Leaving my $285k job was the best thing I ever did

^{By Eli Navarro}

I’m 32 years old, and until six months ago, I thought I was doing everything right.

I graduated in 2015 with a business degree I didn’t love but knew would “open doors.”

The first one it opened was a sales role at a Series B tech startup in Manhattan that sold workflow software to mid-market companies. The office was in a converted warehouse in SoHo with concrete floors, a neon sign in the lobby, and kombucha on tap. The founders wore Allbirds before anyone else in New York knew what they were.

My job was dialing. Dozens of cold calls a day, headset clamped so tightly I’d peel it off and see a red groove around my ears. Scripts were taped to my monitor, but the real goal was to break script — to sound human enough that some VP of Operations would give me ten minutes.

It was brutal, but I was good at it. I had the right mix of persistence and insecurity. Every “yes” felt like a personal validation, every “no” like a direct rejection of me. That kept me grinding — I couldn’t stand the thought of being invisible.

Five years later, the company went public at a $9 billion valuation. I was 27, pulling in about $180k between base and commission. By 30, I’d crossed $285k. I signed a lease on a one-bedroom in the East Village with exposed brick, big windows, and a washer/dryer in-unit.

But instead of feeling lucky, I just felt empty. Quite literally dead inside. Which I hated myself for because I knew this was the life people dreamed about. My grandfather was (and probably still is) cursing at me from above saying, “you ungrateful little shit.” And he'd be right. But my daily routine was far from what I think most people would envy.

I’d wake up at 6:30 a.m., crack open a Celsius, and scroll Slack before my eyes had adjusted to the light. By 8:00, I was in a WeWork conference room rehearsing a pitch deck. At 11:00, I’d Uber to Midtown for a client lunch where we traded small talk while keeping one eye on the drinks menu. At 2:00, I’d be back in the office, dehydrated, trying to sound sharp on a discovery call with procurement people who couldn’t care less.

Fridays felt like the reward. We’d hit quota, crack open beers at our desks, then spill out into bars where we ordered bottle service we didn’t need. At the time, it felt like proof we were winning. Looking back, I see it was just another form of escape. I’d wake up Saturday mornings with my stomach sour from whiskey, telling myself I’d take it easy that weekend, then meet the same friends at the same bars by 10 p.m.

Drinking became my way of existing inside the job. Celebrate wins, drown losses, fill the dead space in between.

The body keeps score

The physical toll crept in slowly. My back ached from planes and stiff office chairs. I’d sweat through my shirts in meetings, anxious before the client even walked in. My Apple Watch kept nudging me about my resting heart rate trending upward, but I turned off the notifications.

One night, after closing a massive deal, I got home at 2 a.m. and couldn’t fall asleep. My hands were buzzing, not from excitement but from something closer to dread. I lay there staring at the ceiling, realizing I didn’t actually want to be rewarded for what I’d just done. The deal meant more pressure, a higher target next quarter, more flights, more hotel lobbies, more client dinners where I couldn’t remember what city I was in.

That was the first crack I couldn’t unsee.

The breaking point

The “ah-ha” moment wasn’t cinematic. No dramatic quitting scene, no big speech. It was a Tuesday morning on Zoom.

We were on an internal pipeline call, 40 little squares on my screen. My VP was rattling off numbers, congratulating one rep, pressing another, and I just… blanked. My camera was on, my face nodded at the right beats, but inside I felt like I was watching a life I didn’t want to live.

In the chat, people posted emojis. Fire emojis for big wins, rocketships for new logos. I stared at them and thought: is this really what I’m giving my life to? Pixelated applause from coworkers I barely knew?

That afternoon, I Googled “how to resign gracefully.”

Unraveling

Leaving was messy. HR wanted an exit interview. My boss wanted me to stay “just one more quarter.” My parents thought I was insane for walking away from nearly $300k a year with no plan. Friends half-joked, “so what are you gonna do, become a yoga instructor?”

What I actually did was nothing. For the first month I woke up late, walked aimlessly through my neighborhood, and tried to notice what it felt like to have no Slack messages waiting. Sometimes it felt like freedom. Sometimes it felt like free-falling.

Money terrified me. I had savings, but every purchase — groceries, subway swipes, toothpaste — felt like a countdown clock. When you’re salaried, the numbers replenish every two weeks. When you’re not, you start seeing expiration dates everywhere.

Conversations were awkward. My mom asked, “so when do you start looking for the next one?” Dates turned weird when people asked what I did for a living and I stumbled through an answer. Friends wanted to meet up after work, and I realized I didn’t technically have an “after work” anymore.

Trying something else

Eventually I picked up freelance work. A friend of a friend needed help running sales for his small consulting firm. Another connection asked me to do prospecting on a project basis. None of it paid like before, but I started realizing I didn’t need it to.

I could buy groceries. I could cover rent. I wasn’t racking up Amex points for another weekend in Miami I wouldn’t remember anyway.

More importantly, I wasn’t waking up dreading my calendar. I had mornings where I made coffee and actually tasted it. Afternoons where I took long walks just because the sun was out. Evenings where I didn’t feel the need to drink myself numb.

There were still moments of panic. Seeing a friend post about a promotion. Hearing someone casually drop their comp number at a party. But those moments passed faster than I expected. And in their place was something quieter, something like relief.

The culture we swim in

What still gets me is how invisible the misery was when I was inside it. Everyone looked fine. Better than fine — polished, motivated, hungry. We were all trading in the same currency: big titles, big deals, big salaries. If you dared to say, “this is destroying me,” you were the weird one.

It’s not just sales, and it’s not just tech. The culture is everywhere. Podcasts telling you to optimize every second of your day. LinkedIn posts congratulating someone for hitting 200% of quota while running marathons and raising twins. The unspoken rule that making money is the highest form of self-care.

I believed it. For a decade, I believed it. Until my body started whispering otherwise. Until I realized that when I pictured my future, the only thing I felt was exhaustion.

What I know now

Six months out, I can’t claim clarity. I don’t have a perfect new career path. I’m not suddenly enlightened or living on a farm or building a wellness startup.

What I do have is a little bit of space. Enough to notice that I feel better when I’m not pretending my worth is measured in quarterly revenue. Enough to admit I want a life I don’t need to escape from every Friday night.

Some days I wonder if I’ve ruined my trajectory, if I’ll regret stepping off the ladder just when it was reaching the higher rungs. Other days I wonder if the real regret would have been climbing all the way up, only to realize the view was nothing I wanted to see.

I don’t know. I may never know. That’s the part I’m still learning to sit with.