Last fall, I stepped into the General Manager role at The Commons, a community space dedicated to meaning-making and self-expression in the heart of San Francisco. The last few months have been filled with experiments and lessons in what it takes to operate a physical space, meet the needs of our members, sustain the business financially, and deliver on our mission of supporting people on their journey in becoming more themselves.

In addition to nurturing our member-designed programming, we also piloted a new experience called Town Square where we partnered with values-aligned practitioners, writers, builders, and civic leaders who are pushing the boundaries of intellectual, spiritual, emotional, and civic development. Our events took shape in the form of fireside chats, book launches, and dharma talk series.

In an increasingly polarized world, the opportunity to welcome leaders across domains and open our doors to the public felt like a breath of fresh air. There are fewer and fewer spaces where we experience the cross-section of humanity. Our remaining public spaces — parks, libraries, transit systems, DMVs — fall short of dignifying our shared humanity. As private social clubs crop up across the nation to combat the loneliness crisis, this project seeks to answer a different, more pressing question: what’s the meaning of it all?

As the new year rolled in, our team returned the drawing board to ponder this question, assess the state of The Commons, and determine where we’re headed. We found ourselves wondering: how can we orient our mission toward creating space for people of all walks of life to coexist, setting aside our differences — if only briefly — to honor our shared human existence?

Since its inception, The Commons has served as an experiential lab for our community, poking at what it takes to safely lose ourselves in the company of others on a similar pursuit, to cultivate Aristotelian friendships, to walk the path toward psychological flourishing, to create spaciousness to slow down, to loosen the grip on our traditional identities, and to playfully experiment with multiple dimensions of ourselves. A place to be ourselves and to become ourselves.

In returning to first principles, we acknowledged that we had strayed from our initial vision of serving as a place to sense make in community, devolving more into a private social and coworking club than a community living room.

With renewed energy, we’re excited to usher in a new era of The Commons — one where we’re contemplating:

• How do we bridge the experience of playful co-working by day and vibrant community meeting house by night?

• What will it take to drive cultural change and usher in new ways of working and playing, offering alternatives to hustle culture and the pervasive bar scene in the form of pursuing work from a place of aliveness and conscious partying with a good book?

• What are the structural conditions needed to seed a culture of individual and collective agency within the space?

• How do we cultivate a place of serendipity and aliveness where evenings can be spent playing a pick-up board game next to a circle in the depths of debating the impact of AI on inner work and humanity?

• How can we sustain this project culturally and financially over the long term and pioneer new business models rooted in healing and self-actualization?

We’re nearly three years in and this is just the beginning. As we continue to experiment with the bounds of what’s possible, we’re guided by the reality that this project is a living, breathing entity, nurtured by the collective wisdom of our community.

The following essay was originally published to .

Where we’ve been 🔮

It’s been nearly three years since The Commons opened its doors in San Francisco. What began as a brainstorm amongst 50 friends for a community living room in the Hayes-Alamo area quickly evolved into a GoFundMe campaign, securing a space at 540/550 Laguna St, and a collective effort by hundreds of friends who built furniture, painted murals, and seeded their hopes for a new kind of community third space.

Together, we co-created a place that harkened back to the feeling of unbounded exploration and curiosity in our formative years: volleying deep questions in a college common room until 2am, mind-melding on beautiful futures that haven’t quite arrived, and communing with diverse, pluralistic, and contradicting perspectives with authentic openness and curiosity. One that could address the growing void in America’s social and "meaning-making" infrastructure left by the decline of churches, clubs, and community spaces.

Thousands of community-created book clubs, juntos, discussion circles, jams, philosophy salons, and workshops later, it's become evident there’s a deeper nexus of phenomena underlying the growth of the space.

The desire to make friends: an effort to mend a fragmented social fabric as urbanites.

The diverse discussions: a need to bring coherence to a dizzying world devoid of overarching order.

From paint nights to writing clubs — a thirst to nurture seedlings of our most authentic selves.

The plethora of co-created programming across the spiritual, intellectual, and emotional — a primordial yearning for wholeness.

The invitation to show up as humans unsure of much — the antidote to all the places in adult life that insist on firm identities.

Not quite a traditional third space, networking social club, secular church, or recreation center — what we are is still emergent and a constantly evolving community experiment (that we’ve loosely defined as a “fourth place”).

Nonetheless, our mission has remained constant: to support people in the process of becoming more fully themselves, rooted in the belief that community is essential to that journey. And to do that in a space infused with playfulness, aliveness, agency, earnestness, abundance, and kindness.

Our next iteration 🔭

Stepping into the new year, we’re excited to share our latest evolution in The Commons’ unfolding toward realizing our mission.

TL;DR: The Commons is evolving from an intimate experimental community into a true “Commons”— a playful co-working space by day that transforms into a vibrant community meeting house by night.

• 🏛️ We’re moving towards more public programming and inclusive membership

• ☀️ By day (9am-5pm), we’re creating a new category of playful co-working that is pro-social, serendipitous, and nourishing

• 🌔 By evening (5-10pm), we’re transforming the space into a Community Meeting House, retaining the heart of our member-created programming while welcoming in more public programming and broader community leaders

• 🍵 We’ll be experimenting with new forms of “conscious night life” beyond the societal conventions of alcohol and partying

• Join us in this new chapter 🎉

🏛️ We’re moving towards more public programming and inclusive membership

To date, The Commons has functioned more as an intimate community than a porous or open one — an intentional choice. However, going forward we’re hoping to increasingly materialize a true “Commons.”

In their early stages, new communities and institutions are inherently fragile, and we prioritized cultivating our culture at a thoughtful, measured pace. This approach allowed us to experiment with programming formats and find the balance between our vision for the space and the emergent, dynamic needs of the community through each iteration.

Today, we believe the reputation and values The Commons represents have grown robust enough to stand independently. Our experiments with programming have also provided valuable insights into the infrastructure and experiments we’d like to run to fully and continuously realize those values.

As an aspiring pluralistic space for self and communal meaning-making, we also want to increasingly invite diverse life experiences, ages, life stages, political views, and ways of being and becoming. Due to the initial network effect of some of our founding cohorts, we veered towards millennial / gen-z age groups in tech and tech-adjacent industries.

Going forward, we’d like to increasingly move towards a true “town square” and more open institution where San Francisco citizens can commune across dichotomies. In today’s climate of dogmatism and division, what’s needed are less private social clubs (the direction we were going down via inertia) and more spaces that cohere people across differences while uniting under core humanistic values.

Here are the changes we’re implementing:

• Broadening membership acceptance: We’ll be accepting more applicants to The Commons given the institutional stability the Commons has created in the last 3 years. With more members, we’ll be ensuring each member still embodies our core values of abundance, agency, kindness, earnestness, and play.

• Expanding public and centrally organized programming in the evenings: In our first 3 years of operations, most of our events were hosted by members for members. Going forward, we’re ramping up on organizing centrally run experiences and expanding our in-space team to create our evening Community Meeting House atmosphere. We’ll also be increasing our evening public programming featuring values-aligned practitioners, writers, creators, and builders across domains who are pushing the boundaries of spiritual, emotional, intellectual, creative, and civic development. Members will receive prioritized access and discounted tickets to these events.

The Commons membership experience:
☀️ By day, we’re creating a new category of playful co-working
🌔 By evening, we’re transforming the space into a Community Meeting House

“An old friend of mine, a journalist, once said that paradise on earth was to work all day in anticipation of an evening in interesting company.” ― Ian McEwan

With this quote as inspiration, we thought to ourselves: How do we create more of these kinds of days at The Commons?

By day, we will be a vibrant neighborhood hub of creative and playful co-working with new and old friends, where the lines blur between “doing” work, mind-melding with others, and simply “being.” We’re for the days where you may have fewer calls, want more creative stimulation, have IRL coffee chats in one of our cozy nooks, or want to take walking calls around the heart of Hayes Valley. At the same time, if you’re looking to be heads down and focused, you are always welcome to carve out your own flow. We’re not here to force serendipity—just to make sure it has a home for those who want it. If some days you want deep focus, The Commons still fully supports that, with plenty of spaces to settle in and immerse yourself in your craft.

The kind of “work days” that are pro-social, serendipitous, and nourishing: meditating mid work-day in our Moroccan lounge, perusing a book for inspiration in our community library, doodling at our art supply station, or striking up a serendipitous conversation while making tea. This is an intentional departure away from the grind-set, remote, and white-knuckled hustle culture that pervades American work culture. At the same time, we also recognize that not every day is the same. Some days are for head-down execution, and others are for spontaneous creativity. The Commons is designed to hold both—so that whether you’re here to laser-focus on a deadline or open yourself up to unexpected encounters, you have the space to do so with intention.

In essence, we want to bring back and reinvent the “watercooler culture” that made work connective and human. In that vein, we’re ushering in a new era of healing and re-defining our relationship to work — one that is flowy, expansive, and holistic.

By night, we transition into an enlivening community meeting house. “Work” as defined by being an artist and doing our art (in the broadest sense) then evolves into communal sense-making. Where the conversations we have in community become mirrors and edifices for self-reflection and expansion, allowing us to show up more authentically in our creations and worldly endeavors. The Commons, by night, is about expansion in whatever form that takes—whether it's engaging in a lively discussion or quietly sketching ideas sparked by the energy around you.

The evening will be enlivened with numerous members only and public events running all at once; for members, we’ll continue to have philosophy salons, board game nights, recurring social rituals, potlucks, and numerous ways to reflect, commune, and explore as a community.

For more public programming: What would it mean to invert the “retreat model”? Instead of going out of town or to disparate institutions to seek wisdom, The Commons becomes a nexus for “elders” to share ideas. A top of funnel function where intros to spiritual traditions, civic matters, philosophical ideas, forms of art, etc. can be shared with the public in a buffet-like fashion. If the intros warrant deeper inquiry, people can then go directly to that elder or institution afterwards. In other words, a node that aggregates energy and then disperses it. Rather than a place of passive consumption, The Commons can be a generative threshold.

In the Fall, we did a v1 of this by hosting over 30+ salons featuring people like Mayor London Breed, Noah Smith, Joe Hudson, Paul Millerd, Gena Gorlin, and Luna Ray. In 2025, we’re hoping to curate a fantastic lineup of new elders embodying “novel ways of being and doing,” offering fresh perspectives on how we live, work, and connect.

Here are the changes we’re implementing:

• Enhancing our co-working spaces: We’re adding a new tea station, an art-making area, and space affordances designed to spark serendipitous conversations along with other playful upgrades.

• Experimenting with playful work affordances: We’ll be experimenting with novel forms of social infrastructure to encourage serendipity and connection during co-working days (i.e. informal lunch squads, “watercooler” prompts, activity breaks, playful stand-ups, etc)

• Balancing member-led and organizational programming: While we’ll continue to support members with resources and space for their events, we’re ramping up on organizing centrally run experiences and expanding our in-space team to support more public events to create our Community Meeting House atmosphere.

🍵 We’ll be experimenting with new forms of “conscious night life” beyond the societal conventions of alcohol and partying

There’s been a subtle but steady shift in the public consciousness towards desiring new forms of evening activities that go beyond the typical excursion to a restaurant, bar, movie night, or club to meet others or convene with loved ones. With a recent warning put out by the US Surgeon General that even small amounts of alcohol can cause cancer, the current alcohol-driven culture of nightlife is rife to go through a huge upending.

What kinds of evening social and physical infrastructure will be created in the wake of this? How can we use different means to meet the same needs for self-connection and connection with others?

We believe now is the time to experiment with novel forms of evening activities: from late night decaf tea houses, evening bathhouses, no-alc dance parties, reading parties, game board parlors to cozy cafes that close at 2am. The Commons is hoping to be at the forefront of this experimentation, opening our space for evening programming that is connective, conscious, and wholesome (with the aims of opening a late night tea house sometime in the future 😉🤫).

Here are the changes we’re implementing:

• More non-alc evening activity experimentation: Expect more experimental evening programming like silent reading nights, analog write-a-thons, powerpoint parties, and rabbit-hole-a-thons.

• Keeping our doors open until 10pm: Most coffee shops close at 5pm and non-alch spaces that are open late are far and wide in between. We plan on keeping our doors open after public / member events end until 10pm so you can continue the discussions into the night.

We’re excited to usher in this new evolution of The Commons’ journey and hope you’ll join us for the ride.

• We’ll be opening our member applications to join our space in Febuary: apply by Wednesday, Febuary 5th, 2025

• Check out our public programming calendar (new events are still in process of being announced & will drop in Feb) + subscribe to our Substack to get updates

• Follow us on Twitter for more updates and good vibes

Warmly,

The Commons Team

The universe delivers us lessons when we’re ready to receive them. These lessons often manifest as internal struggle, triggered by interpersonal conflict, uncertainty surrounding consequential decisions, or existential doubts. A lesson may present itself in new ways, over and over again — it’s only when we’re open to healing an old wound that we can learn what it has to teach us.

2024 delivered me a series of lessons, revealing the ways that I wasn’t yet free. New paradigms I’d stepped into and old dynamics that were ready to be unraveled.

A lesson that had presented itself daily finally came into my awareness: the way I was pursuing aliveness was depleting me.

My search for aliveness has long been tethered to my search for meaningful work. I sought inspiration and aliveness through my work and considered enjoyable activities that took me away from my desk as a reward: an experience to be earned. After I finish this essay. After I send this email. After I wrap this project proposal.

After diversifying my core identity away from a traditional career, I entered a season of life where I filled my days with projects I cared deeply about: writing, studying applied positive psychology, and building The Commons. Work continued to function as my primary vehicle for meaning, becoming deeply entangled with my acts of self-expression. Work that once served as my vessel for creative expression became burdened by the pressure to consistently produce and manufacture meaning. It all had to mean something.

As the lines between work and self-expression blurred, my productivity and desire to create waned under the mounting demands of output and financial sustainability. Although I’d set fire to old scripts, I’d subconsciously began operating from new scripts.

As I’d peeled back the layers of societal conditioning, I came into contact with more of myself — a purer version of who I was underneath all the external shoulds. The trouble was that I hadn’t yet learned that the nature of turning inward is that the shoulds become more and more subtle. As aspects of my life came into alignment, other more subtle shoulds revealed themselves.

The reality that my new portfolio of work had awakened states of aliveness and flow in me spawned a new belief: that work really should be my main source of meaning. As these new scripts quietly took root, they co-opted the progress I’d made in expanding my identity.

At year’s end, when I looked back on the moments I felt most alive, a different truth emerged: it wasn’t the days I spent cranking away at my desk, but the moments I was moving my body, connecting with family and friends, or adventuring in nature. My best days consisted of deep flowy work sessions and awe-inspiring moments with people I love.

Those days, I came to my desk inspired and motivated, dancing toward purposefulness. It all felt inevitable. Yet, for as many days the flow just flowed, there were twice as many days when I forcibly willed myself to dance when no music played.

Despite the fact that the days I spent grinding away all blurred together, I couldn’t shake the notion that meaningful work came above all else.

Clarity arrived in an unexpected way in December: on an emergency family trip. I flew out to Beijing with my mom and brother to be with my grandmother after she was admitted to the ICU. I was amidst finals season at school and yet, I knew with every fiber of my being that I needed to be in Beijing. Despite being jetlagged and grappling with the reality of my grandmother nearing end of life, I found brief moments of flow writing papers in the afternoons, nestled between mornings spent connecting with my mom and brother and late afternoon trips to the hospital. (Fittingly, my final papers investigated what it means to live a meaningful life.)

Back at home, when I suppressed my desire to be inspired and connected, I inevitably operated from disconnection. Yet, self-expression and creativity flow as a byproduct of harnessing possibility and wonder in our lives. Our best work rarely emerges when we’re deprioritizing our bodies and souls. By putting work and self-expression above all else, I closed myself off to drawing inspiration from other areas of my life.

As a result of shaking up my daily routine, I saw the new paradigm I’d trapped myself in with clear eyes. This self-imposed constraint was a defense mechanism that had protected me in an old paradigm.

After a career of early morning meetings, I became fiercely protective of my mornings. When I finally made my schedule my own, I found it deeply nourishing to reserve my mornings for meditating, journaling, and writing. I basked in the morning stillness. Slowly, I pushed my “morning” hours further and further into the day. I became militant about no “distractions” until early afternoon. The restrictions I once needed to recover from having no time to myself expanded to constrain the rest of my day. What was meant to create space and flow became rigid and stifling.

I convinced myself that all my days needed to start a certain way and resisted new ways my day could unfold. When exciting opportunities arose—an interesting call, a new workout class—I clenched to what “worked.”

As I clung to preserving my morning hours, it became clear that the rigidity was contributing to states of contraction. When I held the desire to dedicate the morning to writing and being alone too tightly, I missed signs from my body that were whispering: I’m being deprived of inspiration. I want to work out. I’d prefer to go out for a walk and see what words emerge.

When we’re too precious about maintaining the constraints we’ve set for ourselves, we ignore our intuition and fail to cultivate the self-trust needed to free ourselves from over-optimizing.

The irony of optimizing our lives is that the nature of optimization is rooted in a lack of self-trust. We inherently don’t trust ourselves so we put systems in place to take the thought out of it. While setting constraints is a good short-term solution in bridging our self-trust gap, the ultimate goal is to build a reserve of self-kept promises that help us restore faith in our intuition rather than further optimize a system that keeps us caged.

My morning ritual took shape during a global lockdown when I was checking my phone every few minutes. Now, I no longer have the impulse to check my texts hundreds of times a day — as a result, I no longer need to hold myself back from the desire to take a break after a deep work session to connect with a friend. There’s a difference between following an impulse to procrastinate versus a genuine desire to connect meaningfully.

This year, I’m cultivating moments of wonder and seeking aliveness through moving my body, spending time with people I love, and being in nature, allowing the overflow to spill into my work and self-expression rather than grind on empty.

What lessons did you learn in 2024? What intentions are guiding you this year?

Let me know in the comments or say hi on Twitter :)

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Thanks to Ryan for reviewing drafts of this essay.

Recently, I hosted a Fireside Chat with my friend, , at The Commons in celebration of his new book, Good Work. Paul embodies the spirit of the pathless path and serves as a reference point of what it looks like to break free from a conventionally alluring path in pursuit of his greatest ambitions and aligning with work that matters most to him.

As I read Good Work and prepped for our conversation, I reflected on how my relationship with work continues to evolve and the stories I hold about what it means to do good work.

In the US, it’s common to seek legibility through what we do for work. When we introduce ourselves to strangers, one of the first questions we ask one another is “What do you do?” Not “what do you do” in the sense of how do you spend your time or what curiosities are you chasing, but what’s your role in contributing to our economy? Of all the identities we hold, presenting ourselves as productive workers has become the quickest way for others to gauge who we are and for us to gain approval.

As a result, we derive our self-worth from the titles we hold, the companies we belong to, and the salaries we earn. When so much of our sense of self is tied up in a single identity, it’s easy to feel suffocated by the existential dread that creeps in when what began as a good, meaningful job no longer fuels us.

Paul argues that, as a society, we’ve mistaken securing good jobs for finding meaningful work. Rather than viewing our jobs as the portal to good work, it’s about redefining what work means to us — as acts of self-expression that don’t necessarily bear economic fruit rather than solely as acts of employment.

This isn’t to devalue our employment but rather to disentangle the “good enough” from the truly “good” work. It’s only when we reimagine what work means to us that we can create space to engage in the activities that allow us to flourish and flow.

• Good work: energizing activities that bring us to states of flow — not always easeful, but reliably nourishing

• “Good enough” work: supporting tasks that bring a level of enjoyment, often to help sustain us financially, but not central to our good work

• Supporting work: adjacent tasks that support our good work, but can become a distraction

• “Bad” work: draining work to minimize or avoid, but may be necessary to sustain ourselves financially

Once we have a sense of how each of the activities we engage in fit into these buckets, we can begin to prioritize our energy and time accordingly. In moments of existential dread, we’re likely filling our lives with supporting activities and “bad” work, too depleted to embark on our good work.

finding our good work in the marble

I often hear friends lament that they struggle with identifying what type of work they’d want to do if they had the freedom to do whatever they pleased. Then, they proceed to share a list of meaningful activities they wish they had more time to do.

In my experience, my good work has been surprisingly obvious to me, subtly manifesting as what I do when no one is watching. Once I expanded my definition of work, tapped into my intuition, and created space to experiment, it became abundantly clear that I’ve known what my good work is all along.

When I was in elementary school, I often spent recess writing short stories on the playground with my best friend. As I got older, despite my love for writing, it never occurred to me that I could continue writing even if it wasn’t a “viable” career path.

It took giving myself the permission to write again with no agenda other than self-expression to slip into deep states of flow. Often this feeling is so powerful that when I re-read my essays, I’m met with awe. I know I wrote those words, but I don’t remember how I assembled that sentence or how I arrived at that conclusion. I got lost in the writing and it naturally flowed through me.

The important qualifier is no agenda. When I first started reconnecting with writing, I felt a pressure to grow and monetize in ways that felt misaligned with my purpose for writing. After months of experimentation, I realized it was far more important for me to draw out what felt most alive in me on any given week than commit to a rigid publishing schedule to meet draining growth goals.

Ironically, by giving my relationship with writing space to naturally evolve, I now have far greater (and sustainable) ambitions for writing than I would have by trying to shoehorn it into a profit-making endeavor. Now, writing serves as my vehicle for discovery, expression, and expansion.

I write this coming off several weeks where I struggled to muster the words to piece together an essay. Rather than force myself towards publishing, I gave myself the grace to sit with the discomfort of not having the words, writing and writing until I found flow again.

Your good work exists within the marble slab of experimentation and action, waiting to be revealed. The journey is about patiently chiseling away at the inner and social expectations that keep you from pursuing the work that resonates at the soul level. Allow what doesn’t matter to fall away to make way for what does.

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When you connect with your good work, protect it at all costs. Don’t put pressure on your acts of self-expression by trying to make it your sole source of income. When we buy into the notion that we must spend all of our time and energy doing our most meaningful work, we paralyze ourselves in the search for the perfect thing, ruminating rather than experimenting.

Seek out “good enough'“ and supporting work that afford you time and space to engage in your good work while maintaining the lifestyle you want to live.

The challenge lies not in discovering what our good work is, but in liberating ourselves from the notion that only financially lucrative activities constitute as meaningful work worth doing. Good work recharges our life force, energizes us to connect with our truest ambitions, and serves as our channel to express our humanity to the world.

giving voice to our intuition

All of us have an intuition around what our good work is. The question is whether we’re attuned enough with ourselves to trust that intuition. When we continuously suppress what we want to do in favor of what we should do, it becomes harder to connect with our most genuine desires even when we have the resources to do it.

What do you gravitate towards doing in moments when no one is watching? What came naturally to you as a child?

The best way to unstuck ourselves is to take small steps in cultivating self-trust in the face of “competing” priorities. Rather than thinking about the consequences, take action in building the momentum to figure it out.

Have an inkling to attend the writing event happening tomorrow even though you should work more? Go. Feel drawn to the local pottery class even though you should go to that networking event? Sign up. Contemplating going to the meditation sit even though you should catch up on emails? Meditate.

Evaluate how building self-trust feels in your body. Do you feel lightness or heaviness after acting on your intuition? Each time you honor the quiet whispers that emerge, you strengthen the bridge back to your inner wisdom. Over time, you create reference points of courage that further fuel you towards building a life around the experiences you feel called to.

As we age, the hope is that we gain a progressively deeper understanding of who we’ve been and who we aspire to become. This evolution demands we consciously examine the parts of ourselves that have succumb to societal shoulds. Unshackle yourself from the life you think you should live.

Who are we living and working for if not ourselves?

Here’s to finding your good work. The work you lose yourself in. The work that you do for the sake of it. The work that sets your soul on fire.

Thanks for reading! How do you define your “good work”?

Leave a comment

Let me know in the comments or say hi on Twitter :)

Watch the replay of our fireside chat:

If you enjoy this piece, you may also enjoy my series on Work & Self-Expression:

Thanks to for leading the way in reimagining our relationship with work, to for reviewing a draft of this essay and filming our discussion, and to everyone who joined us for the fireside chat.

Last week, I shared some life updates on what I’ve been up to. This week, I’m sharing a list of big questions that serve as my compass as I grapple with the theory of flourishing and actualize it through building a modern town square.

Historically, I’ve unconsciously allowed societal expectations to drive the work I did and the ambitions I pursued. Now, I think of my career less as a series of milestones to achieve, ladders to climb — more as a set of experiments to run, projects to progress.

To structure these experiments and projects, I sat down last month as I began my masters in applied positive psychology to articulate what questions I planned to center my explorations around.

My intention is not only to answer these questions at the theoretical level through writing, but also to wrangle with them tactically over the course of building The Commons, a community space in San Francisco dedicated to meaning making and self-expression, and through other future projects.

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These are the big questions I’m grappling with and hope to answer over the span of my “career.”

🔭 Cultures of Agency

• What are the structural conditions needed to seed a culture of individual and collective agency within an institution or a community?

• What factors have contributed to the presence of agency in certain communities throughout history? What role do community institutions play in fostering human progress?

• What new narratives can we create around our relationship to work, “economic value,” and true ambition?

• What can we learn from the history of the Bay Area to understand the conditions that have enabled agency to permeate the region?

My interest in exploring agency centers around the core belief that there’s no character trait more essential to individual and societal progress than agency. Agency is the embodied conviction that you have the power to create meaningful change in your life and transform your vision into reality. It’s the engine that powers human progress.

I’m interested in the historical and cultural evolution of agency, particularly in regions like the Bay Area where it’s deeply ingrained in the social fabric. My hypothesis is that the agentic nature of the Bay Area was seeded decades ago and shaped in large part by the formation of America.

In the early days of our nation, the most risk-tolerant immigrants set sail across the Atlantic in search of economic opportunity, religious freedom, and a better life. They held onto the optimism that life would be better in the New World. As our young nation found its footing, society in the original colonies set the tone for early American life while westward expansion came to symbolize even greater opportunity and mobility.

In the mid-19th century, the allure of the Gold Rush drew many of the most entrepreneurial Americans to continue west in pursuit of wealth and reinvention. Call it naivety, greed, or a spirit of agency, the founding settlers of the Bay Area were fueled by an unrivaled level of courage and tenacity.

The region became home to those who embraced risk and innovation, establishing the roots that would shape the DNA of the modern day Bay Area. In the ensuing years, it has served as a crucible for alternative living and movements that swept the nation — from the Free Speech Movement and hippie counterculture movement in the 1960s, to the farm-to-table movement in the 1970s, to the birth of modern technology throughout the 20th century.

Decades later, agency remains on full display with the Bay Area being the center of technological innovation and San Francisco being home to a fifth of all US startups.

Inspired by a city that lives at the edge of tomorrow, I want to uncover the conditions we need to usher in more cultures of agency to foster individual and community progress.

🏛️ Flourishing Communities & Institutions

• In the face of the meaning, loneliness, and meta crises, how can we reimagine and build the town squares and secular churches of the 21st century in support of collective flourishing?

• What are examples of flourishing societies from the past that enabled the pursuit of truth and human progress? What are the core elements of systemic flourishing? What’s the role of the individual versus the collective?

• What were the conditions that allowed individuals like Benjamin Franklin to establish the new age institutions (Penn) and civic organizations (juntos, libraries, philosophy societies) of his time?

• What’s the history of clubs and extracurriculars? How have they contributed to meaning-making and identity formation at the individual and community level?

• What’s the role that societal rituals play in meaning and purpose-making?

• How can we advance the psychology of progress and integrate individual psychological healing as part of the course towards societal progress?

• How can we redefine what it means to gather in community and center around deep connection, aliveness, and introspection? How has the role of hosts and community organizers evolved over time?

Benjamin Franklin, the visionary behind many of America’s earliest civic institutions, conceived a number of our nation’s firsts in his Junto, a discussion group where he convened with fellow intellectuals, artisans, and tradesmen to contemplate solutions to concerns of their time. Among the ideas were our nation’s first lending library, our first hospital, one of the original volunteer fire departments, and an intellectual society.

Societal progress is born from the imagination of an individual, but is actualized through collective effort.

Nearly 300 years ago, Franklin and his contemporaries laid the groundwork for what would become the fabric of daily life in modern America. Today, as we confront the meaning and loneliness crises, along with broader systemic challenges, we have the opportunity to reimagine and reshape our modern institutions to better support collective flourishing.

This set of questions is driven by the notion that systemic flourishing begins with the individual. Flourishing looks different for each of us because it’s about coming home to ourselves. For a community to flourish, each individual must be on their own path towards coming home to themselves. Can we truly flourish if those around us are suffering?

I flourish in the moments when I’m in deep presence and feel connected to the grander scheme of it all. I’m operating consciously and freely self-expressing. Whether I’m writing, working on a meaningful project, hiking in a national park, or spending time with a friend, it’s a feeling of coming alive and being moved by the honor to live this life. These moments are marked by flow and a feeling of being deeply integrated. It’s a homecoming, a grounding, an expansiveness, an easefulness, a peacefulness.

It’s clear to me that others are flourishing when they come alive in ways that give me a lens into who they were when they were children, overflowing with unbridled curiosity, wonder, and excitement. They exude a level of agency and passion that is infectious.

It will take a collective narrative shift and it’s not just up to us to answer these questions alone. We need institutions to support us in this process.

As church participation continues to decline, we can no longer rely on our traditional institutions for meaning-making. More than ever, we are in dire need of new institutions and communities that can guide us in our unfolding and becoming.

That’s precisely what we intend to experiment with and build at The Commons.

🪄 AI & Self-Expression

• Assuming that advancements in AI free up humanity to self-actualize, how can we create social infrastructure and design institutions to support humans in unfolding into their fullest self-expression?

• How will AI elevate human self-expression and agency?

We have early indicators that the commercialization of AI will revolutionize our relationship with work. While I love a good optimistic take, I often hear unwarranted confidence that as AI begins to replace our existing jobs, we’ll have the freedom to find work that’s more aligned with our life’s purpose. This assumes that we’re all in tune with our higher calling — something that’s often subtle and easily suppressed.

After spending the last two years exploring my (previously unhealthy) relationship to work, diversifying my sources of meaning, reconnecting with my self-expression, and refueling my ambition, I sense we’re closer to a full-blown meaning crisis than a liberation.

As a society, we need to step back and reflect on who we want to become once AI automates much of the work that has historically provided us with a sense of purpose, worth, and identity.

If you’ve ever had the opportunity to offboard from a company as your role was being deprecated or backfilled, you know the reality that our contributions fade with time, if not as soon as we move on. Someone replaces us, work is redistributed, life goes on. Regardless of how hard we fight it, we are all largely cogs in the corporate machine.

What is worth fighting for is our liberation from the notion that our worthiness is solely tied to work that generates economic value. Cultivating experiences of self-expression to better understand ourselves and discover who we are beyond merely value capturers will help us gain clarity on who we might become in a post-artificial general intelligence (AGI) world.

Supporting our members in reconnecting with and harnessing their self-expression is another central pillar of The Commons.

And so there you have it, the big questions I’m grappling with in this season of life. I’m certain that these questions will evolve and expand over time.

If you’re exploring similar questions in your work, I’d love to hear from you in the comments or say hi on Twitter :)

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For more on my work, check out:

Thanks to Sam for sharing feedback on this set of questions and to Ryan for reviewing drafts of this essay.

Lately, I've been navigating a season of change and transition. At the culmination of metamorphosis, the caterpillar sheds its skin as its body dissolves into a primordial, gooey nothingness. In this process, the butterfly fortifies its wings as it grapples with the chrysalis, emerging only when it’s ready to take flight.

In the chrysalis of my sabbatical, I lost and found myself again and again, confronting and shedding old identities to make space for my becoming. Only by surrendering to the darkness could I find my path toward a new light.

I'm under no illusion that this is my final metamorphosis. There is no valedictory to our evolution, only a continuous unfolding into who we are becoming. I'm excited to share with you where my latest unfolding has led me.

tl;dr: I’m studying the science of human flourishing at the University of Pennsylvania in the Master of Applied Positive Psychology program and building a modern town square at The Commons as our General Manager.

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Early on in my sabbatical, with the freedom to spend my time however I desired, I began to observe who I was in flow and in ease. I learned that despite being self-aware, I had not appreciated just how out of alignment my prior existence was with the life I wanted to cultivate.

I learned that morning stillness is precious to me. That I love starting my days writing and lost in thought. That I could deepen my meditation practice in new ways. That my shadows desperately wanted to make themselves known to me. That my triggers shined a light on all the ways I was not yet free. That my ambition was sourced from a dirty fuel and a belief that my worthiness was benchmarked to my productivity. That I can only find belonging by first belonging to myself. That I was out of touch with my grief. That I had spent a lifetime shoulding myself.

These revelations led me to reorient how I spent my time and invested my energy. I gave myself the freedom to explore curiosities I’d once dismissed as useless. I began to approach life as a series of experiments, letting go of the notion that there was one way of being, living, and working that suited me.

I spent my early mornings writing with the intent to publish — something I had only recently mustered the courage to do — after years of relegating my words to a private journal, despite having been an avid writer in childhood. At some point, it had become clear that pursuing writing wasn’t a viable career path, as if every single thing I did had to have an associated economic value, so I put down my pen and stopped self expressing through written word.

In rekindling my love for writing, I reconnected with the inner voice I’d suppressed, and by getting in touch with my unbridled self, I felt emboldened to chase other curiosities and intellectual pursuits.

grappling with flourishing

It was during this time that I became conscious of my love for psychology. For as long as I can remember, I’ve been fascinated by our human nature and the inner workings of our soul. This fascination manifested as a voracious appetite for all things “self-improvement” and “personal development.” In my twenties, I consigned this interest to a side quest, reading as many books on the topic as possible, but only in my spare time. I had a narrow view of what I might do with psychology — I didn't necessarily want to become a psychologist so instead, I singularly focused my career on lucrative pursuits like finance and technology.

In the course of a conversation with a friend, I stumbled across the work of Dr. Martin Seligman, the founder of the field of positive psychology. I was deep in my journey inwards, pondering what flourishing meant to me. I picked up one of his books and quickly devoured Flourish.

One quote in particular reverberated within me, planting a seed of possibility:

If we want to flourish and if we want to have well-being, we must indeed minimize our misery; but in addition, we must have positive emotion, meaning, accomplishment, and positive relationships. The skills and exercises that build these are entirely different from the skills that minimize our suffering.

— Martin Seligman, Flourish

The book awakened me to the fact there was an entire research field dedicated to shifting the focus of modern psychology. Following World War II, the spotlight has largely been on curing the pathologies of anxiety, depression, and PTSD, attempting to move us from -1 to 0.

While this work is absolutely critical, we’d spent little time considering what happens when we reach 0. It's not enough to simply pursue arriving at baseline — what about moving from -1 to 1? That path is going to look entirely different. Reducing suffering is just the first step of raising the bar for our existence.

Relative to other sciences, positive psychology is in its infancy with Marty first formally establishing the field in 1998 during his term as the president of the American Psychological Association. As I dove into Marty’s work, I became interested in the idea of studying positive psychology with him. The privilege of studying with the founder of a field and his contemporaries is rare in most disciplines today — so when I discovered he still taught a graduate program, it felt like a stroke of fate.

a masterclass in the science of flourishing

And that’s how I found myself on Penn’s campus at the start of last month, beginning the Master of Applied Positive Psychology (MAPP) program. The program, a full-time hybrid model, brings me to Penn once a month to learn from leading scholars pioneering the field.

On our first day of class, Marty shared the day marked the 60th anniversary of him arriving at Penn to begin his PhD that would pave the way for the discipline. It’s hard to articulate how meaningful it feels to have the honor to be at the edge of the field, grappling with the theory and science of flourishing, on the campus where it was first established.

How I intend to actualize the theory feels equally poetic.

Penn is situated in the city where our founding fathers established our young nation, breathing life into ideals and principles that serve as the bedrock of daily life in America. I’m often struck by the reality that everything that exists in our material world originated from a single idea in someone’s mind.

In the Bay Area, we have the privilege of existing at the frontier of human progress. Several times a day, I pass by self-driving cars or interact with AI technologies poised to revolutionize our lives in ways we have yet to fully comprehend.

Penn was the first university established in America to offer a holistic curriculum including science, public service, and commerce — a departure from the singular focus on theology that the first four US academic institutions delivered. Benjamin Franklin, the visionary behind many of America’s earliest civic institutions, was instrumental in ushering in a new era of academia that ultimately laid the groundwork for higher education as we know it.

Franklin also played a critical role in establishing the Library Company of Philadelphia (America’s first lending library), Union Fire Company (one of the original volunteer fire departments), and the American Philosophical Society (a nexus for scholarship). Many of these ideas were conceived, debated, and incubated at his Junto, an informal club where he convened with fellow intellectuals, artisans, and tradesmen to discuss solutions to civic problems of their time.

Now, nearly 300 years later, in the face of the meaning, loneliness, and meta crises, we find ourselves with the opportunity to reimagine and reshape our modern day institutions to better support our collective flourishing.

building a commons

Two and a half years ago, two of my friends, and Adi Melamed, founded The Commons, a third space dedicated to self-exploration, meaning-making, and self-expression in the heart of San Francisco.

It was intended as an experiment in envisioning what our community’s dream third space could be. With the help of our friends, Rose and Jason, who found the space and the local community who donated and loaned funds to secure the lease, The Commons opened its doors in August 2022. Alongside 100 other founding members, I joined the community, ready to co-create our experience together.

Early on, much of our programming was curated by our members. Our calendar was filled with intellectual salons, artist circles, meaning-making juntos, and film nights. My evenings were spent having lively and intimate discussions with new and old friends. Slowly, my horizon for what was possible expanded. At the time, I was co-hosting SF’s Writing Club on Sundays. I began experimenting with hosting my own community events, book clubs, and salon series from identity work to shadow work.

Prior to The Commons, I had spent most of my journey inward in solitude. I was doing the work, but only when I began sharing my experiences with others on their own paths did I begin to observe a discernible change in my way of being. Part of healing was excavating and making conscious my shadows, triggers, and old wounds — the other part was finding safety in being seen for all of me and holding space for others as they shared their journey towards their own truths. Introspect in solitude, heal in community.

While exploring what the path to flourishing looked like for me, I was also studying how we might foster collective flourishing and the role our communities and institutions play. Day-to-day, I found that while I loved writing and contemplating the theoretical in the mornings, I longed for a way to debate and actualize those ideas in the evenings. For me, it wasn’t enough to just theorize and reimagine what human flourishing could look like in the 21st century — I wanted to go out into the world to debate, experiment, and redefine our modern culture in community with others. Plus, the part of me that loves organization and community building was ready to re-engage.

As fate would have it, soon after I acknowledged that I was ready to partner with collaborators in my next season, an opportunity to join the team and take The Commons to the next level emerged. Over the summer, I joined Patricia and Adi with a focus on upleveling our community programming, external partnerships, and member experience. As I onboarded, we shared our hopes and dreams for The Commons, refined the vision and mission, and debated the role our institution plays in tackling the meta crises.

As we embark on the next horizon of The Commons, I’m spearheading several initiatives as the General Manager to make good on our vision including:

1. Building our Town Square program where we partner with values-aligned practitioners, writers, creators, builders, and organizations across domains who are pushing the boundaries of intellectual, spiritual, emotional, creative, and civic development

   • Town Square events take shape in the form of workshops, fireside chats, salon, lecture series, and everything in between. While our member-run programming remains a cornerstone of The Commons, we’re investing our energy in welcoming more external experts to the space to learn from the forerunners across domains and learn what it takes to be a truly pluralistic square where all perspectives are welcome

   • This gives our members the freedom to channel their most whimsical, playful energy into hosting their own niche events rather than being stifled by a need to put on experiences that cater to the broader community

   • Town Square is designed around four pillars: helping our members 1) explore life’s bigger questions, 2) resolve and integrate our past, 3) expand into new perspectives, and 4) define our purpose in the world and self-actualize

   • Here’s a sampling of our events: A New Psychology of Ambition with , Building a Personal Spiritual Practice with Michael McCord, The Good Enough Job with , The US & San Francisco's Economies with

2. Designing social rituals in pursuit of creating cohesion and a sense of belonging within our community in an era where traditional institutions no longer guide us in meaning-making, celebrating the passage of time, honoring our identities, and mourning the cycle of life

3. Elevating our Commons Clubs, a number of long-standing and emerging member run organizations that have become features of our community experience

   • Over time, we intend to build the infrastructure to support our members as they incubate their unique forms of self-expression. A few organizations at the forefront of piloting that vision are , , and Conscious Tech Collective (CTC)

This is just the beginning. For now, we’ve proven that The Commons is a socially and financially viable experiment. We’ll continue to push the edges of what The Commons can become.

What began as an intention to create a community living room to call our second home — a wholesome alternative to the pervasive bar scene — has transformed into so much more. A space to pause, explore the many dimensions of ourselves, shed old identities, and step into new ones. Since the beginning, thousands of people have come through our doors. We hope that thousands more will find their way here in pursuit of their inner truth and unfolding into fuller expressions of themselves.

If you’re interested in following along, you can find us on Twitter and soon, Substack. Stop by for a public event or apply to join our community!

Substack & the book

In addition to my coursework, writing this Substack will continue to serve as my main outlet for expressing the ideas I’m wrestling with. In the coming weeks and months, I hope to publish more of the academic side of my work as well as some inner workings of my day-to-day. You can expect to see experiments in format and cadence for the foreseeable future.

At the end of last year, I shared that I was writing a book called Joy in Mourning a Life that Could’ve Been. A rookie mistake. I had a few chapters written, but as I sat down to feel into the narrative of the book, I realized that another story felt more urgent and alive in me. And so, as to not make the same mistake twice, I’ll work on the real first book some more before sharing it more broadly :)

Paid subscribers: you’ll receive a signed and dedicated copy of this first book — a big, heartfelt thank you for your support.

And to the nearly 1000 other subscribers (!!) that have joined along the way: thank you for being here. I’ve found my work to be most meaningful when I’m able to keep it largely free and accessible to everyone. Over time, I intend to transition to a buy-me-a-tea model and reframe the paid subscription as a way to support (and fuel) my book writing. In the meantime, I plan to run some fun experiments for paid supporters.

If my writing has touched or inspired you in some way, consider buying me a cup of tea.

Upgrade & buy me a cup of tea 🍵

And so, that’s my current season of life as I know it. Basking in the privilege to grapple with the theory in the city where positive psychology and our nation was birthed while experimenting and actualizing those ideas in a city where we stand at the edge of tomorrow.

Thank you for being on this journey with me. Being seen by this community has played a large role in giving me the courage and confidence to step into my full self-expression and do the work most meaningful to me. I hope to play a small part in inspiring you to step into your own self-expression.

Your support means the world to me. Thank you, thank you, thank you. ♥️ 

These are the questions guiding this season of life:

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Thank you to Tom for introducing me to positive psychology, to Rick, Casey, and Deena for supporting me on my journey to Penn, to the MAPP team for welcoming me into the program, to Patricia and Adi for entrusting me to join you in stewarding us into the next season of The Commons, to friends who have supported me in a multitude of ways, and to Ryan for relentlessly being my hype man on this journey.

At the end of last year, I shared that I’m running a series of experiments in the new year. In the spirit of Year of doing the damn thing, I’m excited to invite you to the first of 2024!

Cringe Club 🫡
I’m hosting an online workshop for paid supporters on Friday, February 9th, at 12:30PM (PT) where we’ll spend 90 minutes surrendering to the cringe and doing our damn thing. Bring a project, an essay-in-progress, whatever’s been calling to you and breathe life into it in community with others. Upgrade to paid to join us! RSVP here.

Upgrade to join Cringe Club

Growing up, I had a fraught relationship with ambition. My deepest fear was not fulfilling my potential. To paraphrase Paul Graham in his Cities & Ambitions, I was one of those ambitious kids who possessed ambition that seemed to precede anything specific to be ambitious about. I just knew I wanted to do something great. I was singularly focused on working hard, being the best I could be, and maximizing my impact in any way I could.

For an immigrant in 21st century America, there are traditional standards of impact to strive towards: become a doctor, lawyer, engineer or go into business. I began my undergraduate career studying economics on the pre-law track. When it became clear to me that economics was largely theoretical and that many of my most ambitious peers were pursuing finance, I swiftly transferred to the business school.

When companies began recruiting on campus, I gravitated towards the highest “impact” jobs (read: highest status and highest paying). I pursued roles at investment banks and investment funds. When I landed my first full-time job at an investment fund, I poured my energy into proving my value as a new graduate. I developed a strong work ethic, prioritizing work over everything else to lay the groundwork for making partner at the firm one day.

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When my interests and ambitions no longer aligned with my career trajectory in finance, I tried my hand at working in venture capital and then in early stage tech. With each pivot, I convinced myself that this new job and company was it — where I would unleash my full ambition and where it would finally flourish.

I would become infatuated with my new role and responsibilities, dreaming of how my future would unfold at the company. Naturally, I’d benchmark my self-worth against the progress I was making towards that reality, measured in the form of expanded responsibilities, promotions, and salary raises. This is what I believed ambition to be: being achievement-driven and outcomes-orientated with a commitment to relentless hustle.

In this paradigm, my ego drove my ambition which was fueled by a lack of worthiness. I thought to be worthy, I must prove that I was extraordinary by societal standards. If I changed the world then I’d be baseline worthy.

When we’re motivated by deep insecurity, we strive towards collecting accomplishments that are deemed impressive by others, but rarely does that lead us towards a life that we would have otherwise chosen for ourself. The sentiment of “I can do more, I can be more” is buoyed by the notion that you should do more regardless of what you want to do. No amount of success will quench our desire to be enough. We keep the hedonic treadmill running, fueled by a bottomless pit of proving ourself to others.

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Ironically, in my attempt to quell the fear of not fulfilling my potential, I inadvertently stifled my ambition by constraining my focus to pursuits that were deemed ambitious by other people. The insidious nature of fueling our ambition from a place of lack is that rather than setting us free, our achievements only amp up the speed on the societal treadmill.

When we channel our ambition towards fulfilling society’s shoulds over our own intuition, we’re actualizing a life that wasn’t meant for us. We feel it in the drain on our life force, the persistent silencing of the things that call to us, the whispers of is this all? Self-actualization doesn’t happen if we’re actualizing for others and not our self.

ambitious to what end?

When we begin to deconstruct why we do the things we do and seek to understand our underlying motivations, it may be surprising to find that the depth of our ambition is quite shallow.

We’re conditioned to believe that to be ambitious is a good thing, but what are we all seeking through our ambition? When it comes down to it: why we’re ambitious and how we apply our ambition matters.

I'd always considered ambition a good thing, but I realize now that was because I'd always implicitly understood it to mean ambition in the areas I cared about. When you list everything ambitious people are ambitious about, it's not so pretty.

— Paul Graham, Cities & Ambitions

Ambition comes in many forms and flavors — each unique to us. When we’re young, we’re taught to see the pursuit of ambition through the lens of what was valued in our family system whether that be starting and owning a business, climbing up the corporate ladder, starting a family, or pursuing the worthy path.

The reality is that there are infinite flavors of ambition and paths to walk. When we begin to see the constraints we’ve boxed ourselves into, we can make conscious the games we’re playing. Make sure that the ambitions you’ve opted into are the ones you want to pursue for the long haul. If they’re not, it’s in your power to release yourself from those that no longer serve you and redirect your attention to playing a new set of games.

The beauty of ambition and self-expression is that it’s distinct to each of us. If we have the courage, tuning into our flavor of ambition has the power to free us. Increasingly, we’re seeing more examples of people who are doing the internal work and creating new reference points for how we can realize our greatest aspirations. The leaders who build companies to change the trajectory of humanity and lead their teams with high integrity, lifting up those around them along the way. The creators and writers who commit their energy to carving new unconventional paths, trading the stability of a 9-5 job for pouring their life force into the work that calls to them and bringing others along for the journey.

When we give ourselves the permission to blaze our own path in service of our purest ambition, not only are we tapping into new levels of meaning in our own life, we’re giving others the permission to focus their energy to make their maybe someday dreams a reality before it’s too late.

the transition to clean fuel

When I started my inner work journey, I feared too much introspection would make me soft and dull my edge. What if being introspective drained me of my ambition? What if I became complacent?

In actuality, putting a witness on my insecurities, triggers, and shadows has given me the power to empathize with my unintegrated parts: the inner critic who pushes me beyond my limits, the night owl who self-sabotages my early bedtime to do just a little bit more work, the impact-obsessed yes woman who takes on too much in an effort to prove herself.

As I integrate these parts, I’m undergoing a purification process: an act of aligning my ego with my will and my soul. My ego is no longer the sole driver of my ambition — instead, its guided by the wisdom of my will and soul.

As I trade my reliance on other people’s barometer for ambition for my own, it feels like a homecoming: a return to my roots, a grounding in my truth, and a transition of fuel source from dirty to clean.

I no longer outsource my ambition to be dictated by everyone else. And as a result, I’m far more ambitious than ever before. My ambition is fueled by my will to redefine what human flourishing means in this century, my soul’s desire to create new reference points of possibility and permission for those around me that pursuing our purest ambition is possible in this lifetime, and my ego’s confidence that it’s time to bet on myself.

The transition to clean fuel has expanded my horizon of possibility. It’s unveiled that there are far more ways to walk the path towards fulfilling my ambition than the narrow path I was marching down. And I trust that my ambition will guide me to places that I can’t even begin to imagine.

By turning towards the unconscious and making it conscious, I’ve gotten underneath my greatest fear. When I ask myself what would I do if I was unafraid of my greatest fear?, a new response has emerged. It turns out my greatest fear is actually pursuing my purest ambitions — trusting that I can rely on my intuition, resourcefulness, and drive to achieve the reality that only I can self express and breathe life into.

In my essay introducing my vision for human flourishing, I shared that:

I want to empower ambitious people to fuel their greatest aspirations from a foundation of wholeness and security.

When we operate from a place of baseline worthiness and enoughness, we have the capacity to tap into our most genuine desires and soften into building a life where we thrive, being bold enough to bet on ourselves and our greatest ambitions.

There are a million ways to honor your ambition. The key is owning it like your life depends on it. No one, no leader, no organization will think about the highest and best way for you to apply your purest ambition. It’s up to each of us to unleash our flavor of ambition in its fullest expression and build a meaningful life along the way.

Thanks for reading! What fuels your ambition? What’s your relationship with ambition? Let me know in the comments or say hi on Twitter :)

Thanks to Ryan for reviewing drafts of this essay.

• Part 1: Knowledge work as an emotional act

In Part I, we introduced the idea of emotional embracement, the act of turning towards “negative” emotions that emerge while we’re working, and why we believe it’s the gateway to unlocking new levels of creativity and self-expression.

By bringing awareness to our body and processing emotions while we work, we can deepen our understanding of how we relate to work, creating more intentionality around how we spend our time.

When we tune into our emotional state, we’re giving ourselves the permission to feel the waves of discomfort and the negative sensations in our body we’ve been clenching. If you find yourself sitting down at your desk, only to feel a sense of dread, there are paths forward other than spiraling into procrastination. Where are you feeling the dread in your body? What is the procrastination trying to tell you?

While we’re not the first ones to talk about this concept, we haven’t found a comprehensive guide on how to apply it to work. This essay serves as our playbook for how to tactically integrate emotional embracement into your day-to-day work.

Through experimentation, we’ve identified four main steps to this approach:

1. Cultivate awareness 🧘

   • Bring awareness to your body and emotional state

2. Journal interstitially ✍️

   • Take notes on resistance and insights that arise

3. Process emotions 😮‍💨

   • Address and process emotions using your existing introspection practices (e.g., meditation, breathwork, Internal Family Systems (IFS) parts work)

4. Update approach 🔁

   • Integrate learnings from Steps 1-3 into your work routine

The ultimate goal of this process is tending to our work in a relaxed state with focused attention. The intention is to develop feelings of loving kindness and non-judgment towards our resistance to work. As with somatic and shadow work, it’s common to feel disdain for our “negative” thoughts and the uncomfortable sensations in our body. But, only by shining a light and putting a loving witness on what’s been suppressed can we begin to dissolve inner conflict and work more intentionally.

A note on personalizing your practice: As with most things in life, there’s no one “right” way to practice emotional embracement. The two of us have wildly different emotional working styles:

• Cissy tends towards an anxious attachment to work. While she finds it easy to start working, under stress, she resists taking breaks even when she’s hit a wall and runs the risk of overdoing it. Her energy may be spent on smaller, inconsequential tasks to procrastinate the meaningful work.

• Pranab tends towards an avoidance attachment to work. While he prioritizes a balanced approach to work, under stress, he resists exertion in the face of too many to dos, overthinking at the cost of getting things done. His energy may be spent seeking other things to do before starting work.

Yet, we have both experienced meaningful changes in our relationship with work as we’ve adopted this approach. Our hope is that by sharing the tactics we’ve found helpful, you can experiment and remix the toolkit to assemble your own emotional embracement practice.

step 1: cultivate awareness 🧘

Start your work session by bringing your attention to your body via a brief meditation and body scan.

• What are you currently feeling?

• What emotions are most alive in you?

• What sensations are you feeling throughout your body?

Think of Step 1 as a warm-up, priming your mind to bring a spacious awareness to your body. We’ve also likened it to tuning into your “inner weather report.” 

The typical start to a work session may look something like this:

1. Open your laptop

2. Review your to do list or calendar

3. Attempt to jump right into a task while battling resistance or the urge to procrastinate

Rather than trying to brute force your way to progress, this step calls for 1) calming the mind and 2) accessing interoceptive awareness. We’re shifting from a cold start to a warm start.

calming the mind

The technique of calming the mind is rooted in shamatha practice, a core teaching found in popular meditation apps. We often think of concentration as a tight, clenched feeling. In emotional embracement, our aim is to cultivate a blend of ease, alertness, and collectedness.

accessing interoceptive awareness

Interoception, or internal awareness, is the ability to perceive and interpret signals from your body as they emerge — being in touch with what you’re feeling while you’re feeling it.

Our interoceptive palette includes:

• Mental: racing thoughts or foggy vs calm and alert

• Awareness: expanded and receptive vs narrow and protective

• Posture: open and relaxed vs tense and collapsed

• Breath: deep, slow, and soft vs shallow and rapid

• Emotion: gratitude, joy, sadness, etc.

— Jonny Miller, The Art and Science of Interoception

All of us have varying degrees of interoceptive capacity based on how often we tap into bodily sensations. For Cissy, it took about one year of actively working with and thawing the numbness she’d developed as a way to adapt to fast-paced work environments before she was able to acutely tune into the signals from her body.

Here are two examples of our inner weather report via interstitial journaling (more on journaling in Step 2):

The good news is that developing interoception comes with practice — the more intention you put into listening to your body and observing the initial numbness, the more sensory clarity you’ll build.

The goal is to create the conditions to allow any and all feelings to emerge, grow stronger, and eventually melt into the background. Approach Step 1 from a place of curiosity, acceptance, and kindness. As you tune into your emotions and bodily sensations, simply observe what subtle feelings are coming up without judgment. It’s natural to resist the emotions coming up, but gently turn your attention towards adopting equanimity.

step 2: journal ✍️

Open up a page in your favorite workspace (e.g., Notion, Obsidian, or Google Docs) and begin a running log of thoughts, feelings, and to dos that emerge as you work. Experiment with stream of conscious and reflective journaling.

Step 2 is about untangling ourselves from our thoughts and feelings. An underlying principle in meditation and therapy is internalizing the fact that we are not our thoughts, we are not our feelings. Journaling allows us to see our thoughts objectively on paper (or screen), freeing ourselves from the deliberations that take up much of our headspace.

Imagine one giant, tangled up monochrome ball of anxieties, questions, and to dos — that’s our mind pre-journaling. The act of brain dumping our thoughts allows us to bring awareness to the giant ball and sort through each thread to begin unwinding that big blob into smaller, tidier, color-coordinated balls. These smaller balls are far easier to tackle and serve as lights illuminating the path forward.

By bringing awareness to the subconscious through journaling, we can begin to name what emotions are alive in us, feel an emotion through fully, and get under why we’re actually feeling a certain way.

The practice of journaling has a wide range of positive impacts on mental health: from processing emotions to reducing stress to increasing self-awareness, journaling has the power to help us navigate intense emotions with a level of safety that may be difficult to access elsewhere.

level 1: interstitial journaling

How might you begin to apply journaling to support your work (even if you don’t currently journal)?

Begin with interstitial journaling, a technique created by Tony Stubblebine (coach turned CEO of Medium). The purpose of this form of writing is to use breaks intentionally. By creating space between when you pause for a break and your next action, you’re making room to tune into your internal landscape before you instinctively reach for your phone or click open a new tab.

The basic idea of interstitial journaling is to write a few lines every time you take a break, and to track the exact time you are taking these notes. For instance:

— Anne-Laure Le Cunff, Interstitial journaling: combining notes, to-do and time tracking

Notice the mix of intention setting (finish the first draft), self-awareness (feeling a bit anxious), reflection (made good progress), and to dos (call Anna) in Anne-Laure’s example.

For the purpose of emotional embracement, we expand the scope of interstitial journaling to beyond breaks. Writing out loud what’s happening internally and externally allows us to proactively bring emotions forward before they begin to fester or become suppressed. Write whenever you feel a dip in momentum whether that’s while working, on a break, or throughout the day.

Journaling is particularly helpful in certain contexts including:

• Navigating emotionally challenging tasks (e.g., high stakes work)

• Moving through self-directed work

• Working through tasks that require high context switching

• Working while experiencing personally challenging situations

• Transitioning roles and responsibilities

level 2: publishing to a public feed

Once you’ve started interstitial journaling on your own, you can experiment with bringing friends along for the ride by journaling to a public “feed.”

There is an online community that I’m in that has an unusual but powerful social technology for asynchronous communication, colloquially called “feeds,” inspired by old-school Facebook walls and RSS feeds.

— Tasshin, Feeds: An Anthropological Report on a Powerful Online Social Technology

Think of feeds like old school RSS feeds, but integrated into your existing digital spaces like Slack and Discord. We’ve found that digital spaces with feeds lower the bar for engaging vulnerably. The ability to scroll through others’ feeds and emoji react allows for passively popping into a friend’s train of thought and see how they’re doing.

Feeds can be just as useful in-person as digitally. During co-working sessions, it’s common to feel conflicted between spending time talking to the friend you’re working with or focusing on the task at hand. The magic of working in a feed alongside others is that it allows for more meaningful connection and deeper focus. If you choose to set up a public feed that others can view, the structure allows for communication that doesn’t interrupt others when you share your thoughts live — your friends can simply scroll through your feed as desired. At the end of co-working sessions, you don’t have to catch someone up on how it went — you see how they’re doing, often in greater detail, allowing for a deeper sense of connection (especially when you see what most resonated through their emoji reacts and comments).

In our experience, scanning friends’ feeds during co-working sessions helped us realize that the waves of “negative” emotions we feel throughout a work session are not unique to us. The reality is we all feel resistance in one form or another — it’s the second derivative feelings of shame and guilt that keep us from moving forward, blocking us from accessing flow when we’re urgently grasping for it.

Here are examples of our feeds in Slack:

step 3: process emotions 😮‍💨

As emotions emerge from Steps 1 and 2, lean on the introspection practices that are most resonant with you to address and process these feelings.

Practices may include meditation, breathwork, IFS parts work, shadow work, etc.

There’s a growing awareness of the importance of therapy, the power of somatic coaching, and the role of acceptance of our parts via IFS and shadow work. But much of that wisdom is locked up in the practice itself (e.g., a morning meditation) rather than embedded throughout our work day.

For the purpose of emotional embracement, we define practice broadly — any type of awareness-enhancing activity, framework, or spiritual belief that you identify with.

• What works well during that practice?

• How can you apply it to Step 3?

• How can you deepen your practice from the lens of emotional embracement?

As mentioned in Part 1, the idea of emotional embracement was born from Pranab’s experience booking time with an emotional coach who supported him while he completed a difficult task. While successful, it isn’t sustainable and is excessive for daily work. Drawing inspiration from facilitated emotional work can help you integrate insights to manage emotional reactions throughout the work day.

Here’s an example of Pranab processing feelings of shame and overwhelm, triggered by a colleague asking about a task in progress:

scale of emotional intensity

As you read this, you may think How will I ever get anything done if I’m processing emotions all day? or What emotions?

The purpose of this approach is not to be a substitute for therapy or somatic coaching — it’s to serve as an extension of your existing practices and invite you to apply what you’re learning about yourself outside of work to work.

On a scale from 1-10, the processing happening in emotional embracement should sit between a 1 and 6. There will certainly be times when you’re experiencing an intense emotion during work, but feeling insufficiently resourced or under time pressure. In those cases, acknowledge the feeling, process what you can, then importantly, gently set it aside with the promise to revisit it later in the day or week.

step 4: update your approach 🔁

Once you’ve moved through a few cycles of Steps 1-3, take a step back to reflect on what you’ve learned. Think back to your body scans and read through your entries.

• What learnings can you integrate into your workflow to improve your current experience?

Here are two examples from our community:

Energy, movement, and creativity

Since committing more of her energy to writing, Cissy has found more inspiration and flow writing first thing in the morning. After a few months of writing consistently, she found herself pushing back morning workouts for fear of “breaking” flow despite hitting a wall some days.

As she adopted emotional embracement, rather than forcing herself to write through the morning, she’s experimented with aligning her writing schedule with how her body is feeling. Now, she sets an intention to get outside by noon, heading out for a walk or run depending on how she’s feeling vs brute forcing her way through a writing session. 

Boredom, time, and value

Recently, Panashe was working on a repetitive task, covering for a colleague. He noticed that the task was incredibly boring, but didn’t feel like it justified an investment in automating it.

When he took a moment to tune into the resistance and boredom, he asked himself, “What’s the value of doing this task?” Asking himself this question rather than continuing to chip away made him realize that he’d spent enough time on it. He didn’t need to continue to invest any more time or energy into it, allowing him to check it off his list and preserve his energy for more stimulating work.

blend your practice with the best of traditional productivity advice

While we’re advocating for upgrading our collective approach to productivity via emotional embracement, we recognize this framework may not work for everyone. We encourage you to experiment with blending emotional embracement with traditional approaches to productivity. From “eating that frog” and doing the most emotionally challenging tasks first, to managing energy based on certain times of the day, to tuning into how your body feels under the pressure of time blocks, there are endless ways to upgrade your relationship with flow.

The intention is to direct your attention to how traditional advice plays out for you and tweak the techniques to intuitively guide you by integrating emotional work rather than simply adopting it at the intellectual level.

Two examples of blended approaches:

Full-bodied pomodoros by Anne-Lorraine

1. Set a timer for 45 minutes

2. Feel tension and numbness in your body. Subtle. Big. In your toes. In your scalp. Try to check in with all of it. You don't need to understand it. Don't force understanding. Do express it: let it shake and move you. Give it the right sounds.

3. If you're grounded in that, start to work. Each pomodoro ends after the set time or when you lose track of your body, grow tense or numb and can't find your way back to soft & supple, surf or flow.

Meta Productivity by Daniel Kazandjian

Daniel’s technique, 5min Dash, involves:

1. List out all the things you’re avoiding

2. Bold the top three hairiest items

3. Break out the explicit next step in tackling these most intense to dos

4. Complete as much of the task as you can in 5 minutes then stop

The idea is to deploy a series of 5-minute dashes to get over the hurdle of starting and build enough self-trust that you return to the task to close the loop vs continuing to avoid it.

This method is part of his larger project, Meta Productivity, which aims to integrate task and knowledge management practices with a philosophical approach to understanding oneself. He shares various strategies and tools that align with emotional embracement.

Thanks for reading! We hope this playbook helps you bring this way of approaching knowledge work to life. If you experiment with emotional embracement or recommend a protocol that would fit into this approach, let us know in the comments.

Stay tuned for Part 3 where we share why emotional embracement matters. We’ll discuss how to strengthen your emotional fluidity, become friends with your inner critic, and draw motivation from “clean” fuel sources — all in support of helping you find meaningful work that’s deeply aligned with your fullest self-expression and upgrading your livelihood. Our final essay of the series will drop in the new year.

Currently, we’re beta testing emotional embracement co-working sessions (virtual and in-person) with our communities. We’re gauging interest more broadly as we roll out new ways to experiment and get involved. If you’re interested in learning more and joining us for co-working sessions, sign up below (separate from subscribing to the Substack). We’ll be in touch!

Sign up here

Thanks to Ryan, Dennis Xiao, and Panashe Fundira for helping us shape this essay and to many others for joining us as we experiment with bringing emotional embracement to life.

• Part 2: Emotions in motion is a tactical guide to embracing your emotions while working

The most productive people work at a pace somewhere between the monk and the stock trader, fast enough to get everything done, and slowly enough so they can identify what's important and then work deliberately and with intention.

— Chris Bailey, The Productivity Project

Productivity has long been viewed as a delicate dance between time and energy management. Buoyed by hustle culture and a world that demands speed, we tether ourselves to high output at all costs, silencing resistance and pushing through procrastination. In an attempt to show up professionally, we train ourselves to celebrate victories with “positive” emotions and dissociate under stress and uncertainty in an effort to maintain composure. In pursuit of flow, we strive to optimize our external environments via productivity hacks while suppressing our internal landscape and “negative” emotions. As a result, we find ourselves trading our humanity for professionalism.

In this series, we’re investigating the question: what if those “bad” emotions and resistance are actually the gateway to inner wisdom, self-expression, and a sense of aliveness in the work we most enjoy?

But first, how did we get here?

current state of productivity

In modern society, we wear “being busy” like a badge of honor. When asked how you’re doing, how often do you default to sharing how busy you are? And how good being busy is?

Despite putting systems in place to turbocharge our efficiency and tackle everything on our to-do list, some days, it feels like we’ve worked or ruminated all day with nothing to show for it.

To keep pace with growing demands on our time and energy, we look to productivity gurus who advise us that it’s all about Getting Things Done starting by Eat[ing] That Frog in pursuit of Four Hour Work Weeks. While productivity hacks and apps promise to keep us afloat, there’s a better way. 

A new, more integrated approach to productivity and work is emerging as a result of a societal trend towards prioritizing mental health and emotional well-being – one where you’re not just trying to stay afloat, you’re gliding through the water.

the history of output-driven productivity

The model of measuring work by input and output is a relic of the Industrial Revolution. 

Fifty years ago, about a third of all US employees worked in factories. In a factory, or in a methodical, assembly-line kind of job, productivity was simpler: the more widgets you produced in the same amount of time, the more efficient and productive you were.

— Chris Bailey, The Productivity Project

Contrast that with modern work where, as a result of massive advancements in technology, a significant portion of the US workforce has shifted to service and knowledge work. Jobs that can’t as easily be measured by inputs and outputs although the Bureau of Labor Statistics certainly tries.

The reality of 21st century knowledge work is that the quantity of output itself matters much less — it’s the quality of what is being outputted that matters.

It may have been possible to brute force our way through manual labor on the factory line, but meaningful knowledge work demands a level of problem solving and creativity that can’t be summoned through sheer force. We won’t find the genius we seek at the bottom of an empty inbox.

The day will never arrive when you finally have everything under control – when the flood of emails has been contained; when your to-do lists have stopped getting longer…and when the fully optimized person you’ve become can turn, at long last, to the things life is really supposed to be about. Let’s start by admitting defeat: none of this is ever going to happen. But you know what? That’s excellent news.

— , Four Thousand Weeks

The ways we’ve been conditioned to work and our relationship with work haven’t caught up with modern work — we’re here to propose a new way of working.

imagining a new way of working

Work has been an act of brute force since the dawn of time. We’re evolved from humans whose next meal was at stake if they spent time tapping into their emotions. As we’ve advanced, knowledge work has inadvertently adopted this same approach: focus on the task at hand, suppress emotional responses, and get through as many to-dos as possible.

After all, work emerged as a means of survival and continues to serve that function today — only now we’ve ascended up the hierarchy of needs, trading the threat of starvation for the pursuit of meaning, purpose, and community. Our ancestors once approached their work in fight-or-flight states — and in the 21st century, we continue to accept these outdated standards which manifest through a culture of numbing ourselves to chase productivity.

Beneath the conflicting drive to be productive and our sticky feelings of procrastination lie unexamined emotions and desires. What if we turned inward and gave ourselves the space to understand what our body and those emotions are telling us? What wisdom have we been ignoring by shoving our emotions to the side when we work?

The idea that our work is emotional may sound counterintuitive if we’ve spent years fighting resistance. The same can be said for the paradoxical act of shining a light on the parts of ourselves that we avoid at all costs as the path to dissolving inner conflict. Bringing awareness to our emotions is the first step in embracing them to understand them, feel them, and accept them.

work 🤝 emotions

What does this look like today?

Many factors contribute to how “productive” we are on any given day: how well we slept the night before, the state of our relationships, the news cycle, the enthusiasm we feel for the work we’re doing, our mood right before we sit down at our desk, etc. 

The adage “Leave your problems at the door” suggests we separate our work and life, hitting pause on our emotional and mental states during the work day. The issue with this philosophy is that compartmentalizing encourages subduing our reality, suppressing creative energy and access to our truest desires.

Detaching ourselves from our internal state and body may feel like a worthwhile trade for getting more done — after all, knowledge work involves being one with our mind, right? 

Turns out, our bodies are far more in tune than we realize which can manifest as:

• Email apnea: shallow breathing and clenching while doing emails, reducing our oxygen intake and increasing stress levels

• Computer vision syndrome: eye strain or headaches as a result of extended periods of time staring at computer screens, causing dry eyes and funny vision

• Tech neck: pain from looking down at a computer, impacting posture and causing neck strain

Our bodies keep the score. When we increase physical tightness, we inadvertently stifle our emotional awareness. Mental tension leads to physical tightness in our bodies and vice versa.

knowledge work as an emotional act

By bringing awareness to our body and processing emotions while we work, we can deepen our understanding of how we relate to work, creating more intentionality around how we spend our time.

When we tune into our emotional state, we’re giving ourselves the permission to feel the waves of discomfort and the negative sensations in our body we’ve been clenching all along. If you find yourself sitting down at your desk, only to feel a sense of dread, there are paths forward other than spiraling into procrastination. Where are you feeling the dread in your body? What is the procrastination trying to tell you?

When we’re feeling disengaged with our work, how do we break a monolithic feeling into pieces? What are we feeling disconnected from? Are we feeling burnt out from repeatable tasks that can be automated? Or frustrated by conversations we’re having? Spending time sifting through these questions allows us to get to a better state where we can move towards work that energizes us. 

Think of it as continual emotional plumbing. By suppressing how we’re feeling, we’re allowing our pipes to back up, slowing the flow of energy and momentum. By taking the time to face and bring loving kindness to our emotions throughout our work days, we’re freeing trapped energy and opening up capacity to work more mindfully.

Beneath our drive to get more done are clues that hold the answers to why we do what we do and how we feel about it. The more emotionally aware we are, the more we can uncover where we want to go with work. Rather than allowing work to become a distraction from dealing with inner conflict, approaching knowledge work as an emotional act enables us to draw wisdom from within and fuel our drive with a clean source of energy.

our origin stories

Pranab’s story

This year has been one of the hardest in my life. For most of my adult life, my family’s been my first priority. This past year, we suffered from increasingly dysfunctional dynamics. While we’re now on the path to healing, Things Fell Apart along the way. It proved impossible to compartmentalize and shield away from work and it exacerbated patterns of avoidance and procrastination that I’ve been long undoing.

Thankfully, I had an amazing support system and an ecology of practices to support me in grounding, healing, and reconnecting to my greater Self.

One such practice was somatic parts work, informed by my non-dual meditation practice. I’d go in feeling stuck and tangled, and leave with a sense of clarity, love, and spaciousness that would last for hours after. The problem was bringing these qualities to the rest of my life. Work often triggered feelings of shame that led to nervous system activation, cognitive thrashing, and acting out old, avoidant patterns.

For example: I procrastinated on a client report for about 2 months. I was grasping for why I just couldn’t do it, and even after bringing it up in a therapeutic session, I continued to not make time for the task.

I eventually paid my emotional coach friend to sit with me on Zoom for a session where the goal was to start the project and embrace the mess of emotions that came with it.

I dropped into my body and asked, “What is this avoidance protecting me from?”

It responded, “Shame.”

I let the emotions flow through my body and started the task. Every couple minutes, tension and constriction would resurface, and I’d repeat the process. When less difficult, I just journaled in our zoom chat, and eventually a silent, focused flow emerged. Though we only talked for 15 of the 60 minute session, I finished the task with more ease than I thought possible, fully completing a cycle of memory reconsolidation.

The act of drawing actionable insight from concept to daily embodiment is called integration. And while I can’t afford to pay a coach every time there was work stuckness, I know there’s a way to get closer to it.

Cissy’s story

I’ve been obsessed with optimizing productivity for as long as I can remember, devouring books about hacking time, beta testing new apps, and redesigning my days in search of flow. I was drawn to this illusion that if I assembled the perfect system, I’d finally be able to tackle everything on my plate. The challenge was that I tied much of my self-worth to work so I had no problem expanding my to-do list, but rarely had the courage to let go of undone to-dos. I found myself on a treadmill running towards a moving goalpost.

As a result of identifying with my work output, I find it quite easy to start working and being in motion. The trouble comes with taking a break to reset and setting boundaries. During particularly intense periods of my career, I’d prioritize work over every other aspect of my life. Rather than tapping out to recharge when I’d hit a wall, I’d further bury myself in work. My anxious attachment to work manifested as me brute-forcing my way to impact, mistaking it for discipline. When I numbed the signals my body was sending me, it rebelled in the form of taking on inconsequential tasks to procrastinate meaningful projects for fear of failure.

The most essential and energizing work was often left sitting on my to-do list until the end of the day when I was drained. I’d chug away at it until it was time to wind down and head to bed, disappointed once again that I hadn’t made meaningful progress on the thing I’d actually wanted to do or was supposed to complete.

The connection between disassociating from my body and the emotional pain of never having enough time eluded me. I supposed I’d just gotten used to living with a perpetual sense of scarcity in time and energy.

Then, over the summer, I started my sabbatical and began to reevaluate my relationship with work. I noticed my body starting to unclench. I had spent the first half of the year in an embodiment mastermind and partnering with a somatic coach, learning to thaw the numbness I’d developed as a defense mechanism. While I was making headway, it wasn’t until the summer where noticeable changes began emerging. For the first time, I had space to differentiate what work I wanted to do vs what I should do, viewing work as an act of self-expression. I hadn’t realized how much I’d subdued my intuition until I came face to face with spending my days doing only the work I cared about.

As I’ve dropped into my body and surrendered to it to help guide me towards my inner truth — infusing meditation, Internal Family Systems (IFS) parts work, and shadow practices with my work — I’ve moved closer and closer to the work that lights up my soul.

introducing emotional embracement

Emotional embracement is all about tapping into the wisdom of our bodies and allowing it to guide us toward finding sustainable ways to work in the days, weeks, months, and years of our one precious life. We’ve drawn from varying introspection practices including meditation, breathwork, IFS parts work, shadow work, and somatic experiencing to unlock a new dimension of capacity within us. Despite having widely different work styles, the act of integrating our minds and bodies has freed up bandwidth for both of us in new ways that allowed us to experiment with new and meaningful approaches to how we work.

We’re in the early days of tinkering with bringing emotional embracement to reality, exploring co-working, asynchronous and synchronous, casual and structured. For now, our community lives in Slack and we’re beginning to host in-person sessions. In the future, we’ll experiment with working with coaches.

So far, the key components are:

1. Cultivate awareness 🧘

   • Bring awareness to your body and emotional state

2. Journal interstitially ✍️

   • Take notes on resistance and insights that arise

3. Process emotions 😮‍💨

   • Address and process emotions using your existing introspection practices (e.g., meditation, breathwork, Internal Family Systems (IFS) parts work)

4. Update approach 🔁

   • Integrate learnings from Steps 1-3 into your work routine

Gone are the days that productivity was all about time management. We’re here to help you build the muscle of tuning into your emotions and move towards unearthing new levels of flow in work and life.

Thanks for reading! Check out Part 2: Emotions in motion where we share the tactics of emotional embracement and invite you to experiment with integrating emotional awareness into your day-to-day work.

Currently, we’re beta testing emotional embracement co-working sessions (virtual and in-person) with our communities. We’re gauging interest more broadly as we roll out new ways to experiment and get involved — if you’re interested in learning more, sign up below (separate from subscribing to the Substack). We’ll be in touch.

Sign up here

Thanks to Melody Song, Dennis Xiao, and Maggie H. for helping us shape this essay and to many others for joining us as we experiment with bringing emotional embracement to life.

This piece is part five of Work & Self-Expression, a series that explores our relationship with work, creativity, and the in between.

• Part 1: Introducing work & self-expression

• Part 2: Who we are without work

• Part 3: Some practical thoughts on diversifying our identity

• Part 4: The art of self-expression

• Part 5: How to sabbatical

As an accompaniment to this essay, I’m excited to share How to Sabbatical: a tactical guide 🧭, a collection of essays and resources from thoughtful folks who have designed and embarked on their own sabbaticals. When I first started my sabbatical a few months ago, I took a leap of faith and had little idea what to expect — over time, I’ve met folks on similar journeys. Inspired by their stories, I’ve curated their work to serve as a guide for others navigating their own in between. I hope this guide helps you find the courage to take the plunge!

sabbatical (n): a break or change from a normal routine (e.g., employment)

The term sabbatical originally stems from the word sabbath, the seventh day of the week observed as the Biblical day of rest. While historically associated with academic professionals taking a leave of absence once every seven years to pursue interests beyond their teaching responsibilities, the idea of a sabbatical has taken on a broader meaning in recent years.

The bounds of the modern day sabbatical are far more fluid, no longer constrained to a timeline of seven years, taken by professionals beyond the academic realm. In this essay, we’ll dive into sabbaticals taken by people who have left their former job with the intention to explore what’s next, whether that’s pursuing their own thing or rejoining the workforce.

step 1: eject yourself from our societal games

When I first made the decision to go on a sabbatical, I had a vague sense of what it might look like. After committing the last decade to working at startups and investment funds, I’d become intimately familiar with structured work days in pursuit of actualizing company visions, but felt like a stranger to the notion of freedom in time and space. My whole career had been spent deriving value from pursuing stable(-ish) full-time jobs — as a result, the idea of walking off on my own felt off limits, like a path not meant for me.

Like many people, I was raised to pursue excellence in everything society expected of me: from school and extracurriculars to work and professional certifications. I followed the well-worn path, defaulting to playing the games that everyone else was playing: pursuing roles with more responsibility, working hard to ascend the ladder, etc. Whether or not we explicitly opt into these games, there’s a part of us that believes that we’ll find happiness or success in “winning” the game. After years of playing to win, I started questioning the belief that investing in this game was the end all be all. I spent enough time contemplating it that it eventually felt like I was betting against myself by continuing to play.

To commit to a sabbatical is to establish a new level of trust with yourself and build the confidence that stepping off the corporate treadmill is the right next step. For those of us who have committed to playing the game, making our full-time jobs our core identity, the journey towards unwinding these entrenched beliefs may feel existential. It takes mustering up the courage to eject ourselves from these games, if only temporarily to gain perspective.

You’ll find yourself in a valley between two mountains, having just descended down a popular, well-paved trail and contemplating whether you’d like to change course to walk into uncharted territory towards an unmarked summit or take a rest before walking back towards the default path laid out for you. Only through tuning into yourself and releasing the external chatter of what you should do can you determine what’s ahead.

step 2: go inward and face yourself

The beauty of sabbaticals is that they materialize in many ways — there’s no one way to do it. Sabbaticals are meant to be a manifestation of your curiosities and a reflection of the journey you’re embarking on.

It’s a time to untether ourselves from fulfilling the expectations of others and ground into our own visions. When we're not conforming to fit the image of a corporation larger than ourselves, we're free to explore and express our depths. Work becomes more than writing memos, sending emails, analyzing data, and driving alignment. Work begins to take shape in the form of a new idea germinating on a midday walk, a conversation with a friend who reminds you of an interest you've lost touch with, or meeting a new person who shares uncannily similar interests.

When you give yourself permission to soften into curiosity and flow, your days become fluid, no longer defined by the rigidity of reoccurring Zoom calls and the deluge of emails to answer. There is a sense of freedom that emerges as you transition into living fully for yourself. When is the last time that you fully lived in pursuit of yourself?

But, this newfound freedom and abundance in time isn’t without challenge. Welcomed or not, the amplified silence may bring forward disorientating waves of emotions and limiting beliefs that had no room to percolate when you worked a full-time job. The real work (and magic) begins when you turn existing limiting beliefs on their head and rewrite your storyline.

There’s a wealth of knowledge within each of us. It’s only when we gently welcome the silence, sitting with ourselves in the face of uncertainty and doubt that our inner knowing dares to surface. Whether it’s meditation, breathwork, journaling, walking, or another form of introspection, being in solitude is what sheds light on areas of misalignment we’ve been enabling. We can either resist what’s unfolding from within or surrender to the resistance and begin to experiment with our self-expression.

step 3: experiment your way to expression

The freedom of a sabbatical can feel paralyzing. The list of things we want to tackle is endless. How does pursuing self-expression fit in and how do we get started?

Self-expression is our vehicle for self-discovery. Our expression comes to life when we own and embody our individuality. Part of the process may involve doing things that are perceived as cringe. Learning to embrace the cringe is half the battle.

Whether we’re aware of it or not, we all have things in our lives that light us up and bring us immense joy — topics that we’d happily spend hours debating, activities that bring us into deep states of flow, projects that send us spiraling down rabbit holes. Sabbaticals give us the space to reignite parts of us we’ve suppressed in the name of prioritizing our full-time jobs and being a Productive Member of Society. Being cringe and experimenting with reviving our long-lost parts is the first step.

A few ways to begin mining for nuggets of expression:

• Curate a list of moments that light you up: as you move about your days, start maintaining a list of moments that you feel yourself coming alive — What are you doing? How does it feel in your body? How can you create more of these moments?

• Visit your inner child: our truest expression is often found in the activities that brought us joy in childhood — before you got serious about life, think back to the things that you spent a disproportionate amount of time nerding out on. What would you have kept doing had you not felt the pressure to “grow up”?

• Ask your trusted others for pearls of insight: turn to people you trust and ask them to reflect back on what they most enjoy learning from you, what they believe you’re uniquely skilled at, and what things seem to light you up

As you experiment, bring awareness to the things that feel like something you want to do versus you feel like you should do. Reflect on the existing narratives that compel you to gravitate towards things that help you feel legible and earn validation from others and what stories you need to tell yourself to orient to internal validation.

a few tactical thoughts on designing your sabbatical

idle time

An interesting thing that started happening with my relationship with time when I began my sabbatical was I became deeply aware of idle time. In my day job, idle time came in the form of procrastinating answering an email, finishing the last 10% of a project, or pitching my team a new idea. While on a recent trip, the friends I was with decided not to take Friday off, preferring to work a few hours in the morning before starting the weekend. As the morning wore on, I observed each of them procrastinating the one last task they had to get done before they were free to log off — meanwhile, I was deeply aware of every passing moment as an opportunity to finalize an essay I was writing. While they procrastinated until noon, the acceptable time to log off, I furiously typed my piece, wishing for time to slow.

Time becomes yours and yours alone. It’s no longer borrowed time, loaned out to your employer for 40+ hours a week. Procrastination is at the expense of embracing your expression and completing your own projects rather than what’s standing between you and your weekend.

structuring the unstructured

Knowing yourself and the conditions in which you thrive becomes important as you design how you spend all your free time. I’ve long lived by my calendar and knew that staring at a blank schedule would send me into a state of paralysis. I traded 30-minute meeting blocks that made up my work days for big open blocks of time. At the onset, I defined buckets of activities I wanted to spend my time doing: inner work, writing, reading, movement & training, projects, community building & friends, learning, emails, and time with my partner.

Each week, I refined my process during my weekly review, constraining myself to the reality of a 24-hour day. Not long after, my days began overflowing with things to do and people to see. While structuring the fluidity has worked for me, I know others who would dread operating off a calendar. The key is choosing your own constraints and recalibrating as often as you need. When the structure of a full-time jobs falls away, you’re free to orient your days to match your energy levels and shed the mentality of time scarcity. Your job becomes preserving your highs and knowing when to recharge to bridge the lows.

location

Shortly after I decided to start my sabbatical, I relocated to the suburbs to housesit for my parents for 2 months. While relocating wasn’t intentional, I found spending time in the suburbs allowed me to turn up the volume on my intuition for how I wanted to spend my time and what I wanted to accomplish rather than amplifying external inputs from other people doing cool things.

It’s easy to get caught up in all the interesting things that other people are doing especially when you live in a city that nurtures agency and you belong to communities filled with inspiring people. While looking to others for guidance and inspiration may propel your exploration forward, be wary that you don’t conflate the interests of others with your own aspirations. Be intentional about self-reflection regardless of who is around.

creativity

As I transitioned to taking my sabbatical, I spoke to a number of people who have gone on sabbaticals of their own. A common theme that emerged was recommendations for books centered around surrendering and cultivating creativity. The Creative Act. Big Magic. The Artist's Way. The War of Art.

While it’s likely you historically didn’t view yourself as a creative, there’s an art to being on sabbatical and often it leads to tapping into a creative side of us that we’ve suppressed in exchange for being a consumer. This is the moment to break down all your existing notions of who you are and who you can be.

For more, check out How to Sabbatical: a tactical guide 🧭.

Thanks to Matt Yao for reviewing an initial draft of this essay.

An update on work & self-expression: Thanks for joining me on this series! I’m so glad you’re here. This concludes the five-part series I set out to write.

• Part 1: Introducing Work & Self-Expression

• Part 2: Who we are without work

• Part 3: Some practical thoughts on diversifying our identity

• Part 4: The art of self-expression

While I’ll continue exploring our relationship with work, creativity, and the in between, I’ll also begin publishing pieces featuring other areas I’m exploring including psychology well-being, human flourishing, modalities of introspection (e.g., Internal Family Systems), communities of agency, and more.

If any of these topics resonate with you, I’d love to hear from you! Say hi on Twitter.

This piece is part four of Work & Self-Expression, a series that explores our relationship with work, creativity, and the in between.

• Part 1: Introducing work & self-expression

• Part 2: Who we are without work

• Part 3: Some practical thoughts on diversifying our identity

• Part 4: The art of self-expression

• Part 5: How to sabbatical

Early on in my career, I never gave creativity or self-expression much thought. I viewed creativity as the work of artists, subscribing to a narrow definition of art. Art was the paintings that hung in galleries, the stories that sat on bookshelves, and the sculptures that lined museums. Self-expression was reserved for the minds and hearts of those who created art, not people who worked in finance and tech — no, we thought in numbers, slide decks, and product requirement documents.

Within the walls of corporations, the name of the game is buy in and alignment. Initial ideas may emerge from the depths of our imagination as pearls of self-expression, but as those ideas make their way towards commercialization, they lose their creative shape. Consequently, when we rely on our mission-aligned jobs to serve as the sole vehicle for actualizing our purpose (read: expression), we find ourselves unfulfilled and longing for more because true self-expression cannot flourish in the face of consensus and external stakeholders. It’s an inside job that defies boundaries and convention, not meant to be locked up in a single avenue of our lives.

pursuing self-expression

Self-expression comes in many forms. In its simplest form, it's the way we lead our lives: how we choose to spend our time, the books we choose to read, the food we fuel our bodies with, the company we choose to keep. In its highest form, it's our innate ability to ground the ephemeral in reality by creating something out of nothing — a piece of writing, a house project, an itinerary.

The truth is we're all creators. Like an artist breathing life into a painting by drawing inspiration from her reality, our expression is drawn from the sum total of our thoughts, feelings, experiences, past and present — an act that brings us closer to our selves.

As with any craft, we must continually cultivate and nurture our self-expression. When we’re young, we begin as blank canvases, filled with unbridled wonder and captivated by our own worlds. If we're lucky, we're encouraged to go out and explore the world beyond ourselves. In our adolescent years, we begin to form our sense of self, creating stories and constructing worldviews to make sense of who we are and how we fit. We develop beliefs and preferences that guide our acts of individuality: the clothes we wear, the music we listen to, the friends we make. Along the way, we begin to look to our outer world for validation and a sense of belonging. The expectations of those around us filter through us and we adopt their narratives as our own.

This constant tension of belonging to our selves and belonging to others is put to the test when we join the workforce. As we ascend the ladder, seeking increased responsibility and promotions, we place trust in others to judge our contributions and allow them to determine our fate. If we fail to develop a grounded sense of self, we run the risk of buying into paradigms that threaten to stifle our originality. We may unwittingly trade our individuality in exchange for validation from people we believe to hold the answers in the form of seniority, getting swept up by the games they play.

Life's a series of games. We're all playing one game or another whether we’ve explicitly opted into them or not. To self express is to awaken to our power to change the rules of the game and free ourself from the societal expectations that nudge us towards a victory of conformity. We can choose to move through life as a pawn, following the rules that others have put into place, or reconstruct the board with an end game that favors us harnessing our truest expression.

a call to adventure: harnessing our truest expression

In a world where we’re anchored to productivity and maximizing output, it’s easy to gravitate to spending our time working on tasks that offer us a fleeting sense of accomplishment, but lack an outlet for self-expression. When we give priority to the things that keep us in our comfort zone and mute our expression, we’re doing ourselves and others a disservice by holding ourselves back from accessing flow and normalizing disconnection. To embrace our originality is to bestow the gift of permission upon ourselves and those around us.

When we view our expression as a vehicle for self-discovery rather than a path towards external validation, it frees us from the fear of judgment and nudges us towards messy action to begin somewhere, anywhere. The more experiments we run, the more we learn about ourselves, the more time we have to get creative with the process and do things that feel like an extension of us.

Only by fully embodying our individuality can we come to understand the full range of who we are and venture to the farthest edges of ourselves. By allowing all of ourself to march to the rhythm of our own drum, we’re providing others with a reference point for how to cultivate their own beat and sparking a culture of agency.

As with making art, the object isn’t merely just to self express. It’s about getting into the wonderful state which makes self-expression inevitable, welcoming every moment as an opportunity to be in alignment with our beliefs and values. When we summon the courage to bet on ourselves and walk towards action, we create conditions fertile for harnessing self-expression. It’s tapping into your true essence. It’s giving yourself the grace to be cringe and look foolish. It’s finding your confidence in the learning curve. It’s playing your game regardless of who is watching.

Up next: How to sabbatical

If this piece resonated, I’d love to hear from you. Say hi on Twitter!

This piece is part three of Work & Self-Expression, a series that explores our relationship with work, creativity, and the in between.

• Part 1: Introducing work & self-expression

• Part 2: Who we are without work

• Part 3: Some practical thoughts on diversifying our identity

• Part 4: The art of self-expression

• Part 5: How to sabbatical

the risk of making it your all

In recent years, we’ve seen a decline in reliance on religious institutions as our primary source of meaning. For the first time in Gallup’s eight decade analysis, the majority of Americans reported having no religious affiliation. The absence of organized religion as our anchor has left our generation in search of new faiths to center our lives around.

Enter: workism. In his essay, Workism Is Making Americans Miserable, journalist Derek Thompson writes of the gravitational pull that work has on shaping our identities. As our generation delays marriage and parenthood in favor of chasing after our career dreams and working from anywhere, our lives are more fluid than ever before — the company we work for and what we do remains one of the few steady constants. Work has evolved into far more than a means of economic production, it’s where we find our community and fulfill our life’s purpose. As our expectation of what we seek in work mounts, it’s become our source of income, healthcare, impact, community, fulfillment, and meaning — our human needs and employment status all wrapped into one.

When we allow one aspect of our life to embody our core identity, the danger is our self-worth becomes tethered to outcomes beyond our control and beyond ourselves — this goes for anchoring our sole identity to our work as well as being a partner or a parent. The laser focus on one aspect of our life going according to plan shrinks our worldview and we begin to view the inconsequential as consequential.

By putting undue pressure on our jobs to fulfill our every need, we inadvertently build a highly concentrated identity portfolio and close ourselves off to other sources of meaning. We seek external validation in the form of more responsibility, promotions, and salary raises that bring a limited shelf life of joy at the expense of betting on other parts of ourselves in parallel — our relationships, starting a family, and exploring other interests.

Many of our contributions to companies we work for will fade with time. When we move on, roles are backfilled, work is redistributed, life goes on. While meaningful in the moment, it’s not always our work that lives on, but the relationships we cultivate and lessons we learn while engaged in that work. What else has staying power? The investments we make in ourselves and our communities.

The danger for high-achieving people is that they’ll unconsciously allocate their resources to activities that yield the most immediate, tangible accomplishments. This is often in their careers, as this domain of their life provides the most concrete evidence that they are moving forward…They prioritized things that gave them immediate returns — such as a promotion, a raise, or a bonus — rather than the things that require long-term work, the things that you won’t see a return on for decades, like raising good children.

…you’ll often see the same sobering pattern when looking at the personal lives of many ambitious people. Though they may believe that their family is deeply important to them, they actually allocate fewer and fewer resources to the things they would say matter most.

— Clay Christensen, How Will You Measure Your Life?

By creating space in our lives to invest in multiple sources of meaning, we can break free from the cycle that demands more of our energy and our time. When we renegotiate our relationship with work, it’s not in sacrifice of our work — in actuality, we’re freeing up space for more of us to become available. It allows us to begin to see the forest for the trees, take a stand, make tradeoffs, and firm up boundaries that enable us to explore paths towards living a fuller, more integrated life. We can’t have our yeses if we don’t own our nos.

tactics to diversifying identity

When we think about opening ourselves up to other sources of meaning, the core work is cultivating a deeper sense of self. It’s about getting to know ourselves and our desires, tuning into our inner voice, and turning towards ourself for validation rather than seeking it in others and institutions.

When you think, “Who am I?,” what comes to mind? What do you identify with? Where do you derive your value? What do you say you value, but don’t act as if you value it? If how you spend your most precious resource, time, is the greatest expression of your values, what would your time allocation tell you about what you valued most?

What roles do you play? Which of your roles is the main character in your life? Who are you without work? What meaning are you in search of that work doesn’t fulfill?

Expand your identity from your job title to what you care about

I recently spoke with a friend who works at a startup reimagining how companies recruit new talent. She was deeply invested in her job and more importantly, the broader mission she serves — so when the pace slowed at work, she started contemplating new ways to further the mission of connecting people with jobs that aligned with their interests. Rather than pigeon holing herself into her day job, she turned towards investing her energy into starting a career coaching business alongside her full-time role.

When we decouple ourselves from our job titles and our organizations, a world of opportunity opens up in ways that are hard to imagine when we’re deeply rooted in chasing after external validation for a job well done, narrowly defined. What does serving the broader mission mean to you? If you untether yourself from your job title, what other avenues might you explore to deepen your skillset and work on what you care about? Your impact has the power to be far more reaching than your job description.

Strengthen your other identities & call in new ones

As you start to examine who you are holistically, determine old beliefs you hold about who you were that no longer serve you: thank them for their service and begin to experiment with shedding them to make room to nurture new identities.

Experimentation can take shape in many forms:

• Adopt a more fluid approach to how you introduce yourself to others: shift away from work being central to your introduction and incorporate other elements of your identity that you want to share with the world

  • Start with subtle changes and observe how it changes the dynamic of your conversations: “I’m exploring psychological wellness and how to construct enduring secular communities. I’m training for a marathon. In my day job, I spend my time…”

• Joke about outcomes you want: it’s easy to focus our energy on what’s not possible — why not focus your energy on breathing life into identities you’d like to embody?

  • Take a page out of Visa Veerasamy’s book and start to joke about the person you’d like to become

• Figure out where people who are “xyz” convene and join them: one of the best ways to begin an identity shift is surrounding yourself by other people who already do that thing

  • Want to be a writer? Register for a writing course

  • Want to be a marathoner? Sign up for a marathon and join a local running club

Get playful about bringing your new identities to life.

Create space for more novelty in your day to day

When our days seem monotonous, it’s easy to slide into tailoring our life to the thing that has the most visible hold on our lives. It’s up to us to create the boundaries that allow other parts of us to see the light of day.

When I first moved to San Francisco, I was in search of communities of people who shared my interests. In that first year, I went to a lot of events and put myself out there in ways far beyond my comfort zone, but eventually, the search paid off and I found my community.

Through it all, consistently experimenting and showing up allowed me to build a life of novelty. In my most balanced moments, work was simply one part of who I was. On the first of the month, I was the hard things instigator. On Sundays, I was the Writing Club host. Life overflowed in ways I hadn’t previously given myself permission to experience — my days were marked with work, meaningful conversations, interesting community events, and adventures in the Bay. Life moved fast. I was in awe of how much I could get done in a day when I prioritized life alongside work.

Whether it’s hosting a monthly podcast club with friends, leading a weekly morning hike, or starting a pottery class, experiment with designing a life doing things that bring you alive like your life depends on it. Because it does. There’s never a good time. Now is a better time than any.

As the seasons change, our existence portfolios are in a state of ebb and flow, making way for new identities and phasing out the old. It’s in harnessing multiple sources of meanings that we give ourselves the freedom to explore new flavors of our essence in pursuit of aligning who we are and who we aspire to be.

Up next: The art of self-expression

This piece is part two of Work & Self-Expression, a series that explores our relationship with work, creativity, and the in between.

• Part 1: Introducing work & self-expression

• Part 2: Who we are without work

• Part 3: Some practical thoughts on diversifying our identity

• Part 4: The art of self-expression

• Part 5: How to sabbatical

I've long believed that the work we choose to do is a meaningful representation of who we are. Throughout my career, my mission has been to find meaningful work that aligns with my values and partner with people who I deeply admire. This approach has brought me closer to alignment with each team I've joined.

On the face of it, this strategy seems logical — work at mission-driven companies as a means of actualizing my purpose. Yet, gone unchecked, I began tethering my identity to the companies I belonged to. I found myself investing the best parts of me in work, tying my self-worth to productivity, output, and more responsibility. Caught up in deriving meaning from my roles, I allowed myself to ignore the reality of working for corporations: there’s a transient nature to our work. With the passage of time and changes in company strategy, the impact of our contributions become like words in the sand, slowly waning, slowly fading, sometimes even before we move on to our next gig.

The truth of it all has the potential to send anyone into an existential tailspin.

When I parted ways with my full-time job a month ago, I sat down to reflect on who I was without work. This experience gave me pause. I felt a surge of panic and shame wash over me.

I’m a Chinese American woman. I’m a wife. I’m a daughter. I’m a sister. I’m a friend.

Who else am I? I’m a writer. I’m a builder. I’m an athlete. I’m a San Franciscan. I’m a community builder. I’m an advocate for psychological wellness. I’m a national park lover. I am many things. I am and will be versions of me I’ve yet to meet.

The panic stemmed from the recognition of what I’ve known all along, which was that my primary identity for the last decade was where I worked and what I did for work. I had spent my career making myself as legible as possible to others and now, I no longer had that safety blanket to cling to. There was something safe about being affiliated with a corporation, a safety net that caught me when I feared betting on myself. The feeling of worth that comes from earning a steady paycheck and belonging to an entity greater than me.

The shame was the result of allowing my primary identity to become so deeply coupled with a fate that was largely out of my control. By entwining my identity with work, I’ve put power into the hands of other people, the small groups of people who make the judgment call on how valuable each of us are to our organizations, and allowing them to dictate who I am and who I should be.

So, why is it that we overindex our identities to what we do for work?

—

For one, we spend a large portion of our best waking hours working or thinking about work. Knowledge jobs have a hold on our lives in ways previously not possible, brought on by the democratization of remote work.

For someone who works 9 hours/day, they have ~60% of their waking hours left to cultivate other identities. But, if we’re not intentional about how we manage our energy, we may inadvertently find ourselves exhausted by the time evening rolls around or too tired to wake up without snoozing.

Even when I prioritized spinning up side projects and pursued hobbies as a full-time employee, it often felt like these other meaningful pursuits were squished into two hours here, two hours there — the rest of my life filled in on the fringes, taking a backseat when work got busy. When the best, most energized parts of me consistently showed up at work, it was no wonder why I’d let work define so much of who I was.

Another reason we anchor our identity to work is simply for ease and legibility.

There's a comfort in identifying with our job. It allows us to neatly put ourselves in a box. It makes for a simple introduction. It gives us something bigger than ourselves to belong to. It reduces optionality and decision fatigue around potential career moves. It keeps everything simple.

When we meet new people and convene with old acquaintances, in a well-meaning attempt to make conversation, “What do you do?” inevitably comes up. It’s easy to give them a well-polished pitch on the job title you hold at that impressive company in search of their seal of approval. It’s these interactions with people we’ve previously known or met in passing that make up our tapestry of societal expectations — moments where we seek validation, making ourselves most legible to people whose opinions won’t really matter to us at the end of the day.

In reality, the people closest to us often care least about our jobs. They care about us — that we’re healthy, happy, and pursuing things that bring us joy and meaning.

And, after all, isn’t that what we strive for? A meaningful life, filled with fulfilling work and a healthy body to sustain us through the years, deep relationships with our community, mastery in hobbies and other pursuits, adventures abroad, and being at peace with it all.

When we more evenly distribute our existence portfolio in accordance with all the things we actually value, what might our lives look like? If we diversify away from concentrating our identity into work, what spaces are we freeing up for other parts of us to flourish?

—

I originally became fascinated with the role that identities play in our lives from the lens of behavior change, how we make decisions, and consequently, how we move through the world.

It seems that many of us are trapped under the illusion that we must hold on to identities that have lived past their shelf life. I’ve spoken with friends who feel stuck and dragged down by inertia as they attempt to grow and outgrow themselves.

Ultimately, it’s in our power to decide who we want to become and take action in alignment with those identities. The first step is getting intentional about who you want to become — the fully integrated you — and then begin experimenting with how to cultivate that identity. With that north star in mind and enough consistent action, your behaviors eventually become automatic habits and an extension of who you are.

The magic comes when we’re able to flow seamlessly between various identities, allowing us to derive sources of meaning beyond one facet of our life. We hold the power to untangle ourselves from one primary identity and step outside the boxes that hold us back.

There is a level of discomfort that comes with abandoning the well-paved trail to prioritize legibility to ourselves over playing the games that society deems worthy. How might we begin our exploration towards a more well-balanced identity portfolio?

Up next: Some practical thoughts on diversifying our identity & sources of meaning

This piece is part one of Work & Self-Expression, a series that explores our relationship with work, creativity, and the in between.

• Part 1: Introducing work & self-expression

• Part 2: Who we are without work

• Part 3: Some practical thoughts on diversifying our identity

• Part 4: The art of self-expression

• Part 5: How to sabbatical

At the start of this month, I kicked off my first ever sabbatical. For most of my career, taking a sabbatical has felt out of bounds. I viewed working at a mission-driven company as the highest and best way I could contribute to society and create tangible value.

I landed at that conclusion after years of following a prescribed path that guided me towards every major milestone: graduate high school —> graduate college —> find a full-time job —> experiment with a few full-time jobs until I find one that feels most aligned with the world I’d like to build, pays a decent salary, and offers a good suite of benefits.

Since childhood, I’ve carefully charted and followed a series of well-trodden paths, seeking counsel from others at crossroads and allowing societal expectations to influence my decisions. While I’ve developed a strong sense of intuition over the years, I’ve only allowed it to guide me within the confines of the well-defined map. Well, what happens if I toss the map and forge a new path absent of trail markers? That’s what I’m off to explore with this series.

In recent months, I’ve tuned into my intuition more deeply, shaking off the rust that’s settled from trust in others over my own inner knowing. Facts that I’ve known to be “true” began to fracture in terrifying and magical ways. Questions emerged within me, breaking my mental models on how we structure our lives, our relationship to work, our perception of time, and why we do what we do. As these questions swirled within me, I felt called to take a beat and recalibrate all that I’ve thought to be true.

When a layoff brought on by changes in company strategy aligned with a long trip back to the east coast, the opportunity to take my first sabbatical unveiled itself. Here was my time to unravel.

Sabbatical is derived from the word, sabbath.

sab•bath (n): a day of observance and abstinence from work, to rest.

For me, to rest is to play and to get to know myself better. To unravel layers of societal conditioning, release the notions of how life should be, and rewire the limiting beliefs that have kept me from blazing my own trail.

work as an act of self-expression

In these early weeks, I’ve contemplated my relationship with work and the legibility full-time jobs have given me. Pursuing roles at companies with missions that aligned with my own has partially been about finding fulfilling work and partially about making myself legible to society. Our job titles give us a clean way to present ourselves — “Hi, I’m [name]. I’m a [job title] at [company name].”

But increasingly, I had been gravitating away from identifying myself by what I do and towards who I am. Who am I without what I do for work? What ideas, thoughts, curiosities uniquely belong to me and define who I am in this moment? What may not exist in the world without me?

I’ve always viewed startups as the expression of what the founders value and their manifestation for how the world should be — my version of founder market fit. For early hires, joining a startup is an expression of alignment with the founders’ values and their vision for the world. Building a company into existence then is an act of self-expression. In recent weeks, I’ve taken a step back to explore what work as our highest form of self-expression means beyond the startup and tech ecosystem.

When you think about it, everything we do, every decision we make is an act of self-expression. It’s how we choose to move through the world.

Slowly, I’m unraveling the belief that the corporation we belong to makes us most legible to society — rather, I believe it’s the courage to walk towards and activate our truest forms of self-expression to make us legible first to ourselves. After all, the life I aspire to live is one where I expand so far beyond what I believe is possible that I can look back periodically and fully appreciate the many layers I’ve shed. To grow and outgrow.

what to expect

Throughout this series, I’ll explore the role that work plays in our lives and our identities, how to revive our intuition and activate our creativity, and the tactics of sabbaticaling.

I hope this series inspires you to start walking. Start wandering down the path you feel called to. Start to venture into uncharted territory.

Up next: Who we are without work: an exploration on identity

Thanks for joining me on this journey! If this series resonates with you, I’d love to hear from you.