The Octopus Test: Real Constraint or Just an Excuse?
Jul 27, 2026
Previously we’ve talked about how the octopus has no skeleton, no bones, no rigid structure, no shell. Nothing to hide behind or retreat into … AND … no constraints on what it can be.
Well, not no constraints, it still has a tiny little beak … but otherwise no constraints. Everything is on the table.
Last week you left with a challenge, to hand something over and not take it back. I would wager that many of you thought about it and then came up with a long and distinguished list of reasons why your situation is unique and why it won’t work for you. Perfectly plausible and rational reasons. And I hate to be the one to tell you this, but other than modeling your business after honey badgers, crows, and octopodes … your situation is not unique. I’m sorry, but it’s true.
You and I both know the truth of those prohibitively limiting constraints. They are self-imposed. And self-imposed, or perceived constraints are the ones that feel structural but are actually just the legacy of habit, history, or discomfort.
The Octopus doesn’t find itself in a tight spot and decide that it’s big, it’s floppy, and it’s just going to be stuck there. It pushes, it tests, it tries everything … It turns into the equivalent of intelligent sea slime and slips through the tiniest of openings and it’s free.
I want you to be free too.
Change is hard. Adapting to change is hard. Especially when you not only have a skeleton, but have to work within the confines of the law, general ethics and morality, and a need to make money. Those are real constraints.
When you look back on the reasons you gave yourself for not handing anything off, everything there is likely a perceived constraint. It’s tradition, it’s scary to give up control, and of course you’ve got the classic “My clients expect to reach me directly, and only I can answer their questions properly.” Most owners carry those with them, almost like armor … never testing or questioning them.
They are effectively like my son when we play Minecraft. There’s nothing I can say or do that will get him to leave the house we built. It’s safe outside. It’s daytime. He’s well equipped … and yet, he won’t explore, he won’t mine or craft. He won’t live.
Unlike him, though, your constraints were probably real at some point. They made sense when you were by yourself, or when your team was new. And that’s what makes those limitations so insidious. You’re the one who created them! And they served you well! But you’ve grown, your business has grown, your team has grown, and those constraints aren’t serving you now … you need to explore, you need to mine, and craft, and you need to live. To be free.
So how do you tell the difference between a real constraint and a perceived constraint? A real constraint doesn’t give or change when you push on it. A perceived one will.
I’ll leave you with this. If you can’t hand off a simple task, you need to question all of the assumptions you’re making that tell you it can’t be done.
Like the octopus (whose cousin the squid exists in Minecraft by the way), do not talk yourself out of progress. Pick one thing you’ve told yourself you can’t do … pick the task you thought about but held on to last week … and push on the rationale behind keeping it. Take all the reasons that came up and push on them. Question them.
Don’t be like my son, refusing to leave a house of our own construction. Be like the octopus who cannot be contained.
If you're an attorney or financial advisor, you already know the version of this that shows up in your practice: "clients expect me personally," "no one else can review this the way I do," "it has to go through me." Test it this week. Pick the one task you're most sure only you can do, hand it off, and see whether the constraint holds or gives. Then hit reply and tell me what happened, or forward this to a colleague who's still carrying everything themselves.
Get Weekly Insights to Grow Your Business
Sign up for actionable strategies and expert tips delivered straight to your inbox every week—designed to help you break free from the chaos and achieve sustainable growth.
We hate SPAM. We will never sell your information, for any reason.