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Yes .. but. I had a great education/CV early in my career, and had the opportunity to interview at some of the top most companies prior to their IPO (some when

Yes .. but. I had a great education/CV early in my career, and had the opportunity to interview at some of the top most companies prior to their IPO (some when they were tiny companies). Google, Facebook, Stripe and maybe 3 more that went on to be billion dollar exits. I screwed up every single time. Either I did not take the interview seriously, or took a more prestigious academic job compared to the start up opportunity. Talk about being in the right place, at the right time and still missing out. I have barely paid off a small fraction of my starter home (no longer in the Bay area). I really wonder if it is just luck or more complex than that. (Good) Luck got me the right opportunity,but it can't just be (Bad) luck that snatched away all those opportunities from materializing? Clear, I made extremely bad decisions, missed out on the greatest wealth creation event in history, and must live with this till my end. Edit. There is a rich-dad, poor-dad point I'd like to make. My parents were extremely bad with investments and not very educated. This made me chase the higher prestige academic jobs as opposed to the lucrative startups. Also, when my white friends (with moderately-rich parents) were buying houses at 5% down, I said they were crazy and I was paying off 5% interest education loans, saving up for a bigger down-payment, buying my car for cash, etc. My parents went through the days of 20% interest and never understood the power of leverage. They passed on risk-aversion to me. Even now, I understand the power of leverage, but am still scared to use it.

bumby 5y ago
I like the phrase "Luck is when preparation meets opportunity". So when you say you made bad decisions, didn't take it seriously, etc. it sounds like you recognize your own culpability in creating bad "luck". There is something to be said for overcoming the inertia of the (bad) ideas we may have been raised with. Malcolm Gladwell wrote in Outliers how wealthy parent raise their children to be more assertive. One of his examples was a "genius" child with a 195 IQ who couldn't reach his goal of a PhD because of the ingrained passivity his parent taught him, which caused him to accept limitations he was told without questioning. To that extent, if we can't overcome those bad ideas, we're creating bad luck for ourselves. And please don't take this as me piling on, because it's fairly clear from your post that you are still bothered by this. I imagine it's because you spend a lot of time imagining "what could have been", but to quote Theodore Roosevelt "comparison is the thief of joy". If you can get to a point where you're grateful for what you have rather than mulling over what you missed out on, you'll probably be happier for it. Genuinely wishing you the best of "luck" in the future.
- throwawaybbq1 5y ago
  Thanks for your kind words. I took it in a positive light, and appreciate your thoughts. I usually bottle it in, but wrote the above post as a release. I'm definitely luckier than a good fraction of the planet. I also truly believe that at some point, we really need to stop blaming our parents, and take ownership for our own actions. It is just really hard some days, to face up to the missed opportunities. Now that I have kids, I imagine advising myself as if I was advising my kids at some point in the future. That has really worked wonders. I'd advise my own kid to say c'est la vie, and move forward in life with optimism and confidence :)

bumby 5y ago

I like the phrase "Luck is when preparation meets opportunity". So when you say you made bad decisions, didn't take it seriously, etc. it sounds like you recognize your own culpability in creating bad "luck". There is something to be said for overcoming the inertia of the (bad) ideas we may have been raised with. Malcolm Gladwell wrote in Outliers how wealthy parent raise their children to be more assertive. One of his examples was a "genius" child with a 195 IQ who couldn't reach his goal of a PhD because of the ingrained passivity his parent taught him, which caused him to accept limitations he was told without questioning. To that extent, if we can't overcome those bad ideas, we're creating bad luck for ourselves. And please don't take this as me piling on, because it's fairly clear from your post that you are still bothered by this. I imagine it's because you spend a lot of time imagining "what could have been", but to quote Theodore Roosevelt "comparison is the thief of joy". If you can get to a point where you're grateful for what you have rather than mulling over what you missed out on, you'll probably be happier for it. Genuinely wishing you the best of "luck" in the future.

throwawaybbq1 5y ago
Thanks for your kind words. I took it in a positive light, and appreciate your thoughts. I usually bottle it in, but wrote the above post as a release. I'm definitely luckier than a good fraction of the planet. I also truly believe that at some point, we really need to stop blaming our parents, and take ownership for our own actions. It is just really hard some days, to face up to the missed opportunities. Now that I have kids, I imagine advising myself as if I was advising my kids at some point in the future. That has really worked wonders. I'd advise my own kid to say c'est la vie, and move forward in life with optimism and confidence :)