50 Things I'd Tell My Younger Self
Hard-won advice on faith, family, business, and the fight to keep growing.
A Thought...
I’ve been thinking a lot lately about growth, aging, and how different I feel from the kid who started his first business. Back then, I moved fast because I didn’t know any better. I took risks because fear hadn’t caught up yet. It was raw, messy, and full of momentum.
Now? I’m older. I’ve got a wife of 10 years, two incredible kids, multiple exits under my belt, and hundreds of employees across different continents. The stakes are higher. The noise is louder. The weight of responsibility is real.
But here’s what I’ve learned:
You don’t stop evolving just because you’re comfortable. Or successful. Or older. You only stop if you choose to.
We all look back sometimes and wish we’d known more, moved differently, thought bigger, or simpler. And that reflection? It’s worth paying attention to. Because if you don’t, life repeats the lessons until you do.
50 Things I’d Tell My Younger Self
In 2014, I wrote a list of 16 things I’d tell my younger self. A decade later, I’ve got a lot more to say.
Let’s dive in.
Get serious about your health early. Nothing else matters without it.
Your wife will be your greatest asset—treat her that way every day.
Saying “no” is a superpower. Use it often and without guilt.
Speed is good. Endurance is better.
Your kids won’t care about your work, they’ll care if you were there.
Don’t fake confidence. Build competence, it’s quieter and more lethal.
Everything is sales. Learn how to sell early.
You’ll never regret over-communicating.
Build things that outlast you.
Rest is a tool, not a reward.
Learn to sit with discomfort, it’s where growth happens.
Take the meeting. But don’t take the bait.
Integrity is expensive. Pay it anyway.
Hire slow, fire fast. Always.
Forget perfection. Speed of iteration wins.
You don’t need motivation. You need systems.
Watch your circle. Who you spend time with writes your future.
Your instincts are better than you think, trust them.
The best deals happen off the record.
Ownership > Titles. Every time.
Being a father will break you open in the best way. Let it.
Learn to love boredom, it’s where clarity is born.
Stay out of debt unless you’re using it as a tool.
Don’t outsource your values.
Build things that make you proud to tell your kids about.
Reputation takes years to build and seconds to destroy. Guard it.
The loudest person in the room usually knows the least.
Stay dangerous, complacency kills edge.
Never stop learning, even when you think you’ve “made it.”
Don’t let success make you soft.
Build margin in your life; financial, emotional, and physical.
People will copy you. Let them. Execution wins.
Be kind, but don’t mistake that for weakness.
Chase peace, not just happiness.
Track your wins, but study your losses.
Comparison is poison. Run your own race.
Your greatest ideas will come when you’re outside, not behind a screen.
Work out your own definition of success earlier.
Stay humble. The market can humble you overnight.
Make time for friends who sharpen you.
Never stop asking: “What’s the worst that can happen?”
Don’t take criticism from people you wouldn’t take advice from.
Learn to love the process, not just the result.
Money solves money problems, nothing more.
Build things worth talking about.
Don’t chase trends. Build what matters.
Slow down when things get overwhelming, speed up when you’re clear.
Make sure your calendar reflects your priorities, not just your obligations.
Talk about money more, you’d have saved yourself a lot of headaches.
At the end of it all, it’s not about exits or accolades. It’s about the people who love you when everything else is stripped away.
I actually came up with 117 things, but we’ll stick it to 50 for today.
What I’m Listening To
Beatboxing has taken over my household lately, our eldest is fascinated by music, instruments, and sound itself. We’ve been watching video after video, and honestly, the skill level in the scene keeps blowing my mind.
Vahtang’s take on Black Betty is next-level. And if you want a deeper dive, check out Chezame’s reaction videos, they break down what makes these performances insane.
Question I’m Pondering
Am I building a life my kids will want to model or just one they’ll inherit?
Until Next Time
Keep building what matters.
Love your people well.
– Jacques
P.S. If you enjoyed this, share it with someone who thinks like you.
Check out other things I’m busy with:
We Edit Podcasts – A full-service B2B podcasting agency that helps brands turn listeners into customers.
Hunting Portal – Your next hunting adventure starts here. Outfitters, taxidermists, gear heads, and more.
Halalisana — We help township-based businesses grow, scale, and thrive in South Africa. We offer conferencing, co-working, and a coding academy.