Lawless Thinking brings you insights, tools and encouragement direct from my world of bold C-suite strategy delivery.

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Thought of the Week

“I’ve never been in there with him. But I believe the world is round and they all believe the world is flat. Maybe I’ll fall off the world at the horizon but I believe the world is round.”

 

Muhammad Ali

(I found this moving comment in David Remnick’s autobiography of Ali. It was made in a hotel room before the Sonny Liston contest in 1964. It is in stark contrast to his press conference statements.)

If you read Lawless Thinking, you leave the harbour and enter the choppy waters of uncertainty. That guarantees you’ll have moments when your confidence wavers.

The switch that can flick between ‘It’ll be ok’ and ‘You can’t do this thing’ in a heartbeat is mysterious. That’s why sports people, and maybe you too, have a pair of lucky pants.

So, I sat down in my garden and searched for moments when my confidence deserted me.

And like Alice on the riverbank, my mind swiftly began tumbling down the rabbit holes. Moments when my feelings of inadequacy to the task tried to overwhelm my mind and biochemistry.

I’m sitting in my car waiting to start the engine and go to a racing yard. It’s December. Dark and cold at 5.45am. I got bolted with the last three mornings. The other riders aren’t talking to me anymore. It’s raining hard on the windscreen. Time to go, but I can’t bring myself to start the engine. What do I do?

I am in the front row at a low-key event about to speak. The carefully chosen words my partner sent me to work with, again, have destroyed me. I don’t feel worthy to walk out there. Who on earth do you think you are to go talk to them? What do I do?

It’s 3am and I’m wide awake. Day one did not go as planned. I’m halfway through a two-day high-performance design with an executive team that simply won’t fire, and nothing in my toolkit has cracked them. In five hours I’m back in that room, and we have to land a result by the end of the day. There’s no day three. What do I do?

I think that ‘confidence’ is the thoughts we have about ourselves and our upcoming challenges after drinking a volatile cocktail of skills acquired, specific preparation, ‘self-worth’ (including the comments of others) and our emotional state at that moment.

If we don’t like the taste, our emotional state shifts to fear. The cocktail becomes more bitter. A cycle can begin. It can spiral into dangerous levels of anxiety that will prevent performance. We must be able to manage the situation.

But if we are going to leave the harbour and sail the seas of life, we need to be able to manage things when the cocktail our minds serves up is bitter.

1. When the challenge seems too big.

My riding mentor, Gee, only got angry with me once. She asked why I never seemed afraid, learning to ride one-ton animals in the dark and cold, getting bolted with or thrown several times a week.

I told her I was often afraid. Her tone changed. “How can I help you if I don’t know what’s going on?”

She wasn’t angry that I was scared. She knew that every brave jockey can get scared (I did not yet know this). Courage isn’t the absence of fear; it’s doing the thing anyway. She was angry that my need to show up perfect was damaging our coaching and putting the goal we’d both committed to — the racetrack in a year — at risk.

We tore up the next day’s plan. Instead, she let me talk. I let her in. She gave me tools. We cancelled riding out and went to the gallops together instead, in daylight, and she taught me things to try, there and then, on horseback.

When the challenge feels too big, my first recommendation is vulnerability.

Not a performative confessional in front of the team, they may not need to see your full frailty until the thing is delivered, but a quiet conversation with someone you trust. Open up. Let someone in.

My second is to ask for help. Find the person who’s sat on more racehorses, been in the room more often, stood on the stage, led the team. They can help you. They will also understand the fear and how to move past it. High performers empathise because they have done it. The friend in the bar may not.

2. Finding your self-belief when the pressure is on.

Most of us carry some shame, and it loves to ambush us at the moments that matter most. What you need then is a tool, not someone to blame. This is where therapy can sometimes leave you stranded. My tool of choice is boundaries.

Not the Instagram kind: the one-sided proclamations of what you “will not tolerate.” Real boundaries work inward. They’re the filter that decides what you let in from others and what you keep out. And they run the other way too: knowing when to stay quiet, because it isn’t always your place to speak and offer another human your view of them.

When your self-worth vanishes because of the comments of others, or your own demons coming out to play, first put up the boundary. This is not reality. You do not have to pay it any attention.

Then go to the evidence. You’re not in that room because they needed a warm body and you happened to be there.

You’re there because you’re the right person. Others saw it clearly, even when you can’t feel it. So remember why you’re there, how you earned the right, how you prepared. Remember why you are unique – and you are, in some special way that matters for this moment – perhaps because of those very demons and how they help you to think: then deliver.

And if you haven’t done the work? There’s no honest trick I can offer. Pretending to be ready when you’re not isn’t confidence, it’s acting. That’s a different topic.

Secondly, there are tools that can help you feel stronger here. I heard this week that the England football team’s striker coach tells them there is no goalkeeper. Don’t even see him. He cannot get to a well struck ball in time. He is an irrelevance. Just shoot at the empty goal before you!

I use music in my hotel room or headphones before a big presentation. And I always know what I am going to say in the first 30 seconds and where I will stand on stage. That occupies my mind and gives me a solid start I can control.

So, it could be music, a controllable foundation, a thought pattern cue like the England strikers – but finding something to focus on other than ‘can I do it?’ can be extremely helpful in a clutch situation where you cannot afford your confidence to dip.

3. The 3am Self-Doubt Club.

Your situation may be different. But I suspect you’ve found the late night confidence attack when you discover you are not up to the task – in your imagination.

First, let’s name what 3am actually is. Your brain in the dark is a catastrophe machine — it strips out every resource and shows you only the cliff. Nothing you “decide” now is real, so decide nothing. This isn’t the situation; it’s the 3am version of it.

Then put the weight where it belongs. The result here was never mine alone to force. There’s a room full of capable people, and a breakthrough is a shared job, not a solo rescue. You can’t control whether they fire-up. You can control your preparation, your presence, and your first move at nine. Control the controllables; release the rest.

And trust the evidence. Your process has worked before, with rooms that looked just as stuck. If yesterday’s approach didn’t land, that’s data for today’s -not proof I’m finished!

Whatever your version of the confidence attack at 3am may be, log it, close the chapter, and let it go until morning. The work is done. You’ll figure it out. Now focus on breathing deeply, relaxing your major muscle groups and enjoying that you get to do exciting work and take on exciting challenges!

Sleep is part of the preparation, not a betrayal of it.

It’s going to be ok. Let’s enjoy the ride while we can!

My Fortnight

Presentations have taken me and the DARE Loop from 1500 people in Munich at a large, celebratory EMEA sales jamboree to an intimate conference room in the UK where the newly merged finance leadership teams of two great organisations were working in detail on the Decisions and Actions required to delivering their ambitious and stretching strategy to become one.

I have welcomed a new exec team advisory client to the fold which is very exciting and brings me close to capacity for 2026.

My Symmetry team are working hard on re-launching our training for team leaders across the organisation who need to generate ownership, accountability, clarity and performance at speed: INSPIRE.

Book of the Week

Are you too busy? Is everything important and urgent – and being done badly whilst good people ‘burn out’?

A strategy is a set of clear choices to deliver a prize. ‘Pre-made decisions’ that guide us under pressure and in moments of almost unbearable opportunity cost temptation to ‘do more’.

But most enterprise strategies are a committee/trend driven Vision, Mission and Values statement with a long list of goals attached.

“Good strategy requires leaders who are willing and able to say no to a wide variety of actions and interests. Strategy is at least as much about what an organization does not do as it is about what it does. Bad strategy is long on goals and short on policy or action.”

This is where I operate with my advisory clients. Then we build the Second Strategy: how we’ll deliver the enterprise strategy through our people.

One of the books that I often gift to clients is Rumelt’s Good Strategy / Bad Strategy.

It is an easy read providing solid principles and a clear guide to how to spot a good, and a bad, strategy and the difference between them.

Write Your Story 🖋️

Jim