I can’t think my way out of this

Welp.

Here I am again.

Another fork in the how-I-make-a-living road.

My current work contract ends in about a month. I may or may not be offered a permanent position, but staying on doesn’t seem fair to the team or myself because on the scale of Fuck Yes or No, I’m at a Fuck No. So I’ve been brainstorming what the hell I’m going to do next. And when I say brainstorming, I mean circle-jerking my thoughts into the ninth circle of hell, trying to future-proof my next decision as if I’ll end up on the streets if I get it wrong (which is false btw).

The last time I made a major shift, AI was a novelty. A mere knick knack. But things have changed and ChatGPT has been a trusty companion in bouncing ideas back and forth. Thankfully, AI’s patience is limitless because if it wasn’t I fear what sort of furious, CAPS-LOCK laden messages I might receive back.

After realizing I’ve been hammering the thing with hundreds of variations of the same question, I thought I’d give it a chance to tell me what it really thinks about me.

The Prompt: Given everything you know about me and my career issues, roast me and then offer some advice that I need to hear to make my life more beautiful and happy.

The Roast: You’ve spent more time researching businesses and skills you might enjoy than most people spend actually mastering one. If decision fatigue were an Olympic sport, you’d podium and then ask if you should pivot to speed walking or bobsledding instead. You’ve considered pest control, tile setting, sauna-building, wealth management, AND bookkeeping… but the only thing you’ve consistently built is an empire of Google Docs.

The Advice: Stop trying to outthink your way into happiness—start acting. You don’t need more ideas; you need direction and commitment. Choose one path that aligns with the life you actually want, and stay with it long enough to get good. Build your future around freedom and energy, not what feels practical or “safe.” You already have the skills—what you’re missing is belief and messy action. Life gets better the moment you stop optimizing and start living. Pick the thing. Go all in. And quit stalling behind analysis.

Oof.

You’re not wrong Mr. Robot.

I spend so much of my time researching, researching, researching… finding new reasons why my scheme of the month will fail.

But where is the goddamn execution, good sir?

I literally don’t know what will happen if I start doing things. Yet I try with every fiber of my being to capture certainty before acting. A hopeless cause, indeed.

On the bright side, I am fully aware that this is my modus operandi. Which means I can take steps to change my behaviour. Part of this is understanding that no matter what I do, as long as I’m “doing”, then I’m on the right track. It’s also understanding that there will be many, many twists and turns along the way that I can’t predict, but as long as I stay adaptable, I’ll be just fine.

Maybe.

I hope.

In the spirit of taking one small step instead of manifesting my entire life before it happens, I’ve settled on a direction. Nothing fancy. Maybe even kinda sketchy in the era of AI. I’m keeping it under wraps for now until I’ve passed through the regulatory hurdles and can hang my hat, but I’m feeling the right kind of nervous excitement. Just need some follow through.

There’s this great quote from Derek Sivers that I plan on revisiting as I continue to walk this path and it’s this:

”Never forget why you’re really doing what you’re doing. Are you helping people? Are they happy? Are you happy? Are you profitable? Isn’t that enough?”

There’s no crystal ball, but those questions can act like a flashlight, illuminating a few steps in front of me so I don’t walk off a ledge or something.

The truth is that I can’t think my way out of this.

But I can do my way out of this.