Issue 78: What an octopus can teach you about your career

ISSUE 78

18 MARCH 2026 | READ ONLINE

Hi there Reader,

An old friend was in Seattle this week.

Phil Le-Brun. We've known each other for about 20 years. And he did the most Phil thing imaginable -- he made sure I ended up with a signed copy of his new book, The Octopus Organization, co-written with Jana Werner.

That's just who he is. Generous, thoughtful, always thinking about the people around him.

I read it yesterday (well, skim read - I want to dig deeper with my highlighter when I get a chance). And honestly? It got under my skin a little bit.

Not because it's a brilliant business book -- though it is. But because it kept pulling me back to something I care deeply about: the gap between how organizations say they work and how they actually work. And what that gap costs the people inside them.

Here's what Phil puts his finger on:

Most large-scale transformations don't work. What starts as a plan to drive meaningful change becomes an all-consuming distraction -- a value-destroying set of activities that, even when it's obvious they're going to fail, must still be completed at any cost.

I've been inside those transformations. I've led inside them. I've watched talented, committed, genuinely brilliant people burn themselves out trying to make a broken system work -- because somewhere along the way, they started believing the problem was them.

It wasn't.

And if that's where you are right now -- exhausted, underestimated, wondering why your best efforts aren't landing -- I want you to hear this: sometimes the system is the problem. Not you.

Phil's answer is an octopus.

The octopus is smart, endlessly adaptable, highly resilient -- with eight tentacles that work together beautifully, but where each arm can also think for itself. The intelligence isn't sitting at the top waiting to be handed down. It lives everywhere. In every person. Every conversation. Every decision is made close to the ground.

So many of us have spent years waiting for permission to use ours.

Waiting to be asked. Waiting for the right title. Waiting for the system to finally recognize what we already know we're capable of.

What if that wait is the thing worth examining?

Phil and Jana identify 36 antipatterns -- conditioned habits that keep organizations stuck -- and offer practical levers that create meaningful improvement. But what struck me most is how many of those patterns live inside us, too. The reflexes we developed to survive rigid systems. The habits that protected us once, but quietly limit us now.

That's the real career conversation. Not just how do we change our organizations -- but how do we notice what those organizations have done to us, and choose something different.

A Small Experiment for This Week

Option A: The Permission Check

Think about something you've been holding back on in your career -- an idea, a conversation, a move you keep almost making. Ask yourself:

What am I actually waiting for?
Who do I think needs to give me permission here -- and is that really true?
What's one thing I could do this week that only needs my own green light?

Option B: The System vs. Self Audit

Think about somewhere you've felt stuck or frustrated lately. Sit with these honestly:

Is this a me problem -- or a system problem?
If it's the system, how am I navigating it -- and is there a smarter way?
If it's me, what's one old reflex I'm ready to loosen my grip on?

The most courageous career move isn't always the big, visible one. Sometimes it's quieter than that. It's deciding to trust your own intelligence -- and stop waiting for the system to catch up.

Pick up Phil's book. It's the kind of read that changes the questions you ask yourself.

See you next week,