A letter to the past
February 7, 2026, 2:15 pm
10 years ago, I wrote a letter to my past self, because 10 years before that I had done the same thing. This will be my third letter to myself.
The first letter (2006)Think back 10 years, how old were you?
I was 34 when I wrote the last letter. I randomly remembered it while looking back through my blog. I was working in San Francisco and I made myself a calendar reminder to do it again today. I got a notification yesterday, and then almost forgot again if not for another reminder today.
These days it's hard to remember my life timeline without Linkedin. It catalogues where I was when. At a certain point where I was mattered for my timeline, and for the last decade or so it was where I worked. In 2016 I was working full time at the Academy of Art. I worked there for 9 years and then was unceremoniously dropped at the start of COVID.
If you ran into yourself at that age, what would younger you say?
He would tell me to keep drawing. He would be upset that I got divorced again. He would probably be surprised I got married again. They would be so surprised I was still in San Francisco. He had been telling everyone that I would never live anywhere longer than 7 years.
He would be glad that I had made a whole comic book, but probably pissed I never released it. He'd be pissed that life had caused me to burn through my nest egg, especially in almost the exact same way my dad did.
What would you say back?
Being good to your coworkers is important in life. Having your team's back and trusting that they have yours is everything. No company has your back. Every company will drop you on a dime. Don't stay in a comfortable job forever if you can do better.
Friends are so important. Basically the most important thing. Pick up golf earlier. Don't push away friends for ego, and don't expect that anyone owes you anything. Least of all any of the women in your life. None of them owe you anything. But maybe if you can be humble good things could happen.
Stop talking over other people. Allow others to be generous to you, and be generous to everyone you can. You'll need their generosity when your ability to be generous dries up.
When I look back at this letter, I will be reminded that this was a real low point in my life. In a life of peaks and valleys, the whole world and me included are going through a real rough patch. It's been a real bad second half of the decade. I just hope things can pick up soon.


