The Paradox of Progress: Why Having More Can Leave Us Wanting
When I started my first company, I thought freedom would follow. No boss, no office hours, no one telling me what to do. Just me, my laptop, and the wide-open promise of autonomy.
Instead, I found myself working more than ever.
The irony of our age is that we’ve made breathtaking progress—technological, medical, and otherwise—under the banner of freedom and ease. Yet many of us feel more trapped, more anxious, and more overwhelmed than ever before. The things designed to liberate us—the smartphone, the cloud, the work-from-anywhere ethos—have also shackled us to a perpetual mental treadmill.
We can work from anywhere, which now means… we work everywhere.
The Great Prediction That Got It Wrong
Nearly a century ago, John Maynard Keynes predicted we’d all be working 15 hours a week by now. Automation, he said, would eliminate the need for toil. Machines would handle the dirty work, leaving us to explore leisure, art, and family.
What happened?
Well, we did make the machines. But instead of slowing down, we sped up. We started multitasking and “optimizing.” And instead of choosing peace, we chose productivity—over and over again. Because beneath the convenience and speed of modern progress lies something far older and deeper: craving.
The Craving That Never Quits
Buddhism and Taoism understood something that our data-driven culture still hasn’t fully grasped: craving is insatiable.
The moment we hit one milestone—title, income, square footage—we see another gleaming just out of reach. So we push forward. And the more we achieve, the more convinced we become that just one more thing will bring peace.
Spoiler alert: it won’t.
This is the hedonic treadmill. You climb one peak of accomplishment only to see a higher one waiting. So you climb again. And again. Until you realize you’re not chasing success—you’re being chased by it.
As the Tao Te Ching reminds us: “He who knows he has enough is rich.” And yet, how few of us ever pause to truly ask, “Do I already have enough?”
Imagining Loss to Remember What We Have
There’s a Stoic practice called premeditatio malorum—imagining the loss of the things you hold dear. It sounds morbid at first, I know. But bear with me.
Imagine losing your eyesight. Or your partner. Or your health. Not as an exercise in anxiety, but in appreciation. When you truly see how fragile everything is, you also begin to see how precious it is. How enough it already is.
We rarely do this in our progress-obsessed culture. We focus on what's next. But peace doesn’t live in what’s next. It lives in the gratitude for what is.
Yes, Progress Is Amazing—But It’s Not the Point
Don’t get me wrong. I love progress. I’m fascinated by what AI can do, by what science is curing, by what we’re building together as a species.
Progress is a gift.
But it’s a terrible master.
If you tie your happiness to outcomes, you’ll always be at their mercy. Win the deal? Joy. Lose it? Misery. Get the promotion? Elation. Miss it? Defeat.
This rollercoaster is exhausting. It’s also unnecessary.
In Get Out of My Head, I talk about this exact trap. We give away our peace—not to bad things, but to good things. Success, ambition, growth. These aren’t enemies. They just make lousy landlords when we let them rent out our minds.
Work for the Process, Not the Prize
The ancient Stoics, Buddhists, and Taoists weren’t against progress. They were just clear-eyed about where happiness comes from. Not in the external world, but in how we relate to it.
As I learned firsthand building my company, the moment I stopped obsessing over the outcome—and focused on how I was showing up each day—everything shifted. I found more clarity. More presence. Ironically, more success too.
The key wasn’t more hustle. It was more equanimity.
Progress should be pursued for the love of the process, not the thrill of the prize. And when the prize does come? Great. Celebrate it. Then let it go. Don’t let it define you. Because nothing outside of you can.
What to Do With This
So how do we escape the trap?
Here are a few things that help me:
- Set boundaries. Just because you can work from bed doesn’t mean you should. Your mind needs places and times to rest.
- Practice negative visualization. Picture losing what you have—not to scare yourself, but to spark gratitude.
- Check your craving. Ask: “Am I chasing this because it brings me joy, or because I think it will finally make me enough?”
- Return to now. The only place you ever really own is this moment. The future is a dream. The past, a ghost.
Owning Your Journey
Progress will continue. It should. But let’s not confuse having more with being more. Let’s not mistake motion for meaning.
You are not your job title. You are not your calendar. You are not your inbox.
You are the thinker behind the thoughts. The being behind the doing. And when you can root yourself in that identity—not in your outcomes—you become unshakeable.
So climb that next mountain. Build that next company. Write that next chapter.
But do it because it brings you alive—not because you think it will finally make you whole.
You already are.









