I opened my habit tracker yesterday and saw two numbers sitting next to each other.

925 days of reading.

6 days of journaling.

My first thought? Gotta start somewhere.

My second thought? I’d be lying if I said that big number wasn’t a little intimidating. 925 days is over two and a half years of not missing a single day. It doesn’t even feel like a habit anymore. It’s just part of who I am now.

But 6 days ago, “WRITE IN JOURNAL” was exactly what “READ A BOOK” was on day one. Nothing. Just a decision.

Here’s what I keep coming back to.

Every big thing in my life looked like nothing on day one. The habit. The move to Lisbon. The financial plan that gave us the freedom to actually make the move. None of it looked like much at the start. It never does.

In 2023, Jamie and I took a scouting trip to Lisbon and came home calling it our “4-year plan.” Then in 2024 Jamie got laid off, and what felt like a setback turned out to be exactly what we needed to make it real. A 4-year plan became a 2-year plan became a one-way ticket.

The 4-year plan was day one. Lisbon was day 925.

But none of it would have been possible if we hadn’t started. Not when it felt safe. Not when we could see the whole path. Just started.

I think about this every time I talk to someone like one of my favorite clients, Joie.

Before I even met him, he filled out his intake questionnaire and wrote something that stopped me cold.

On our first call he said: “When I think about being in a role like this for the next 30 years it makes me really sad.” And then: “I’m annoyed already on behalf of my future self.”

He was making a great salary. RSUs. Strong benefits. By every external measure, things were good.

But he was stress-buying hobbies and toys to cope. He and his wife Sarah were taking trips to Mexico just to sit at a resort and decompress. Not even doing much. Just trying to reset enough to go back and do it all again. They felt guilty spending money on anything that made daily life easier, like hiring a house cleaner, because it always felt like they were spending money they didn’t have.

Sarah was burned out and working part time. Joie felt like he had to keep pushing to keep the household afloat and was starting to burn out too.

They didn’t have a vision for the future. Just a vague hope that it would be more fun than this.

After a few sessions, Sarah told me she never realized how dissatisfied they actually were. They were just on autopilot. She said looking at their spending honestly felt like, and I’m quoting her directly here, “opening moldy yogurt from the fridge. You just have to do it though.”

That was their day one.

For a long time, whenever I asked them what they wanted to build toward, the answer was immediate and instinctive.

“Not this.”

They couldn’t see beyond the day-to-day. So we started there. Got everything in one place. Automated the basics. Built a system that let them actually see where their money was going for the first time.

It took one month of real data for Joie to look at what they spent on restaurants and say: “Huh. I guess it’s not that much.”

That was the moment.

Once the leaks were plugged and the guilt spending was gone, there was genuinely more left over every month than they expected. Real numbers. Real breathing room. And almost overnight, “Not this” became “We want this. And this. And this. And this.”

The dream was always there. They just needed proof it was possible.

Here’s where they are now, three years later.

Somewhere along the way of chasing hobbies to cope, they fell in love with sailing. Not as an escape. As a life. They take real trips now, filled with experiences instead of resort lounges and recovery drinks. Every dollar of excess income flows directly toward their goals. They are almost done building an ADU on their property that will generate passive income indefinitely. They cashflowed the entire build. No debt on the investment.

They have accelerated their retirement date by over 15 years.

None of that was visible on day one. They just needed to start.

I’ll let them tell the rest.

I talk to people every week who live in their own version of “Not this.”

So buried in adulting they can’t even dream about something different. But the glimpses are there.

It’s day four of a week of PTO, right after the nervous system finally calms down and just before the dread of returning creeps back in. It’s the “what if” hiding inside the joke about selling everything and living van life. It’s the real longing, tucked beneath the envy, when a friend mentions their company gives every other Friday off in the summer.

They followed the formula. College. Career. House. Family. Cars. Hobbies. Vacations. Stuff. More stuff.

But no matter how many boxes they check, they don’t feel any closer to the finish line. They’re not even sure where the finish line is.

So they tell themselves this is normal. That if they just keep going, work harder, earn more, advance further, then someday they’ll be able to stop and enjoy what they’ve built. Just make it through this week. This quarter. This sprint. There’s PTO to look forward to.

“Just a little more” keeps them marching.

What they’re marching toward? If you asked them right now, the most honest answer they could give you is probably “Not this.”

Sound familiar?

I spent way too long living that same narrative. Until I hit a breaking point and chose to do something different.

For the last 5 years I’ve been helping people just like you, and just like Joie and Sarah, build something different. Not someday. Now. With the finances to actually back it up.

Over that time I’ve taken everything I built, and everything I’ve learned working with clients, and refined it into something that creates the greatest impact in the shortest amount of time.

Next week I’ll share exactly what that looks like.

And how you can use it to turn your own “Not this.” into something you’re genuinely excited to wake up to.

Day one is enough. Start there.

— Joe

P.S.

If this already resonates and you don’t want to wait until next week, just hit reply. Tell me where you are right now and I can show you how to get to your day 925.

I read every message personally and I’d love to hear your story.

Joe Maddux

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