Getting what you wanted and feeling nothing

You hit the thing. The title, the money, the move, the island. And then you're standing in it and it's the same view.

I've done that twice.

First one was a middle management job in tech. Six figures, business development, flying everywhere, corporate card, an apartment in Sydney and another one in Melbourne. Everything I could've wanted on the money I was making. And I got there burnt out, lost, confused, wondering why I felt so trapped by the exact thing I'd spent years chasing.

So I did what most of us do with that feeling. I set a bigger goal. Quit, went into remote consulting, made more in a week than I used to make in a month, moved to Bali. Living on a tropical island with everything sorted, at least visually.

Second time was worse. Because by then there was nowhere left to put the blame. I had everything I thought I wanted and I kept coming back to the same problem. Everywhere I went, they were my problems. Common denominator was me.

Two things are usually going on when this happens and they're worth pulling apart.

One is the goal got picked for how it reads from the outside. You can show people a title. You can't show them a feeling. So you go after the version that can be shown, you hit it, and then there's nobody to show it to who makes it mean anything.

The other one is you inherited it. Somebody sold you a picture of the good life, you picked it up without ever really looking at it, and then gave it years. That's what happened to me with the whole laptop lifestyle thing. Do what you want, when you want, with whoever you want. It wasn't a lie exactly. It was just somebody else's, and if you ask me now what I want, it's not that, and it never was.

So this is about what comes after. And why the next goal doesn't fix it.

• Why do I feel empty after achieving a goal I worked years for?

  Because the goal was measured by how it looks from the outside, and the experience you wanted from it was never named. You hit the target, the view st…