Jul 7, 2026

Success was supposed to feel better than this

Ron Pratt

It was December 23rd. I was on one of the higher floors of a building in Hudson Yards, finishing a deck.

Not writing it. Finishing it. The kind of finishing where you're just moving the mouse around at that point — tightening a headline, re-checking a number, hitting Control + S (save) and Control + P (print) out of muscle memory because you've done it so many times your hands know the keystrokes better than your brain does. We needed it out the door before the holiday. I needed to be at JFK in three hours.

I remember checking Google Maps on my phone more than once. Hudson Yards to JFK, at that hour, cutting through Brooklyn. I already knew it was going to be close.

I finally got the deck out, got feedback, made the last round of changes, and jumped in the Uber. Three hours before my flight. An hour and a half of traffic sitting between me and the gate.

And somewhere on the BQE, sitting in that traffic, I noticed something that wasn’t about my job, or even the stress of holiday travel, but about what I felt in my body. I noticed I wasn't relaxed. My shoulders were up near my ears. My jaw was tight. I'd been tense for so long I'd stopped feeling it as tension (it just felt like any other Tuesday).

And then I had a thought, seemingly out of nowhere: this was supposed to feel better than this.

I'd done the thing. Good grades, good school, the MBA, the consulting firm — the whole path, followed in order, exactly as advertised. By every metric anyone had given me, I was doing it right. And I was sitting in traffic on the way to a flight (which I ended up missing by the way!), having just finished a deliverable I didn't care about, feeling like I might lose it if one more thing went wrong that day.

That thought wouldn’t go away. It was eye-opening, disorienting even. My perspective shifted, like when you stare at a W and realize it’s actually an upside-down M. A magic-eye picture that suddenly comes into focus out of scattered parts.

For a while I didn't do anything with that thought. I didn't quit my job. I didn't have a plan. But I couldn't stop thinking about it. And once I started exploring the thought, I had an even worse one: this wasn't new.

I could trace the same pattern back through every job I'd had. Each one started the same way — genuine excitement, real engagement, the high of learning something new fast. And each time, once I got up the learning curve, my energy and enthusiasm started to drain. I'd stop caring about the actual work. I'd notice the culture didn't quite fit how I naturally operated. I'd start counting down instead of leaning in.

I used to think that was just what a job eventually feels like once the newness wears off. Now I realize it was information I didn't know how to read yet.

There's an image that circulates on LinkedIn every so often — a lineup of animals about to take an aptitude test, and the test is: climb that tree. There's a monkey, an elephant, a penguin, a fish, and a few others, all being judged by the same standard. I imagine the monkey is up the tree in seconds. The elephant is standing there confused. The fish, obviously, isn't participating in this exercise at all.

It's a simple image, but it names something precisely. When you put an elephant in a monkey's test, the elephant doesn't fail because something is wrong with the elephant. It fails because the test was never built for how it's made.

That's closer to what was actually happening in those jobs than anything I was telling myself at the time. It wasn't that I lacked discipline, or gratitude, or the ability to be happy with a good thing. It was that I kept measuring myself by a scoreboard that reflected achievement, while expecting it to show me fulfillment. It was never going to. Each time the gap showed up, I read it as a personal failing instead of a sign I was tracking the wrong number.

If any of this sounds familiar, if you've had your own version of that Uber ride, your own moment where something you were promised would feel like satisfying instead felt empty — I don't think you should be more grateful, I don’t think you should be able to ‘power through’, I don’t think you should be able to ‘deal with it’ because the people around you are dealing with it, I don’t think you’re just bad at being an employee, and I don’t think you need more discipline. I think you've just been assessing yourself through the wrong lens.

Most of us were taught to ask: what else do I need to accomplish to finally feel the way I'm supposed to feel? That question keeps you climbing. But climbing was never going to answer it, because accomplishment and fulfillment turn out to be two different things that are tracked differently, felt differently, and not guaranteed to move together just because one of them is going well.

I didn't have a fast answer to that when it first showed up for me. I'm not sure a fast answer to that really exists. I spent years figuring it out on my own, and it cost me more time than it should have. I wish I'd had someone who'd already done this to help shorten my path.

I built a tool for people who want a quicker path than I had — it's called the Career Restlessness Decoder and you can access it here.

But before any tool, the more useful thing is just this: noticing which scoreboard you've actually been checking. They're not always the same one.

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