How to sabbatical

Part 5: The inner workings of the in between

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

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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.

credit: Tim Urban (Wait But Why)

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.

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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.