You're Spending Your Life Earning Things You Don't Have Time to Enjoy
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At some point, the earning and the enjoying diverged. You kept optimizing for one and forgot the other existed.
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A guy I know bought his dream house last year.
He’d been working toward it for a decade. Saving aggressively, turning down vacations, saying no to weekends off for years. The house was the goal. The tangible proof that all the sacrifice was worth it. Four bedrooms, a backyard, a home office with a view. Everything he’d been picturing since his late twenties.
He moved in on a Saturday. By Monday he was back at his desk working 12-hour days. I asked him a few months later how the house was. He laughed in a way that wasn’t really laughing and said “I wouldn’t know. I leave before sunrise and come home after dark. The nicest room in the house is the one I see the least.”
He’d spent a decade earning the house. He didn’t have the time to sit in it.
I keep thinking about that. Not because his situation is unusual. Because it’s the norm. People spending years of their life earning things they don’t have the time, energy, or presence to enjoy. And by the time they notice, they’ve built an entire life around the earning and have no idea how to stop.
The Divergence Point
There’s a moment in everyone’s career where the earning and the enjoying split.
Early on, they move together. You get your first real paycheck and your life gets better in ways you can feel immediately. The apartment without roommates. The vacation you pay for without checking your account balance. Earning more and enjoying more are on the same track, moving in the same direction.
Then at some point, they diverge. You keep earning more but you stop enjoying more. The raise comes with more responsibility, which comes with more hours, which comes with less time for the things the raise was supposed to fund. The promotion looks great on paper and erases your evenings.
You cross the divergence point without noticing because the earning keeps going up. The paycheck increases, the title improves, the house gets bigger. The metrics that society uses to measure success keep climbing. So you assume the trajectory is right.
But the enjoyment flatlined somewhere behind you. You blew past it while chasing the next milestone. And the distance between what you’re earning and what you’re experiencing grows wider every year.
The Upgrade Trap
The mechanism that makes this so hard to escape is simple. Every time you earn more, you upgrade your life. And every upgrade creates new obligations that consume the time and energy you’d need to enjoy the upgrade.
The bigger house needs a bigger mortgage, which demands a bigger salary, which means a bigger role and longer hours. You bought the house so you’d have a beautiful place to spend time. The house is the reason you have no time to spend. The thing you earned and the capacity to enjoy it move in opposite directions. Each upgrade tightens the ratchet.
Psychologists call the underlying mechanism the hedonic treadmill. Humans adapt to improvements in their circumstances remarkably fast. The new house feels amazing for about three months. Then it’s just your house. The raise feels life-changing for about six weeks. Then it’s just your salary. Each thing you chased delivers a burst of satisfaction that fades faster than you expected and gets replaced by the next thing to chase.
The treadmill never stops because the adaptation never stops. And the only way to keep feeling the high of the upgrade is to keep upgrading, which keeps requiring more earning, which keeps consuming more time. You’re running faster to stay in the same emotional place. And you keep running because stepping off feels like falling behind.
“I’ll Enjoy It When...”
There’s a sentence that runs underneath all of this. You’ve probably said some version of it today.
“I’ll enjoy it when things slow down.” Or after this quarter. Or once this project wraps. Or when you hit a number that, if you’re honest, will be replaced by another number the moment you reach it.
The enjoyment is always conditional. Contingent on a milestone that keeps moving. I’ve done this for years. I told myself I’d take a real break once the podcast hit a certain number. Then I hit it and set a new target. The break never happened because the target was never the point. The point was having something to chase, because chasing is the only mode I knew how to operate in.
Bronnie Ware spent years as a palliative care nurse, working with people in the last weeks of their lives. She recorded their most common regrets. The second most common one, right after “I wish I’d had the courage to live a life true to myself,” was this: I wish I hadn’t worked so hard.
Not earned more. Not bought the bigger house. Worked so hard. The people at the end of their lives weren’t looking back wishing they’d earned more. They were looking back wishing they’d been present for the life that was happening while they were earning.
The Presence Deficit
Even when we’re technically “enjoying” something, we’re often not there.
You’re on vacation but checking email between courses at dinner. You’re at your kid’s soccer game but mentally drafting a message to a client. The beautiful house you worked a decade to buy becomes the place where you scroll through your phone, not because anything is happening on it, but because being still feels wrong.
The problem isn’t just that you don’t have time to enjoy things. It’s that you’ve trained yourself out of the ability to enjoy them. The muscle for presence has atrophied. Being present requires you to stop thinking about what’s next, and if you’ve spent the last 10 years optimizing for what’s next, stopping feels like falling behind. The anxiety of not producing is so loud it drowns out the thing you’re supposed to be experiencing.
I felt this on a trip with Gina last year. We were somewhere beautiful. No work obligations. Nothing urgent. And I couldn’t stop reaching for my phone. Not because anything was happening on it. Because the silence made me uncomfortable. The absence of productivity made me anxious. I was sitting in a place I’d been looking forward to for months and I couldn’t be in it because my brain was still at my desk.
That was the moment I realized the problem wasn’t time. It was capacity. I’d spent so long in earning mode that I’d lost the ability to shift into anything else. The switch was rusted shut.
What You’re Actually Optimizing For
When you step back and look at how you spend your hours, not what you say matters but how you allocate your time, the picture gets uncomfortable.
The earning system has perfect feedback loops. You earn more and the number goes up. You get promoted and the title changes. Every step is measurable, visible, and socially validated. People congratulate you. Your parents relax. The scoreboard updates in real time.
Enjoying has no feedback loop. Nobody congratulates you for being present at dinner. There’s no promotion for taking a weekend off. No metric tracks how fully you experienced a Tuesday evening with someone you love. So enjoyment gets deprioritized, not because you decided it didn’t matter, but because it doesn’t have a scoreboard. And in a life full of scoreboards, the thing without one quietly disappears.
You end up optimizing for metrics that nobody on their deathbed has ever wished they’d improved.
The Recalibration
I’m not going to tell you to quit your job or sell your house or dramatically downshift your life. That’s not realistic and it’s not the point.
The point is noticing where you are on the treadmill and asking whether the next upgrade is going to make your life better or just more expensive.
The next time a bigger role, a bigger purchase, or a bigger commitment is on the table, run it through one question: what does this cost in time, and is that time currently spent on something I value? Because the cost of the upgrade isn’t just the price tag. It’s the hours. And the hours come from somewhere. Usually from the parts of your life that don’t have a scoreboard.
And if you’ve been telling yourself “I’ll enjoy it when...” for more than a year, stop and look at the pattern. You’ve said this before. You reached the milestone, didn’t enjoy it, and set a new one. The sentence is a loop, not a plan. Recognizing it as a loop is the first step to stepping off.
The Metric Nobody Tracks
The metric that matters most in your life is the one nobody measures.
Not your income or your net worth or your title. The metric is: how much of your life are you present for? Not watching it pass by while you think about work. Not enduring the week until the weekend arrives. Present for. Feeling the weight of an ordinary evening with someone you care about and knowing, in that moment, that this is the point of everything you’ve built.
The house doesn’t matter if you’re never in it. The income doesn’t matter if it funds a life you’re too busy to live.
You know this. Everyone knows this. It’s the most obvious insight in the world. And almost nobody lives according to it because the treadmill is loud and the present moment is quiet and we keep choosing the loud thing over the quiet thing until the quiet thing isn’t available anymore.
Bronnie Ware’s patients figured this out in their final weeks. They had absolute clarity about what mattered and zero time left to act on it.
You still have time. The question is whether you’ll use it to earn the next thing or to experience the things you’ve already earned.
The earning will always be there. The time to enjoy it won’t.
Thank you for reading,
Scott
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