For the last few years, I've run culture of innovation sessions where failure and innovation get talked about as inseparable twins. You cannot have one without the other, I'd say, and rooms full of leaders would nod. Try things, some will not work. That is the cost of building anything new. It was a good session. I believed every word of it.

Then a few people, in the last few months, asked me some version of the same question. Are you really going to give up a steady income to go out on your own? And I noticed something uncomfortable in my own hesitation before I answered. I had spent years giving other people's failure a soft landing while quietly reserving a much harder standard for mine.

That is the norm worth rewriting. Leaders extend permission to fail as a cultural good, a thing to be encouraged in others, while treating their own failure as a different category of event entirely. Something to be avoided, managed, minimised. I have watched too many leaders run this exact split without noticing it. Do as I say, not as I do, dressed up as strategy.

Real leadership is taking your own medicine. It is not standing at the front of a room telling people to embrace failure while you personally have not risked anything in a decade. You model the behaviour or you should not get to teach it. Lead from the front means your own decisions carry the same risk profile you are asking of everyone else, not a version of the advice with the actual cost engineered out.

Here is the actual maths, stripped of sentiment. If I try this and it does not work, it costs me something. Time, some money, a run at a senior role I could otherwise have kept. That cost is real and I am not pretending otherwise. But it is bounded. If it works, there is no upside limit on what that means for the business I am building or for the work I get to do. Try, fail, improve, try again is not a slogan I use in workshops. It is the actual shape of the bet.

I'm backing myself for the next chapter of my career, and I'm incredibly fortunate to have a wife who is backing me too. Most of the leaders I have coached through their own version of this decision had that same asymmetry available to them. Bounded downside, unbounded upside, and they still could not make the call, because the rule they applied to their own risk was never the rule they taught.

There is a version of me that keeps running culture of innovation sessions from a safe distance, advice fully intact, own skin fully out of the game. That version gets to keep the title and skip the medicine. I would rather be the version who can say I did the thing I told you to do, and here is what it cost, and here is what it is teaching me. That is the only version with any standing to keep walking into rooms and asking other people to try.

So the rewrite is simple to say and harder to live. Give yourself the same terms you give everyone else. Not a lecture about resilience. The actual maths, taken as your own medicine. Credibility comes from living the advice before you teach it.


— Cindy Schwartz

Founder, Executive Excellence Group | Rewriting Leadership Norms