For Years, This Is What I Wanted from My Work. Then a Bike Ride Made Me Question Everything.
We work hard. We work a lot. But we don’t often ask what the point of it all is.
This story appears in the September 2026 issue of 91.
My friend has been working like a dog for decades. He’s made some money. He’s had some success. But lately, he told me, he’s been asking himself a big question: What am I actually working for?
The obvious answers are there: He’s ambitious. He’s growing his company. He’s making more money. But again, to all of that — what for?
The question nagged at him, because he wasn’t sure of the answer.
When he told me this, I recognized it immediately. After a career in which I’ve pushed myself relentlessly, often thinking about nothing but work, I’ve been asking myself the same thing.
Then I told him something I’d never quite put into words before: “Whatever I’m working for, I think it’s time to start enjoying that.”
That stopped us both. I want to share why.
About five summers ago, my family and I were visiting my parents in Colorado. I set myself up outside in a chair, anchored to my computer as usual, and worked all day, every day.
One afternoon, a neighbor rode by on a bicycle and asked if I wanted to join him for a ride. I said, No thanks, I’m working. He took off.
The next day, the same thing happened. So I asked him: How does he have time for a bike ride in the middle of the day?
He said he just makes the time. He works hard, has some free time, and uses it like this. Then he took off again.
On the third day, he invited me again. And I realized something: For years, when people — including my wife — asked me what I wanted from work, I’d say, “I want full autonomy of my time.” I wanted to spend my time however I saw fit.
And yet there I was, sitting in that chair, not doing anything meaningfully different with my time. What was the point of having full autonomy if I did nothing autonomous with it?
So I went on the bike ride. Then more bike rides. I slowly started to build extra flexibility into my days.
If you haven’t asked yourself some version of this question, I encourage you to. So I’ll write it again: What am I doing all this work for? And is it time to start enjoying whatever that is?
Are you working for money? Great. How are you spending it?
Are you working for flexibility and time? Great. How are you spending that time?
Are you working for personal satisfaction? Great. Are you doing the things that actually satisfy you?
So often, we put off the purpose of something until later. We think of now as “grind time,” as if it’s all for some future version of ourselves. But if we never stop to actually appreciate it and to take advantage of it, we just keep working toward an unknown future. And then, truly, what is the point?
I’ve met people at the tail end of their careers who worked tremendously hard and never stopped. I’ve met billionaires in their 90s still grinding. I’m sure they got things along the way — money, status. But was that what they actually wanted? Was there something else along the way they could have paused to enjoy more?
I always wonder: Did they ever even ask the question?
Lately, I’ve been trying to answer it myself. It’s time to use the time I’ve worked so hard to reclaim. I’ve gone on lunches with friends. I’ve gone on long walks. I’ve said yes to more things, just because they sound enjoyable, even if they leave me with a little less time to work.
I’d encourage you to do the same: Ask yourself what you’re actually working for. Not what you’re doing, not what your goals are — but the real outcomes all this effort is supposed to deliver.
Then go take advantage of it. Because the work will always be there. But your time won’t.
My friend has been working like a dog for decades. He’s made some money. He’s had some success. But lately, he told me, he’s been asking himself a big question: What am I actually working for?
The obvious answers are there: He’s ambitious. He’s growing his company. He’s making more money. But again, to all of that — what for?
The question nagged at him, because he wasn’t sure of the answer.