Last month, I shared an essay on taking risks.
The angst I wrote with was fueled by my move to New York and ongoing deliberation about career change. At the time, it all felt like one giant emotional soup. It still does.
But after hours of journaling, self-reflection, and conversations—with both like-minded and dissenting peers and mentors—I’ve come to realize that “risk” is fractured into three distinct subcomponents within my psyche:
Social Risk
Financial Risk
Emotional Risk
Each and every day I take deliberate actions that inch me closer to all three. Lately, I’ve gotten close enough to smell their breath—sweet yet pungent, like cough syrup or rice-based alcohol. But as someone whose frontal lobe is still raw in the center, the stench makes my heart race, with both fear and wonder.
[1] Social risk is the judgement that comes with challenging the status quo.
When you talk about leaving the acceptable path to success, people regard you with a mix of curiosity and skepticism.
The pessimist in me believes that some part of everyone—however small—wants to see you fail. Maybe not to the point where you deeply suffer, but just enough to reaffirm that their decision to stay the course was right.
After all, if we are rational agents, we must also wake up every morning with the strength to go about the day, believing in the choices we’ve made.
An unexpected way I’ve felt social risk is through the fear of being perceived as arrogant. That I think I’m too good for my job, or I’m looking down on the corporate path that my friends are on. That I’m making some type of grand statement by opting out like a big-ole drama llama.
In reality, I think I’m kinda bad at my job, and I truly believe that self-made work has greater upside for me.
There is vulnerability that comes with being perceived as trying, and both sides can feel the tension. To know that one party cares so much about a belief, a product, a philosophy that they are willing to trade ultra-stability for just a shot at it is disarming.
Is anything more fragile than unproven hope laid bare?
[2] Which segues us nicely into financial risk.
I think of financial risk as the blind spot between the stress of paying rent and the dream of making a living doing what you love.
The more challenging concept to overcome for me is one layer deeper: am I really ready to break free from the hedonic treadmill of 5% yearly salary bumps for the rest of eternity?
When faced with financial risk, it’s hard to plan for the future. I already know of kids my age who are getting engaged and putting down payments for homes. The constant which supports these long-term commitments is the expectation of steadily increasing income.
Our society is paranoid about money, and rightly so. The deeper I plan into the future, the more important money becomes. It’s the one thing I feel I can control, a guarantee of baseline security when everything else—relationships, careers—feels uncertain.
Having “enough money” is the single most important need. But “enough” is slippery. We stretch planning timelines decades ahead, obsess over savings goals and interest rates—all while holding zero understanding whatsoever about the things that actually drive satisfaction in older age. What will your hobbies be? How will you find meaning? Will you have the energy to start that café you keep talking about?
To take a financial risk, then, is to temporarily (or permanently) say fuck it this long-term commitment between time, money, and satisfaction.
To bet on the parts of your life that actually bring you joy, and in doing so, set yourself up for a more meaningful life.
One that better aligns the flow of money into your account with the flow of your energy into the world.
[3] Then there’s emotional risk.
Will I be able to keep my head together once I finally make the leap?
I’ve wondered numerous times to myself how I would behave when my back is against the wall, when I no longer have petty excuses via corporate constraints to make up for the fact that I’m not chasing after what feels right.
Right now, my job lets me be passive. It gives me a socially acceptable excuse to delay, to not post, to not try as hard as I should. It allows me to romanticize the struggle without having to live it.
Soon I will leave my job, and the excitement will be electric. But what happens when the high wears off? When plans go sideways? When it starts to really hurt?
Will I have the resilience to keep going?
The clear and obvious answer right now is: of course. Of course I will press forward!
But this certainty is theoretical, it hasn’t been tested yet in the heat of the moment.
And slowly but surely, I feel the temperature rising.
"[W]e must also wake up every morning with the strength to go about the day, believing in the choices we’ve made." Searing and beautiful, as always, Raymond. A favorite Latin phrase comes to mind: "Dum spiro, spero!"