Fitness: lost 50lb, which moved me from obese to normal BMI, then put on enough muscle to squat 1.5x my bodyweight for reps. Then got into running just enough to be able to run 3 miles on demand and 10 miles with a little lead time to prep. This all took maybe five years. Now I'm hopefully 18 months out from starting a thru hike of the Appalachian trail. The feeling that I can just trot into a run at any time just feels so good after a lifetime of obesity. Plus now exercise just feels so good, my biggest issue is overuse injuries so I'm constantly mixing up my routine to fight that.

Finances: started saving more than I spend, so I can take off time as needed to do big expedition projects like a 6-9 month thru hike. Also have learned a huge amount about finance and economics, which helps a lot with knowing what to do with saved money.

Location: moved from nowhere TX to the big city. Best decision ever. I was making 29k a year as a programmer there, immediately doubled that when I moved. The more I made, the more I could pay off debt.

Got debt free ASAP: paid off 200k student loan debt by living with my grandmother as her cook, handyman, and cleaner for 3 years. This was awesome, I got to learn a lot from her in those few years she was still pretty coherent.

Food: started writing down everything I eat, this helped me break my emotional attachment to eating that plagues my whole family. Now I'm 5+ years out from losing 50# and still fitting in my new clothes. Also got good enough at cooking that I can feed myself without getting bored, so I only really ever eat out socially, maybe 2-3 times a week.

Drastically reduced drinking alcohol and caffeine: drinking makes me feel bad, costs a lot of money, and caffeine makes me anxious. Today I drink less than a beer a week, and I feel like crap when I do, so I rarely do. It's a bummer too, because I'm a pretty handy bartender and barista after years of food service work.

Engineering: got serious about my programming skills 10 years ago, and worked hard to get much better at it. Finished SICP, Let Over Lambda, a couple of Haskell books, and a million TDD katas. Now I'm extremely fluent in several languages, and can solve most technical challenges encountered in a typical software shop. I'm surely not a PhD in CS, nor am I master leetcoder, but I'm pretty handy with unit tests and a repl in pretty much any environment. This makes my day job so much more rewarding, and I'm able to work a chill job with some fantastic coworkers.

Marriage to the right person: I'll never marry anyone else, but I choose to remarry this woman every single day, 13 years later. She doesn't care about money and isn't materialistic. She isn't addicted to social media. She likes to work hard, then loaf on the sofa with me and play WoW. We're effectively 100% financially compatible. This is so important it's silly. This takes out maybe 99% of potential stress between us. She's effectively already had kids (raised her two much younger sisters, woot they just graduated college!), so we're childless and really happy with that.

Career: learned progamming, made really good money doing it. Taught friends and family how to program, now they've got careers too and are escaping poverty. Feels pretty amazing to help my family really learn how to fish.

Art: picked up violin at age 30, taking lessons every week, I've gotten good enough I can reasonably site read a lot of easy pop pieces. Learned enough painting and drawing to really enjoy figure drawing sessions and portrait painting. Both have helped complement my life considerably.

Materialism: been working on reducing this in myself. I've gone from a medium house filled to the brim with crap down to a small apartment with just a few select high quality items. My day to day emotional enjoyment has increased substantially. It's easier to keep tidy, which helps a lot.

Mental health: I realized that I suffer from anxiety and an in progress with doctors and therapists to sort out how to let go. I'm expecting high dividends from this, so far it's better but not great.

Location: just moved a few miles away, but now I'm surrounded by forest. This is amazing and I love it.

Old car: I just don't care one wit about looking cool or socially signaling with a car. This saves money for actually cool stuff like violin lessons.

What didn't pay off as much as I'd hoped:

Writing a blog then some books: eh it was fine, but didn't even scratch 1% of what I could earn in the open market as a developer. That time better would have been spent focusing on my career.

Baking: contributed to my obesity in my mid twenties, even baking bread is still a hell of a lot of empty carbs

Winter sports: eh they're fine, but really expensive and ultimately something I enjoy just once or twice a year. Also I now have a limp when I sit for too long from a pretty bad snowboarding accident. It goes away when I warm up, but that freaked me out enough to say mostly it's just not worth it for me.

Moving upwards in the tech ladder: became a director of a whole office a few years ago in medium software company. It largely made my life worse for little benefit. I'd previously read the Gervais-Mclod series by michaelochurch and believed it, but wanted to see for myself. Just started the process to step down last month, couldn't be happier. I'd rather be a "loser" than "clueless". Plus engineering is awesome, managing managers and budgets just isn't as appealing to me. As Jack in Stargate says, "I've spent my whole life sticking it to the man. If I do this, I'll be the man. I don't think I can be the man."

Buying a house: this was a wash, netted about the same, and I was pretty careful about it all. Houses have a lot of unexpected costs. I'm glad I did, and glad it's gone.

What I'm hopeful for:

Sailing: I want to get a liveaboard small sailboat. I expect this to be a decent amount of work, but I love sailing and being near the water. Hoping to try this for a year in 2023. Helps that my wife is am A&P mechanic, and she's excited at the prospect of having a project always to work on.

Thru hiking: I plan to attempt the AT in 2022, I'm hoping this becomes a big part of my life. I'm expecting to get into the culture of it, then earn money to live on over winters. I've started several years ago doing more overnight and weekend hikes to get used to it. I'm crushing a 45lb ruck every day to build up tendon/muscular strength, with the goal of building up to a consistent 60lb every day. Already my endurance is really increased, so I'm hoping it's a good way to prepare in advance. Also my gear is pretty locked in at <25lb total, so I'm hoping the heavier rucks translate easily into endurance.