What Would Your 18-Year-Old Self Think?

Three weeks into the Challenge, closing out the money leg of 5-5-5

If you’re new here, welcome to The BOLD Life. Each week I write about building wealth in money and in life, because the goal was never just a bigger account balance. It’s a life that actually feels rich. If someone sent this your way, I’d love for you to subscribe.

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My mom grew up in an Italian neighborhood in Pittsburgh, in a household of six that shared one bathroom. Bath time meant everyone used the same tub of water, one after another, and because she was the youngest, she got to go first, while the water was still clean. Her father, who had come through Ellis Island with little more than a bag of clothes and worked hard as a concrete finisher, got to go sixth and last, in the cold, dirty water. But he was happy because all he wanted was for his kids to have a better life than he did. My mom became the first in her family to go to college, then a schoolteacher, and eventually she built a career that gave me a very different childhood than the one she had.

My mom (center) with her two sisters, her brother, and her dad. Nonnie was likely behind the camera

The Treadmill

I think about that bathtub whenever I catch myself measuring my life against the wrong thing. You close the deal, you get the raise, the stock finally pops, and for a few days you feel like the richest person alive. Then you adjust. The new number becomes the new normal, and some quiet part of your brain starts looking for the next one before the last one has even settled in.

Psychologists call it hedonic adaptation. I just call it the treadmill, because that is exactly what it feels like once you notice it. I have run on it myself more times than I can count, and you can run as fast as you want while the scenery never changes, because the finish line keeps moving with you.

Me and my boys on actual treadmills. Not getting anywhere, but enjoying life together.

The fix is not one more win. I have chased enough of those to know that the top of the mountain always reveals another mountain behind it. The fix is where you point the comparison. Most of us compare up and forward, to the next milestone, the next number, the neighbor’s newer Range Rover in the driveway next door. Compare that way long enough, and you will feel behind no matter how far you have actually come. The comparison that actually works points backward instead. Measure yourself against where you started, and if you are willing to look a little further back, against where your family started, not where someone else is now.

Luckier Than You Think

My mom got the clean water because she was the youngest. Right now, roughly one in four people on this planet lack reliable access to safe drinking water, something you and I get by turning a handle in the kitchen. We live in the richest country the world has ever produced, and simply being born here put you ahead of a staggering share of humanity before you ever earned a dollar of your own.

I am not saying that to guilt anyone, myself included. I am saying it because we lose sight of it constantly. No matter where you sit financially today, somebody else on this earth would trade places with you in a heartbeat. We all have a lot more to be grateful for every day than we sometimes think.

What Would Your 18-Year-Old Self Think?

This is the question I think about when the treadmill starts speeding up. Not what does the guy two rungs up the ladder have that I don’t. What would eighteen-year-old me, or fifteen-year-old me mowing lawns around the neighborhood, think if he could see this exact life? The house. The family at the dinner table. The freedom to build what I want to build. He would not be unimpressed. He would be blown away.

That question works because it changes the direction you are measuring in. The version of you further down the road will never run out of things you don’t have yet. The version of you further back is a fixed point, and against that fixed point, almost everyone reading this has already done something remarkable. You do not have to wait for the next milestone to feel it. You can feel it right now, about the distance you have already covered, and still want to cover more ground tomorrow.

The Balancing Act

None of this means stop striving. I am not interested in a version of contentment that looks like giving up on growth, and I do not think you are either. Wanting more is not the problem. Wanting more while forgetting to notice what you already built- that is the problem. That’s why two of my favorite words are gratitude and progress. Together, those two words lead to happiness. Tony Robbins famously says that “progress equals happiness,” and I have a slight twist on his formula. For me, it’s “Gratitude + progress = happiness.” Appreciation is not the opposite of progress. It is what makes the progress worth having in the first place.

If you are so locked onto the finish line that you never look up and notice the race itself, you will cross every line you set for yourself and still feel like you are losing. Life is a journey. Enjoy the miles you are on right now, and keep pushing for more ground tomorrow, because both are true at the same time, and neither cancels out the other. Gratitude for the mile behind you and hunger for the mile ahead are not in competition. They were always meant to run together. Be grateful for what you have, but stay driven to keep making your future better.

Back to the 5-5-5 Challenge

This is where the money leg of the 5-5-5 Challenge comes in. Hopefully you have spent a few minutes each day for the last three weeks thinking about your money as part of the challenge. Those few minutes are part of the progress side of the formula. It is a small habit, but being conscious of your money rather than letting it drift on autopilot will have long-term positive repercussions. Remember, money compounds over time, and so does the positive daily habit of managing it. When you combine deliberate action with compound investing, your money can truly grow over time.

And why are we growing our money? To use it to magnify our values and live the life that matters to you. Minor in money, major in life.

Your Turn

Picture your eighteen-year-old self standing where you are right now, looking at your life today, your family, your work, what you have built so far. Tell me in the comments, in one line: what would they say?

Start Bold

1. Write down one thing in your financial life right now that your eighteen-year-old self would consider a miracle. Not the goal you haven’t hit. The one you already have.

2. The next time you catch yourself comparing up to the bigger house, the newer car, the louder success story, catch it, and consciously flip the comparison backward instead.

3. Do your five minutes on money today, whatever that looks like for you this month, and let it be driven by gratitude for how far you’ve come as much as ambition for where you’re headed.

We build financial wealth not for status or scorekeeping, but to fuel the areas of life that matter most: family, health, growth, generosity, joy. You are almost certainly further ahead than you give yourself credit for. Keep building anyway. That is The BOLD Life.

Don’t drift. Live boldly.

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