🤑💰 unshackling myself from golden handcuffs

leaving a high-paying job to wriggle around and figure life out.

“A worker held by golden handcuffs, digital art” | DALL-E 2

I.

I’m often asked the same question:

How did you leave that much $$ on the table?

Having worked in the temple of tech, I’m intimately familiar with the reasoning behind this question. I worked in a land that treats TC (total comp) as the cost of salvation. Get the right offer or job title and all your worries will be quelled and you too can cry yourself to sleep on your satin, anti-aging pillowcase. See, the tenets of this game are quite simple—you hitch a ride that puts coins in your wallet, or you build that train yourself. Sure, there’s fancy talk of missions and visions, but the cold truth is we were all attracted by the rewards. At least partially. The culture is one of ever-increasing numbers—more users, more ad revenue, bigger paychecks, more stock. The game is the game. You’re expected to take pitstops, to swap jerseys with rival teams and to flirt with the opposition to get counter offers. This expansionist, accumulative culture isn’t unique to tech per se, but tech offers the addiction of RSUs (stocks)—the sweetest drug in all the world.

RSUs are like little balls of decadent chocolate that slowly fall into your mouth on a predetermined schedule. A Payroll rep blindfolds you and carefully places sinful treats on your tongue. (Okay, so maybe that was a dream I once had.) Imagine a conveyor belt that brings self-dispensing sweets to your doorstep. A fondant pie this month, a human-sized tiramisu the next. Mileage will vary depending on the weight of your grant. But it’s simply a prize you’re given for remaining employed until a certain date. On vest day, there is no fanfare—a dull email crashes your inbox and the ganache will ask you to devour it. There’s a mad rush the first time this happens. That chocolate truffle is now laced with caffeine, pumping adrenaline through your veins. But like any drug, your body starts to normalise the effects after a while. You get used to it. You yearn for a higher dose for the same high. You crave that asymptotic high—one you will certainly chase but will never quite reach.

The tech world is inundated with talk about “exits”. Basically, an exit is when you cash out from the game and get to do whatever you want. But I’ve always found this weird. If we’re constantly talking about our desire to leave…doesn’t that tell us something about where we currently are? Doesn’t that imply displeasure with your current location? Where are we trying to go? Is that place inaccessible to us right now?

To its credit, tech douses you with many addictive comforts and rituals to soften any discomfort. You’ve heard about the beer and wine on tap, but do you know about the dizzying array of sparkling waters, smoothies and sunflower seeds? The ridiculously-complicated machine that makes custom mocktails? The free cafe where buzzing baristas will prepare any drink of your imagination. The nap room (yes, you read that right). The library where you never study. The catered lunches with multiple meat, pescatarian, vegetarian and vegan options. The Uber Eats discounts. The shipping room that turns every half-baked adult into a returns specialist. The soft seating and plush poufs that make sure you never rest your bum on bare metal. The salad bar with a devious supply of avocado. Even the bloody stationery was perfect. Those firm-grip-yet-soft-touch pens stare you down and demand you jot down all your bad ideas.

You don’t need me to tell you that these perks are not heartfelt gifts borne of love. I mean, your company doesn’t hate you. The truth is more blasé. A company is a legal construction that was birthed in Delaware. How could it have feelings for you - good or bad? To them, you’re irrelevant in the same refreshing way that you don’t matter to Jupiter. The money, the treats, the perks are the terms of a deal. You bring your smarts, energy and optimism and hopefully, that helps the greater organism to expand. The hope is that the perks keep you at the office long enough to do more work, maybe even better work than if you had to stress about how to ship your ASOS returns.

In any game, especially if it’s a game worth playing, there is that which is seen and that which is unseen. The seen stuff shines bright in daylight and everyone can see its lustre. Then there’s that which is unseen, undercounted and often ignored. In this little dance between sought-after employee and opulent tech company, the seen cost is quite obvious. The companies shell boatloads of cash to feed, flirt with and seduce employees. The unseen costs lurk underneath the surface and are silently borne by employees. But nobody really talks about this in the open.

Money is supposed to be freeing. It’s supposed to let you imagine better futures that work on your terms. It should bring you closer to living in alignment with your interests and your values. It should not be bondage. For far too many, a high-paying job becomes a prison that drains your life satisfaction and wellbeing. I know several people in this boat. How could they be imprisoned by money, you ask? Well, the covid pandemic was an accelerant. When you strip away all the frills and glitz from your job and are faced with the reality of how you spend your workdays, the outcome is often disappointing. The happy hours, the perks and the lunches medicated you into managing until the weekend. But when your work is one lifeless, inconsequential Zoom call after another, then even the weekend is too far away. 

Trapped by the weight of their grants, they lied to themselves about when they would leave. “Oh I’ll just wait for two more vests then I’ll leave”. I’m not judging, I did this very thing myself. Constantly drawing new lines in the sand. Doing all kinds of justification gymnastics to tell myself that it would be worth it in the end. Spreadsheets tried to talk sense to my logical brain, and narratives swayed and seduced my emotional brain. The reality is that it’s difficult to give up money. And that makes sense from an evolutionary perspective. We’re wired to protect ourselves and loved ones. Remember, for most of history, we did not live very long. Surviving the winter was not a foregone conclusion. If you have extra fat or extra grain, your brain wants you to store that for the days of rain, cold and famine. But the issue is your brain is running outdated software. It doesn’t know how to account for the realities of today, the true costs and value of money, your mental health and the other opportunities you have. 

So what do you when your money becomes your prison? When you’re zooming through life endlessly yearning for weekends that are always too short? When you’ve run out of vices to quell the pain? How do you reckon with the finiteness of your life - you don’t know when you’re going to die so what the hell is the point of accumulating wealth if you hate your present days? Is that future money worth it if you’re gonna be depressed when you’re wealthy?

It is here that I want you to sit for a moment. In this uncomfortable space where you reckon with the value of money in your life. I won’t pretend to know what season you’re in or what your priorities are. You could have huge financial obligations that demand you earn as much as legally possible. Or you might enjoy the corporate game and dream of fishing for bigger salmon in the open seas. Who am I to tell you otherwise? 

But I know that there will be others. Others who feel completely disconnected with the stories we tell ourselves about work. Those who continue to excel at work and are rewarded with more work that they hate. Those who recoil at the idea of being called a “resource”. Those who dream of using the totality of their skills at work - not just an engineer, not just a writer, not something that exists on a career ladder. Those who don’t fit squarely into the neatly divided holes that the corporate world prescribes. Those who feel at odds with the options they have, who know that there must be much more out there for them. Those too talented, too inquisitive, too rebellious to sit and twiddle their thumbs with inconsequential work.

Consider the end of your life. If that’s too dark for your taste, consider someone else on their death bed. What do you guess they might regret about their life? Shots they never took? Grudges they held too long? Money they didn’t earn? Work they hadn’t done? Hopefully, you and yours are not dying anytime soon. But research consistently tells us that the dying often regret having the courage to live their authentic life. The life truest to themselves not the life expected by others or dictated by society. Not the one where you’re merely adopting the narrow, singular definitions of success that society prescribes us. So don’t shortchange yourself by endlessly sacrificing the present for a tomorrow you’re not certain you’ll have. Spend your today doing what you were put on this planet to do, or at least trying to figure out what that is. 

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II.

“Beach balls always rise to the surface”.

My therapist said these words to me on a random Tuesday. I was taken aback because I live in foggy San Francisco where there are no actual beaches. Instead, there are stretches of sand that present as mirages, tempting us to dip our toes in the water only to be met with frigid cold. So I asked her to explain the concept. She obliged and I felt completely understood.

I tried many things before I decided to leave my job. I used two coaching services ironically provided by my ex-employer. I wrote painfully honest journal entries for my therapist. You know the kind that you try to edit before sending because you’re concerned about what it might say about you? I found a few friends who liked their jobs and badgered them with questions. “So what do you mean, when you say you enjoy your job?” I talked about leaving for so long that it had become a running joke with my close friends that it would never happen. I’d be there when the stage curtains were being closed, turning the lights off and drinking the applause as the credits rolled in.

In the summer, I was in denial. I thought changing roles would help mute the pain and propel me forward. Over the years, I’d been told by many people - mentors, coworkers and a manager that I’d be a great product manager. So one day, I climbed out of my abyss and told my manager that I wanted to pursue that direction. He supported it. Until I reckoned with myself while in the shower one day. Would this new role really change much? Was I avoiding something? Pursuing a shiny distraction instead of doing the introspection I desperately needed? Setting a new goal and going after it was intoxicating, but I could see myself three months in feeling the same way. I decided not to go down this route.

I learned how to game my own mind. I’d look at the calendar and JIRA board and would see several things I didn’t want to do. So I’d incentivise myself with rewards from other parts of my life. “It’s Monday so at least you’re playing soccer tonight”. Just hold it together until the evening and you will feel a bit better. Voila! A future dose of dopamine…something to look forward to. Then I’d wear my corporate makeup and put on a theatrical performance to try to drag myself across the finish line. Often I’d fail. Focus and motivation were at an all-time low. My workdays were simply the hours I spent waiting for things that would give me a little life. What a horrible way to live. Whether it was soccer, or hanging with friends, I tried to stuff the void with things I liked. But all fun things end at some point and that bleak Monday cloud always found a way to stalk, return and hover. It would be a stretch to say I was surviving. I was a tiny notch above functional.

Then, I came to understand what my therapist was saying about beach balls. I’ll spare you the high school physics lesson about upthrusts and pressure. But the gist is this: no matter how hard you try to submerge a beach ball underwater, it shoots back up. I had succeeded at temporarily convincing myself to shut up and do the work. To follow the incentives and play the game for the rewards. To sacrifice the short term for future fruits. I had quietened my dissenting voice that yearned for other fruits. Even if I didn’t know what those fruits were, I knew this current thing wasn’t for me. While my logical brain could accept this tradeoff, my soul could not. It flared up in bouts of indifference, inaction, depressive thoughts and general sadness. And this was profoundly uncomfortable for more than a year. When I calculated my expected payouts, I never counted the cost of misery and dejection. Just because those don’t come with price stickers doesn’t make them any less costly.

I had my fears about leaving. I mean, tech companies are decimating entire teams and slowing hiring across the board. And here I was, voluntarily trying to leave my (as-far-as-I could-tell) secure job. The timing felt odd. But once I took the time to evaluate my fears, I realised that they were mostly unvalidated. Fears try to help us to protect ourselves from danger, but they are low resolution, they can’t see the real details. At the time, I was concerned about next steps - what I’d do, where I’d go, how much money I’d need, how I’d explain this, how long I’d need before getting a “real job”. But none of those are real concerns, I made simple backup plans in case things got really bad. In case we got into a two year recession and engineers suddenly became undesirable. And I convinced myself that I could get another tech job next year if I really needed to. So then it became a simple question: could I bet on myself? Could I take a leap of faith to figure out my journey? What would it look like for me to take advantage of this time? Whisper it, but what if I actually thrived on this journey? How could I say no to this opportunity? Saying no is saying yes to toiling and lingering in the hopeless place with no direction. I couldn’t do that to myself.

Ultimately, I decided to leave because I needed to. For my own survival and because the cost of staying was far higher than I could be paid. My light would be too dimmed, outlook too pessimistic and aura too muted, and to what end?

What’s the point of flying first class on a crashing plane?

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