5 Hard Truths That Built Me (and Broke Me)

If you're reading this, you're either avoiding work on a holiday week or you genuinely care.

Main Story:

The 5 Philosophies That Built Me

If you’re reading this, you’re either avoiding work on a holiday week or you genuinely care. Either way, thanks for being here.

Most people don’t really know me. They might know the content, the startup, the memes, the financial advice, or the funny takes on LinkedIn. But they don’t know the moments behind the curtain.

So, here it is. I turned 30 a couple weeks ago. And I wanted to share five core philosophies that shaped my 20s. Plus one behind-the-scenes story from the early Habits days that I’ve never told anyone. Not because it wasn’t important. But because it was too raw to package nicely into a TikTok.

This isn’t a life highlight reel. It’s not a playbook. It’s what I learned from ten years of f**king around and finding out. So if you’re in your 20s, 30s, or hell—just figuring it out, I hope something here sticks.

The Story No One Saw:

Let’s go back to 2023.

I was three months into running Habits full-time. I had just dumped my entire 2022 bonus—about $100,000—into the company. A dumb decision? Depends who you ask. My old manager still texts me once a year to remind me how much I’d be making if I just "stuck it out" in banking.

Staring Episode 2 GIF by The Office

me every xmas when my old manager texts me what my comp package would look like

Anyway. That $100k disappeared in five months.

Our product wasn’t working. Sales were worse. We didn’t know what the hell we were doing. And one day, Veera (my co-founder) and I sat down in Chicago for what started as a regular sync and turned into a 45-minute straight-up intervention.

He looked me dead in the eye and basically said: “This isn’t a f**king game. I have a family. A mortgage. And I’m betting on you to lead. So get your sh*t together.”

It was humbling. And terrifying. And exactly what I needed.

That was the day I stopped acting like a founder and actually became one. Not when I quit banking. Not when our first video when viral. Not when we raised capital. But when I realized the implications of our startup.

Truth #1: Nobody Knows What the F*ck They’re Doing

I’ve worked with execs making $50M/year and 22-year-olds trying to get their first credit card. And I promise you…everyone is guessing. Some are more confident guessers, but they’re still guessing.

Once you realize that, you stop trying to impress people. You start showing up as you are. Loudly. Imperfectly. Consistently. The people who pretend to have it all figured out? Usually the ones hanging on by a thread.

Life is hard. We’re all just trying our best.

Truth #2: Be Happy

The happiest people I know are anchored in something bigger than themselves.

I've seen people who made millions before 35 and still ended up lost. Because when you don’t have a reason to get up in the morning, life gets heavy. Fast.

Comfort feels good for a while. But it’s a slow killer. Give me hard days that mean something over easy days that don’t. Any time.

You don’t need to have all the answers, but you do need to figure out your why.

Truth #3: Everyone’s Life Looks Easier From the Outside

You might look at someone’s life and think: “Damn, they’ve got it made.” Truth is, they’re looking back at you thinking the same.

Everyone’s overcompensating for something. Everyone’s dealing with something you don’t see. I used to think business owners or startup founders lived some sexy freedom-filled lifestyle. Turns out, it’s mostly anxiety, customer support emails, always being strapped for cash and eating lunch at 4pm if you remember to eat at all.

Don’t let the social media highlight reel fool you.

Truth #4: Stress is a Currency

This one slapped me in the face the hardest. You don’t get to opt out of stress. You just choose where to spend it.

You can stress about whether your boss likes you. Whether you’re posting too much. Whether you’re wasting your degree. Or you can stress about building, learning, risking. Either way, it costs you something.

So pick the stress that pays you back.

Truth #5: The 85% Rule

This is the one I still try to master daily. I used to live in extremes. All-in or fully off. Sprint, crash, repeat. Now? I shoot for 85%. All gas, just not flooring it into a wall.

You can’t win if you’re constantly recovering. And you don’t need to be a machine. You just need to be consistent. It’s not sexy. But it works.

Long term consistency beats short term intensity.

The Corniest Part Of Me

The one thing I do every single day that I’ve never really shared publicly:

I love cold showers. I mean, I f**king love them. Not because I’m some wellness hardo. But because it’s the one ritual that makes me feel completely alive.

Before every cold shower, I say to myself: "Do what is easy and your life will be hard. Do what is hard and your life will be easy. Choose your hard."

Then I turn the water to the coldest it can get, take a deep breath, and step in. I started doing it when I didn’t have the money for a fancy cold plunge setup. I just needed something. Something that shocked my system. Something that said, "Wake the hell up."

It hurts. It’s uncomfortable. It makes me hate my life for 30 seconds. But afterwards? I feel unstoppable. Like I just took a shot of espresso and a punch to the chest at the same time.

It’s a small act. But it’s mine. And it’s become the tiny thing I do every single day.

So yeah—it’s cheesy. It’s embarrassing to admit. It’s probably from a TikTok. But I don’t care. It works.

Find what works for you.

Feedback for Jack

Did you like this email?

You can add additional feedback after selecting one of the options below.

Login or Subscribe to participate in polls.

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?

I’ve been experimenting with email campaigns, strategies around our middle of funnel management, and will dive further into my learnings to date.

Sharing Is Caring

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