I first stumbled upon identity work during my 2022 annual recalibration, an end of year ritual where I slow down to reflect on how life has unfolded over the last 365 days. In previous years, I spent the majority of my recalibration crafting new goals for the new year. I came into last year’s annual review in a different headspace. In November, I had an affecting revelation that I’d long suppressed a core identity of mine (more on my shadow work in an upcoming essay). As I excavated the identity of being an Asian American woman, I realized how little time I’d spent in previous recalibrations sitting with who I’d become over the past year. Always forward looking, never retrospecting. This made for a shaky foundation to build new ambitions off of.
Life was a treadmill of goals to do. Did I accomplish that goal? Check. Move on to the next goal. On and on it went. I focused so intently on arriving that the journey felt like a grind, a constant feeling of Are we there yet? What about now?
It never occurred to me how one dimensional goal setting was, centered around defining what we want to achieve with a secondary emphasis on who we aspire to become. Years of relying on goal setting to dictate the direction of my life left me with a scattered sense of self and no cohesive narrative around the person I wanted to grow into. I found myself becoming detached from goals that a past me set — some no longer relevant, others no longer motivating. As a result, I’d turn inwardly critical when I failed to achieve goals that no longer had a place in my life.
The dawn of the new year brought hope that next year could be different. I craved a more playful, experimental approach. As I explored ways to catalyze meaningful change through my annual review, I found resonance in infusing a more introspective approach to augment goal setting.
Enter: identity aligning.
tabula rasa & alter egos
Think of the last time you set out in pursuit of actualizing a great ambition. What feelings emerged? Boundless excitement? Dreadful fear? Suffocating scarcity? What was it about the goal that made you gravitate towards committing to it? Were you called by an internal knowing or was there a societal script that made you to believe you should pursue it?
When I’ve found myself at the starting line of a new ambition, my body often serves me a cocktail of contradicting emotions — a dash of bitter, a splash of sweet. In the face of particularly grand aspirations, the flavors of resistance and discomfort have overpowered the thrill of starting something new. This friction born from the incongruence I’ve felt between who I strove to be and who I believed myself to be. It felt like stepping into an unfamiliar reality and reaching for an identity outside of myself.
i·den·ti·ty (n): being repeatedly
Yet, every one of us enters this world tabula rasa, as a clean slate. Sure, we have dispositions, preferences, and intuitions that contribute to shaping who we become, but the experiences and knowledge acquired along the way are equally powerful agents.
If identity is the act of being repeatedly, we simply need to find paths to explore new ways of being on our pursuit to grow into new identities. Impostor syndrome commonly strikes at the start of something new, but by approaching a new experience as a series of experiments imbued with our inner knowing, we can take the pressure off of needing to be immediately competent.
Think of your heroes and luminaries. None of them came into the world as who they've become. Leonardo da Vinci wasn’t born a polymath, Albert Einstein wasn’t born a theoretical physicist, Carl Jung wasn’t born a psychiatrist. They found their way through a lifetime of experimentation.
Experimentation comes in many forms. One variety is role playing with alter egos and distinct identities beyond ourselves. Giving yourself the permission to try on new identities like new outfits allows you to envision yourself wearing a different style, creating a new reference point for new parts of you to come alive.
a wardrobe of identities
Our identities are far more fluid than we’re conditioned to believe. When I faced my first professional pivot early in my career, I worried that after committing five years to working in finance, transitioning to tech would kick me back to square one. Despite being eager to begin a new chapter of my career, I viewed the transition as an act of spring cleaning rather than an opportunity to expand my wardrobe, leaving me feeling guilty for abandoning my finance self.
In actuality, I was adding new outfits to my wardrobe alongside the suits and blazers that lined my former closet, pairing old outfits with new garments to curate new ensembles. Eventually, I became comfortable sporting the new outfits I experimented with and was ready to fully shed my finance identity along with the conditioning that came with it — but that didn’t come until several years after my initial move. Learning how to mix and match my way to a new identity served as a reminder of who I had been on my way to becoming who I’d be.
role playing as a series of experiments
You are under no obligation to be the same person you were a year ago, a month ago, or even 15 minutes ago. You have the right to grow.
— Alan Watts
We often spend a lot of intellectual energy contemplating our path towards a new reality, thinking about how we can de-risk our dreams over taking the first step. Role playing suggests there’s another way. While it’s helpful to have a roadmap guiding us in the direction we want to head towards, “things come toward you when you walk.” Standing still won’t bring us closer to our destination — progress happens when we’re in motion, in experimentation. The more inputs we gather, we more confidence we cultivate in our new identity.
Early on in my time in San Francisco, I felt called to join and build more communities. I loved living in the Bay Area, but felt untethered to the city as a result of a lack of meaningful friendships. I traveled often which made my time in SF feel disjointed. It was challenging to maintain momentum with new friends because we were all on the road so frequently that our schedules only realigned again after a month or two. After two years of the status quo (and some social distancing brought to us by COVID-19), there came a time when I realized the novelty-seeking adventures I pursued in the form of travel were happening at the expense of the grounded community I was craving at home.
I began to grapple with the question, “How would someone who has an established community in San Francisco live?” The answers were easy: live in SF, stay in SF, attend events in the city, host events with new friends. The same month that this clarity emerged, a spontaneous opportunity to travel to Finland arose when my partner had a last minute work trip come up. Torn between my identity as a spontaneous travel person (a lived identity) and a SF community builder (a desired identity), I found myself in a moment of turmoil. I was drawn to Finland because I thought I should take the opportunity to attempt to work from a different time zone while exploring Helsinki. It had been some time since I’d traveled internationally and I had long wanted to return to Europe. On the other hand, I felt a deeper calling to root down and truly make San Francisco home.
After a few days of back and forth, I decided to meditate on whether or not to buy the plane ticket. As I imagined myself on the flight and walking around Finland, I felt a tension build in my body. I then imagined myself in SF with no plane to catch, slow mornings, and a calendar wide open — a subtle sense of ease came over me. Trying on these two scenarios allowed me to tune into the clarity that lived in my body. It was the wrong moment in time for me to go to Finland — saying no to Helsinki now didn’t mean no forever.
Three days after I declined the trip to Finland and started rooting down in San Francisco, no less than five invitations to events in the city landed in my inbox. When I set a boundary of who I was becoming, opportunities that I would’ve otherwise had to say no to while traveling magnetized towards me.
When I first moved to San Francisco, I didn’t really have a reference point for what my life would look like as a community builder. It had been years since I was in the position where I convened new friends, spending most of my last few years in Boston hanging out with best friends from college, colleagues, and my partner’s friend circle. An important part of this process is gently asking your ego to step aside during experimentation. Rather than asking yourself what you should do, expand the question beyond yourself. Bring an objective lens to the approach by asking, “What might someone who wants to do [xyz] do?” When you’re able to separate your sense of self from role playing, you can get creative about approaching the how in pursuit of the why.
ride the learning curve towards your own style
Any pursuit worth chasing comes with a learning curve. It’s easy to judge ourselves for our lack of coordination as we start something new. The reality is that in the beginning, we’re at the very bottom of that curve and it’s inevitable that we’ll fumble. How can we look to others who are further along the curve and transmute our doubt into a sense of agency?
Draw inspiration from those who have come before you. Understand the minds of those who exhibit the identity you’re seeking. Pablo Picasso painted over other artists’ works which served as inspiration that led to his own original paintings. Hunter S. Thompson rewrote every word of F. Scott Fitzgerald's The Great Gatsby to experience what it felt like to write a Great American Novel. In the early innings, immersing yourself in the work of those who embody the identity you seek allows you to develop an intuition about how you would do things differently. Over time, as you build the reps, you can refine the work to develop your own style.
In a recent interview with writer David Perell, entrepreneur Sam Parr shared how he approaches writing boldly. Before writing a piece that demands audacity, Sam picks passages from Anthony Bourdain’s book and writes them by hand in preparation to write his own bold takes. A pre-game ritual of sorts as he steps into the identity of a courageous writer.
embodying & role playing with others
Knowledge is only a rumor until it lives in the muscle.
— Brené Brown
Once we’ve intellectually experienced trying on a new identity, it’s time to embody that experience. We can’t just think our way to becoming. Practice embodiment with trusted others, while meeting new people, and in passing. Cast votes of confidence towards the identity you seek by voicing it to others and you’ll begin to see it reflected back at you.
During a period when I was struggling to get to bed earlier, a friend asked me if I wanted to go to dinner one evening, but then immediately acknowledged, “Oh wait, I forgot you’re a morning person and go to bed early. Want to go for an afternoon walk instead?” By having a friend hold up a mirror to my identity as a morning person, it strengthened my belief in myself.
Begin experimentation in solitude and invite others to role play along. The more cheerleaders you can get on board, the more cohesive your narrative becomes. Figure out who you want to show up as, refine it every opportunity you have, and eventually, the reps will allow you to embody and internalize what it feels to be that person.
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Every day, every week, every month, every year is a chance to thank an old identity for all it’s done for you, bid it farewell, and welcome the arrival of a new, expansive identity. Living a life where you bend to no one’s expectations but your own is just on the other side of a few costume changes.
Thanks for reading — let me know what you think in the comments below or on Twitter!
Check out two related essays: Trading goal setting for identity aligning and The Annual Recalibration.
Thanks to Ryan, , , and Diana-Maria Demco for reviewing initial drafts of this essay.