The hardest thing you ever do

A maxim for your professional life:

“If you insist on getting credit for the work you do, you’ll never get far in life. Don’t confuse yourself with the idea of getting credit.”

​A heuristic to help you think better:

“If you want to understand something, take it to the extremes or examine it’s opposites.”

What a good teacher really teaches his students:

“Do not write it as a formula. Write it as a way to teach officers to think, to think in new ways about war. War is ever changing and men are ever fallible. Rigid rules simply won’t work. Teach men to think.”

These are all valuable ideas from Robert Coram’s biography of John Boyd. There are more: 

– The “To Be or To Do” speech.
– The OODA loop. 
– The idea of destruction and creation. 

If you’re interested in strategy, hunting the truth, getting things done in a static environment, or adapting to change and challenge, you need to read this book.

There’s another idea from the book I’ve been thinking about recently. It’s this: you need someone to red team your work. 

What does “red teaming” mean? Here’s a definition from the team at

“Historically, a red team was a group of military personnel playing the role of adversaries, the role of the enemy or opposing force team (“RED”), as opposed to the friendly forces team (“BLUE”). With time, the red teams mission and capabilities evolved and they turned into a force tasked with challenging the security posture of military bases, outposts and other “targets”.”

And what do they do?

“Both government and private organizations use red teams not only to test the current state of their physical and digital security but also to continuously challenge the plans, defensive measures and security concepts/policies. These exercises result in a better understanding of possible adversaries and help to improve counter measures against them and future threats. A key aspect of the red team operations today is the adversarial way of thinking, the “Red Team Mindset”. Red team members think outside the box; they are not bothered by rules or laws. They look at a problem from multiple perspectives at the same time, often probing the sides of a problem – or solution – that was never considered. Today, different government organizations and Fortune 50 companies use red teams to analyze and poke holes in a plan or concept of operation at pre-design, design, and final phases. In some cases, red teams are used to try to analyze a competitor’s point of view. Red teams recognize contingencies and bring them to the forefront of analysis by asking the right questions and challenging underlying assumptions.”

Or, as I prefer to think of it, the red teamer’s aim is to take you down. They try to maximise disorder and uncertainty and capitalise on it. They do the unexpected and knock you off balance. 

But how does this help you? Here’s a passage from the book on Boyd. Emphasis mine.

“Then Boyd began showing his briefings to to Sprey and asking for an opinion. Sprey often ripped the briefs to shreds. And he did it in such a calm and irrefutable manner, reason stacked atop reason, logic atop logic, that it was impossible to disagree. Boyd referred to a Sprey critique as the “Pierre Sprey buzz saw.” But he knew Sprey was making his work stronger and more focused and virtually impervious to attack. “We’ve got to do our homework, Tiger,” Boyd often said to Sprey. “One mistake and they will leverage the hell out of it.””

This goes beyond feedback. Beyond commentary. It’s about attack. About vulnerability. You need someone who has the ability and the willingness to attack your work with the same fervour as a sworn enemy. 

If the subject under attack is something you’ve created, it’s going to be hard. Your ego could get bruised. But this is where you can develop your intellectual courage. This is where you can learn to separate your ego from your ideas. Where you can teach yourself to absorb what reality is telling you about the strengths and weaknesses of your work.

Find someone to hunt down the weak spots. To challenge the assumptions. To check the evidence. To highlight the flaws. To subject it to every kind of biased and unbiased attack. You need someone to conduct a rigorous and unflinching investigation of the validity of your work. But such a person is hard to find. 

Often, you’re the only person who cares about the work as much as you. Which means you’ve got to learn to switch modes. To go from creative—someone who builds upon the work, to destructive—someone whose aim is to tear it apart.

When I played basketball in college, I learnt about the ideal difficulty of training. It’s the same in jiu-jitsu. Training should be the hardest thing you ever do. Because then, when it’s gametime, you don’t have to step your game up. You’ve already endured and prevailed over greater trials.

Evaluating your work or strategy is like training. So find someone to red team your work. To deconstruct it and test it for vulnerabilities and missing pieces. And don’t flinch when they find that what you’ve created could be better. Embrace that knowledge. Encourage them to attack. Because if you allow yourself to stumble in the shadows, you give yourself more chance of triumphing when there’s something important on the line.