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Last week felt like a note to my younger self. I was at Purdue University speaking at their Executive Forum. Which, if you know me, is objectively hilarious. I am 30. I am not a Purdue alum. And I am definitely not a Fortune 500 C-suite executive.

My title says CEO. But CEO of what? A handful of employees, some money in the bank, and a stubborn belief that the future can look different. Still, there I was.

To understand why it meant something to me, you have to go back a bit.

I grew up in a household where both of my parents dedicated large portions of their careers to the nonprofit world. There was a rule in our house. You are either in a sport, in an extracurricular, or you get a job.

Being the least athletic and arguably the least dedicated of the bunch, my summers were often filled with volunteering. Senior centers. Helping my mom at the Patty Turner Center. Visiting seniors in assisted living facilities. Playing cards. Just showing up.

My parents instilled this idea that you’re part of a community whether you like it or not. Shovel the communal sidewalk. Hold the door. Be useful. Contribute. Somewhere along the way, building a startup messed with my head. Content. Product. Hiring. Firing. Pivots. Travel. Capital raises. Analytics. Board decks. It never stops. And if you’re not careful, your entire life becomes output. Efficiency. Leverage.

The one thing that quietly disappeared was donating my time.

Busyness can quietly crowd out the parts of you that used to feel most grounded.

A couple years ago, I decided to fix that in a very unstructured way.

I opened up my calendar every Saturday. Free reign. Any aspiring founder, content creator, Wall Streeter, student, whoever. Grab a cold brew. Go for a 2-hour walk. Shoot the shit. And it exploded.

Over 1,000 people filled out a HubSpot form in 6 months to meet. I couldn’t keep up. So I started doing Instagram Lives. TikTok Lives. Zooms with clubs. Visiting universities.

It slowly became my favorite form of giving back.

Because when I was 20, I had every question in the world. And I felt like everyone gave me polished, hindsight answers. Not malicious. Just disconnected. It’s easy to connect dots looking backward. It’s harder to remember what confusion actually feels like. So when Purdue invited me, I said yes immediately.

When I arrived at the Union Hotel, operated by students, I was exhausted. It had been a long few weeks internally. Operational shifts. More hours. More pressure. In true Jack fashion, that meant nights and weekends. I got escorted to my room. There was a welcome basket. Snacks. A chocolate choo choo train. I don’t care how old I am, it will always be called a choo choo train.

I had 20 minutes to freshen up before dinner with Dave Randich, a faculty member at the Daniels School of Business at Purdue.

Dave moved to Europe at 29 and spent decades scaling companies across borders. The kind of life that fascinates me. I’ve been fortunate to travel. 6 months in the south of France during exchange. Shanghai for banking. Traveling Europe on my last dollars after graduation. Consulting across Asia, the US, Europe. Speaking at an accelerator in a castle north of London.

Travel isn’t glamorous to me. It’s grit. It’s discomfort. It’s learning to operate without familiarity. It’s eating food you can’t pronounce and being away from your support systems.

Dave and I had whiskey and oysters in West Lafayette, Indiana, which feels illegal to say. They were fantastic. That night, I fell asleep to the Interstellar soundtrack like I always do after a couple drinks. Something about floating in space alone feels peaceful. Probably says more about me than it should.

Perspective expands when you put yourself in unfamiliar rooms.

The next morning was chaos.

Instead of a small fireside chat with 50 students, there were hundreds. Cameras. Moderation. Recording. Before that, 3 hours of rotating groups. Students. Faculty. 1:1 conversations. It felt like JPM super days all over again. I had student guides walking me from room to room like I was on a red carpet. People kept thanking me. Saying it must be exhausting.

Are you kidding me? This felt like a vacation. I was being asked to talk about myself and Habits for hours, and it was met with encouragement and curiosity. That’s not exhausting. That’s energizing.

Then it was showtime. For 45 minutes, I laid it out there. Unfiltered. Not the corporate version. Not the LinkedIn version. Just me. There’s a weird freedom in that. The same freedom you feel with childhood friends. No performance. No filtering.

At one point, I got nostalgic talking about being 20. Sitting there dreaming about working on wall street. Becoming a CEO. Traveling the world. Watching Gary V clips thinking that was the blueprint. And I realized something in real time.

I did make a lot of those things happen.

But the best parts? I never predicted them. The relationships. The weird pivots. The uncomfortable moves. The mistakes. My core message was simple.

The plan you obsess over at 20 won’t look like the life you love at 30 and older.

Afterwards, about 20 students and some faculty gathered for lunch. While there, one student asked a question that stopped me cold.

“What’s a memory that didn’t feel like a big deal at the time but stuck with you as you got older?”

It took me a full minute to answer. If you know me, 10 seconds of silence feels like an eternity. A minute felt brutal.

I told them about being a 2nd-year analyst at JPM in Indianapolis. I had pulled an all-nighter building a 50-page deck for a CMO of a massive pharma company who was about to become a startup CEO. I was exhausted. I had canceled Friday night plans. My girlfriend was pissed. My mom had just lectured me about how work isn’t more important than relationships (always listen to your mother).

Nobody opened the decks except my executive director, who noticed a smudge of blood on his copy. I had cut myself binding the books at 11 pm because the local office didn’t have printing support.

At the end of the day, that CMO grabbed my arm and said, “You never introduced yourself.” He told me how lucky I was to be in that room. That even if I was the lowest guy on the totem pole, that proximity mattered. That the work would pay off. Just not on my timeline.

I didn’t fully believe him at the time. I do now.

The moments that feel small at 22 often shape the person you become later in life.

If there’s one thing I’d encourage you to think about is how you can give your time away.

Mentor someone. Take the coffee meeting. Answer the DM. Visit the school. Say yes to the uncomfortable room. Someone helped you get here. Even if you don’t remember exactly when.

The least you can do is return the favor.

You never know which 5-minute conversation will echo for the next 10 years.

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