Jack's Journal (1/9)

A lot of you have asked for this so I'm going to try my best to make it happen

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A Mini Series…

This week, I’m kicking off a 4 week blog series about the personal philosophies that keep me (mostly) sane while building Habits and navigating life. Expect some deep truths, awkward lessons, and the occasional ‘wow, they really let this person run a startup?’ moment. Think of it as life advice, but from someone who still Googles “how to fold a fitted sheet.”

Q&A Section

Q: What keeps you up at night? Are you thinking about work 24/7? What do you stress most about? - Alex

A: Years ago I made peace with the fact we can’t control what happens in this life. Across the good, the bad, the ugly, the only thing you can guarantee is the effort you put into each day. - JB

It’s All A Game

But play it intentionally

Life is a game, some people are out here playing chess (btw if you’re on chess.com DM me), some are mindlessly on Candy Crush, and the bulk are just mashing buttons like it’s Super Smash Bros.

I’ve always believed life is about making intentional moves—not just rolling the dice and hoping you don’t land on that one Monopoly space that wipes out your cash. The point is, you don’t win by winging it. You win by knowing the game you’re playing, what you’re after, and how to avoid completely screwing it up.

Find the balance between yes and no

This lesson didn’t hit me in some zen, life-changing epiphany. Nope. It was more like repeatedly walking into the same damn wall until I realized, “Oh, maybe I should stop doing that.”

In college, I said yes to everything. Clubs, internships, fraternity life, studying abroad, interning abroad, finance competitions and group projects with people who couldn’t even figure out Google Docs—because hey, opportunity.

But you know what? Most of it was a waste of time. It only clicked when I started saying yes to the right things—and no to the garbage. Intentionality is the cheat code: it doesn’t guarantee you win, but it keeps you from rage-quitting.

How this relates to startup life

This philosophy has been my north star for building Habits. Startups are chaos. If you don’t know your game plan, you’ll end up spending your time on stuff that doesn’t matter (trust me, I’ve been there). Every hire, every product feature, every TikTok post has to align with our mission—helping people play the financial game smarter. Otherwise, it’s just noise.

(And noise doesn’t pay the bills)

And it bleeds into all areas of your life

And it’s not just work—intentionality applies to everything. I used to hang onto relationships out of guilt, spend money because I had plenty of it, and rewatch The Office because it felt easier than making a decision.

But over time, I realized these habits weren’t serving me. Letting go of draining friendships, spending money with purpose, and even choosing new shows to watch helped me take back control of my time, energy, and joy.

Why it matters so much to me

Here’s the thing: most people don’t even know the game they’re playing. They’re out here grinding at jobs they hate, chasing goals they don’t even care about, and wondering why they’re burned out. Life is short, and spoiler alert—you don’t get a redo. So figure out what you actually want, and stop wasting time on things that don’t get you there.

At Habits, we’re building tools to help people do just that—play the financial game with purpose. It’s not about being perfect; it’s about making moves that set you up for the life you actually want. Want to splurge on that vacation? Cool. Want to buy a house someday? Also cool. Just don’t wake up one day wondering where all your money (and time) went.

So, here’s my challenge to you: stop reacting. Start playing. Figure out what the hell you’re aiming for, and move like you mean it. Life’s too short to sit on the sidelines.

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Find Your Financial Advisor

If you’re somebody on the sidelines or are not sure if a financial advisor makes sense for you or your family, just shoot me an email at [email protected].

Or… visit our website and book time with us!