The days are long but the decades are short

That's about half my own age, which I try to keep in mind when everyone here seems insane to me. :-)

Scott Adam's is slightly more pragmatic. I took his quote as meaning your chances of success are higher if you are a generalist than to pigeonhole yourself with only one skill set.

I don't think the two quotes are conflicting pieces of advice.

Experience something horrible.

I grew up in a ridiculously perfect fantasyland. My parents, who have an ideal marriage, told me I was the best at everything, encouraged every dream I had, paid for college and insulated me from all of life's difficulties re: money, stress, etc.

To make matters worse, I excelled right along with the praise -- made good grades, got into a top-10 college, started a company after college which was lifestyle-profitable for 7 years. (It could have been a major score if I'd executed better, but that's beside the point.)

When my company started to decline post-2008, I had to go get a job. I excelled at it, but got crossways with my boss for entirely personal reasons and was fired.

This back-to-back double-whammy was by far the worst experience of my life. I'd never experienced failure or rejection and my psyche/ego simply didn't know how to handle it. I sunk into a depression for 3 years. It's not hyperbole to say I almost didn't survive it.

But I'm on the other side of it now. The darkness is receding. I know this because I know the double-whammy was entirely necessary for me. The spoiled brat is gone. I empathize with others. I care about the journey people have taken to the point where I meet them. None of that mattered before. It was all me, me, me, the worldbeater.

Yeah I'm in my mid 30s now and the past 5 years were tough. But I'm glad I've already spanned the chasm now than in my mid-50s. Now I'm better prepared for things to come.

One slightly separate piece: I used to have massive entrepreneurial angst. I was a person who looked at those who have "made" it and got angry. Angry at lack of co-founders. Angry that my school's alumni network doesn't have the best SV connections. Angry at perceived ageism in tech circles... But now I know that all advantages others might have on you -- better schooling, younger, lucky career breaks, etc -- can be trumped by one thing: traction. It doesn't matter if you're white, black, purple, one-armed, blind, gay or republican -- If you have something worth investing in, you can find investors. Period.

I get that this is aimed at the startup crowd, but I've always felt that this sentiment is pretty privileged. We, the elite, get to cherry pick our work and do what we like. But I bet 9/10 people will never feel they have this luxury, and 8/10 will be right.

> Most people pick their career fairly randomly...

And in the truest sense of "most people" I would bet that "most people take whatever work they can get, and sometimes something sticks" is probably more accurate.

I know these sentiments are a bit cynical, I just can help but feel sometimes that it's irresponsible to dump the "you can be/do anything!" sentiment on our youth when the reality is nowhere near that for most of them. I understand we need ideals and motivation to make them a reality, but more flowery advice doesn't seem to be the best tactic.

Regardless, Sam is an amazing individual who has done an enormous amount for others and the startup community. This isn't meant to disparage his views or advice; ironically, I think it's just hardest to give truly sage advice when you're trying to be sage.