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Thank you for sharing your story. I tend to do this (attempt to transfer my failed dreams onto my kids), and it's helpful to have such a powerful reminder of how selfish and unfair that is. Thank you.

Wow, this was exactly what my dad did. He also was very well educated, and he also became bitter by his sacrifices as I got older. I came to appreciate his sacrifice when I became a father but I promised to never blame my kids for any choices I make. The difference between my father and myself is that I already feel like I have proved enough by becoming a father. If I died today, I would have no regrets. He passed away at 56 when I was in college and I know he had regrets. Like you said, I would rather have had an absent father than a bitter one too.

What would have been the correct balance for you Dad to strike between working and being with you?

Ideally, I would've liked it if he had done exactly what he did do up until about age 8 or 9, and then gone back to work. As I grew up, my needs shifted from someone who would love me unconditionally and give me lots of attention to a role-model who could teach me how to interact with the outside world, and someone whose life is completely coupled to yours is neither the best role model nor someone who knows a whole lot about the outside world.

The trick is not to go for success at all costs so you don't "have something to prove" which you force on your kids, it's to grow out of the need to "have something to prove." It's possible, and will result in less wasted time and fewer tears.

But it's often much easier to grow out of that need if you've made a sincere effort to actually go for it.

I founded a startup at age 25. Worked my ass off on it for a year and a half. It failed and went nowhere, as many startups do.

But I felt that in many ways, the experience set me free. I'd kinda coasted through school, college, and my first job half-assing whatever work I felt like, because I figured that at some indefinite point in the future, I'd found a startup and become a millionaire, and so nothing I did really mattered. Whenever things didn't work out, there was always some reason - "The material wasn't challenging" or "The professor didn't like me" or "It's not what I want to do anyway" or "We're using the wrong technology stack" to explain it away.

When it was just me & my cofounder though, the material was challenging, it was what I wanted to do, there was nobody else to blame, and if we were using the wrong technology stack, I damn well better change it.

So even though it didn't work out, I felt that I gave it my best effort and made a sincere shot at it. And that set me free to give my best effort on other things, because really, the consequences of it not working out were pretty minor (I got hired by Google). It wasn't the outcome that mattered, it was the process of figuring out what I was capable of when I really put my mind to it.

I'd much rather figure that out at 27, when I'm single, living like a college student, and have my whole career ahead of me, than when I'm 40 with a couple kids, a mortgage, and a string of dead-end jobs behind me. And I'd much rather figure it out at 40 than when I'm dead.