As you get older, you get wiser, right?
Well, I hope so, and that’s what this video is about. I turn sixty this month.
On the one hand, that sounds impossible to believe. On the other hand, of course, I’m turning sixty. As the old song goes, “Every time I look in the mirror, all the lines in my face growing clearer.”
Yep. The decades really do fly by. Some things never change. Ssix-year-old me (below) grilling t-bones over charcoal has morphed into 60-year-old me still loving a great ribeye and my Big Green Egg.
I want to offer 10 reflections, life lessons if you will, that I think my younger self would want to know, and perhaps you, as someone with a few fewer decades under your belt, can learn from them too.
With that said, here are 10 life lessons I’ve learned in six decades.
1. Character, Not Competency, Determines Legacy
Here’s what haunts me:
Your kids won’t pull out your subscriber count at your funeral.
They won’t replay your best podcast episodes or mention that presentation you gave. Instead, they’ll talk about who you were—how you loved them, whether you were actually there for them or not.
Character isn’t just important—it’s pretty much everything. While knowledge puffs up and achievements fade, character lasts.
That promotion you’re chasing? The glow fades before you’ve told the last friend about your new title. The platform you built? Someone else’s will be bigger next year.
Honestly, the hedonic treadmill is real.
But character—the slow work of becoming more like Christ—that’s what transforms your legacy.
If strangers on social media love you, but your kids don’t, you win at the wrong game. If you’re crushing it online, but your spouse feels alone, something’s deeply broken.
Sanctification isn’t just an esoteric theological construct—it’s God chiseling away at who you are, not fuelling what you do.
Without character, what’s left? Just a pile of stuff heading to Goodwill and achievements nobody cared about as much as you did.
As good as you might be at whatever you do, your character, not your competency, determines your legacy.
2. Give The People Closest To You Your Best (Not Your Leftovers)
Here’s the danger: the people you love most are the ones you’re most likely to cheat.
You skip dinner because “they’ll understand.” You work through vacation because you have “important things to do.” After all, you’re a big deal, right?
I fell into this as a young leader, and it nearly destroyed my family and me.
Here’s what nobody tells you: at eighty, if you’re lucky, all you have left is family and a few close friends.
Those “important” work relationships? They vanish the moment you leave your role. Just ask any retired CEO whose phone has gone silent.
Arthur Brooks nails it: there’s a massive difference between *deal* friends and *real* friends. Deal friends stick around for what you can do for them. Real friends are “useless but not worthless”—they can’t advance your career, but they’re the ones who actually care about you.
That’s why I made this decision: I want the people closest to me to have the best experience of me, not some random follower on social media.
So ask yourself, are your closest relationships getting your best, or are they getting your leftovers?
3. Understand That Everything Compounds (Literally, Everything)
Understand that everything compounds with time. Literally everything.
Life gets better or life gets worse in direct proportion to the decisions you make in your 20s, 30s, and 40s.
On the eve of my fiftieth birthday, a friend who had a few years on me said, “Your fifties are going to be fantastic.”
I pushed back: “Buddy, you’re not a prophet.”
His response haunts me: “I’ve seen this pattern hundreds of times. You did the hard work in your thirties and forties. Now you’ll reap the benefits.”
Turns out he was right. My fifties have been my best decade, hands down. I just wish I knew what I know now when my kids were younger.
Everything compounds.
Those ‘small’ compromises with integrity? They become character implosion. The debt you’re ignoring? It becomes a financial prison. The marriage tensions you’re avoiding? They become divorce papers or the icy staring into space you’ve seen too many elderly people embrace.
But the opposite is also true. Every time you choose character over compromise, health over comfort, or relationships over success, it compounds. Every single time.
So make your choice now.
4. Avoid Magical Thinking (See Your Past As the Best Predictor of Your Future)
You know what’s seductive? Thinking tomorrow will somehow be different while doing nothing about it today.
I see this all the time: leaders who think they’ll magically wake up more disciplined, more present with their family, or more financially stable. As though somehow their marriage will be transformed while they sleep, or that God will intervene without them taking any responsibility (possible, but not likely).
But life doesn’t work that way.
Your future isn’t created by wishing—it’s cultivated by habits.
Want to know what your life will look like in five years? Look at your calendar, experiences, and bank statements from the last six months. That’s your real trajectory.
- Your marriage in a decade? It’s being shaped by the conversations you’re avoiding right now.
- Your legacy? It’s being written in the small decisions you’re making this week.
- Your waistline in five years? It’s determined by what you’re eating today.
If you’re waiting for magical intervention, you’ll wait forever.
5. Wisdom Is A Better (But Less Popular) Teacher Than Pain
Pain is an expensive teacher, but at least you’ll never forget the lesson.
I’ve learned plenty this way: words I can’t take back, decisions that haunt me, relationships I destroyed thinking I was right. Pain taught me a lot.
But here’s the truth: wisdom is offering you and me the same lessons, minus the scars.
What strikes me after reading Proverbs annually for 25+ years? A full third of the book is basically Solomon begging us to choose wisdom before pain forces our hand. It’s like he’s watching a train wreck in slow motion, pleading with us to change tracks.
Yet, most of us default to learning things the hard way. We nod at wisdom, then dive headfirst into the very disasters it warned us about.
The irony? Pain is expensive. Wisdom is free.
And here’s the kicker: there’s never a line for wisdom.
Pain’s got a long line of people waiting for the next lesson. So save yourself some time and potential catastrophe: choose wisdom as your teacher.
6. Seize Your Internal Locus of Control
There are two kinds of people. People who blame everything and everyone for their misfortune and those who look inward to see what part of the challenge might have been them.
Bad day? Blame the weather.
Team issues? Clearly their fault.
Marriage tension? If only she understood my work better.
I struggled with this until I discovered what experts call an internal locus of control—the idea that I have agency. That regardless of circumstances, I could choose my response.
When I embraced the seven words “as far as it depends on me,” suddenly, I wasn’t waiting for the world to change. I was changing my world.
Instead of “Why is this happening to me?” ask “What can I do about this?” Instead of waiting for perfect conditions, create better ones.
You won’t control everything. But you’ll stop being a victim of your circumstances and start making progress.
7. Examine Your Motives
No matter how hard you try, your motives will always be mixed. Even recording this now, hoping to help others, I can feel that familiar tug – wanting people to watch it, to share it. I’ve fought against selfish ambition for years, and while it’s quieter now, it still shows up uninvited. Ugh.
You may never fully get rid of mixed motives, but you can see them clearly. Get honest about what’s really driving you, then surrender the drive again and again.
Why does this matter? Because…
Unexamined motives drive you until they destroy you.
Sure, you can end up with a story of redemption, but why drift into the conditions that create something in need of redemption in the first place?
8. Work Toward Mastery
Most of us start as generalists in our twenties, appropriately saying yes to (almost) everything. But moving through your thirties and forties does something interesting – it refines and narrows your passion, helping you zero in on what you’re truly gifted at.
I’m looking at my sixties differently. I see them as a chance to pursue real mastery, to get as good as I possibly can at just a handful of things. Think about a samurai swordsmith – it takes a lifetime to perfect that craft. That’s what I want – the chance to achieve mastery in one or two areas of my field.
As you age, narrow your focus list, put your foot on the accelerator, and learn and hone as much as you can. Your 10,000 hours are accumulating. Direct them.
9. Advance (Don’t Cruise or Retreat)
I have seen some friends, over the years, unchecking boxes of things they used to do that they no longer do. I get it. Everyone’s health and desires change with time.
But what if you saw the season of life you’re in as a chance to discover and try new things? Curiosity and newness make you better as you age.
I’ve never been particularly athletic, but at 55, I took up downhill skiing again (largely because my wife never gave up skiing, but her friends had mostly given it up). She wanted to be able to ski with a friend, so why not me?
At 58, I skied the Rockies for the first time in decades, and at the local ski hills now (i.e. not the Rockies), I routinely do black diamonds.
Throughout my fifties, I’ve picked up other new experiments and hobbies (from weightlifting to snorkeling, smoking brisket, playing with AI, becoming more financially literate, learning how to sharpen kitchen knives, and brewing first-rate home coffee).
So, as you get older, you’ll drop things that you no longer want to do but keep adding new experiences and skills so you don’t stagnate, grow bored, or grow old.
10. Retirement: Consumption Is a Trap, But Contributing Isn’t
Retirement is an interesting concept (and a relatively recent construct). Throughout most of history, people worked until they died because they had to, and they generally died younger.
I’m fortunate that I love what I get to do (build in to leaders), and we’ve joked with friends that we’re taking our retirement as we go. I’ve taken July off for the last decade, and my wife and I tack extra days onto business trips. Six weeks a year is plenty of retirement for me.
Heading into a new decade, I have no plans to step back. Instead of seeing the decades ahead as a chance to consume, I’m viewing them as a chance to contribute. To mostly give, not mostly take. To make a difference instead of taking endless victory laps.
Sure, there may be a day when speaking invites stop and time passes my “market value” by. But market value isn’t the same as value. At eighty, I might meet with pastors and leaders for coffee, gather young leaders, mow my neighbor’s lawn, or just brush snow off a stranger’s car in a Toronto parking lot.
The longer I’ve thought about it, the more I think retirement is a trap.
So, instead of imagining the decades ahead as a chance to consume, I think of them as a chance to contribute. It’s a chance to give, not mostly take. It’s making a difference instead of taking a victory lap or five.
You can only lie on a beach for so long.
Meaning is found in the giving far more than in the getting.
Whatever decade you happen to be in, everything compounds
What changes do you need to make now to have a better, more fulfilling future years from now?
