What Falls Apart Reveals What Holds

Two friends, a birthday, a diagnosis, and considering the question many don't think about until it's too late.

“I turned 64 today, and I’ve lived almost seven years longer than my father did.”

That’s not my line. Those are the words of my friend and colleague Gary Karr, who published a piece on his birthday yesterday called The Big Boy Job. Gary is one of the sharpest communications minds I’ve ever worked with — we go back to our days in government — and his writing has always had a way of cutting through the noise to land somewhere uncomfortably true.

His piece is about chasing status. Specifically, about taking a corporate job in Hartford for the wrong reasons — the stock options, the title, the validation — and watching it collapse nine months later when a reorg wiped his position out. The guy he reported to resigned two weeks in. The whole thing unraveled.

But here’s the part that stuck with me: what Gary kept wasn’t the job. It was the friendships. The church community in New England. The colleagues he still talks to. He even visited one couple — twice — in Munich. The stuff that looked like it mattered disintegrated. The stuff that actually mattered held.

Gary quoted Charlie Munger on envy being the worst sin because it’s the only one you can’t have any fun at. I felt that in my chest. Because I’ve been there. I’ve scrolled LinkedIn and seen someone land a role I wanted. I’ve compared numbers. I’ve let that comparison quietly erode my peace before I caught it.

And I’ve learned — the hard way, like Gary — that giving in to that envy always costs you somewhere else. In your clarity. In your marriage. In your relationships. In the decisions it pushes you toward next.

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I’m thinking about this today because of another friend.

Randy Skoglund is one of those people whose career you look at and think, how did one person do all of that? He’s the founder of Orange Hat Group, a digital agency out of Alexandria that’s been nationally recognized — their work’s been featured in PC World, The Washington Post, The Hill. They built the first platform that let citizens contact Members of Congress through Twitter. They won the Platinum Award from the Publicity Club of Chicago for Best PR Campaign. Randy’s done political digital strategy at a level most people only read about.

But that’s not how I know Randy.

Randy and I grew up in the Midwest together. We reconnected in Washington. When I was building DC Dog Sitter — before it was a seven-figure company, before I had any idea what scaling really meant for small businesses — Randy helped me with my first Google ad campaign. His family used our pet service. That’s the kind of guy he is. Award-winning strategist by day, calling you to help figure out your first ad spend because he believes in what you’re building.

This past May, Randy was diagnosed with cancer. Last week, his family shared that he’s entered hospice care. They’re managing pain, draining fluid from his torso, trying to give him comfort. He’s behind on messages but wants everyone to know he appreciates them.

I’m not sharing this for sympathy. I’m sharing it because it’s the realest possible version of what Gary wrote about yesterday.

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Gary’s piece ends with this: “Having reached a birthday my father never got close to, I am more keenly aware of dwindling time than I’ve ever been. I’m trying to spend it chasing what lasts.”

I think about that line differently now than I would have even a few years ago.

In 2016, I was deep in the build. Scaling a business from the ground up with no investors and no fail-safe. Running at a pace where “what lasts” was a concept I’d get to eventually — once I had the revenue number, the exit, the proof that I’d made it. I was collecting credentials the way Gary collected that Hartford job. Not because they were wrong, but because I thought they’d say something about me that I wasn’t sure I could say about myself.

Then I landed in the ER at Sibley Hospital in Washington, DC. They did a chest X-ray. The doctor came in, put her hand on my leg, and said, “We need to talk.”

Many people in life at some point will have that moment, the “we need to talk” moments. What happens next will usually radically alter the course of their life — drastically. It did mine.

Here’s what I know now that I didn’t know then:

The titles don’t hold. The revenue number doesn’t hold. The LinkedIn announcement doesn’t hold.

What holds is the friend who helped you figure out your first ad campaign when you had no idea what you were doing. What holds is the colleague who tells you the truth when everyone else is being polite. What holds is the community you built in a city you moved to for a job that didn’t work out.

What falls apart reveals what holds. Every time.

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Randy is fighting. Gary is reflecting. I’m writing.

And if you’re reading this and you’re in the middle of your own build — chasing the title, the number, the validation — I’m not going to tell you to stop. That drive built everything I have been able to accomplish. But I will tell you this: pay attention to what you’re building alongside the business. The relationships. The people who show up when the reorg hits, or the diagnosis comes, or the thing you built falls apart.

Because those are the assets that appreciate. Everything else depreciates the moment you stop feeding it.

Build something that can’t be broken. Start with the people.

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Gary Karr’s full piece, The Big Boy Job, is worth your time. And if you’re the praying type, Randy and his family could use them — you can follow his journey on CaringBridge.

If this resonated, subscribe to The Jenn Files. I write about business, money, resilience, and grit — cutting through the noise so you can build something that can’t be broken.