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Simon Says

Winformation This Week...

I once described to someone my plans for the next 5 years and their eyes narrowed, and she said, “you’re really ambitious, aren’t you?” You could tell it wasn’t a compliment. She didn’t see it as a positive. I think ambition gets a bad rep, and you can see why. Ambitious people on socials (especially men) these days, are producing voice over reels with clips of them kick boxing or speeding away in a green lambo. You can see ambition and aggression weaved into each other. But it wasn’t always this way. In today’s One Idea to Win in Business we look at how to be fiercely ambitious without becoming a narcissist!

Being aware of yourself, how you are viewed and the impact of your presence in any situation is a superpower. In today’s One Idea to Win in Life we talk self-awareness and how to harness its almighty power.

One Idea to Win in Business

How to Be Fiercely Ambitious Without Becoming a Narcissist!

My entrepreneurial hero growing up was Richard Branson…ok that could possibly be the nerdiest thing I ever said…But as an outsider looking in, you wouldn’t have Richard Branson down as an overtly aggressive guy. And I think we can all agree he’s one of the most ambitious people in history. These days people with huge ambition can often be viewed in a really negative light. Here’s how to be fiercely ambitious without becoming a narcissist!

1. Anchor your ambition to a purpose bigger than you

Real ambition, the biggest there is, is always about others and not about yourself. Our company really took off when we (eventually) started seeing the impact it had on our team and the community. That’s when we doubled in 12 months. Ambition rooted in totally selfish reasons, comes across very negatively and ironically will keep you small. When ambition is rooted in genuine impact, it stays healthy, and explodes the size of everything you are working on.

2. Stay coachable because success is not a graduation certificate

Narcissists believe that success means they have nothing left to learn. Truly ambitious people know the opposite is true. The moment you stop asking questions or start believing your own hype, your growth stalls. Curiosity and humility keep you moving forward.

3. Make others bigger, not smaller

Narcissistic ambition needs all the credit, which is why it eventually hits a ceiling. Healthy ambition grows by lifting others and creating an environment where people feel confident to contribute and take ownership. When you make the people around you better, you multiply your own success.

4. Choose discipline over drama

Real ambition reveals itself through consistency, not noise. It is shown in quiet progress, reliable output, and the ability to stick with the work when nobody is applauding. Narcissistic ambition needs attention. Genuine ambition needs standards.

5. Remember that winning is not a personality trait

Ambition becomes narcissism the moment you start treating success as proof that you are special. You are not built different, you are behaving differently. Responsibility is what converts ambition into achievement. That is what makes ambition something to be proud of, rather than something people roll their eyes at.

The Winformation truth

You can be incredibly ambitious without turning into the kind of leader people secretly hope will fail. Anchor your ambition to meaningful outcomes, stay open to learning, lift others, prioritise discipline, and keep your ego on a short leash. Do this consistently and you will not only move further, you will move with people who want to see you win.

One Idea to Win in Life

Want to Improve Fast? Here’s the 5-Step Self-Awareness System That Works

Self-awareness is one of the most underrated performance tools you can develop. It is the ability to tune into your thoughts, emotions, and behaviour and understand how they influence the decisions you make and the relationships you build. It also makes you, well, far less annoying.

1. Make everyday count

Time moves quickly, but each day is a building block in whatever you are trying to create. Spend ten minutes reflecting on how the day went, what challenged you, how you felt, and what you learned. Writing it down trains your mind to recognise progress, patterns, and wins, as well as the areas that need attention.

2. Know your superpowers and your kryptonite

Checking in on your strengths and weaknesses is not about creating a list, it’s about holding up a mirror. When you understand what you naturally excel at and what regularly trips you up, you give yourself a huge advantage. You can double down on what you do best and be intentional about the areas that need strengthening, which is the foundation of real growth.

3. Live by your own compass

Life is full of choices, and clarity comes from knowing what you stand for. Define your core values and let them guide your decisions, especially when things feel messy or uncertain. When you are rooted in the things that truly matter to you, the right direction becomes much easier to recognise. If family and health are your top priorities, taking a job abroad with a lifestyle that contradicts them will never feel aligned, no matter how appealing it looks on paper.

4. Ask for feedback and make it count

Generic questions lead to generic answers, so be specific when you ask for feedback. Try asking what one thing you could have improved or whether your pitch was clear and engaging. Choose the right moment, ideally one where the person has seen your work and can offer meaningful insight. The more intentional you are in how you ask, the more powerful the feedback becomes.

5. Keep learning even when it hurts

Setbacks feel unfair in the moment, but they are often the fastest route to insight. Rather than slipping into the “why me” mindset, ask what you can learn from the situation. If something has not gone the way you wanted, take the free lesson. Growth is rarely comfortable, but it is always valuable.

Win or Wonder?

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Until next week! 

Let’s win, together!