The “one that works out” can also give you a misrepresentation of how the world works and a false sense of how lucky one should expect to be over a long period of time.

At an earlier point in my life, I had been applying to many well-known big tech companies right out of school (not a top school either). I never got a reply from any of them so I ended up accepting a local job with a non-tech company after months of searching.

But I didn’t give up my hopes and kept applying to big tech, and while I did manage to get the occasional interview with some mediocre companies or the random startup, I also miserably failed all of them too.

At some point during my long period of despair at never getting a better job, my very top pick (and arguably one of the best tech companies in the world at the time) reached out to me. Even more miraculously, I somehow passed their interview (the only tech interview I passed in the prior year) and accepted a job there.

I really enjoyed working there. Some of the best years of my life. And my performance reviews were great too, so the imposter syndrome from having failed so many tech job interviews sort of faded into the background. But after a while, perhaps due to the “hedonic treadmill” mentality, I thought I could do better. So I left to join a startup.

Well, the startup failed, as startups tend to do, but what I didn’t expect and what caught me off guard was that I was now back in the same situation I was in right after graduating from college. Don’t get me wrong—having “the name” on my resume now meant I could get at least one chance at an interview about anywhere. But much like the first round that I tried to forget about, I once again failed all the interviews.

Unfortunately, this second time around never procured a “get out of jail free” card.

So I guess my lesson is: 1) there’s a lot of luck involved in these things, 2) if life gives you a winning lottery ticket at some point, don’t throw it away for the chance to win an even bigger lottery, and 3) that famous saying about “the only actions regretted are those not taken” is absolutely, totally wrong—almost all of my regrets in life relate to taking some action I shouldn’t have rather than inaction.