You’re Not Behind. You’re Just at Halftime.

This is tmrw — a weekly note on money, decisions, and what tends to matter over time.

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You’re Not Behind. You’re Just at Halftime.

The Super Bowl is happening this week. Over 100 million people will tune in and watch. I hardly remember last year’s game, but I vividly remember the halftime show, and maybe more than that, the puzzled look of my friend’s parents watching Kendrick Lamar.

While the world is already debating this year’s halftime show, the real work is happening in the locker rooms. Players resting up, eating PB&Js, and tweaking the playbook for the second half, either to come back and win or extend the lead.

Over the years, I’ve noticed that some people have a really good sense of where they are financially, where they’re headed, and what needs to happen next.

Others don’t.

Then there is the armada of social media influencers, regardless of age, who seem to “always” be on the up and up.

As I’ve been writing these recent editions, thinking through the work we’re doing for clients and what I am personally working on, I’ve been thinking about how time and seasons intersect. Not in a soft or abstract way, but in a practical one. How do you know what season you’re in financially? And how do you know when that season has changed?

Since launching Fjell in 2020, we’ve onboarded over a hundred new families across the U.S. What I’ve always found interesting isn’t just who reaches out, but when they reach out. Families somewhere in their 50s are more common than not. They’re not panicked. They’re not failing. Nothing is broken. Actually, the opposite is usually true, things have never been better. They’ve found themselves at halftime, winning the game.

But something feels different because things are different.

They’re watching coworkers they’ve known for years retire. They can see the end of their career in a way they couldn’t before. Their relationship with work changes. They still work hard, but they know the clock is winding down, and they can start seeing blocks of free time on the calendar and all the fun things they could do with that.

They say:

“I know I don’t have unlimited time left.”
“We don’t want to work forever.”
“It feels like it’s time to get serious (about retirement planning).”

What they’re experiencing, whether they have language for it or not, is the midpoint of their financial life.

It’s precisely here where people can misread the season they’re in, miss the point of halftime, and spend their time working on the wrong things.

Last week, I wrote about compounding and regret, and about how regret is a terrible guide. When people fixate on what didn’t work and try to fix the past, they often miss the fact that things have changed. Markets change. The tax code changes. Life changes.

When you look across the spectrum of time, a strategy that made a lot of sense in your 40s can become a liability in your 50s, which can cause permanent damage in your 70s.

When families come to work with us, or when clients move from one phase of life into another, a lot of the work is simply helping them see that the game is different now. Not in a dramatic way, and not by tearing everything down, but by acknowledging that the rules have shifted. The tax code you live in during your accumulation years is often very different from the one you live in later. Estate planning strategy changes significantly as asset levels grow. If you don’t adjust for these, you can end up paying more in taxes than you ever expected, which means less flexibility later on.

Again, think of the players this weekend and what they are going to be doing while we all watch the show at halftime. They step off the field. Coaches are dialed in with the plays they are going to run in the second half. Players roll through what could have been better or how they are noticing an opponent play. Regardless of whether they are winning or losing, halftime usually means doing something differently in the second half.

When people misunderstand the season they’re in financially, the effects don’t always show up right away. Like many things with money, they happen slowly over time. I’ve helped clients with decisions where the value won’t be reaped for years. On the other hand, I’ve also watched families adjust risk and immediately feel more freedom, knowing they locked in profit. Those outcomes aren’t accidents, nor do they come from random chance. They come from walking off the field and revisiting the game you are playing. You can’t go back and replay the first half. But you can spend the second half solving the wrong problems.

What people need is usually more context. One of the harder parts of building wealth is that context disappears the wealthier and older you get. Fewer people around you are dealing with the same decisions you are presented with.

Everyone reads the same news, but the implications are different depending on where you actually are. People can get stuck in accumulation mode. They keep playing the same game they played in their 40s, even as their career starts to wind down and their assets are just reaching halftime.

The tricky part about halftime is that while you can’t change the first half, the second half gives you fewer chances to fix mistakes. In your 60s and beyond, there’s no new income from work to bail you out. There’s less time. The dollar value of potential losses grows exponentially alongside your assets.

Yes, the habits that built wealth still matter. But the game becomes more nuanced because of the winding down of life itself. Unlike an actual game with predetermined stopping points, there’s usually a moment that brings this into focus. A thought that won’t go away. That thought turns into Google searches. The Google searches turn into conversations. Eventually, people show up asking a very specific question, even though the feeling underneath it is broader.

“I don’t want to work forever.”
“My kids are getting older.”
“I want to enjoy what I’ve built.”

The shift isn’t fear, and it’s not a lack of ambition. It’s a mixture of contentment and urgency. The same drive that built a career, but pointed in a different direction.

Winning in the second half of life doesn’t have a universal definition. There isn’t a shared scoreboard. Halftime is about taking stock, strengthening what’s already there, and making changes slowly and intentionally. Over time, those adjustments tend to lead to a retirement that feels planned instead of accidental.

In a lot of ways, halftime is just the beginning of retirement, even if it’s still years away. Life without earned income requires preparation. And preparation starts with being honest about the game you’re actually playing.

If something feels different, it probably is.

If you’d like to talk through how this applies to your own financial life, you can learn more about our work at Fjell Capital here.

And if you found this edition useful, let me in the poll below or reply with a quick note—I read every response.

More next week.