Why Retirement Planning Isn’t About Keeping Up

I coach both of my sons’ little basketball teams. This year, my 10-year-old son’s team made a decision: they wanted to get more competitive.

For the past two seasons, we had felt like we’d reached the ceiling with the organization and schedule we were playing in. So we decided to take a leap and enter some tournaments.

At our first tournament, we were blown out. Not just beaten—blown out. The kids we were playing against were unreal. Bigger, faster, sharper. It was one of those moments where you look around and think, If this is the level, what’s the point of even playing?

That feeling—discouragement, comparison, doubt—is incredibly familiar. And it doesn’t just show up on a basketball court.

It shows up all the time in retirement planning.

When Comparison Steals the Joy

In the weeks after that tournament, we took a step back. We didn’t quit. We didn’t lower expectations for effort or growth. But we did adjust the level of competition we were playing against.

And something interesting happened.

The games became competitive again. The kids started to grow. They gained confidence. They learned what it felt like to work hard, improve, and see progress pay off.

That first tournament wasn’t “wrong.” It just wasn’t aligned with our goals.

The same thing happens in retirement planning when we compare ourselves to everyone else.

You see someone retiring at 55.
Someone else traveling nonstop.
Someone with a bigger portfolio, a nicer house, a more “impressive” lifestyle.

And suddenly, instead of feeling proud of what you’ve built, you feel behind. Unsettled. Like no matter what you do, it’s not enough.

Comparison turns planning into pressure.

Progress Beats Perfection

Our goal as coaches was never to turn these kids into the best team in the state overnight. The goal was to help them progress. To teach them how to compete. To show them that hard work leads to improvement.

Once we got clear on that, the path forward made sense.

Retirement planning works the same way.

The goal isn’t to “win” retirement.
It’s not to match someone else’s number.
It’s not to live the retirement you see on social media.

The goal is to design your retirement—and then build a plan that supports it.

• What do you want your days to look like?

• What matters most to you—freedom, security, flexibility, legacy?

• What level of risk actually lets you sleep at night?

Those answers are far more important than how your plan compares to someone else’s.

Define What’s Right for You

When you’re clear on your goals, decisions get easier.

Just like with the team, once we understood what we were trying to accomplish, we could choose the right level of competition, the right schedule, and the right expectations.

In retirement planning, clarity does the same thing:

• It helps you save with purpose, not panic.

• It helps you invest with intention, not emotion.

• It helps you measure success by progress, not comparison.

A “good” retirement isn’t universal. It’s personal.

And the most successful plans aren’t built by chasing someone else’s version of success—they’re built by consistently working toward your own.

Those kids didn’t need to be the best team in the tournament to grow. They needed the right environment, the right goals, and the belief that effort leads somewhere meaningful.

You deserve the same in your financial life.

Stop playing someone else’s game.
Decide what your retirement should look like.
And then build toward that—one intentional step at a time.

Because the goal isn’t to keep up with everyone else’s good time, it’s to create one that actually feels like yours.

Shean