15 Years at Prime Time: 15 Things I’ve Learned

LinkedIn reminded me this morning that I have officially been at The Prime Time Agency for 15 years. Fifteen. I actually stared at that number for a minute.

For roughly eight of those years, I was an Account Executive, learning this business under Teds direction. And for the past seven, I’ve been on the other side of the desk as the owner of the agency.

Eight years plus learning. Seven years leading. WOW.

And my first thought wasn’t, Look what I’ve accomplished. It was: Does this mean I’ve made it?

And almost immediately: Am I behind? Should I be doing more? Should I be doing less?

Funny how that works. We spend so much of our careers looking toward the next thing. The next client. The next goal. The next hire. The next big idea. The next revenue number. You tell yourself, When I get there, I’ll feel successful.

Then you get there. And “there” moves.

I didn’t walk through the doors of Prime Time in August 2011 knowing that years later I would have the opportunity to buy the agency. Back then, I was learning. Clients. Media. Budgets. Deadlines. Creative. Relationships. How to solve problems before the client even knew there was a problem. Mostly, I was learning from Ted.

Then came 2019, and suddenly the lessons weren’t theoretical anymore. The decisions were mine. So were the risks, the payroll, the mistakes, the sleepless nights and the responsibility of carrying forward an agency someone else had spent decades building.

There have been really good years. There have been really hard years. There have been moments when I felt completely certain about what I was building and others when I wondered what in the world I was doing.

So instead of trying to decide this morning whether I’ve officially “made it,” I started thinking about what those 15 years have actually taught me.

Here are 15 of them.

1. You never really feel like you’ve “made it.”

The finish line has wheels.

Every time you reach the thing you once thought would make you feel successful, there’s another goal waiting behind it. Ambition is funny that way. I’m not sure that feeling ever completely goes away.

2. Who you learn from matters.

I had nearly eight years working under Ted before I became the owner of Prime Time, and I didn’t realize at the time how much of what I was learning would eventually shape the way I run this agency.

Some lessons were about advertising. Some were about clients. Some were about business.

And some you don’t even realize were lessons until years later.

3. Owning the business is very different from being good at the business.

This one deserves to be printed on something.

You can be great at your job and still have absolutely no idea what it feels like to be responsible for all of it.

Payroll. People. Cash flow. Clients. Decisions. Problems. Opportunities.

And ultimately, the buck stops with you.

4. Relationships will take you farther than any sales pitch ever will.

This business has changed dramatically in 15 years.

Relationships haven’t.

People want to work with people they trust. They want to know you’ll answer the phone. They want to know you’ll tell them the truth. And they want to know you care about their business beyond the invoice.

5. Sometimes the client you don’t get is a blessing.

You usually don’t know it at the time. At the time, you’re disappointed. Maybe even a little mad.

Then six months later you think, Well. That worked out. Not every opportunity is your opportunity.

6. Revenue isn’t the same thing as success.

This took me a while. A bigger number doesn’t automatically mean a better business.

Sometimes more revenue brings more overhead, more stress, more people, more problems and less of the work you actually enjoy doing.

Growth matters. But good growth matters more.

7. You have to learn to say no.

I was much worse at this 15 years ago.

No to the wrong client. No to the wrong project. No to something that doesn’t make financial sense. No to something that takes your team away from where they need to be.

Every yes costs something.

8. People remember how you handle things when they go wrong.

Maybe even more than they remember when everything goes right.

Mistakes happen. Problems happen. Campaigns change. Deadlines move. Technology breaks.

How you respond when things aren’t perfect says a lot more about you than how you behave when they are.

9. You are allowed to change your mind.

About a strategy.

About an employee.

About a client.

About a goal.

Even about what you want your business to become.

Changing direction doesn’t always mean the first direction was wrong. Sometimes it means you know more now.

10. The business will take everything you’re willing to give it.

It will never tap you on the shoulder at 5:00 and say, Kerry, that’s enough for today.

There will always be another email. Another idea. Another problem you could solve. Another thing you could make better.

Learning when enough is enough may be one of the hardest parts of owning a business.

I’m still learning this one.

11. You need people who will tell you the truth.

Especially when you’re the person signing the checks.

You need people around you who aren’t afraid to say, “I don’t think that’s a good idea.”

You need people who challenge you, question you and occasionally save you from yourself.

“Yes” is easy to find.

Honesty is much more valuable.

12. There will always be somebody doing more than you.

Making more.

Growing faster.

Winning something you wanted.

Opening another office. Landing the big account. Posting about another record year on LinkedIn.

Comparison can make a pretty good life feel inadequate in about 30 seconds.

Their timeline isn’t mine.

And mine isn’t theirs.

13. Experience doesn’t mean having all the answers.

It means being a lot less afraid when you don’t.

Fifteen years ago, not knowing the answer could make me panic.

Now I know we’ll figure it out.

We’ve figured out a lot of things.

14. The work changes. The fundamentals don’t.

The advertising business I walked into in 2011 looks very different from the one we’re working in today.

Platforms changed. Media changed. Consumer behavior changed. Technology changed. Now AI is changing things all over again.

And something else will come after that.

But good ideas still matter.

Strategy still matters.

Understanding people still matters.

Trust still matters.

And doing good work still matters.

15. Maybe staying power counts for more than we give it credit for.

This is the one I’m thinking about most today.

Fifteen years of showing up.

Of learning and then leading.

Of adapting.

Of surviving hard seasons.

Of taking chances.

Of making mistakes and getting better because of them.

Of watching an industry reinvent itself and continuing to reinvent right along with it.

Of taking something someone trusted me with and making it my own.

And after all of that, still being excited about what we can do next.

That has to count for something.

So, have I made it?

I still don’t know.

Am I behind? Probably by somebody’s definition.

Should I be doing more? In some places.

Should I be doing less? Absolutely, in others.

But this morning, I’m trying not to immediately turn 15 years into another goal.

Eight years learning. Seven years leading. Fifteen years growing alongside a business that has become such a big part of my life.

Maybe the 16th thing I’ve learned is that every once in a while, you should stop moving the goalpost long enough to look back at how far you’ve carried it.