Tired of feeling like you’re in the wrong room? A Practical Guide to Definitively Deal With Imposter Syndrome (template included)

As a mentor at the Oxford Foundry, I run weekly one-to-one mentorship sessions with fellows. Each of these talented young students is from a group underrepresented in entrepreneurship.

After ten or so of these calls, I’ve noticed a distinct pattern. Each starts with my mentee commenting on my career or LinkedIn profile, implying that I’ve figured out my career and what I want to do with my life. One student even thought I was still a practising surgeon in addition to my startup (I’m not!). The truth is that instead of following some Well Considered Plan, most of us — myself included — are figuring it out as we go.

I recently found myself making the same assumptions about my own mentors.

As I caught up with one recently, I made a similar comment about his achievements (McKinsey partner, exited entrepreneur, fund manager). He had the grace to share his recent struggles with me, both professional and personal. Why do we make these assumptions about others, despite knowing all too well the ways we haven’t figured our own lives out?

You see, our minds have evolved to fill gaps in our knowledge. Let’s take vision as an example. You don’t notice your actual blind spot because your visual cortex extrapolates from what you can see to fill in the gap.

Similarly, when we look to our mentors and those we admire, we catch glimpses of the complete picture of their lives. We have no idea what their inner struggles are. We fill in the gaps…

This is a problem, and I want to talk about it.

In this piece, I’ll unpack this thought and look at why many of us experience low-grade anxiety and a sense of inadequacy. I’ll also share approaches to overcome these feelings, including a template that I use to overcome these feelings (linked at the bottom).

The loveliness of others

As humans, we have an incredible ability to convince ourselves of the loveliness of others.

Every crush, every idol, every peer or mentor we’ve thought has it all figured out and can do no wrong — in each case, we’ve glimpsed just a fraction of their reality such as a blog post, a video clip or a podcast. And we’ve filled in the gaps.

If you reflect back on your life, I’m certain you’ll find many examples. A crush that turned out not to be as warm and friendly as you hoped. A teacher, boss or manager whose struggles overwhelmed them from time to time.

My own experience is no exception to the rule that the people we admire most are often those we know least well.

Contrast this with the balanced and more critical views we hold about ourselves. Most of us wouldn’t consider ourselves worthy of that kind of attention.

Embracing the messy reality

These unrealistic views set us up for disappointment and cause two problems.

First, we create unreasonable expectations for ourselves. Unless we come close enough to see the flaws in others, we assume that they’re somehow above the mistakes, the anxiety and the folly we find ourselves in. We go on to blame ourselves — our decisions, our life circumstances, our friends and family — for the lives we have. The truth is life bends us all a little out of shape — our crushes included.

Secondly, when we come face-to-face with the flaws of others, an inevitable letdown follows. We’re more likely to be cynical: Why admire anyone when they always let us down? It seems a reasonable question.

The truth is that nothing — and no one — is as perfect or as whole as they seem from the outside. In the internet age, each of us is just one filter and two airbrushes away from perfection.

The celebrated French philosopher Michel de Montaigne (1533–92) put it more eloquently in his Essays (translated):

“Kings and philosophers shit, and so do ladies.”

The point is that no one — not a King, a philosopher or a lady — is above the foulest and most embarrassing aspects of human nature.

I don’t know who needs to hear this right now, but the people you look up to are, like everyone else, full of flaws and imperfections. The slightest triggers bring out their defensiveness, anxiety and insecurity… and that’s ok.

Look closely enough and you’ll find some redeeming qualities.

Rather than holding those we don’t know in such high esteem, extend your knowledge of those closest to you. Assume they are, like you and everyone else, full of irrational expectations, covered in scars and yearning for something.

The roots of imposter syndrome

“Imposter syndrome” describes when we feel that we’re not worthy of responsibilities or successes offered to us. This belief stems from assumptions about authority figures that take root in childhood.

As children, we’re taught that our parents and elders are not like us. They’re sensible, knowledgeable and taken seriously by society. We struggle to picture them as foolish children making the mistakes we do.

We assume they’ve always had things figured out, like how to fix a leak, pack for a holiday or pay bills.

On the other hand, we see ourselves as foolish, constantly making mistakes and needing correction. These ideas continue to shape our view of the world as adults.

We’re lucky if we have any friends that share their vulnerabilities with us. This is why being vulnerable is so powerful — it’s profoundly reassuring to know that we’re not alone in our struggles.

This is also why it’s essential to treat children like whole people, fully deserving of attention and respect. More on that another time.

Overcoming imposter syndrome

Accepting that everyone is flawed, anxious, uncertain and “making it up as they go” is the only way to break out of feeling like an imposter.

This is necessary if you seek to get comfortable creating opportunities for yourself rather than waiting for an invitation to pursue your dreams.

What could this look like in practice?

• Reaching out to that senior leader whose work you admire rather than waiting for them to notice you.
• Writing to the CEO of the company you want to join and offer something useful to them, instead of applying to a vacancy through their website.
• Making the first move to get to know someone you deeply admire.

Recognise that there is nothing fundamentally different about you compared to the people that you look up to.

Only by believing that you are equally capable of success and worthy of fulfilment will you have the best chance of finding it.

The Definitive Guide to dealing with imposter syndrome

One of my mentors is an engineer and exited founder. On a recent call, he gave me some practical advice on how to deal with imposter syndrome. I’ve turned that advice into a structured thought experiment that I’m happy to share below.

This approach has helped me identify reasons to feel more confident in the face of any challenge or opportunity. It has helped me find tangible reasons to feel confident and identify specific actions that make me more qualified for the role.

👉🏽 Click to access the Google Doc

There are four simple questions to answer. Coupled with the suggestions above, I’m sure this approach can help you deal with feelings of imposter syndrome.

It’s simple, but it works.

Good luck, and feed it forward.

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