^{Sponsored Ad Emergency Broadcast}

Back-Up Blog!

Very similar to my post-Morningstar blog, this one is coming to you after a cancelled flight, two deplanings, and the quickest (and most fun) 36hr visit to our new office at One World Trade Center in NYC.

It’s 3am, I’m exhausted…so I’m sending you my “back-up blog,” which is something I put together a month ago knowing I may need one for situations like this.

So instead of a half-assed sponsor write up, using this as a shameful plug for Habits.

TL;DR find your financial advisor at www.usehabits.com 

^{Top Content}

7 Figures Is The New 6 Figures

Last week, I wrote a post on LinkedIn that exploded, so it encouraged me to make a post for Instagram and TikTok.

Agree? Disagree?

^{Main Story:}

The Guy in Cargo Shorts Was Right

I. When Work Becomes Your Whole Life

18mo ago, my calendar was a nightmare. I was hosting back-to-back Zoom calls with strangers, families, individuals, curious Habits enthusiasts…all of them funneled through me. We didn’t have a product-led flow, no automated sign-up process. If you wanted to experience Habits, you had to book a 1:1 call with me.

That was the MVP.

At first, it felt like momentum. Strangers were booking time with a stranger. They’d found us online. They were curious. It felt like validation. And it was for a while. But as the calls stacked up, I realized I wasn’t just running a company. I was the company. And slowly, without even noticing, I had tied my identity to it.

Every Saturday morning, I opened up my calendar to anyone who wanted to chat. I told myself it was noble. That it was just what scrappy founders did. But what I was really doing was burning out. Not for the first time. And definitely not for the last.

Your job will take as much as you're willing to give it. If you're not careful, it will swallow your entire sense of self.

II. Letting Go of a “Good Job” Isn’t Easy

When I was 26, I had a job people envied: big company, solid paycheck, upward path. It looked great on paper. And for a while, I believed that was enough. That being at a "great company" meant I was doing great personally. But deep down, I felt stuck. Not because anything was obviously wrong. That was the problem. Everything looked fine. Comfortable, even.

But “comfortable” is dangerous when it keeps you in a place you’ve outgrown. It lulls you into complacency. And when you finally realize the role or company doesn’t fit anymore, you’re often already too deep. You start to think it’s too late to switch. That you’ve invested too much.

The scariest part? I didn’t hate the job. I just hated who I became when I built my entire life around it.

I eventually left. Because the longer you stay somewhere that no longer serves you, the more you forget what it feels like to choose your life on purpose.

A “good job” isn’t always good for you, especially if it keeps you from becoming who you’re meant to be.

III. The Lifestyle Trap You Don’t See Coming

Speaking of that banking career, I upgraded everything as my salary/bonus structure did. Nicer apartment. Nicer coffee. Nicer weekends. I stopped thinking twice about expensive cocktails or impulse purchases. I told myself I earned it. That I was just “enjoying the fruits.” And to some extent, that was true.

But lifestyle inflation doesn’t hit all at once. It creeps. You normalize comfort. You begin to depend on it. And before you know it, the freedom you thought you were earning turns into pressure. Pressure to maintain. Pressure to earn. Pressure to perform.

At some point, I realized I wasn’t just working hard — I was working scared. Scared to lose the job or business that paid for the lifestyle I had convinced myself I needed.

It’s easy to confuse success with stability. But if your income is fueling a life you can’t step away from, that’s not success. That’s a gilded cage.

If your lifestyle owns you, your freedom is gone…no matter how much you make.

IV. When You Stop Exploring, You Start Dying

In my early 20s, I thought the goal was to climb. Pick a job, prove yourself, keep moving up. Rinse and repeat. But the truth is, the riskiest move in your 20s/30s isn’t trying something new. It’s never trying anything at all.

At some point, I stopped exploring. I stopped learning for the sake of it. I stopped saying yes to things that didn’t fit into a tidy plan. Because I thought I had to be efficient with my time. Strategic. Focused.

But building Habits reminded me that the best things I’ve done — the biggest leaps — didn’t come from sticking to a plan. They came from detours. From curiosity. From leaning into uncertainty even when it made no sense on paper.

That’s the gift of early chapters. You’re supposed to wander. You’re supposed to pivot. You’re supposed to try shit, fail at it, and learn something you didn’t expect to learn.

If you’re not exploring, you’re coasting. And coasting always ends the same way: stuck.

Your 20s/30s or wherever you are in life are for building optionality — not perfect resumes.

V. The Identity Reboot Nobody Talks About

No one warns you what happens when you stop introducing yourself by a well-known company name. When I told people I worked at J.P. Morgan, there was instant credibility. They didn’t need a backstory. The brand spoke for itself.

Now I tell people I’m at startup or that I work in sales, and I get questions. So many questions. Some genuine. Some skeptical. Some clearly laced with, “Is this a real thing?”

And that’s fine. That’s part of the deal. Because when you build something of your own, you also have to build a new version of yourself. A version that doesn’t hide behind corporate logos or job titles. One that can explain who they are without name-dropping a brand.

It’s awkward at first. And honestly, a little lonely. But it’s also freeing. Because the person I’m becoming is someone I chose, not someone I inherited.

Let go of the job title. Let go of the LinkedIn polish. Let go of who you were supposed to be.

You don’t find your new identity, you build it by leaving behind the old one.

VI. Peace Over Prestige

At 16, I swore I’d never become that guy in cargo shorts walking his dog in the middle of a weekday. I thought he had settled. I thought he’d given up.

Now? I see him and think: He figured it out.

He’s not flying through Terminal B on four hours of sleep. He’s not stuck in another fake-dinner with people he doesn’t respect. He’s not chasing titles. He’s walking his dog. At 2pm. On a Tuesday. Because he can.

I used to idolize the guy always “making deals.” The one who always looked busy. Always on the grind. But now? I’m trying to build a life that looks more like freedom than urgency. A life that feels light. Spacious. Quiet, even.

I'm not fully there yet. But I'm a hell of a lot closer than I used to be. And I think that counts for something.

The real flex isn’t building a life that looks impressive — it’s building one that feels peaceful.

Feedback for Jack

Enjoyed this newsletter? Forward it to a friend and have them signup. Alternatively, use the referral link at the bottom of this email.

What’s Coming Next?

Originally, this week’s post was meant to be about my biggest priorities for 2Q25, sharing some screenshots from our investor deck (+ hoping to get that Morningstar presentation recording…still on hold for that) and biggest concerns.

Stay tuned for next week!

Sharing Is Caring

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