Photo by Anastase Maragos on Unsplash

This is so crazy, it might just work. COROLLARY: If it’s not crazy enough, it probably won’t.

My old uncle was a phenomenally successful real estate developer and architect.

Entirely self-taught. I think he did a few university-level courses, but just enough to learn what he needed to know, then he went back to whatever project he was working on.

Due to some unfortunate family politics, I didn’t get to mix it up with him much as I was growing up. If I had, it might have changed my course significantly.

He had an outsized personality, and that’s understating it. He filled whatever room he walked into, and dominated every conversation. If he couldn’t find one to dominate, he started one.

And he had a temper to match. I never saw it at full throttle, but I heard the stories. His adage was Follow, or get out of the way! I’ll do the leading.

Someone like that inevitably makes enemies, within and without. I learned to look past the tough exterior and see the genius. Toward the end of his life, I had some access to him. We spent three days driving around the English Cotswolds, bouncing ideas off each other. It was three days of magic. We cast off the fetters and dreamed big. (I cast them off anyway; I don’t think he ever allowed himself to be shackled by anyone.)

His skill and reputation was such that when the British government was seeking someone in the 1980’s to develop Canary Wharf, he was invited to bid on the project. He declined, deciding that it was too big for him . (Wisely? It would eventually bankrupt the Reichmann brothers who took it on.)

He told me that whenever he was invited to bid for the design of a new development, he would submit three design concepts.

The first two would meet the requirements exactly.

But for the third, he would throw the requirements out the window, and let his imagination run wild.

Inevitably, he said, the concept that the client would select was the third.

Folks, pay attention. This is powerful. (In a Steve-Jobsian way.)

What it means is, his clients thought they knew what they wanted, but didn’t really, until my uncle showed it to them.

I occasionally drive through neighbourhoods that he built. The houses are strikingly different. Gently slanted rooves inspired by traditional Japanese architecture, smoothly sloping berms instead of fences, to give the feeling of a gentle breeze while reclining in a lawn chair on a summer afternoon.

Nothing like any other neighbourhood in town. They stand out, and make you feel that you own something special. That you are special.

In the last conversation I had with him before he fell ill, he said that he had slowed down to just 40 hours of work a week, and that he wanted to take on a project so big that it had the potential to bankrupt him.

Slowed down to 40. Bankrupt. Remember, he’s an octogenarian already.

Was he secretly envying the Reichmanns? Had they in fact made the right decision, even though it cost them their fortune? Was he ashamed that he’d backed down from the challenge, and wishing for a second chance?

Work worth doing, work that is fun . . . . has to be crazy enough. It has to be bigger than you. Much bigger. It has to be unachievable.

Work worth doing has to be an adventure.

It has to kill you.

Peter Drucker was still publishing a book a year, right up until his death. And after, actually. The Five Most Important Questions came out three years after he passed. There’s productivity for you.

What would possess a man to work that frenetically right into his nineties?

Simple. Lust for adventure. An overweening desire to push the envelope. To release their inner James T Kirk, and boldly go where they have never gone before.

Most of us don’t think we’re capable of much. We’re born into a system that discourages us from exploring the outer limits of our personal universes.

And it’s only by sheer chance that we occasionally have experiences that make us wonder if we’re capable of far more than we realized.

Usually we squash those thoughts as quickly as possible, before they can do any damage. Or if we’re foolish enough, we vocalize them to a few people we trust, and THEY squash them for us. Why? Because THEY’VE already squashed those hopes in themselves. They don’t want the shame of anyone close to them succeeding at something they never had the guts to try.

Paul Rosenberg, of, tells the story of Dick Woit, a ex-NFLer who, when injury cut his career short, turned personal trainer. Before long, out-of-shape men, including some who were desperately ill or disabled, were streaming to Woit’s door.


Woit’s approach was to scream foul-mouthed insults at his customers during training sessions, to the point where they wanted to kill him as they sweated (and sometime vomited) their guts out. 150 pushups? Is that all? You call yourself a $%^&@*¢ man? You’re not leaving this floor until I’ve counted 200!

And then, when he’d counted 200, he’d allow, All right, not bad, but if you had two lungs I’d force you to do 400! (The subject only had one lung.)

Why do this? Why behave in such a way, especially to the men who are paying you?

Because he knew that human beings are capable of far more than they think they are. Far more.

And he knew that human beings are their own worst enemies. They need a push, sometimes a hard one.

Dick Woit never wanted for customers. They streamed to his door, and before long he was getting press attention. NFLers would come to train, and often find themselves shown up by old-age-pensioners. If they lasted through the first few sessions, they became committed regulars. Dick Woit earned their undying respect for revealing the precious secret that no-one else had.

I found this out myself when I went on a 15/3 mountain climbing expedition. Fifteen peaks in the hills of Snowdonia in north Wales, in three days.

The last peak was Snowdon itself, the highest peak in Wales. By then, I was terribly sore and stiff. Fifteen minutes up Snowdon, I hit The Wall. the Snivelling Brat in my mind rebelled. I told my climbing mates that I was through, I’d had enough. I’d wait for them at the bottom.

For ten minutes, they tried to talk me around.

And to this day, I don’t know what possessed me, but I finally agreed to keep going.

That act, of pushing through the Wall, of ignoring what I thought was my own better judgement, was my salvation.

When your brain is yelling at you that you don’t have anything left in the tank, that this is cruel inhumane punishment, it’s lying.

You do, and it isn’t.

What I regret most about that experience is that it came when I nearly fifty. Nobody before ever pushed me hard. Count yourself lucky if you have encountered such a tyrant early in life.

Crazy. Push.

Your biggest mistakes will almost definitely be of the not-crazy-enough or not-hard-enough varieties.