Looking For Freedom or Finality? Let's Talk About Your Future Retirement

My dad retired four different times.

He was a professional pilot, and his great love was flying airplanes.

Each time he retired, he thought it was the right moment to slow down. But after a few months, he'd find himself at home, bored, ready to get back to work, and my mom ready to kill him because of "too much togetherness." He always found a reason to go back to flying. Retirement for him was never an ending, it was always just a pause.

That’s something I see over and over again with high-performing people.

We’re told that the ultimate goal is to build something valuable, sell it for a big payout, and then enjoy the good life. And for about six weeks, most people do just that. They travel, relax, spend time with their grandchildren, tackle a few projects. But then something shifts. Boredom sets in. The loss of routine, purpose, and daily decision-making hits hard.

I’ve rarely met a truly driven person who retired and was genuinely fulfilled long-term. Especially not the kind of person who’s built a business from the ground up.

You don’t have to stay stuck in the day-to-day. But you also don’t have to sell just because the world tells you it’s time. In Episode 269 of the IA Forward podcast, Shane and I talk about the difference between selling of your agency versus setting it up to deliver perpetual revenue. Instead of selling and walking away, what if you restructured your business to continue generating income, like an annuity? What if you hired the right people, delegated well, and pulled back just enough to enjoy your time while still having purpose and control?

Are you looking for freedom or finality? Because those two things are very different.

If it’s freedom you want, you may already be sitting on the perfect vehicle to deliver it. You just need to shift how you drive it. If it’s finality you’re after, and you’re truly ready to close the book, then make sure the financial return and personal readiness align. Because walking away too early might mean walking away from both income and identity, two things that are hard to replace.

My dad didn’t keep going back to work because he had to. He went back because he wanted to. Flying wasn’t just a job. It was joy. It was purpose. It was who he was.

That’s why I encourage agency owners to think long and hard before they sell. Don’t just build a business worth buying. Build a business that supports the next chapter of your life, whether that includes a full exit, a partial step-back, or just more time in the metaphorical sky.

Be fearless!

Tonya

Be sure to check out Episode 268 of the IA Forward podcast at iaforward.com, YouTube, Spotify, or Apple Podcasts.