I am writing this after 4.5 years working at startups. For about the last three, whenever I talk about work my uncle has asked me if I think I’m ready to get a “normal job” again.

My answer each time has been no.

It’s reasonable for him to ask. Most people prefer in-person to remote work (compared to myself, who asked Caesars in 2019 if I could work remote from Boston). My startup jobs have all been remote. The three startups I’ve worked at have never been profitable, and were often struggling to meet financial expectations. Most “normal jobs” are at companies that make money. And a handful of my managers were…not good. I can see how someone links that to the nature of startups.

To someone from an older generation, I sound like I’m putting myself through misery.

Others who ask this question will sometimes point to my experience at Caesars. I seemed to enjoy the work, and had friends in the office.

But Caesars was a unique situation. I found myself on the exact perfect team for me in the exact perfect role. That team no longer exists. We played cards for two hours a day in the office, in part because we had a good group and in part because the company was taken over and was in the process of a sale (leaving many of us lame ducks). Being a lame duck for too long started to wear me out.

Why I prefer startups

While it’s been a rocky path in tech, I believe it’s been a better move for my career than had I stuck it out at a “normal job”. Reasons include:

Remote work

I knew since college that remote work was something I wanted to try. I’m not against going back into an office, but I think I’m past working in productivity-sapping open office plans. I hated my commute; now I reclaim that time. I sleep longer. I have more time to cook and exercise.

“Normal jobs” seem to want you back in the office five days a week. Some startups do as well (or offer hybrid), but others embrace distributed teams.

Location independence

Location independence is the idea of needing to live in a specific city to work at a job. Part of wanting to leave Caesars in 2019 was to get out of Las Vegas.

One thing remote work has enabled is opening up job opportunities that I wouldn’t have otherwise had available or been willing to consider. I would not have relocated to Bend to join Dutchie in 2020. I would not have relocated to San Francisco to join Future in 2022. But I was thrilled to join them from Philadelphia, where there weren’t a ton of tech opportunities.

More money

Hard to pretend like this one doesn’t exist. Before leaving Future in June 2024, my salary was four times greater than my starting salary at Caesars in August 2018. I could barely pay my bills and couldn’t really afford to go out in Las Vegas.

Startups valued what I could bring more than normal jobs (perhaps too much). Taking a 50% salary reduction to go back to a normal job would require almost everything else being perfect.

Different coworkers

Startups tended to attract more more young, smart, and ambitious people than normal jobs. I liked that.

Better scope of work

I got to take on way more responsibility at startups way earlier than I would have at normal companies. Overachievers like myself crave that opportunity.

More learning

In part due to better scope of work, I learned more and faster.

Trying to “win”

I like the growth aspect of startups. I like being the underdog. It’s more motivating to me than preserving the market share an incumbent already has.

Upside and downside

One thing I might have put in that list at previous times was the concept of equity. At startups, you are issued stock options and if the company does well, you could make some extra money.

Long story short, I think what we’ve seen recently with valuations and liquidity events tend to be less friendly to employees like me. It’s still better than not having stock options, but not something I’ve gotten utility out of thus far.

But that leads into my broader point of how we think about upside and downside with “normal job” vs. job at startup.

My assumption is most people think the startup is high upside, low floor and the normal job is low upside, high floor.

In the 2020s, the startup upside is probably less likely to produce completely outsized returns. So maybe we call it medium upside. The floor is definitely still low. While I was lucky to avoid layoffs the last few years, each of my companies had them, and a lot of the places I interviewed at had them too. And the startup job market has been brutal the last year and a half.

Meanwhile, the “normal job” still has low upside. But I think the idea of a high floor is deceptive. And take a shot, I’m bringing up Nassim Taleb.

In Antifragile he offers the scenario of a taxi driver vs. someone working a stable job. The latter has a more consistent income, but they’re quite fragile. (I recommend reading the book but you can see a quick summary here) As we’ve seen recently, some of the people working “stable” jobs were just as likely to get laid off.

Even after we’ve discounted the upside of the startup job, once the floor gets taken out on the “normal job” it’s clear you’re sacrificing some EV.

Of course, the answer probably is neither. It could be fair for someone to say the startup job has a similar risk profile but with a higher salary.

Where to go from here

Just because I’ve found startup jobs to be a better fit for me than “normal jobs” doesn’t mean I should get complacent. Hopefully I continue to learn more about what works and doesn’t for me.