• HOME
  • ABOUT
  • EXPERTISE
  • SIGNAL
HOMEABOUTEXPERTISESIGNAL
SIGNAL · OCT 2026What 23 Years of WorkTaught Me AboutGetting AheadSIGNAL · DAN WENTZ

What 23 Years of Work Taught Me About Getting Ahead

10/7/2026Dan Wentz

I've been working full-time for 23 years, and I'm starting to feel old. So, like every well-intentioned mid-life crisis conqueror, I'm going to dish out some advice I'd like the rest of the world to hear.

No one says it, but we're taught to be selfish early. Win the game. Get better grades than the kid next to you. Beat the other people who want your job. Nobody's going to look out for you, so look out for yourself. Outside of family and a few close friends, not many people are cheering for you. And, some days, even they're a little quiet.

So we set goals. Land the title by 30. Hit the salary by 35. Grow the 401(k). Plenty of us hit those marks, too. And the win feels great for about a week, maybe two. Then the next goal shows up. There's always something more to do.

So what outlasts the sugar rush of hollow achievement?

I think it's human connection. Caring about people, and having people care about you. Not as a networking trick. Not to build up favors you can cash in later.

Think about those who shaped your career. I'll bet it wasn't the person who beat you out for a promotion. It was someone who took an interest in you when they didn't have to.

I can name three without even thinking.

Bob Zimmerman, who has since passed, was a Hall of Fame broadcaster in central Pennsylvania. He'd made it by any measure. Big house, nice cars, and investments most people can only dream about. He had nothing left to prove. Still, he kept making time for Penn State students like myself. He'd coach us on careers and explain how the media business really worked. A guy at his level could have spent those afternoons on the golf course. He spent them with college kids instead.

Kelly Nolan Rock was my sales manager at Clear Channel in Pensacola. She's the one who taught me sales could be fun, and not just a pit in your stomach. She'd ride with me to the middle of nowhere in Florida and Alabama to meet people we both knew weren't going to buy. We spent hours in the car for a guaranteed "no." She didn't have to do that. She did it because those drives were a chance to teach and connect.

Then there's Keith Allen, my radio Yoda for 7+ years. I owe a big part of my media career to him. He recruited me to the South with promises of MTV's Spring Break in Panama City, FL. It wasn't quite as I had envisioned; there was plenty of hard work, early mornings, and late nights. I had little experience working as a team in a professional atmosphere, but he remained patient and showed me the ropes.

None of them had to do any of it. They put time into someone who probably wasn't worth it yet. I'll remember all three for the rest of my life. Not for their titles or their bank accounts. But, for the grace they showed to a young, enthusiatic, developing human.

Here's the thing, though. That kind of care looks different from a volunteer day. Serving at a food bank or pitching in at church is good, and people need that help. But let's be honest. A lot of the time, we walk away feeling great about ourselves and go right back to normal. The harder version happens on a random Tuesday, with the people already around you.

What does that look like? It's checking on the coworker who's been quiet lately. It's asking "How are you really doing?" and sticking around for the answer. And it's paying attention to the people who seem fine. The top performer. The friend with the perfect Instagram. The neighbor who always waves. Everybody's running a hard race, and the ones who look like they've got it handled are often carrying the most. Nobody thinks to ask them.

This isn't a new idea. The Bible talks about it a lot. Your grandparents probably told you the same thing. It's just hard to believe until you live it. And we don't see it much anymore. We've got phones that connect us to everyone, and somehow we feel further apart than ever. When someone takes a real interest in you now, you notice.

When people invest in each other, it comes back. Not on a schedule. Not always the way you'd expect. But it holds up through job changes, bad years, and market crashes. Bob, Kelly, and Keith are proof of that for me, years after I last worked with any of them.

Your title will change. Your salary will go up and down. Most of your goals will fade from memory. But somewhere out there, someone might still be telling stories about the time you showed up for them.

So be honest with yourself. Will anyone say your name the way I say theirs?