What I Wish I Asked at 23

What's on my mind?

My nephew Alex called me Saturday night on his way to dinner with his parents.

He’s in his early twenties. Engaged. No kids yet, but you can feel a family sitting somewhere out on the horizon — like a season that hasn’t started, but you’re already watching the sky.

He works in agriculture and he wants to stay there. Not just “work a job” in ag either — he wants to own and run something of his own someday. What that “something” is… that’s part of what he’s trying to figure out.

And I could feel it.

Not one specific sentence he said, but the energy underneath the conversation. A quiet sense that he’s standing at a decision point. He doesn’t want to make a mistake. He’s seeking advice from people he trusts.

I’m flattered that he called me. I really am. It means something when someone asks for your perspective — especially when you know how much the next few years can shape a life.

But after we hung up, I had a very honest thought:

I did more telling than asking.

If I could have a do-over, I’d start over and ask more questions. I’d listen longer. I’d try to understand what success actually means to him before I offered my version of it.

Because here’s the thing… I love work. I always have.

Alex works a lot. And he likes working a lot. That part made me smile, because it reminded me of myself.

There’s nothing wrong with a strong work ethic. In fact, it’s one of the few advantages you can choose on purpose. You can’t always control talent. You can’t always control timing. You can’t always control who opens the door.

But you can control whether you show up. Again and again and again.

And I believe something else too — something that lives right alongside that truth.

Work ethic is powerful… but it can also become a hiding place.

After that call, I remembered hearing the founder of Jersey Mike’s say that balance doesn’t really exist when you’re building something of your own. It’s a grind. It’s all of it. If you want it, you have to be willing to work harder and longer than anyone else.

I understand that. I’ve lived it.

But I also know what it costs when you don’t stop to define what you’re working for.

Back in my early twenties, my definition of “success” was simple: more money.

That was it. More money.

I didn’t even know what I would do with it. I just wanted it. I wanted to be the top earner at the dealership. Then I wanted to be the number one insurance agent. Neither of those things came true, by the way — but I chased them like they were the only scoreboard that mattered.

And I did have an advantage.

I don’t have a college degree. But that doesn’t mean I’m not educated.

While other people were in classrooms, I was working. Seven days a week. Learning how to sell. Learning how to listen. Learning how to handle customers, rejection, pressure, competition, momentum — all of it.

There have always been people in the room smarter than me.

But there haven’t been many rooms I’ve been in where someone was willing to work harder or longer.

That was my edge.

It might take me four times as long the first time. But once I understand the process — once I can see it clearly — it’s hard to stop me. Because then the work ethic has something to grab onto.

The problem is… in those years I thought I had goals, but I don’t know if I ever really chose them.

I had the kind of goals successful people are supposed to have.

Have a goal, right? Chase it. Win. Repeat.

What I missed for a long time was the deeper question:

What is this goal actually going to feel like if I get it?
And what will it cost me on the way there?

Because I spent years chasing goals… and hitting them… and still not feeling happy.

I sacrificed a lot to meet those goals. I missed important things.

One year, early in my agency, I got a lead at the end of the day. I could see the sale sitting right there if I just stayed and did the work. I made the decision to stay — even though my gut was alerting me.

It was obviously the wrong decision, and I missed my wife's birthday that year.

At the time, I didn’t know what I know now. I thought “doing whatever it takes” was the whole point. I was too early in my career to realize I could have just been honest.

I think about that moment the same way I think about when I stopped taking Saturday appointments.

It felt like it was going to be the end of my agency. I thought it was my advantage.

But then I started saying something simple and true:

“I can meet with you on Saturday… but I get to spend time with my wife and kids on the weekend. Is there a time during the week that we could get together?”

Every customer I said that to scheduled at a time that still worked for both of us.

They totally understood.

And honestly, I think they respected me more because I said it. Because it was the truth.

That’s one of the lessons I wish I could go back and hand to my younger self:

Sometimes the “advantage” isn’t working more.

Sometimes the advantage is being clear about what matters… and living like you mean it.

What’s different now?

Time, mostly.

Time has taught me that the journey matters more than I was willing to admit.

I used to believe the journey had to be sacrifice, pain, and suffering — because that’s what made it “worth it.” Like if it didn’t hurt, it didn’t count.

Now I think something different.

I think the journey should be the best part.

Not easy. Not lazy. Not “no pressure.”

But alive.

Because if you can’t design a path that feels meaningful while you’re walking it — if the whole thing is just a grind you’re trying to survive — I’m not sure the destination is going to be what you think it is.

It’s not that hard work is wrong.

It’s that aimless hard work is expensive.

And that brings me back to Alex.

He mentioned seed sales. He said he’d love to do it full time, but he also said something that’s common for someone young and hungry: “I don’t know a lot.”

I pushed back.

Because that’s not true. He knows more than he realizes already. And even if he doesn’t know enough yet — that’s not a character flaw. That’s just the starting line.

I told him something I believe deeply: if you find the specific thing you truly enjoy, you can become great at it faster than you think. Not because you’re a genius — but because you actually show up.

And I think that’s the real advice I was reaching for with Alex — even if I didn’t ask enough questions to get there the clean way.

Not “work less.”

Not “grind more.”

But this:

Get focused. Ask others — but ask yourself too.
Because everyone has advice and most will give it freely, but none of it matters if it has nothing to do with the journey you want to be on.

You get to choose… everything.

Choose wisely, but don’t worry about choosing incorrectly. You will do that too. It’s the mistakes you learn from.

Question everything — especially the things you think you know.

Stay open to change.

I’m still working on my own definition of success, but if I had to write it down today, it would be something like this:

To live, learn, and share in the amazing life I’m allowed to live.

And maybe that’s the question I should have asked Alex on Saturday night as he drove to dinner:

What are you building — and who do you want to be while you’re building it?

I’ll admit something else too.

After that call, my mind kept drifting back to how people get paid in agriculture — and what that does to the kind of advice a young guy like Alex is surrounded by.

That might be a separate post. But it’s connected. Because incentives shape behavior… and behavior shapes outcomes… and outcomes shape the life you get to live.

Because the danger isn’t hard work.

The danger is climbing the ladder fast… and realizing it was leaned against the wrong wall.