The Paradox of High Ambition and Self-Doubt

Self-Doubt: A Bug or a Feature?

Self-doubt is completely normal, even though very few people openly admit to experiencing it. This is because self-doubt is often viewed as a crack in our armor—something that stands in stark contrast to the highly praised qualities of confidence and self-assuredness.

But if self-doubt is so common and pervasive, how do we manage it effectively so that it doesn’t negatively impact our ability to achieve our goals or diminish our overall quality of life?

Today, I will explore the nature of self-doubt and offer strategies to better manage it.

Self-Doubt as a Call to Reflect and Prepare

It’s important to recognize that self-doubt isn’t all bad. In fact, it can be a powerful tool for reflection and preparation. When experiencing self-doubt, ask yourself: Where is this stemming from?

Identify the core factors causing your doubt:

- Do you feel underprepared?

- Have you overlooked potential risks or failed to create contingency plans?

In this way, self-doubt can prompt you to invest more time and effort into preparation. However, as any ‘recovering perfectionist’ will tell you, there is a point of diminishing returns. Beyond a certain threshold, using self-doubt as a tool to prepare stops being helpful and becomes a hindrance.

I think of a client who puts so much pressure on himself to “get it perfect” that, despite being prepared, he becomes highly stressed in the days leading up to company presentations. He struggles to sleep, switch off, and constantly loops on the 'what if'. In situations like this, self-doubt often points to deeper issues such as anxiety or a lack of confidence.

Self-Doubt & the High Achiever

But what about confident, ambitious individuals? What happens when they experience self-doubt?

This is an area I consider myself well-versed in—not only because I work with many high-performing individuals, such as entrepreneurs and professional athletes that deal with self-doubt, but also because I’ve had to learn to manage this in my own life.

Here, self-doubt rears its head occasionally during the process of building towards a vision. You might be confident and have high conviction that you will achieve your goal, but at times that conviction and confidence wavers. You may find yourself questioning:

- Is this possible?

- Am I truly capable?

- Am I following the right process?

- Am I wasting my time?

In these cases, self-doubt doesn’t stem from underpreparation. Instead, it’s triggered by pursuing something entirely new—a goal that stretches far beyond your current reach. It’s a natural reaction when striving for something big that you have never personally done before.

Managing these moments is crucial if you want to realize your vision. You need to keep moving forward even when self-doubt is amplified.

Strategy 1: Build Conviction

You have to convince yourself that you can and will succeed. I call this tool ’selling yourself.’

Sell yourself on your dream daily. Remind yourself why it’s possible, why it matters, and why you will make it happen. This is a powerful buffer against self-doubt.

One way to do this is by studying the biographies of great individuals and their persistence in the face of doubt and adversity. Listening to motivational audios in the morning or channeling energy into a hard gym session can also help quiet the voice of doubt and build certainty.

For me, selling myself daily is part of my routine, often through physically challenging exercise. I have realised that breaking through mental resistance by doing something hard first thing in the morning quiets the inner critic, setting the tone for the rest of the day. This echoes the advice of Brian Tracy, who famously recommends tackling the hardest task first—“eating the frog.”

Too often, beginners make the mistake of trying to convince others instead of themselves. The journey to achieving your big goals is heavily reliant on how well you manage your own psychology - your mental and emotional state.

Build your own conviction first, and the results will follow.

Strategy 2: Get Comfortable with Rejection

Rejection and setbacks are inevitable. Self-doubt often surfaces when things don’t go as planned—whether it’s a deal falling through, criticism from others, or outright failure.

Understand that rejection and setbacks are part of the process. They are not a personal reflection of your worth or an indicator that you can’t succeed. Often, rejection and criticism trigger deeper insecurities rooted in childhood, which then spiral into full-blown self-doubt.

Remind yourself that you are no longer that vulnerable child—you are a capable, resilient person who will find a way to make it work.

One of the best ways to prevent rejection and setbacks from derailing you is to build a solid foundation of self-trust.

If you can’t detach from others’ opinions, withstand rejection, or persevere through moments of isolation, then the path to achieving your impossible may not be for you. This journey isn’t for the faint-hearted.

Strategy 3: Lean on Your Highlight Reel

When self-doubt strikes, lean on your past evidence of success. Reflect on the big and difficult things you’ve overcome before. Play highlight reel in your mind’s-eye, reminding yourself that you will make it happen.

Success breeds success, and you can draw power from past accomplishments—even when facing unrelated or new challenges.

In this way, success becomes a pattern, just as failure can. Each win makes the next victory possible.

This highlights the importance of creating ongoing small victories and taking on intentional challenges.

Learn to play at the edges of your comfort.

A Final Reminder

These tools—building conviction, handling rejection, and drawing on past victories—have been invaluable on my journey. I might not be at the top of my next mountain yet, but I have summited a tremendous amount of personal peaks that at one time seemed impossible – and I can assure you, learning to manage self-doubt played a huge role in it.

All of these tools build on and reinforce each other.

When you notice self-doubt creeping in, practice compassion. Often, it’s not that you can’t or won’t succeed—it is just a natural part of striving for something big and meaningful. But now, you have a set of tools to get your mindset back to one of determination and belief next time self-doubt wriggles its ugly face.


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The Psychology of Self-Belief