40 Things I’ve Learned (So Far)
On turning 40, and what life, leadership, failure, and love have taught me—so far.
I turned 40 this week.
I’ve always loved the annual birthday reflections Ryan Holiday shares—raw, simple lists of what life has taught him so far. I’ve read every one of them over the years. So this year, I figured I’d try my own. Not as a copy, but as a way to mark time. To take stock.
This isn’t a highlight reel. It’s not a TED Talk. It’s just what I’ve learned the hard way—through faith, leadership, marriage, parenting, business, books, and a few gut punches I never saw coming.
Some of these are obvious. Some I had to suffer to understand. All of them feel more true at 40 than they ever did at 30.
Here goes.
Faith & Perspective
Faith is the anchor.
Not just religion, but belief in something bigger. A higher power. A deeper meaning. It gets you out of your own head and keeps you grounded when the ground gives way.
Tragedy clears the fog.
Loss has a way of revealing what actually matters. What stays? Love. Time. Meaning. The rest fades.
Suffering is not the enemy—it’s the instructor.
Pain reveals what you care about. What you’re made of. And what needs to go. It’s not something to avoid. It’s something to learn from.
You’re not your worst moment. Or your best.
You’re the habits in between. The decisions you make when no one’s watching.
Don’t worship comfort.
The easiest life is rarely the best one. A little discomfort now and then means you’re still growing.
Family & Love
The person you marry is the most important decision you’ll ever make.
Marrying Nicki changed everything. She’s my partner, my anchor, and my closest friend. She believes in me when I can’t, and tells me the truth when I need it most. Life is better, deeper, and more grounded because she’s in it—and I wouldn’t want it any other way.
Kids don’t need a perfect parent. They need a present one.
They remember if you looked them in the eyes. If you showed up. If you were in it.
Living for others is the real path to joy.
Selfishness looks easy but feels hollow. Serving people—your family, your team, your neighbors—that’s where the meaning is.
The little moments are the big ones.
It’s the shared meals, the inside jokes, the bedtime stories. The ordinary stuff that feels forgettable in the moment—but ends up meaning everything.
Love is not a feeling. It’s a choice.
Made daily. Through action. Through forgiveness. Through showing up.
Leadership & Work
The job is never just the job.
How you show up to work is a mirror. Do it well, no matter what it is.
People don’t follow titles. They follow energy.
Your presence matters more than your position.
Feedback only works if it’s specific.
“Great job” helps no one. “I’d like to see more structure in your next pitch deck” might actually help someone improve.
You are what you tolerate.
From others. From yourself. Raise the bar.
You can’t think clearly if you’re exhausted.
Rest isn’t a weakness—it’s a weapon. You can’t solve problems if you’re barely holding it together.
Talent without character is dangerous.
It’ll get you attention. But it won’t keep it. Trust is what lasts.
Your job as a leader is not to be impressive—it’s to be useful.
To clear roadblocks. To speak truth. To protect your people and stretch them.
Most people aren’t playing chess.
They’re reacting. That’s not strategy. Don’t confuse chaos for depth.
Character & Integrity
Honor is underrated.
There’s still value in doing the right thing, just because it’s right. Even if no one sees it.
Don’t lose yourself trying to belong.
If fitting in costs you your voice, your values, or your edge—it’s not worth it.
Keep your heart open.
Letdowns happen. Don’t let them close you off or pull you under. Stay soft. Stay strong.
Don’t be afraid to walk away.
From bad deals. From bad culture. From people who drain you. That’s not quitting—it’s leading.
Self-control is a superpower.
The people I trust most are the ones who can hold their tongue, hold their temper, and still get the job done.
You become what you repeat.
Practice doesn’t just build skill—it shapes identity. Train what you want to become.
Humility is stronger than confidence.
People trust the leader who listens more than the one who talks.
Don’t just read about values—live them.
You either walk the walk or you don’t. There is no in-between.
Mindset & Growth
Mastery takes longer than you think.
If it’s worth doing, it’ll take years. Start the clock.
Small steps add up.
Forget breakthroughs. Focus on 1% better, over and over again.
Growth requires discomfort.
If you’re comfortable all the time, you’re not changing.
You don’t have to know everything. Just keep learning.
Beginners ask better questions anyway.
Discipline is freedom.
The more structure you build, the more space you create—for creativity, family, peace.
It ain’t the years—it’s the mileage.
Indiana Jones had it right. Wisdom doesn’t come from time alone. It comes from doing the work, taking the hits, and staying in the fight. Experience is earned, not aged into.
Comparison is poison.
Don’t measure your life by someone else’s highlight reel. Stay on your track.
Make your life hard in the right ways.
Choose the strain of building something meaningful over the ache of regret.
Reflection & Presence
Write it down.
Thoughts are slippery. Writing makes them real. Make sense of your life on paper.
Go for the walk.
It clears the head. It slows time. I’ve never regretted taking one.
Read old books.
They last for a reason. They’ll outthink most of the voices shouting today.
Be where your feet are.
Don’t miss what’s in front of you chasing what’s next. Regret and anxiety thrive in places you’re not.
Take your time—this is it.
Life’s not a warm-up. Time isn’t the enemy. It’s the medium we live and lead in.
The clock is running.
You don’t get forever. Use your time. Be grateful for it. Make something that lasts.
Final Thoughts
Forty years in, I’ve made more mistakes than I can count. I’ve learned some lessons the hard way, and others by grace alone. But I’ve also built a life I’m proud of—family, love, work, friendships, and a sense of purpose that feels hard-earned.
If I’m lucky enough to get 40 more, I hope I spend them still learning, still growing, and still doing the hard things that matter.
—Chris