You’re Lucky if You’ve Seen Some Things Done Right, and Some Things Done Badly

A naive belief is that you’d be lucky to have only seen things done the right way, as if that’s some kind of assurance that you’ve only learned correct lessons. If you’ve only ever seen things done the right way it doesn’t mean you’ve learned the right way. It means you’ve severely under-sampled the parameter space of success/method, and you probably underestimate the role of chance. You don’t know how far you can get from the right way before things go awry, and worse you may not know the signs of things going awry. Or even worse you may not appreciate the value of doing things the right way - i.e. you may not understand the compounding effects of bad (or even just subpar) practices.

People who’ve seen things done the wrong way don’t have these shortcomings. They know the price of subpar engineering practices and bad processes. They can spot at least some of the warning signs of problems piling up. What might seem like a perfectly reasonable shortcut to a person unfamiliar with Bad Things, often appears as a flashing red strobe light to those more experienced.

Relates to why so many VCs say they value a founder who’s led a failed venture over one who’s starting fresh - if you’ve failed then you know how hard things are.