Last week I said I’d noticed another pattern. Here it is:

My investing comes in bursts, with long silences in between.

January 2021: NVIDIA. I started buying it because I knew it was a good buy. Then I got tired of looking at stocks and moved on with my life. By the time it exploded, I wasn’t watching.

August 2024: LULU. After a few years away, I started looking again. About thirty minutes in, I found Lululemon, and my first thought was no way I found something this quick. That’s wishful thinking. So I spent a lot of time trying to justify it, including a trip to the mall to count the line. What finally tipped me was seeing NVIDIA’s gains and using it as evidence that maybe there was something to this.

Early 2025: the newsletter, and MU. I started publishing monthly stock picks, and Micron was one of the few that I recommended AND bought. But the issue was there wasn’t a screaming buy to recommend every month. So by June 2025 I’d stopped. “Here’s the best I could find this month” isn’t how I invest. My attention had moved on anyway, first to buying private businesses, then to rental properties.

June 2026: CRM. About a year later, I looked back at my old picks and saw that Micron had done amazing. So I went looking again, and found Salesforce almost immediately. And again I doubted it. They say success bias is one of the great faults of the business world, and I didn’t want to rest on my laurels. So I sized my position modestly, and the price ran away before I had a full position.

The cycle goes like this:

  • I look after a long absence

  • See a screaming buy

  • Doubt myself

  • Dip my toe in

  • Then it either….

    • Jumps right away or….

    • It stays put, I get bored, find nothing else, and life moves on. Then I look back and it did extremely well.

The feeling

Each time I look back, I think: if I did this full time and was always hunting for opportunities, I could make so much more money. And that comparison leaves me feeling down and rough on myself.

But I know the full-time version of me would also have had the boredom and the false positives.

The question I can’t answer

It doesn’t feel right to forget about investing, check in every so often, and expect another winner. So was it blind luck? Or was I subconsciously sensing upheaval in the world and recognizing it as opportunity rather than being scared of it? The truth is I don’t know.

I’ve actually been spending less time on stock research and more time writing fiction, and I can feel its pull growing. Which means I’m in the cycle again: getting bored, leaving it alone, and waiting for something to trigger me back.

Right now, I don’t have anything big on my radar. LEN is the biggest position, and that’s a timing issue hinging on interest rates, not a thesis problem. Bitcoin was something I was researching for a while, but that recently fell through. I plan to talk more about that next week.

Happy investing.