The biggest mistake I ever made.

We tend to hide our failures, but I’m going to share one of my biggest.?

I didn’t pick up the phone.?

That’s it.?

Sounds small, doesn’t it??

But the biggest failures (this one cost me $20,000 in the end) always start as they mean to go on: with a small thing that didn’t happen, and didn’t happen every day until it’s too late.?

I’ve learned now, in the most expensive MBA you’ll ever do (it’s called ‘life running a business’) that when someone has gone quiet on you, you pick up the phone.?

And you keep picking up the phone every day until you hear what you need to.?

The project that failed was one being managed by an architecture partner. They make the lion’s share of the money on these things, they carry the most liability, so it makes sense on some level that they manage the project.

My team had largely finished our work. We just had to help the architect bring things in to land.?

But things weren’t going well. A quiet word from the Head to me let me know that they weren’t being heard, that design work was happening that they hadn’t asked for, that they didn’t want.?

And up until that point I hadn’t picked up the phone when, all along, my gut had been screaming at me that something was awry.?

And, if I’m going to be kind to myself, they didn’t pick up the phone to me, either.

So it was the same mistake, repeated on both sides, for days. For weeks. For a couple of months.?

Nobody picked up the phone.?

This week I’m Washington, D.C. at the AAIE conference, learning from Heads of School from across the world, and sharing some stories of my own.

Most people will talk about their successes. But I’m more interested in the things that failed. And the often trivial failures early on that led to the blot a few weeks or months down the line.?

The late Jim Rohn was an entrepreneur. He became a millionaire at 30. And lost it all by 33. And then he became a millionaire again. In 7 Strategies for Wealth and Happiness has this to say on failure:

“Failure is rarely the result of some isolated event. Rather, it is a consequence of a long list of accumulated little failures which happen as a result of too little discipline. Failure occurs each time we fail to think today, act today, care, strive, climb, learn, or just keep going … today.

“If your goal requires that today you write ten letters and you write only three, you are behind by seven letters … today.

“If you commit yourself to making five phone calls and you make only one, you are behind by four phone calls … today.

“If your financial plan requires that you save ten dollars and you save none, you are behind ten dollars … today.

“The danger comes when we look at a day squandered and conclude that no harm has been done. After all, it was just one day. But add up these days to make a year and then add up these years to make a lifetime and perhaps you can now see how repeating today’s small failures can easily turn your life into a major disaster."

The most fatal small errors are not the one or two the senior leader makes each day. It’s the one or two every day that their 20 middle leaders might be making, hidden from plain sight.?

In Leading from the Middle, we help those middle leaders and their senior leader bosses learn how to spot the mistakes they’ll make, before they even make them. It’s called “doing a pre-mortem”, to make sure the project won’t die.?

Does it prevent all failures? No. But it gives you a fighting chance of spotting them when they appear.?

And worst case, you’ll learn to pick up the phone when your gut tells you to.?

We close for new participants on February 14. After that, we don’t return until 2026.?We don’t need more managers in schools. We need leadership. There are just two weeks left to grab your places. Aspiring, middle and accomplished leaders welcome.

So pick up the phone (or buy online or send an email: [email protected]) to get your spots.?

This appeared days ago in our free Monday newsletter, The Provocation. You just need to sign up so that you start your week with some inspiration or a reminder of what really matters. Keep your head above the whirlpool of change and sign up now. You can always change your mind later.