Most career advice on the internet is from people who had some sort of meteoric success. Why read advice from someone who’s had a mediocre career? But there’s massive sampling bias. All this advice will try to draw grand, sweeping narratives and also typically fails to sufficiently factor in luck.

I worked at a struggling tech company for a couple years, and spent a lot of hours with my friends (also in similar situations and colleagues examining what we would’ve told our past selves. Below is a quick distillation of wisdom if:

Your company is struggling

If you get a retention offer, take it and start looking immediately. DO NOT act like you’ve already earned the money. Those 6-12 months will destroy your soul. At one point, I was calculating how much extra I was making, per remaining hour, to keep myself in meetings. “They’re paying you $200 to be here, just shut the fuck up and nod…” The company is not your family. Some of the people in the company are your friends in the current context. It’s like your dorm in college. Hopefully some of them will still be your friends after. But don’t stay because you’re comfortable. Don’t think that there won’t be politics because there wasn’t politics before. Politics emerge when the players believe the game is zero sum. In a recession, the players are more likely to believe the game is zero sum. Maybe the turnaround will work. Maybe it won’t. You have to decide whether it’s worth waiting for. Your existing time is sunk costs.

You’re not sure of how much risk you want to take

It’s okay to go for the safe job. Sure, Airbnb was founded during a recession. 50% of the time, you’ll survive the charge across no-man’s-land and reach the enemy trench. It’s also okay to take risks. Staying at a company that’s slowly dying has its costs too. Stick around too long and you’ll lose your belief that you can build, that change is possible. Try not to learn the wrong habits. Just… try not to fuck up the ratio. You can take the risk but if you do so, demand some of the upside.

You’re finding a new job

“When a management team with a reputation for brilliance tackles a business with a reputation for bad economics, it is the reputation of the business that remains intact. - Warren Buffett, maybe

When picking a job, yes, your manager matters. But if you have an amazing manager at a shit company you’ll still have a shit time. In some ways, it’ll actually be worse. If they’re good at their job (including retaining you), they’ll keep you at a bad company for too long. And then they’ll leave, because they’re smart and competent. Maybe they’ll take you with them. Your equity package is a lottery ticket with expected value of zero. VCs are salespeople for a living, are constantly talking their own book, and only have to be right 1/10 of the time. Even the ones you trust to have your best interests at heart are often wrong. Don’t ever join a company solely on the recommendation of a VC. Even if they’re a board member. It’s the nature of boards that they ignore (externally) problems until their hand is forced. “Take any role, at any pay, on a rocketship and everything will work out” is only sort of true. It’s the Hollywood model… do it for the exposure and it might be great! Technically true, but it’s also a way for people with more information to offload the risk of bad companies onto… you. Seriously, you have to form your own opinion. Hyped = hiring good PR != successful. Every time I’ve outsourced my thinking for a job change (n=2), I’ve missed out on 5-6 figures of equity appreciation. But, who the fuck knows.

Lastly, it all tends to work out, on average, eventually.

If you thought this was useful, please share it. Or tell me your own stories, and I’ll share them in a follow-up.

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