At some point, two people with two incomes, two sets of goals, and one shared life realize that winging it financially isn't a strategy anymore.

It usually hits around the same time everything else does. The mortgage conversation. The kids question. The "wait, where did that money go" moment at the end of the month.

Habits matches couples with vetted financial advisors who actually work with people in your stage of life. Not generic advice. A real conversation about what equitable looks like for the two of you specifically.

Do I believe AI is going to take over the world? No. Absolutely not.

But do I believe the combo of layoffs, AI agents, massive capital raises, energy requirements for data centers, and insane company valuations, are a little spooky and give reasons for a lot of us to speculate about the future? Yep…

See it on TikTok or YouTube!

This past weekend our whole team took a long weekend. No agenda, no deliverables. Just time. I spent it doing the kind of stuff that sounds boring when you say it out loud but feels genuinely restorative when you're in it. Hosting, visiting museums, watching college basketball, eating at places that don't take reservations. And somewhere in the middle of all of it, my phone kept buzzing with a group chat I've had going since elementary school.

Ten of us. All grew up within a bike ride of each other, some just a few blocks apart. Most of us still remember each other's home phone numbers from twenty years ago, which is either impressive or a sign that our brains peaked early. Over the years we've traveled together to places like Peru and Costa Rica, watched each other's lives unfold in real time through a thread that has logged somewhere between daily and hourly activity since we all left for college.

The ten of us went in pretty different directions. Finance, medicine, consulting, private equity, architecture. One joined the Marines, became a forest firefighter, and is now a sheriff out west. Another joined the Israeli Defense Force and eventually came home to his family's business. And then there's me, semi-content creator and startup founder. But over this particular weekend the chat got unusually real. Someone was sharing how they're moving into a new apartment they're genuinely excited about. Someone shared, in just the saddest way, that they had to put their beloved yellow lab down. Someone had eloped in Japan and was just now telling us. And then the rest of the thread was the usual chaos, March Madness takes flying in from every direction, the kind of noise that means everyone is alive and paying attention.

But mixed into all of it was this quiet, unplanned outpouring of gratitude. For the group. For the fact that we still talk. For the simple reality that these people exist in our lives. And then someone said what I think a lot of us had been feeling for a while. That we feel a lot older than we actually are.

Here's the thing about being a millennial, especially if you're on the younger end of it like I am. Born in 1995, technically still in the generation but closer to its tail than its head. Every generation has had its version of hard. The Great Depression. World Wars. Hyperinflation. Gas lines. But there's something specific about what our generation absorbed, and I don't think we talk about it honestly enough.

We grew up knocking on each other's doors. Memorizing phone numbers. Doing homework on loose leaf paper and scantrons. We had CD players, then Limewire, then somehow the family computer got a virus and nobody talked about it. We were sent home from school on 9/11 and watched our parents navigate the financial crisis while our older siblings tried to find jobs that didn't exist. We went to college the same year the App Store launched and spent the next decade watching the entire world compress itself into a seven inch supercomputer that followed us everywhere. To bed. To the bathroom. Into every quiet moment that used to just be a quiet moment. A dopamine machine running 24 hours a day, always one notification away from pulling you back in.

The pace of that change is hard to fully articulate. It wasn't gradual. It was a full rewrite of how human beings interact, spend money, find love, consume information, and understand themselves, all within one generation's conscious memory. And somewhere along the way most of us signed up for it enthusiastically. More convenience. More options. Faster everything. One click solutions. We wanted it and we got it.

And now a lot of us are sitting in group chats quietly admitting that we kind of want to go back. Not to be younger. Just to live more simply. The park ranger fantasy. The local bookstore. The general store where someone knows your name. The weekend with no content to post about it.

Here's where I have to tell you about Sunday, which I realize sounds like a non-sequitur. Bear with me.

While the group chat was blowing up all weekend, I was with my family at NASA. And I don't mean that lightly. There's a lot of buzz right now around the Artemis missions, Artemis being the sister to Apollo in Greek mythology, the program designed to get humans back on the moon, test bigger rockets, build long term infrastructure up there, and eventually go further than any living thing from Earth has ever gone.

We started in an IMAX theater, fifty minutes narrated by Tom Hanks, which sounds like something you'd describe to a kid but genuinely stopped me in my tracks. And then we got on a tram and they took us to Mission Control. Not a replica. The actual room. The same room where a group of engineers and flight directors sat on July 20th, 1969 and talked two human beings down onto the surface of the moon. NASA has kept it perfectly preserved. The ashtrays are still on the consoles. The pencil sharpeners are still bolted to the desks. Every screen, every gauge, every instrument has been maintained so they can replay exactly what those displays looked like in real time. And they pipe in the audio, the actual recorded audio, of Mission Control talking to Neil Armstrong and Buzz Aldrin as they descended.

I stood in that room with my family and could not stop thinking about the group chat. About the ten of us. About what it means to be alive right now, in this specific moment, on this specific rock.

Because that's what NASA does to you. It recalibrates everything. You remember that we are on a planet that, in a universe of effectively infinite size and mostly cold darkness, happened to land at exactly the right distance from exactly the right star, with exactly the right atmospheric conditions, at exactly the right moment in cosmic time to produce oceans and oxygen and eventually a group of engineers who figured out how to land on the moon using computers less powerful than the phone buzzing in your pocket with March Madness takes.

If you're reading this, you're probably somewhere in your late twenties to mid-forties. You probably work in tech, finance, corporate America, a startup, or something adjacent. You likely have a household income that puts you somewhere in the middle class to upper percentiles of American wealth, which means you have more options, more decisions, and more noise competing for your attention than almost any human being in history. And you probably feel behind in some version of it. Some quiet background hum of not quite enough yet.

I want to tell you, and I'm telling myself this too, that it's all going to work out. Not in a bumper sticker way. In a real, grounded, cosmically absurd way. The fact that you're here, navigating this specific moment in history with the specific people in your life, is so improbable that it almost argues for its own meaning. The ups and downs are real. The pressure is real. The exhaustion of living through five once in a lifetime events before turning 35 is real. But so is the group chat that buzzes every day. So is the friend who just eloped in Japan and wanted you to know. So is the 50 degree April Saturday that still somehow feels like the best day of the year.

We spent our whole adolescence watching the world speed up. Maybe the move now is to stop waiting for it to slow down on its own and just decide, quietly, to live a little slower anyway. To knock on the door instead of texting. To put the phone down at dinner. To let the weekend be a weekend without documenting it.

The universe is 13.8 billion years old. You get maybe 85 of them. Spend them with people who still remember your home phone number.

The most radical thing a millennial can do right now is be present for something that isn't being recorded.

Enjoyed this newsletter? Forward it to a friend or use the referral link below!

Do me a favor, if you enjoy this, share it with a friend!