When was the last time you said YES while everything inside you was screaming NO?

Not a small yes. A real one. A board seat. An investor. A hire you knew was wrong in the first ten minutes. A dinner. A merger. A marriage.

Take a second. Actually look for it.

You probably can't find the date.

That is not a memory problem.

↳ You can't find it because you've done it so many times it stopped registering as a decision.

It became automatic. Like breathing. Like blinking. And somewhere along the way you started calling it something noble.

Being reliable. Being professional. Being a grown-up.

I did it for twenty years. I have nine companies to show for it.

And I could not tell you which of them I actually chose.

The part that makes this hard

Most leadership writing about people-pleasing gets one thing badly wrong. It treats the mask as a lie.

It isn't. Your mask is made of your real strengths.

You genuinely are the reliable one. You genuinely do carry more than your share. You genuinely can hold a room, absorb someone else's panic and make a decision when everyone else has gone quiet.

None of that is fake.

↳ What happened is that you froze a real quality into a fixed role — and then you got paid for it.

That's the trap. Nobody sells their soul in one transaction. You rent it out in small, sensible pieces and every piece gets applauded.

The reliable one gets promoted. The one who never causes friction gets the bigger territory. The founder who absorbs everyone's anxiety without complaining gets the term sheet.

The market pays you, generously, to keep the costume on.

And then one morning at 3 AM you're lying there fully awake, running a company you built, and something underneath the sheets asks a question you can't answer:

IS THIS IT?

Where the costume was actually stitched

You didn't invent this at 35 in a boardroom. You learned it before you could form a sentence.

The paediatrician and psychoanalyst Donald Winnicott described it in 1960 and I've never heard a better description of what happens inside a founder. He called it the False Self: the structure a child builds when their spontaneous needs are consistently met with irritation, absence, or coldness. The child works out - without anyone teaching it - that being what's wanted is safer than being what you are.

Carl Rogers called the same thing conditions of worth.

• Love arrives with terms attached.

• You learn the terms.

• You meet them.

• You survive.

  
  

The False Self is not a fantasy. Winnicott was clear about that. It is a caretaker. It exists to protect something underneath and it is built out of genuine compliance and genuine capability.

Which is exactly why it works so well.

And it keeps working, all the way up. It gets you through school. It gets you hired. It gets you funded.

↳ It just never lets you off the stage.

• The actor (you) plays the role so long he starts eating breakfast in character.

• He negotiates in character.

• He fathers his children in character.

• He goes to bed in character.

• And one day he wakes up and can't find himself without the costume.

  
  

Read that again.

Now look at your calendar this week and tell me which version of you is in those meetings.

You are not weak. You are standard-issue.

In 1951, Solomon Asch sat people in a room with actors and asked them to compare the length of three lines. The answer was obvious - a child could get it right (NB! This illustrative example is found by using AI :-))

The actors, one after another, confidently gave the wrong answer.

About 75% of the real participants went along with them at least once. On the critical trials, roughly a third of all answers were wrong - not because people couldn't see, but because everyone else in the room had already spoken.

These were not fragile people. They were people with functioning eyes.

↳ The pull toward agreement isn't a character flaw. It's the factory setting.

That should make you feel better for exactly four seconds and then much worse. Because if agreeing is the default, then every leadership position you hold is a position that requires you to override your own wiring, in public, repeatedly, while people watch.

Most leaders never do it. They just get very good at sounding like they do.

I know, because I was very good at sounding like I did.

What it actually cost me

I built nine companies across agriculture, IT, retail, sales and biotech. I've built and led over 600 sales teams. I built the world's largest outdoor medicinal mushroom plantation.

By every number on the outside, the strategy worked.

What the numbers didn't show:

• I destroyed my health.

• I was present at almost nothing.

• My relationship with my own father is two men who know each other's names and nothing else. And I watched my sons start drifting away from me exactly the way I drifted from him — because I had never learned how to be reachable, so I couldn't teach it.

  
  

I wasn't building companies. I was building evidence.

Nine separate arguments for why the version of me everyone approved of deserved to keep existing.

↳ You can't win an argument you're having with your own childhood. You can only fund it for longer.

I know how that reads. I know some of you just felt the reflex to close the tab, because this is getting personal in a way LinkedIn usually isn't.

That reflex is the subject of this whole series.

The one question that breaks the spell

Forget "who am I?" for now. That question is too big and it lets you philosophize instead of answer.

Use this one instead, in the moment, before you respond to anything:

Whose voice is this yes for?

• Not "is this a good decision."

• Not "does this move the metric."

• Just: who is watching, and what am I buying from them?

  
  

Do it for one week. Every yes. Every meeting you accept. Every time you soften a sentence before you send it.

You will find that a shocking amount of your calendar is procurement. You are buying approval, in small instalments, at a price you never negotiated.

Where this lands in the work I do

At INLIBRIUM, my co-founder Monika Jakobson and I run a six-month, medically supervised program for founders and executives. Psychedelic-assisted therapy is part of it - two supervised sessions in each of three seven-day residentials in Jamaica, with a full clinical team.

And I'll tell you the part most of the industry won't.

The compound is roughly 20% of the work.

I've been in this space since 2016 - as an investor and personally, through more than a hundred experiences. I have watched brilliant people take a massive dose, have a beautiful night, cry, feel reborn, fly home and be exactly the same man six weeks later.

Because a substance can show you the costume.

↳ It cannot take the costume off. Only months of unglamorous, professionally supported, deeply boring work does that.

That's the whole thesis of what we built. The container matters more than the compound.

Your move, leader

Go back to the question I opened with. You've been carrying it this whole time.

• When was the last time you said yes when your whole body said no?

• Who was in the room?

• And what, exactly, were you afraid would happen if you'd told the truth?

  
  

If you have to think hard to answer, that is information.

If your honest answer is "I don't do that anymore, I'm past it" - that is the loudest information of all and I'd gently suggest asking your spouse whether they agree.

You have one life. You are not obligated to spend it being useful to people who never asked to meet you.

↳ Live it. Don't perform it.