What have I got to lose?

“Let management take care of this,” he interjected.

The internal rumblings to quit, similar to grumblings on an empty stomach, began shortly after an unsatisfying talk with my manager regarding the lack of innovation on our service.

“If you need to worry about something, worry about your promotion,” he continued.

He consistently used my impending promotion as an ongoing basis of encouragement- our meetings largely revolved around getting him enough data points to submit a promotion proposal. “We’re so close,” he said, “I can see it happening next quarter.”

My work was regularly interrupted by my manager’s constant push to insert myself in places where people could see me say or do things that would help someone up the ladder approve my promotion:

  • If someone had an idea for how to improve our DevOps pipeline, I should try to come up with a better one that required an unnecessary overhaul of my own resources. 
  • If there was a meeting being held that I thought didn’t relate to my work, I should show up and pretend to be involved anyway. 
  • When there was a lack of opinions around the room because the answer was obvious, I was asked to obviously state it.

I constantly needed to show myself around the room to display reach and take part in a pageant of trivial opinion and redundant discourse.

Meanwhile, I was pushing back on leadership to focus on improving the core technology to expand beyond our current services. However, I was told it wasn’t my job. Management was too busy caught up in making small wins against the confines dictated by our, ironically, internal competitor. 

We were repeatedly banging our heads against a wall on the losing end of this internal battle until an unexpected external competitor sprung up with the technology I had been pushing for all year.

So I had to quit. What have I got to lose? I no longer have to take part in the pageantry. I no longer am forced to be rerouted by short-sighted leadership.

In the midst of my contemplation, I visited an old friend who had also been having thoughts on leaving her company, but for the last three years. “I don’t wanna just leave to leave. I like my job enough,” she told me in an illuminating discussion. Inevitably, she chose to remain for another busy season to “think it over”.

She cited imposter syndrome to be the culprit behind her decision to stay throughout the years.

Similarly, I was constantly plagued with feeling my skills and engineering experience could only be matched with similarly insufficient roles.

But I found that these feelings often occurred as a consequence of pursuing growth within the confines of the corporate ladder, similar to the way we pursue prestige within the education system.

If you aren’t good enough to stand out and accelerate above the crowd of your peers, you’re like every other gummy bear on the conveyor belt. Only few earn distinction to accelerate forward; these occasions are rare in such structured environments where space is limited to forge your path. You end up, for quite a few years, sitting at a job you’ve outgrown long ago, with the desire to move dulled into an ache in the pit of your still empty stomach.

“Most people live in a very restricted circle of their potential being. They make use of a very small portion of their possible consciousness, and of their soul’s resources in general, much like a man who, out of his whole organism, should get into a habit of using and moving only his little finger.”

William James

While my friend chose to remain within the environment that limited her beliefs as a place of security, I chose to find a way to quickly let go of mine.

This is probably how people end up in cults or in remote communities where they fart in communal fart bags to save the planet. (I’ve heard enough stories.)

But to save myself from this, I returned to first principles. I scoured the internet for people whose thoughts and feelings reflected my own- and did something about it. I knew I needed to feed off of their passion to gather enough activation energy to confront inertia on my own path.

I had to go out and find my people, surround myself with them and deconstruct my own identifying beliefs about work, security, and purpose.

I began to connect with many people who were forging their own way- an unfamiliar path I only dreamt of for myself: founders, nomads, solopreneurs, writers, creators, artists. As I keep bumping into them, I get to keep replenishing on that burning energy to strive for more.

I quickly realized a common denominator that kept them all afloat. You can’t be an imposter if your job is to capitalize on the advantages that come with being yourself. You can’t be worried about being an imposter if the work is more important than what you think of yourself or how you think it fits on your resume.

We grow by making small bets on ourselves to make bigger bets on things we are passionate about. In these spaces, there’s no one you can imitate. Is there anyone who can act like me… better than me?

So I had to quit. What have I got to lose? I no longer needed to feel like an imposter, trying to forge my way through a path already worn out by so many.

But there was still one thing left on my mind: money. I struggled against these feelings of inferiority and stagnation in my competition-driven workplace for so long, the competitive salary had been the main source of comfort. I deserved to take as much as I can. At least in compensation, I was winning.

But monetary consolation is like a smoker’s urge for nicotine. You don’t really need more money, but you want it to relieve yourself of the rat race all the more quicker. For all the crap you have to go through at work, you are at least entitled to see that deposit amount in your bank account at the end of each month.

And if you could squeeze more out of your employer, or even from another potential employer, and pit them against each other to fight for your well-oiled limbs and broken spirit? Even better.

These “big” wins are irresistibly finessed at the margins, like a kid at the 20% discount candy store with rotting teeth. But to truly break out of this cycle of addiction, similar to quitting smoking, your brain needs to get used to not having this monetary consolation around entirely. You have to deconstruct these rituals around money as the main motivation and define a new reward to structure your life around.

During the months before quitting my job, I had to ask myself, “What about my job am I addicted to? What does it provide me that I feel I can’t live without?” The answer was obviously monetary: a steady income, unvested stocks, and an impending promotion.

The unvested stocks would never be vested with the promotion. And I don’t believe the promotion would have mattered for where I was going. I really only needed income and I had enough money set aside to go without one for six months. This meant six months to throw myself into finding a new job. Doable.

So I had to quit. What have I got to lose? I didn’t really need to waste away a couple more years for monetary self-affirmation at the expense of self-acceptance.

So I did.

I quit.

I chose to put all my energy into finding something better to do.

Removing myself from the 9 to 5 rat race provided natural clarity- good enough is not an option. Sure, there is a gamble for what I want to do next, but I wasn’t stuck on the proverbial hamster wheel.

I took a bet on myself to find something better through trial and error. I chose to surround myself with people whose mindsets inspire me to actively find out. There is no grinding dullness here.

The work is playful from the start. I embrace and pursue the odds against me because they are natural obstacles I must face for being myself.

I don’t need to keep resharpening my stale pencil for the promise of “later on”. My pencil is both sharp and dull, depending on which edge I use, learning and experimenting with writing, coding, designing, and knitting.

My curiosity for these endeavors have since exploded and I am ever so adjusting to my needs.

Perhaps the question I am asking myself all along isn’t, “What have I got to lose?”, but rather “What have I chosen to lose?”


Thank you to Chris Wong, Martyn Bromley, Jonathan Miller, Ashni Patel, Alexander Tran, and Bob Barnard for your feedback at the terrible beginnings of this article. Much much much appreciation for you all.

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