My Greatest Accomplishments at 50
I turn 50 today. I built more than I ever dreamed. None of it made this list.
I know I usually send out posts on Tuesday. But today is my 50th birthday, and I have some reflections as I think about this milestone. So you are getting a special Monday edition this week.
I expected to feel proud of what I’ve built financially when I turned 50. The businesses, the wealth, the life we’ve created. And I do. But when I sat down to reflect on what my greatest accomplishments actually were, none of that showed up. It was one of those moments that quietly reorders everything.
Here is what actually made the list.
Being a father. Nothing makes me prouder than watching my boys grow up into good human beings. They are kind, thoughtful, and genuinely amazing kids. When I stop and think about the fact that I had a hand in that, it hits me in a way that’s hard to describe. It’s one of the most powerful feelings I know.
Marrying the woman of my dreams. She’s beautiful, and I knew from the moment I watched her around kids that she was the one. I knew she would be the most incredible mother, and she is. I’ve written about this before, but the person you choose as your spouse is the single most important decision you will ever make. You will spend more time with that person than anyone else on earth. Make sure they make you happy, challenge you, and make you better. And make sure you are aligned on money, because that matters more than most people admit before they get married.
Taking care of my dad. I gave him the best life I possibly could, despite his physical challenges. Moving him to North Carolina to be near his grandkids. Buying him a home in our neighborhood that was wheelchair accessible. Caring for him when he could no longer care for himself. Giving him joy by letting him live vicariously through our family, sharing pictures and stories of our adventures. He was always so happy for us, so proud of me. He was my biggest fan.
Working alongside my mom. I get to see her almost every day, which is something most people don’t get. I have friends who see their parents a couple of times a year, and I get to see my mom at least a couple of times a week. I’ve read that one definition of success as a parent is your kids wanting to spend time with you when they become adults. My boys aren’t there yet, but I hope they will. In the meantime, I know my own parents succeeded, because I have always chosen to be around them.
Having an extraordinary network of friends. I still keep in close contact with a handful of people I’ve known since childhood, including my best friend, who is also my business partner in our construction business. We joke with each other every single day. We have been telling the same jokes for decades, and they never get old. Beyond that, I have built friendships at every stage of life, friends who started as clients, friends I met at the gym, friends we’ve made through our boys. Some of these people I have only known for a year, yet we connect as if we’ve known each other our whole lives. Jana and I have countless group text threads humming at all times. It’s one of my favorite things about our life.
The friendships that came through work. When I first started in business, a couple of people I respected as leaders gave me the same advice: keep work and personal life separate; it doesn’t end well. I understood their reasoning, but I quickly realized that wasn’t going to be my path. I started making genuine friends with clients, business partners, subcontractors, and employees, and I wouldn’t trade those relationships for anything. I have several close friends today who used to work for me but no longer do, and that change never touched our friendship.
The restaurant I owned is a good example. From a pure business and financial standpoint, it was a mistake, and I’ve told people plainly not to go down that road. But I met more people running that restaurant than almost any other venture in my career, and many of those friendships are still thriving today. It turned out to be worth it, just not in the way I expected when I opened it.
I think the reason work has produced so many lasting friendships for me is simple: I don’t separate work from my personal life. I am the same person no matter where you meet me. My values don’t change depending on the room I’m in, and because of that, every room has been an opportunity to find people worth keeping.
The trip that made it real.
This past weekend, we took a few days in Cancun with family and some close friends to celebrate. It was everything a milestone birthday should be, surrounded by the people who matter most, sharing meals, laughing, and making memories that will last. That is what your money is for. Not to sit in an account and look impressive, but to create moments like that one.
And this one was extra special. Jana and I share the same birthday. We also met at my 30th birthday party, which means this trip wasn’t just a 50th celebration. It was twenty years since the night we met. If I hadn’t thrown that party two decades ago, we might never have found each other. I think about that sometimes.
Did I have to go to Cancun to enjoy turning 50? Of course not. But doing something intentional, throwing a party, taking a trip, gathering the people you love, transforms an ordinary occasion into something you’ll carry with you for the rest of your life. Twenty years from now, I’ll look back on this weekend and feel exactly what I feel right now. That’s the whole point.
My mom likes to say there is no U-Haul behind the hearse. She’s right. You can’t take any of it with you. What you can do is spend it on the people and experiences that make life worth living, and then hold those memories close for as long as you have.
One more thing I’ve learned to do on the big ones.
I love anchoring major life events to something larger than the celebration itself. The trip, the party, the gathering of people you love, those are all worth doing. But I’ve also learned to pair those moments with generosity, and that combination is hard to beat.
When Jana and I got married seventeen years ago, we didn’t do a wedding registry. Could we have used the gifts? Honestly, yes. I recently found a spreadsheet from our wedding where I tracked every dollar we spent. But I’ve always preferred giving to receiving. So instead of asking for gifts, we funded a Make-A-Wish for a seven-year-old girl named Dakota who had been dealt a very difficult hand in terms of her health. We sent her to Disney. She loved every minute of it. She’s alive today and still remembers that trip.
For my 50th, we’re doing it again. This time for a local six-year-old named Milo who just finished three years of fighting leukemia and won. We’re sending him to Hawaii.
If you’d like to be part of it, here is the link: Milo Make-A-Wish
Money never showed up on the list.
As I finished that list, I realized something I wasn’t fully expecting. I have successful businesses. I’ve built more financial wealth than I ever imagined. I have a beautiful home, cars I enjoy, and all kinds of things that used to feel like distant goals. And not one of those things crossed my mind when I sat down to think about what I’ve actually accomplished. Not one.
I plan to keep growing, keep getting better, and keep living as fully as possible for at least another 50 years. But what this birthday reminded me is that life is genuinely short, and the things that matter when you pause and look back are almost never the things you thought would matter when you were in the middle of building them.
Build the wealth. But never lose sight of what you’re building it for.
Start Bold.
For my birthday, I have one ask. If you know me personally, drop a single word in the comments that describes our relationship. If we haven’t met yet, I hope we do one day. In the meantime, I’d love to hear one word that describes something you’ve taken away from this newsletter.
One word. That’s it. It would mean the world to me.
Rap-worthy
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