At 35, I had everything a successful person is supposed to want. I owned three businesses, had a platform, made good money, and a decade of work I was proud of. I’d written books. People asked me to stand on stage and speak. By every external measure, I had made it.
I was also exhausted and miserable.
When I told people I was thinking of shutting it all down, they had suggestions. “Become an advisor, or an investor,” some said. (No thanks!) Learn to play golf,” said others. (lol, no chance.)
In desperation, I did something that seemed crazy to my business-owner buddies. I gave away half of what I’d built.
Turns out, it was the smartest thing I’d ever done.
Tzedakah and The Giving Paradox
There’s a principle in Christianity that I like, which basically says that we never own anything.
All that exists is a loan from God. Everything was God’s property before we arrived and will be returned to him after we die.
I like this because it puts into better perspective the concept of ownership. Getting more isn’t the point. Being more useful and enjoying more of what we have during our short time on this earth is the point. Which, in turn, frees us from the burden of ownership.
Tzedakah is a Hebrew word meaning “righteousness.” While charity is generally understood as the act of giving money, tzedakah differs in that it is an obligation to do what is right.
Giving isn’t just about financial gain or karma. It’s about enabling us to keep doing the work that we love with people that we enjoy being around. What I’ve found holds people back from giving is a notion of whether it’s fair or not.
In the case of my businesses, I started them, funded them, took all of the risk, and then gave away half of each to somebody else.
My business owner friends laughed at me. They thought I didn’t get it. I knew they didn’t.
Whether or not something is fair financially is only part of the conversation. My goal is to maximize the quality of my output while never missing a minute with my wife and kids.
So what if somebody else wins big and I could have possibly gotten a better deal? As long as the deal that I got was good and the deal that they got was good, that’s cool.
The Giving Paradox: Give more, get more.
What I gave away had real and tangible value. What I got in return went beyond money. I got more time, less stress, and more freedom to pursue mastery.
This sentiment crosses borders and religions. The most important sentiments always do.
In Chinese philosophy:
“Give a man a fish and you feed him for a day. Teach him how to fish and you feed him for a lifetime.”
The Islamic practice of sadaqah suggests its followers:
“guide the blind” and “support the weak with the strength of your arms.”
The giving paradox of giving more to get more is said in Judaism, Christianity, and Islam to bring you closer to heaven, God, and Allah respectively.
Ironic that the things that bring us closer to divinity also tend to improve our quality of life here on earth. Maybe all this talk of a greater power is just a handy way of nudging you toward being a better person for yourself and others. Kind of like Santa Claus, but for adults.
If an aspect of what you do is holding you back, give it away without care or consideration of whether it’s a fair financial trade. What you’ll gain goes far beyond money. And the most striking aspect is that it very often leads to more money too.
Having more often leaves us with less
Once I had some space to breathe, I could clearly see what I’d been doing wrong:
I had been trying to find happiness by accumulating more. More influence. More output. More responsibilities.
It wasn’t working. It was never going to work.
The counterintuitive truth is that having more often leaves us with less. Less presence, less fulfillment, and less of what actually matters.
Researchers have a term for what I experienced: hedonic adaptation. It’s our tendency to return to a baseline level of happiness regardless of positive changes in our circumstances.
- You get the promotion, and after a few weeks, it’s just your job.
- You buy the dream house, and by summer, it’s just your house.
The hedonic treadmill keeps spinning, and you keep running, but you never actually arrive.
Here’s a formula I come back to again and again:
Satisfaction = What you have ÷ What you want
The secret, counterintuitively, is to shrink the denominator. Want less. Not wanting something is just as good as not having.
But here’s some data from the American Time Use Survey what made me change my ways. It tracks how we spend our days as the years go on. These images come from my next book, Unhinged Habits.
Time spent with our children spikes in our thirties — then falls off a cliff.
Meanwhile, time spent with coworkers stays flat for decades.
We trade the irreplaceable for the replaceable.
The cruelest part is that the work that feels urgent today is usually something we won’t remember in five years. But our kids will remember we weren’t there.
The life you’re postponing isn’t waiting for you
“When I finally get the promotion, I’ll have time for my kids.”
“When I finally finish this project, I’ll call my parents.”
“When I finally save enough, I’ll take that trip.”
I told myself these stories for years. I suspect you have too. Consider a few more of the most common “When-I-Finally” traps:
But “when I finally” never comes, does it? The goalposts keep moving.
I’ll never forgot a lesson my Dad told me. Made me stop in my tracks.
We were on a walk and I said that once I hired a general manager, I’ll have more time.
He laughed. Then, my dad, a career manager (and man who I’d never heard say a swear word before) said:
“Jon. Problems never go away. Business is just one f***en thing after another.”
Promotions lead to more responsibility, not less. Projects get replaced by other projects. Savings goals revise upward.
Meanwhile, the window closes. Your kids grow up. Your parents get older. The trip never happens.
What you can do
1. Recognize the trap.
The first step is admitting that more — more success, more stuff, more commitments — isn’t the answer. It never was.
2. Audit your “when I finally” list.
Write down what you’re postponing and how long you’ve been waiting? (Be honest. I wasn’t, for years.)
3. Ask the subtraction question.
Instead of asking “What should I add to my life?” ask “What should I remove?” Maybe it’s obligations that drain you, possessions that clutter your attention, or professional commitments that crowd out the people you love.
4. Read this book.
My next book is called Unhinged Habits: A Counterintuitive Guide for Humans to Have More by Doing Less.
It captures something I believe deeply: the path to a fuller life runs through strategic subtraction, not endless accumulation. As the Harvard professor and #1 NYT bestselling author on happiness, Arthur Brooks, wrote in his endorsement, “This beautiful book will help you reorient your life around what matters most.”
If you liked Atomic Habits or Essentialism, you’ll love this book. Same lane, but a contrarian spin with more focus on the deeper values of relationships, health, and purpose.
Thanks for reading,
-Jon
