My whole life is regret and I found the article very insightful. I heard a religious quote that I wish I could remember: it's better to earn gold along the way by investing in relationships than to bet it all on a gold mine.
As a hacker trying to win the internet lottery since.. 1992-ish, I put all of my eggs in one basket most of the time, and I've been part of at least a dozen ventures that all failed. It's like flipping a coin and getting tails 30 times in a row, which feels like 1 in a billion odds of losing to this extent. My best years were invested in techs like C++ that nobody even uses anymore, and I wouldn't use because they don't provide enough leverage. I only have the smallest bandwidth now to get anything at all done, and 90% of that is a waste of time due to conceptual flaws in languages, frameworks, operating systems, hardware, etc. In a very real sense, my most impactful choices were in the beginning, but I chose poorly or lost, so now it's too expensive to get back the sunk cost that I've invested. Making it ever-harder to keep going. Sometimes it feels like regret is all I have.
Unfortunately the winners usually don't have this experience. They don't have the gumption to lose for a lifetime. So they don't go through the same healing and growth process. Vanishingly few wealthy people can step back and use their money for social wellness altruistically.
Meanwhile some of us stumble onto concepts like duality and see through the matrix. We grok that there's no way to opt out of reincarnation. Then we look around and wonder why everyone is acting so strangely, having strong attachments to materialism in the 3D. The more we have, the more we cling to our ego and accomplishments, eventually living in fear of losing it all. While the people with nothing are more likely to lose their risk aversion and live in service to others.
Which means that the wealthy and powerful often live in a fear-based reality, while the poor often live in a love-based reality. Which works out well for the rich, while the poor suffer under systems of control they have little say in.
Zen Buddhism and Taoism touch on the idea that life is suffering, and suffering comes from attachments. So something that helps me is to go into situations knowing that I'll likely fail, but trying anyway, without expectation of outcome or regret.
So that one day if/when the win comes, I don't waste it like so many others. And maybe, just maybe, we can change the world.