The 44-Year-Old You Should Be Designing Your Life For

Hey folks, this is a different style newsletter to my normal one. I have some really amazing people in my life so I wanted to ask them for some guidance that I could share with you all. This is the first letter of this series. I’m still regularly posting on Patreon, but I wanted to ensure everyone received this letter who hasn’t yet changed platforms.

Pete and I met during my days working for the startup Bounce where we solved many problems together with my other great friends and colleagues there.

Pete has helped to build multiple billion dollar startups and now spends his time with his family in Austin, advising startup founders, and writing his first novel - you can follow that journey here https://petehancock.substack.com/" 

For most men at 30, there are only two people worth designing your life around.

The person you are right now. And the person you'll be at 44.

Everyone else — the 37-year-old with the weekend house in Tahoe, the rando on LinkedIn with the impressive title, the founder friend on the Forbes list — is a distraction. You're not thinking about what you actually want when you see those people. You're thinking about what you don't have.

This leads to too many men in their 20s and 30s optimizing for the wrong time horizon. Too short on one end, too vague on the other. They sacrifice today for some goal that's six months out, then repeat that cycle until one day they look up and a decade has passed and they don't remember what they actually wanted in the first place. The goalposts kept moving.

The fix isn't better goal-setting. As Rob likes to say — it's asking better questions.

Question one: Are you actually living right now?

Not performing. Not deferring. Actually doing it. Going to the concert. Showing up at your friend's house on a Tuesday with a six-pack. Disappearing to Paris for Thanksgiving with your girlfriend because you can — and someday you won't be able to. Getting your ass to the gym the next morning anyway.

This isn't about being reckless. Joy is available to you right now. Don't put it off because you think you need to earn it first — and don't assume it'll still be there tomorrow.

Question two: What does 44 actually look like for you?

Go find a few men in their 40s you respect and buy them a drink. Ask what they'd do differently. I promise the answer won't be I wish I'd bought a nicer car at 31. It's always some version of the same three things: I wish I had more time with family and friends. I wish I'd taken better care of my body and mind. I wish I hadn't stopped doing the thing I loved.

Time. Health. The thing you love.

Everything else, the title, the brand, the status, the stuff, is just noise that felt important at the time. Your priorities change permanently as you get older, and it's refreshing.

Why 44? Because building real financial freedom takes time. It takes even a top earner about 12 years to make their first million (see below¹). So if you're 30 today, you're not solving for 33. You're solving for 44. And the question isn't how to accumulate more stuff by then. It's how to build a life where you have time to enjoy what you have.

Every dollar you don't spend on your ego is a dollar buying back your time. And time is the whole point.

Live simply now.

Build toward a vision that's 10+ years out. And that vision should match what you'll actually want then, not the distractions in front of you today.

Do that, and you can give yourself the time and freedom everyone in their 40s craves, while your kids are still in the house.

The path to painful regret is spending the next decade lost in the middle — too busy chasing the next goalpost, too focused on other people's lives, too distracted to build your own.

Don't do that.

¹ The math: If you are a top earner making $400K annually in California (not bad!) and max out your 401K, post-contribution and post-tax you're taking home about $211K per year. Set aside an additional 20% into a brokerage account after that and 12 years later you're a millionaire in real dollars (assuming 8% growth, 3% inflation, 5% real return on your 401K and brokerage). Alternatively, work at a startup, hit a $2M equity jackpot, pay your taxes, and walk away with $1.2M — about $1M in today's dollars. Liquidity events don't come fast, and if you get one at all, expect it to take multiple tries. Either way: 12 years.

- Pete