
40 Lessons at 40
Aidan O’Brien Shares Insights from his Masterclass to Celebrate his 40th
At 40, I decided to reflect, not just on my life, but on the lessons that shaped decades of coaching leaders, realigning high-performers, and challenging organisations to raise their standards. Here are a couple of the key takeaways that are leadership-specific.
In a world that’s designed to distract you, my priority is always clear intention. To find our truth, we have to look beneath the surface. 40 Lessons at 40 are based on the insights, lessons, challenges, behaviours, and growth I’ve seen first-hand across industries and continents. The people change but the lessons don’t.
Key Themes from the 40 Lessons
1. Self-Awareness is the Ultimate Advantage
Most people are busy trying to fix external problems, when the real leverage point is internal. Awareness is not a soft skill - it is the most powerful tool in leadership. When you know yourself, you trust yourself. And when you trust yourself, your decision-making sharpens. Execution accelerates. Confidence becomes quiet and clean.
2. Truth Over Comfort
One of the most transformational lessons I’ve learned is this: a hard truth will always move you forward faster than a convenient or easy lie. Leaders who choose clarity over confusion, honesty over image, and constructive feedback over ego are the ones who create sustainable success. Always tell yourself the truth. Especially when it’s uncomfortable. Your growth depends on it.
3. Visionaries Move First and See Further
Visionaries say yes before all the evidence is there. They're not reckless, they just know what they're capable of. I coach my clients to be vision-led, not reality-bound. It's about creating urgency. Asking better questions. Acting from clarity. Visionaries ask better questions and make fewer conclusions, and that is a major change maker within an organisation.
4. Lead Yourself First
The first person you need to lead is yourself: your identity, your calendar, your choices. High performers don’t compromise their standards. They work in seasons - short, focused sprints with clear intention. They replenish their energy, stay connected to purpose, and design a rhythm that fuels performance.
5. Relationships Run on Alignment
Great relationships don’t just happen. They are built on Values, Character, and Vision (VCV). If those aren’t aligned, miscommunication, mistrust, and misalignment follow. Whether you’re leading a team or building a family, your relationships rise or fall based on how well those three elements align.
6. They Don’t Wait for Permission
One of my non-negotiables of exceptional leadership is: you can’t wait to be knighted as a leader. You must move first. High performers and leaders move. They take action from clarity, and with certainty. It’s not about being reckless, but it is about not standing still and waiting. Waiting is not a strategy.
After 20 years in rooms with world-class performers, I can tell you this: the most important work you can do is on yourself and on your teams. Specifically, investing in developing mindset and skills is a game changer for your business.
Quick-Fire Lessons from 40 at 40
- You don't know what you don't know. Stay open. Stay curious. Keep a beginner’s mindset.
- Not everything you believe is true. Challenge your thinking, question your beliefs.
- Self-exploration sets you free. You can’t lead if you don’t know who you are & what makes you, you.
- Visionaries say yes first, then figure it out. Realists wait for perfection that never comes; visionaries create the circumstances and adjust as needed.
- Communication and imagination are the highest forms of value creation. Don't get caught in "work mode"; get into creative mode and create leverage.
- Make decisions from love, not fear.
- Truth is always the right strategy. Even when it’s uncomfortable.
- Work in focused, high-intention seasons, not lukewarm years.
- Don’t just learn for knowledge. Let learning change your behaviour.
- Your job should be a vehicle for expression.
- Leverage and urgency should be a priority for health, fitness, and business.
- High-value conversations can open doors you could never open by yourself.
- Be interested before you try to be interesting.
- Sales is something you do for other people, not to other people.
- The secret to greatness is in the service of others.
- Sometimes belief comes after the action. Don’t wait for belief to start - it might not come until later. Let belief catch up with your action.
If you take one thing from my workshop - 40 Lessons at 40, let it be this: you must stay a student of yourself. Keep learning. Keep applying. Be willing to question everything. Let go of what's not working and put your attention on what is working and what will move the needle. Don’t wait for permission. Move. Lead. Decide. Your future, your team, and your results are waiting on your clarity. And clarity begins with the courage to look within and change what's not working.
And while this journey of leadership is personal, it doesn’t have to be walked alone. That’s why coaching and personal development matters. Not because leaders are necessarily weak, but because great leaders are smart enough and humble enough to know they can’t see everything.
Mentorship provides the mirror to shift the perspective and show the blind spots when necessary. To remind you what's important and what's not. To hold you to your highest standard when things are moving fast and pressure is on.
Having a strategic coach isn’t a compromise. It’s a seriously competitive edge. It’s how you protect your clarity, multiply your execution, and stay in alignment when everyone else is distracted.
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