How I Won and Lost My Last Decade

A Review of My 20’s as I Step Into My 30’s

Jake Daghe
22 min readMay 24, 2022


Photo by Martin Reisch on Unsplash

“I try to do the right thing at the right time. They may just be little things, but usually they make the difference between winning and losing.” — Kareem Abdul-Jabbar.

I am on the precipice of entering a new year of life. In all reality, it’s no different than any other birthday. Another revolution around the sun, another run around the bases. But turning 30 feels different. It feels more like a doorway and less like a lap. More like a checkered flag and less like a pit stop.

Although it is technically just one additional candle to add to the birthday cake, this one seems weightier, like it’s the one candle to rule all other candles, the one that finds them. The one to bring them all together, and in the flames and celebration, to bind them. Bonus points if you get the reference.

The closer the actual day has gotten, the more I’ve come to be settled in the truth that turning 30 is just another inch on the ruler of life. Nevertheless, it does provide an excellent moment to reevaluate and recalibrate. It is a meaningful “when” if you’re a fan of Daniel Pink. If Chip and Dan Heath are more your style, it is, by definition, a “powerful moment.

So, this is me taking inventory. This is me doing a multi-point inspection of the beautifully messy life that I’ve gotten to live and the ways that I’ve won and lost my last decade.

There will be some goals that I hit and some that I missed. Some outputs and behaviors I enjoyed, and some things that took away from my happiness. There will be some stories, some quotes, some cheesy references, and most importantly, a lot of gratitude to the people who contributed or shaped me along the way — namely my wife, Lindsey.

Jimmy Dean once said, “Do what you say you’re going to do. And try to do it a little better than you said you would.” I’ve found this to be a good definition of my twenties. So much of this last decade has been the experience of just showing up. Of building brick by brick.

You’ve likely heard the quote that “many people overestimate what they can do in 1 year but underestimate what they can do in 10.” When I look back over my twenties, I see this truth in action. I’ve…



Jake Daghe

Creative Engineer writing working hypotheses | I write what I wish I could have read when I was younger | Join my newsletter ‘I/Q Crew’ on Substack.