Years ago I had a client tell me that he hadn’t been out of the office for more than a week in nine years. I had to ask him—was he proud of this, or regretful? He’s a multimillionaire. He’s also divorced, had an affair with a woman at the office, and is now alone in his 50s.

I think about him sometimes, especially when I hear men talk about what success looks like. On paper, he has it all. But when you strip away the accolades and the balance sheets, what remains? His life became a singular pursuit, a marathon of work without a pause, and in the end, it cost him the things that couldn’t be measured in dollars. It makes you wonder, what’s the real currency of success?

Another friend—who’s married to a major celebrity,  just posted publicly that last week was the first time he’d been away with his wife for more than a weekend alone since their honeymoon. Think about that for a second. That’s almost three decades of a life so busy, so filled with obligations, demands, and the pursuit of success, that they never took the time to truly be together. And for what? Fame? Adulation? Influence? What’s it all worth when the person next to you, the person you’ve chosen to spend your life with, barely knows who you are anymore? The dichotomy was that this was supposed to be an announcement that the doors are now finally open to more of this. 

Just yesterday, I read a post from a friend whose son I coached in Little League. He wrote about his retirement after 33 years with Pennzoil and Shell Lubricants. It was a nostalgic post—full of pride in the roles he’d held, from a young process engineer to plant manager at one of the largest production facilities in the world. He thanked the countless people he worked with over the years, acknowledged the impact they had on him. But when I read it, all I could think about was 33 years of waking up every day to go to work for the same company, making lubricants. Three decades of routine, of showing up, of doing the job.

On the surface, it’s another success story. A career well-lived. A job well-done. But beneath it, there’s that lingering question—what did it cost? What did he give up to spend three decades in the same industry, waking up every day to the same job? I wonder what his mornings feel like now, without the rhythm of work to guide him. Does he feel liberated, or lost?

These stories aren’t unique. They’re versions of the same tale I hear from men in midlife over and over again. The choices they’ve made, the decisions they’ve committed to, all come with costs. Success is celebrated, but rarely do we talk about the sacrifices made in its pursuit—the marriages that falter, the relationships with children that feel distant, the friendships that wither under the weight of time.

The choices we make and the actions we take. There’s always something we’re not seeing, something we don’t account for in the pursuit of whatever it is we’re chasing. We celebrate the wins but often ignore the toll. We frame success as financial or professional, but rarely do we measure it in terms of personal fulfillment, of joy, of connection.

I don’t have all the answers, but I know this—everything has a cost. The question is, are we willing to pay it? And if we are, will we look back and say it was worth it?

We only get one shot at this thing. One life. One chance to make the most of it. The men I’ve talked to, the stories I’ve heard, they all remind me of one simple truth: it’s not about what you have, it’s about how you live. 

So do with this what you will. Success is defined differently for all of us. But before you keep pushing, before you say yes to that next deal, that next job, that next achievement, take a moment to ask yourself—what’s it really going to cost? And is that price worth paying?

Because at the end of the day, the real question isn’t what you’ve accomplished. It’s whether you’re proud of the life you’ve lived.

In Health,

Greg

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Greg Scheinman is the Founder of Midlife Male. His mission is to help men maximize middle age. He does this through one-on-one coaching, a podcast, and a newsletter. He is a best-selling author, speaker, entrepreneur with two successful exits, athlete and thought leader on life over 40. Most importantly, he’s a husband and father.

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