The Constant Lesson: You Only Ever Learn the Hard Way

You would think that when you are close to 50 years of age you have everything figured out. That you make less mistakes. But here I am older and not feeling much wiser than I was 20 or even 30 years ago.

This is in regards to relationships, family, friendships, business, as well as personal finance and investing. I’ve made some progress but the way life seems to work is that the minute you figure something out, everything changes. So what used to work does not work anymore.

Or nothing has changed except you. You get cocky, arrogant and sloppy. You start thinking you can do no wrong.

This was me in February & March 2020 as I came off 2 very good exits in my portfolio at 500 Startups. High on that and a few keynote talks I did at some big tech conferences. Of course, that was right before the pandemic lockdowns and my own personal financial difficulties. But I recovered financially by the end of that year and jumped hard back into investing in 2021.

It was a nutty time and I got caught up in it. I made some good investments but I also did some really stupid ones. Investments in businesses and teams I never would have done in prior years. Like many investors during that bubble, we lost discipline and, well, our portfolios show it. I have never seen such a fast and steep J-curve that happened the year after in my time as an investor.

That is why there is a much used aphorism in investing, “there are two kinds of investors, those who are humble and those who will be humbled.”

The point is to own up to it, take the lesson and keep going. As the saying goes, pain leads to knowledge. Or said even better by old Roman Titus Maccius Plautus: “not from age, by capacity, is wisdom gained.”

This is probably a good thing. I’ve learned to just keep pushing forward. Besides, life would be pretty boring if it was predictable and static. Like water when it’s still, it only leads to staleness, stagnation and decay.