When I was a young attorney, a good friend gave me a much-needed talking to: Take time off because vacations create memories for your kids.
I had a law degree, a shiny new shingle, and a work ethic fueled by espresso, ambition, and just enough Catholic guilt to keep me going long after everyone else had turned out the lights. I was launching my own practice, building it from the ground up—client by client, contract by contract, paper cut by paper cut.
In those early years, I worked like a man possessed. Nights, weekends, birthdays, anniversaries—I was there, in the office, elbow-deep in court documents and correspondence while the rest of the world barbecued and went to baseball games.
I hadn’t taken a real vacation in years. Not because I didn’t want to, but because I thought I couldn’t. Time off? That’s for other people. People with bosses. People with paychecks. People whose livelihoods didn’t depend on them being a one-person legal machine. I had bills to pay, a reputation to build, and besides, if I didn’t do the work, who would?
Enter Donnie.
Donnie was a good friend and a self-employed electrician—gruff voice, calloused hands, smarter than most of the folks who wore ties and liked to tell electricians what to do. We met through some mutual friends, and I liked him immediately. Donnie had this habit of telling the truth, even when it was wildly inconvenient.
One day, we were talking about summer plans. Or rather, he was talking about his. He and his wife were taking the kids to the beach—boardwalk fries, cheap T-shirts, sand everywhere.
He asked me what I was doing. I laughed and said, “Work.”
And that’s when he scolded me.
“You can’t be serious,” he said. “What do you think your kids are gonna remember when they grow up? The Tuesday you spent at the office reviewing somebody’s will?”
I opened my mouth to argue, but he wasn’t finished.
“Regular summer days blur together,” he said. “They’re just one long hot stretch of cereal, TV reruns, and whatever’s in the fridge. But vacations? That’s where the memories live. The time Dad cannonballed into the pool and lost his sunglasses. The night we all stayed up too late eating ice cream on the boardwalk. That weird hotel room with the flickering lamp and the closet that smelled like crayons. You remember that stuff. You hold onto it.”
He was right.
Children—and adults, for that matter—don’t store their fondest memories on spreadsheets or in filing cabinets. They store them in moments that break the routine. Moments that are out of the ordinary. Moments that feel, in the best sense of the word, useless.
Because that’s the point of a vacation: it isn’t productive. It isn’t efficient. It isn’t “leveraging synergy.” It’s time spent being instead of doing. And that, my friends, is where life actually happens.
The Self-Employed Delusion
Now, if you’re self-employed, you probably know the voice I’m about to describe. It lives somewhere in your frontal cortex. It says things like:
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“If I don’t do this today, I’ll fall behind.”
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“Clients are counting on me.”
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“I’ll rest when I’m dead.”
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“Just one more email…”
We treat ourselves worse than we’d ever let an employer treat us.
If you interviewed for a job and the employer said, “By the way, we don’t offer vacations—ever,” you’d politely back away and look for the hidden camera. But somehow, when you’re the boss, it feels noble. You think, This is what it takes to succeed. You wear exhaustion like a badge of honor.
But success without sanity is just self-inflicted punishment. And here’s the real kicker: your family doesn’t see your grind as a virtue. They just see that you’re not around.
I’ve seen plenty of successful entrepreneurs build empires and lose their marriages. I’ve seen go-getters with five-year plans and twelve-hour workdays miss the small, beautiful stuff: the cannonballs, the late-night ice cream runs, the “remember when” memories.
The truth? A business that can’t run without you for five days isn’t a business. It’s a hostage situation.
Vacations Are Philosophy in Action
Taking a vacation is more than a nice break. It’s a philosophical statement. It says:
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I believe life is more than productivity.
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I believe relationships matter more than revenue.
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I believe I’m a person, not a project.
When you take a vacation, you teach your children something powerful: that rest is not laziness. That joy is not optional. That presence is not earned—it’s offered.
A vacation is an act of radical rebellion against the tyranny of busyness. It says, I don’t need to answer every call. I don’t need to monetize this moment. I’m just going to sit here with my toes in the sand and be absolutely useless for a while. And that’s beautiful.
The Donnie Doctrine: Carve It Out
Donnie’s advice was deceptively simple: Take the time.
That was it. Not “if you can.” Not “someday when things calm down.” Just take the time.
You don’t need to go to Hawaii or take a cruise (though if you do, bring me back a T-shirt). Sometimes the best vacation is a weekend in a cabin. Or a few days visiting friends. Or just staying home but acting like you’re away—no phones, no chores, no errands, no work.
And for heaven’s sake, put it on the calendar. If it’s not scheduled, it doesn’t exist. Plan your vacation like you would a deposition—firm, immovable, and non-negotiable.
You Will Never Regret It
You will never say, “I wish I had worked through that summer trip.” But you might say, “I wish I’d been there more.”
You’ll never regret walking on the beach with your spouse, or sitting in the backseat listening to your kids argue over who gets the window seat, or watching fireworks from a cheap motel parking lot. These are the moments that make life sticky. The glue between generations.
My own kids still talk about trips we took when they were small. I barely remember the work I sacrificed to go—but I remember the laughter in the back of the rental van, the bad diner food, the sunset over a lake I couldn’t find again if I tried.
When I retire, nobody’s going to throw me a party because I was always available. But they might raise a glass to the fact that I was present.
Final Thought: From One Maniac to Another
If you’re self-employed, I get it. You work for a maniac. Evenings or weekends of work still happen. But Donnie taught me this: even maniacs need margin.
Take the trip. Carve the time. Vacations create memories.
Someday, your child will describe their childhood to someone else. Let it include the words: “We always took time together.”
Trust me: no client will love you the way your family does.
And no vacation will ever cost as much as the regret of not going.
