6 months of surrendering to the unknown

Reflections on the four stages of sabbaticaling

Glacier National Park — October 2022

At the start of my sabbatical, I wrote a series called Work & Self-Expression to make sense of who I am without work and how work could become an act of self-expression. At the time, I didn’t have many reference points for others who had ventured off the well-paved path. Along the way, I’ve met thoughtful humans who have designed and embarked on their own sabbaticals. Inspired by their stories, I curated their writing back in August to serve as a guide for others navigating their own in between. I’m excited to bring back an updated How to Sabbatical: a tactical guide 🧭 with many more essays and perspectives — all new resources highlighted green.

This month marks six months since I first kicked off my sabbatical — six months of dancing with my greatest ambitions, shining a light on my darkest shadows, and seeing myself clearly for the first time. An unlikely journey in cultivating a level of intuition I hadn’t thought possible.

When this season of life first began in June, it wasn’t clear to me how it would all unfold. I’ve always been someone who was guided by a loosely defined five year plan. The idea of surrendering control and trusting that I’d figure it out along the way was a big departure from the person I’ve strived to be my whole life.

In my 20s, I was convinced that in order to “get ahead,” I needed to have it all figured out. To fast track this process, I chased prestigious, well-paid jobs at companies with inspiring missions. The trouble was that while each job was fulfilling and meaningful in its own way, existential dread eventually caught up with me each time, whispering this isn’t your path.

I suspect that when we’re following a path we think we should be on, we clench to make it work at all costs. Rather than flow and ease, there’s friction and pressure. The idea of surrendering to the unknown simply never crossed my mind because I truly believed if I wasn’t actively accelerating, everything I’d worked so hard for would collapse. I didn’t trust that I could move through life with ease without having it all figured out.

Fast forward to December: last week, I was running through Golden Gate Park in the pouring rain when I felt a deep gratitude wash over me. There’s no where I’d rather be than running through Golden Gate Park in the pouring rain right now. Not working remotely from the jungles of Costa Rica. Not reading on the beaches of Bali.

For so long, I dreamed of the future and oriented my life in service of what I had not yet achieved. Now, I dream of the present. I dream of being here, doing the work and being with the people that set my soul on fire in this moment. I surrender to the reality that I don’t yet know how this will all unfold. By choosing the present and following my intuition, I trust that a path more beautiful than I could've ever imagined will emerge.

clear intentions, no expectations

For me, taking a sabbatical was about exploring new realms of possibility. For others, it may be about recovering from burnout before kicking off a new job search. The important thing for me was clearly defining my intentions and aligning every ounce of my energy to the phase I was in (more on each stage below) to dispel any doubt of whether I should be spending my time differently.

My intention was to carve out an undefined period of time, likely through the end of 2023, dedicated to understanding myself better and exploring my draw to writing, psychological wellness, and human flourishing. I wanted to understand what really drove me subconsciously and why I had tethered so much of my identity to work.

Intentionality about why I was on sabbatical gave me the permission to avoid unnecessary input from others. In other moments of my life when I couldn’t sit comfortably with lack of clarity, I sought advice from everyone else, relying on them to pave a path for me that wasn’t theirs to pave.

I knew I had a lot of deprogramming to do after a lifetime of shoulding. My first step was entering this season of life with both clear intentions and no expectations.

introspection as a full-time job

Prior to June, I spent nights and weekends doing the work, working with an embodiment coach on shedding the armor I’d acquired to numb myself and with a somatic leadership coach to learn how to lead from a place of intuition.

As I started my sabbatical, I expected inner work to be a side pursuit that I’d dabble in. In reality, turning inward started and continues to be a significant share of my time.

I’ve always been a relatively introspective person, but I used to live out the same old patterns over and over. My inner work felt circular like I was tracing the same path endlessly. Everything changed when I deepened my commitment to getting to know myself. Soon, the work felt like walking up a spiral staircase — as I look out, I see a similar landscape, but from a new height each time.

Developing a consistent introspection practice — however uncomfortable it is — and welcoming the existential dread is my gift to my future self, saving her from a midlife crisis by doing the hard work now to build an existence I’m proud of.

borrow from the confidence of others

As I entered unchartered territory, it was time to take a good hard look at my core belief system and the scripts I was reading from. Part of the experience of untethering myself from a legible full-time job was getting very comfortable with answering questions about how I was spending my time.

Because I truly had no idea who I was without a full-time job six months ago, I engineered my environment to be conducive to becoming illegible. Serendipitously, I started my sabbatical the same week that I moved back to the east coast for two months to housesit for my parents in the suburbs. I spent much of my time alone during the week, decompressing from a life where I was always on, and weekends celebrating friends’ wedding and seeing old friends who could care less about my (lack of) job title. I couldn’t have been more grateful for the timing.

Surrounding myself with people who may not have understood the journey I was embarking on, but supported me and filled me with confidence nonetheless allowed me to focus more on the journey than trying to weave together a narrative about the (unknown) destination I was heading towards.

the four phases of the sabbatical

Despite not knowing how it would all unfold in June, it’s clear to me now that I moved through four very distinct stages. Each stage uncomfortable, insightful, and expansive in its own right.

• Phase 1: Rest & Mobilize (June)

• Phase 2: Exploration (July - August)

• Phase 3: Experimentation (September - November)

• Phase 4: Execution (December onwards)

phase 1: rest & mobilize (June)

In June, I was coming off a particularly intense season of startup land and appreciated — needed — a moment to catch my breath. For the five months prior, I had become one with work, deprioritizing everything in life that interfered with my productivity. I was ready for the pace of my days to slow, albeit with some reluctance for insecurity of taking a step back.

I spent that first day reading How Will You Measure Your Life by Clayton Christensen, an apt way to ring in a new era where I sought to spend time grappling with the grand scheme of life and step out of the day-to-day grind.

That first month, I read a lot. After How Will You Measure Your Life, it was The Creative Act. The Big Leap. Big Magic. The Pathless Path. Whereas I previously turned to others for advice on what I should do next, I opted to ground myself in the words of authors who painted beautiful visions of possibility beyond the worlds I knew. I borrowed from their confidence that I too could breathe life into a reality I did not yet know.

I journaled. I introspected. I meditated. I wrote. I walked. I ran. I cooked. I watched The Matrix. I called and saw friends. I caught my breath.

Each day was a new opportunity to rewrite an old narrative. I slowly began to let go of the notions of the life I thought I should be building and opened myself up to the life I could build, starting with detaching myself from the idea that meaningful pursuits were locked up in a 9-5 work day.

I had a good inkling for the spaces I wanted to spend my time exploring. In the second week, I created a Collab with Me document that I shared with friends to give them a sense of how I’d be spending my sabbatical and to pass along to their friends who were interested in similar spaces.

A snippet of my original Collab with Me doc.

Crystalizing my Collab with Me doc took a huge weight off my shoulders. By articulating what I was seeking in this next season of life, it gave me a clear sense of what to say yes or no to. Friends could then connect me with potential collaborators in their communities.

For example: I knew I wanted to spend my time thinking about psychological wellness and human flourishing. If an opportunity to chat about enterprise tech (a focus of mine in a prior life) surfaced, I could confidently pass knowing that I was freeing up space to focus on the most energizing conversations.

I had spent the month contemplating who I was without a full-time job and turns out, I was many things. I had long sought purpose and belonging in the form of aspirational company missions. In that first month, I realized what I’d been searching for all along was the freedom to express. I was ready to start writing about it and exploring.

By the end of the month, I emerged from my cocoon of thoughtful consumption to create. On the last day of the month, I introduced my first project, Work & Self-Expression, a series exploring our relationship with work, creativity, and the in between.

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.

phase 2: exploration (July - August)

As July rolled around, I found more solid footing around how I wanted to spend my time. I was writing more and growing my community. I started exploring new identities and getting comfortable with the unknown. I had a lot of hypotheses and started throwing them against the wall to see what would stick.

I continued writing my Work & Self-Expression series. I wrote hypotheses on how I could contribute to raising the baseline of our collective psychological health. I chatted with people who shared similar dreams. I sought out new ways to introspect, applying for a 10-day Vipassana meditation retreat. I explored ways to balance doing and being, searching for activities where doing fueled my being rather than doing for the sake of doing.

I continued to keep to a schedule, planning my days the night before to give my life structure. This has worked incredibly well for me although others on sabbatical often opt to set themselves free from their calendar.

Around this time, I met up with a friend,

Matt Yao

, who put words to a new feeling that was emerging: “High confidence, high uncertainty.” I’d spent most of my life driving towards specific outcomes, but for the first time (ever?), I felt my whole body unclench, welcoming the uncertainty with curiosity.

phase 3: experimentation (September - November)

After much exploration and a 10-day meditation, I started to build confidence in what I wanted to experiment with in a more systematic way.

The 10-day Vipassana retreat brought a new level of clarity. I considered pushing it off until October, but ultimately decided that I couldn’t think of a better way to spend ten days than turning inward and stepping away from the material world. Those ten days gave me the space to solidify hypotheses I had and as a result directly informed how I spent these following 3 months.

Around then, my travels for the year were winding down which freed me up to go hard into experimentation. I did a lot during this phase. There were moments I wondered if I was doing too much, but now that I’m on the other side, I realize that I did just the right amount for that phase. Importantly, I was committed to each thing I was doing.

I wrapped up marathon training and ran 26.2 miles through Chicago. I started building a psychological wellness community called Psych Club. I started a coaching training. I took a writing course. I took a nervous system course. I started publishing essays weekly. I co-designed and led a workshop on shadow work. I collaborated on bringing to life the idea of embracing our emotions while working dubbed emotional embracement. I hosted a series of community events.

The life that I was calling into reality was beginning to take shape.

phase 4: execution (December onwards)

Now, as I enter my season of execution, I’m winding down several projects in favor of double downing on the bets I’m feeling particularly drawn to and optimistic about.

I spent the first two phases of sabbatical largely self expressing in solitude and the third phase in community with others. As I now transition to execution, I’m excited to blend the two.

When I’m asked the question of when my sabbatical will end, I don’t have a gratifying answer (for others). As a result of untethering myself from specific outcomes these days, it’s become less obvious when it’ll “end.” In many ways, I view this more intentional approach to how I’m living and working to be a mainstay of how I’ll continue to move through life. There was life before this sabbatical and life now. To “end” my sabbatical feels like I’ll return to the way life was before — that I know for certain will not happen.

My intention is to roll right into the execution phase and go from there. I’m highly confident that the uncertainty will soon take a new form and dissolve. I suppose once that happens, I’ll call it wraps on this era more formally.

…to actually accomplish at your full potential, you have to start doubling down on particular bets long before you know that you can follow through. You won’t see the whole path when you begin. You will have no way of knowing whether it exists, or whether what you are pursuing is even possible. If you have more certainty than that, you aren’t aiming high enough. You have to bet your life on faith that the universe will provide if your vision is good enough.

— Wolf Tivy, Quit Your Job

I’ve always dreamed of spending my life force on extraordinary things. It wasn’t until now that I realized that it’s solely up to me to define my extraordinary. I won’t stumble upon it along a well-defined path. It’s up to me (and every one of us) to decide what’s worth sacrificing in pursuit of finding our freest selves.

As for what’s next, stay tuned for updates over the next few weeks :)

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If you’re in the Bay Area, I’m hosting a SF x Pathless Path meetup this Wednesday, 12/13, sponsored by

Paul Millerd

in Hayes Valley. Join us!

Check out the Work & Self-Expression series:

• 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

Thanks for reading! If you’re on a sabbatical or considering kicking one off soon, what have you learned so far and what questions do you have? Let me know in the comments or say hi on Twitter.

Thanks to Ryan for reviewing initial drafts of this essay and for being my fiercest sabbatical hype man.