Introducing Work & Self-Expression
Introducing Work & Self-Expression
Part 1: Cissy’s sabbatical field notes
This piece is part one of Work & Self-Expression, a series that explores our relationship with work, creativity, and the in between.
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.
"Things come toward you when you walk.”
— William Stafford
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.