A Few Regrets but We'll Be Grand

Episode 14May 1, 2026

In Episode 14 of Friends in Low Places, we tackle a topic that hits close to home for anyone in their 40s: regrets.

Not the dramatic kind. The quiet, everyday kind.

The choices we made. The paths we didn’t take. The expectations we carried for far too long.

What Counts as a Regret?

It’s not always about big life decisions.

Sometimes it’s:

  • Not listening to yourself earlier
  • Living the life others thought you should live
  • Spending too much time trying to be someone you’re not
  • Waiting too long to figure out who you actually are

The Regret That Sticks

One thing came up again and again: not trusting yourself sooner.

The lads talked about:

  • Following paths because they seemed “right” on paper
  • Doing things because that’s what was expected
  • Taking decades to realize you had permission to just… be yourself

And the frustration that comes with realizing this could have happened earlier.

But Here’s the Thing…

You can’t go back and change the beginning.

But you can start where you are and change the ending.

That’s the CS Lewis quote that wrapped up the whole conversation.

And it’s not just philosophy—it’s something the lads are actively doing.

The Parent Perspective

Having kids changes how you think about regrets.

Because now you’re watching them navigate the same expectations, the same pressures.

And you’re thinking: How do I make sure they don’t spend 20 years figuring out what I’m only realizing now?

It’s not about giving them a perfect life. It’s about being more intentional about what you pass on—and what you don’t.

The Key Is When You Start

The moment you decide to change something… that’s when the change starts happening.

It doesn’t matter if you’re 25 or 45.

What matters is that you’re trying.

Final Thought

Maybe the real wisdom isn’t in avoiding regrets.

Maybe it’s in not letting them define you.

And in knowing that it’s never too late to start looking forward instead of back.


“This time next year, Rodney… we’ll be millionaires.”

And to quote Édith Piaf… well, you can guess what that translates to.

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