The Tentacle Economy | Okulez

Essay<br>Published July 22, 2026

The Tentacle Economy

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I am afraid of losing my job to AI. Most people I know are, even the ones who won't say it out loud. But<br>when I sit with that fear long enough, a second one shows up underneath it, and the second one is worse:<br>what do I do after?

I watched my father retire. He had given his whole working life to one thing, honestly and completely,<br>the way his generation was raised to. And the day it ended, everything slowed down. Old age seemed to<br>arrive all at once, not his body first, but the days themselves. There was suddenly nothing pulling him<br>into the next morning. That is what happens to anyone when the one thing they were handed gets taken<br>away, and in his time a man was only ever handed one thing.

I don't want to be caught the way his generation was caught.

Here is what took me a while to see. The fear of AI taking my job and the fear of retirement emptying my<br>life are the same fear wearing two faces. Both come down to this: you build everything around one thing,<br>and one day that one thing gets cut. AI cuts it early and without asking. Retirement cuts it on a<br>schedule. Either way, if that one thing was all you had, the whole animal stops.

That was the honorable deal in his day. One job, given everything, for a lifetime, and he kept his end<br>of it completely. But the deal only ever handed a man one arm. An octopus with a single tentacle isn't<br>really an octopus. Cut the arm and there is nothing else reaching into the world. My father never had the<br>choice I have now. That is the only thing that changed. Not him. The times, the tools, the deal.

So the answer, at least the one I've landed on, is to stop being a one-armed animal while you still can.<br>Grow more reaches. Not frantically, not a hundred shallow side-hustles, but real tentacles that touch<br>different parts of the world, so that no single cut can stop all of you.

I am not writing this from somewhere safe. I am afraid too. This is just what I have decided to do about<br>the fear instead of sitting in it: take on more projects than my one lane, and grow the arms now, while<br>the choice is still mine.

Start at work, because that is the arm you already have. Stop guarding one narrow job. The person who<br>does one thing perfectly and touches nothing else is the first one a model does perfectly instead. Reach<br>into the next project, and the one after that, until you are the person who understands how they all<br>connect, the one who is a pain to remove. That is not ambition. It is cover.

Then grow something that isn't your salary. Invest. Turn a hobby into money. And here is the one most<br>people skip: if your day job is digital, in IT, in front of a screen, put one arm somewhere physical. A<br>real business, with hands and inventory and a street address. That sounds old-fashioned right up until<br>you notice which jobs the models are coming for first, and it is the screen jobs. If your paycheck and<br>the thing eating paychecks both live on the same screen, you have not diversified, you have doubled down<br>on the target. The physical world is the one place the models can't reach yet.

Now, if you have ever heard me talk about investing, this sounds like a contradiction. I preach<br>concentration. One or two high-conviction bets, don't spread thin just to feel safe. And I still believe<br>that, completely. But growing tentacles isn't spreading thin. It is a search.

You don't yet know which reach is the one worth concentrating on. So you try. What if real estate clicks?<br>What if the small product idea clicks? You can't know it from the armchair, you have to put an arm in the<br>water and feel. Most of them won't click, and that is fine, that is the plan, as long as you keep each<br>one small. It is the same discipline I use on the flyers, the speculative corner of my trading: keep each<br>one small, expect only a few to land, and let the one that lands pay for the rest. And a tentacle is<br>kinder than an option. An option that misses expires at zero. A reach that never turns into income still<br>leaves you the skill you built and everything you learned growing it. None of these arms get cut off. You<br>keep them all. That is where the risk management lives: you cap what each reach can cost you, you let the<br>winner run uncapped, and even the reaches that never pay leave you stronger than you started. You grow<br>tentacles to find the one that hits. And when one hits, then you pour in. The concentration comes after<br>the search, not instead of it.

Here is the part people get wrong about moving fast. They think the tools mean you can build anything<br>fast. You can't. What you can build fast is the thing you have secretly spent years getting ready for.

This product took me a few months to ship. It also took twenty years, and a pile of things that never<br>made it. I had tried to build software before, more than once. I hired developers, some offshore,...