DAILY PILLAGE
Monday, November 17, 2025
HUMILITY MEANS MORE THAN SUCCESS
At 31, looking back on five years of building a property management and vacation rental company reveals lessons money can't teach. In our twenties, we started with more ambition than experience. The numbers that followed seemed surreal: 130 properties under management, millions in real dollars generated for our clients by leveraging their assets.
Here's what five years taught: the higher you climb, the more you realize what actually matters along the way.
The Weight of Growth
When the company was managing over a hundred properties and producing at the highest level, something unexpected happened. What should have felt like success came to be felt as cost. What should have brought confidence brought frustration.
Client expectations rose with every win. The better we performed, the more was expected. Externally, we were crushing it—the numbers proved it. Internally, the story was different. Market sentiment was shifting beneath our feet. Personal battles with self-worth that had been there since childhood didn't disappear just because the business was growing—they amplified under pressure.
The normal complexities of partnership added another layer to navigate. Expectations came from every direction: clients who trusted us with significant assets, friends and family that needed us present and a church community that goes and goes. Every milestone that should have been celebrated felt like another plate to keep spinning.
The company was succeeding. Personally, there was work to do that success couldn't solve.
The Other Side of the Coin
None of this is to say it was all struggle. We had a ton of fun along the way. There were client wins that felt incredible—property owners seeing returns they never expected, getting thank-you messages that made the long hours worth it. Clients were stoked, and that energy was contagious.
We traveled, celebrated milestones, had moments where we looked at each other and couldn't believe what we'd built. Managing 130 properties meant 130 different challenges, and solving them was genuinely satisfying work. The systems we built, the relationships we developed with vendors, the way everything came together when it worked—there was real satisfaction in that.
The happy memories are just as real as the struggles. The difference now is understanding that the fun parts don't require sacrificing the peace parts. We can have both.
When Everything Shifted
Becoming a father recalibrated everything. Holding my son for the first time made it clear that none of the numbers mattered the way we thought they did. The 130 properties, the millions generated for clients, the validation from growth—all of it paled in comparison to being present for him.
In the last year we scaled back the vacation rental portion of the company entirely. The part of the business that had defined much of our early success, the piece we'd been most proud of, we let go. The market was shifting, and rather than chase volume in an evolving landscape, we chose to focus our energy where we could serve fewer clients better—with more presence and less pressure. Some people thought it was crazy. Others understood.
The truth was: priorities were finally aligning with what mattered most.
Peace as Income
These days, wealth gets measured differently. Peace has become our greatest income. The peace of watching those first steps. The peace of being home for dinner. The peace of knowing that family gets the best of us, not whatever's left after ambition takes its share.
Success without peace is just expensive anxiety. There were years of that. Peace wins every time, and it makes everything else—including business—better.
The Humility That Changes Everything
At every peak of success, at every moment when it would have been easy to take credit for the growth, humility kept trying to break through. Sometimes it came through personal struggle that success couldn't solve. Sometimes through recognizing that childhood wounds don't heal just because adult bank accounts grow. Sometimes through the simple truth that performing well externally doesn't mean thriving internally.
Real humility is understanding that success sits on a foundation we didn't entirely build. It's acknowledging the incredible clients who took chances on us, the market conditions that were favorable, the cleaning companies, handyman services and vendors who showed up reliably so we could scale, the systems and automation that made managing 130 properties possible.
Humility is staying curious when there's every reason to feel certain. It's listening more than talking, especially when holding the most success in the room. It's treating vendors and service providers with the same respect as the investors writing checks.
Humility means recognizing when to scale back, when growth is costing things that can't be bought back. It means admitting that external success doesn't fix internal struggles, and that's okay—they're separate journeys that both deserve attention.
What Gets Carried Forward
Everything else turned out to be conditional. The money, the growth, the number of properties under management—all of it could shift. Market conditions change. Industries evolve. What worked at 25 might not work at 35.
Humility is portable. It works in every season, at every stage, whether building or rebuilding. It makes business better while keeping us teachable. It makes relationships better while keeping us grateful. It makes life better while keeping us grounded.
Most importantly, it helps recognize what actually matters before too much of it gets sacrificed on the altar of ambition.
At 31 with a son who won’t know how many properties we manage (until he’s 16 lol) or how many millions we generate for clients, the math is clear. He'll remember whether we were present. Whether we were humble enough to prioritize him over proving ourselves. Whether we understood that peace is the greatest income.
The path taught humility through years of learning that external success and internal peace are different pursuits—both valuable, both necessary. Our son is giving us the chance to live that lesson intentionally. The clients we serve today benefit from that growth.
The business continues. The numbers still matter. The difference is understanding what they measure and what they don't. Success looks different now—quieter, more grounded, more sustainable. That's not a retreat from ambition. It's ambition that finally knows what it's actually after.
We're building something that internally feels different now—focusing on our long-term residential management with owners who appreciate the same shift we've made. Fewer properties, deeper relationships, same succesful outcomes. If that sounds like the kind of partnership you're looking for, we'd love to connect: www.johnsonpacific.com
Everything = Everything
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