The Lie Everyone Believes About Turning 50
We’ve been taught to expect less as we age. I think that’s exactly backwards.
Hi, I’m Chris. I’ve spent the last 25 years building businesses, wealth in real estate, and learning what actually matters along the way. Most people don’t fail; they drift. Here, I share how to create wealth and live a life that doesn’t decline.
We’ve been sold a quiet idea about life: that it peaks early and everything after is just a slow decline. That the best years are behind you. I don’t believe that.
The second half can be the best part, if you don’t miss it.
But I didn’t always see it this way.
This is the shift.
When I was in my twenties, my soundtrack was Prince. There was a defiance to it. No matter what tried to pull you down, you kept pushing up. I was building, learning, and going all in on what was in front of me. It was a season where everything felt possible, with real energy and momentum and a sense that the future was wide open. And whether we say it out loud or not, most people assume that’s the peak.
For my 40th birthday, my wife threw me a surprise party. When I walked in, it was 80’s themed and she had a Prince costume waiting for me. Prince music blared. For a few hours, it felt like stepping back into that earlier version of my life. Prince died the day after that birthday. And it stayed with me.
In that moment, it felt like that season of life, the one defined by raw energy and forward momentum, was clearly behind me.
Or was it?
What culture gets wrong about midlife.
Most people don’t ask what’s next. They just assume the answer, because that’s what culture has fed us. They hit mid-life and expect a slower version of the same life. Less vitality, less growth, and less to look forward to. They may not say it out loud, but they live like it’s true.
Yes, things change. You can’t treat your body at 50 the way you did at 25. It takes more intention now, discipline, and clarity about what actually matters. But you also have advantages you didn’t have at twenty: experience, perspective, and a better sense of what’s worth your time.
If you use what you’ve learned in the first half, the second half doesn’t have to be a step down. It can be better. Colonel Sanders franchised his first restaurant in his 60s. The difference isn’t time. It is trajectory.
Lifespan is how long you live. Healthspan is how long you actually get to live well, with the energy, clarity, and ability to do the things that make life worth living. Most people say they want to live longer. What they really want is to live better for longer. That doesn’t happen by accident.
That realization changed how I think about the second half of my life.
The next fifty.
I turned 50 last week. Somewhere along the way, my soundtrack shifted from Prince to country, and I keep coming back to Tim McGraw’s My Next Thirty Years. He wrote it at thirty about living intentionally.
I’m hearing it at fifty, and it lands differently. At thirty, you assume you have time. At fifty, you realize you need to use it. If he was aiming for thirty more great years, I’m aiming for fifty more. I want to live to 100 and make the most of this life.
That’s not a dream. That’s a plan.
I’ve had 50 healthy years, and I’m not taking the next 50 for granted. I want to reach 100 still moving, still sharp, still able to do the things that make life worth living.
Still skiing.
Build for the life you actually want.
Klaus Obermeyer founded Obermeyer, one of the world’s most iconic ski apparel brands. He is 106 years old and still skiing the slopes of Aspen. His philosophy is remarkably simple: one hour of physical exercise every day, all your life. “The longer you ski, the longer you live,” he says. He also says skiing is easier than walking.
I want to be that guy. I want to ski with my family well into my seventies, my eighties, and beyond. I want to hike out to the Delicate Arch again when I am in my 90s. I want to travel the world with Jana, see places we haven’t been, and keep making memories that compound the same way good investments do. I want to be the guy in his eighties still in the gym, still training, still showing up, because I have seen what that commitment looks like in real life, and it is one of the most inspiring things I know.
I don’t want to miss my life. If you are here reading this, I don’t think you want to miss yours either.
From where I’m standing, the next fifty years are about building something better. Most people accept the default arc. Less energy. Less ambition. Less to look forward to.
I don’t.
You either build or decline
If you want to live that expected narrative, that life declines as you age, then that is easy. You don’t have to do much. But if you want to live an exceptional life, the time is now.
I’m building toward being the kind of father my boys choose to come back to when they no longer have to. I want to see Max and Mason grow into intentional men, meet their families, and hold their kids. If I live to 100, they’ll be in their early sixties, and every healthy choice I make today is an investment in being there for that.
I’m building a marriage Jana and I are both proud of, knowing it grows when you invest in it and erodes when you don’t. I’m building businesses, a foundation, and a culture where people grow and do the best work of their lives. Something that outlasts me. I’m building a life defined by generosity, because giving returns more than any balance sheet ever will. And I’m building the kind of life that earns the memories, the meals, the laughter, the trips, and the ordinary nights that turn out to matter most.
This isn’t something I’m hoping happens later. It’s something I’m building now.
What I Know Now
I am fifty years in. The soundtrack has changed. The goals have deepened. Life is richer in every way that actually counts.
And here is what I know now. No one wakes up and decides to miss their life. They just never decide not to.
If you’re honest, you already know what you don’t want to miss. What is it? Leave it in the comments. I’d love to read it.
A Favor
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Yes, yes, yes. 👏 In midlife, we have the great advantage of wisdom. More confidence knowing where we should spend our time. Less fear. More intention. More meaning. I feel more alive in my late 40s than I did in my 20s, and it has taken intentional choices. I’m excited to build what lasts longer than me in this second half. Loved reading every bit of this.
The health span movement is definitely gaining strength, but it takes will power and discipline. At some point in your life you have to decide to make sacrifices that will set you up for more years of doing! (And the sooner the better) Even if it is counter-culture and takes gumption. Maybe this is starting to change, but for the most part, McDonalds is still winning.