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Imposter Syndrome in High Achievers (With Aaron Ross)

Imposter syndrome (n)

The persistent inability to believe that one's success is deserved or has been legitimately achieved as a result of one's own efforts or skills.

Also recognised as:

A collection of feelings of inadequacy that persist despite evident success.

In other words, imposter syndrome is not being able to acknowledge that the hard work you put in every day to learn and develop your skills should result in you deserving recognition or holding your job title.

Instead, it can leave you feeling like you’re somehow tricking those around you into believing you’re better at your job than you really are. An imposter who doesn’t deserve to be there.

It can happen to anyone, in any level of the organisational hierarchy - in fact, some research has suggested it could actually be more prevalent in those in higher-up positions. 🤷‍♀️

We wanted to bring this subject to the forefront, spark important conversations and highlight why imposter syndrome is so prevalent in high achievers. We spoke to Aaron Ross to get his insights.

Keep reading to find out more ⬇

Who feels imposter syndrome?

According to research, as many as 70% of us will experience imposter syndrome at some stage in our lifetime.

That’s the majority of us - and yet it seems to be so under-discussed.

Imposter syndrome in your early career kinda makes sense. You’re just starting out, you’re getting to grips with your working life and building your confidence as you go.

You maybe aren’t quite sure what you’re doing yet, so it’s understandable that you might feel insecure in your job role.

However, you have a lot less pressure put on you at this stage in your career; people don’t expect you to have all the answers quite yet.

What’s interesting is that imposter syndrome doesn’t appear to dissipate as you progress through your career. In fact, in many cases, it tends to rear its head more often.

The people who, from an outsider's perspective, have ‘made it’ are just as (if not more!) susceptible to imposter syndrome even though they’ve proved themselves to be successful, achieved great things and hold important positions in their workplace.

Aaron shares his experience as imposter syndrome started to crop up:

“When I was younger, I always wanted to get to the next level. I want to be a manager, then a VP, and then a CEO, or an entrepreneur.”

“As humans, we want to grow. That’s a good thing. But I think sometimes we forget that once we get to these next stages, there is always going to be a bit of a learning curve.”

“More responsibilities, influence, and decision-making that we have to take on. Heightened pressure to perform. Often pushing boundaries.”

“I actually don’t think I felt much imposter syndrome when I was younger, because I knew that I wasn’t really meant to know what I was doing yet.”

“I was much more aware of it as I got older, especially seeing other executives dealing with the same.”

Aaron mentions a couple of people in high-up positions, for example an executive of a $100 million software company who he has talked to about having imposter syndrome.

His hypothesis? High achievers such as this are in positions where they need to be doing something differently to everyone else in order to get traction in today’s climate.

They aren’t seeking the easy route because that likely won’t equal growth.

Aaron quotes:

“Comfort is the enemy of growth.”

“Therefore you must step out of your comfort zone to achieve growth.”

When you’re attempting something new that hasn’t been done before - let’s say a new B2B marketing campaign - that has no defined route, no pre-written action plan, and no guaranteed outcome, you can understand why someone might feel a bit out of their depth.

That’s not because they aren’t good at their job.

It’s because it's brand new; there’s more to be learned. The outcome is not yet known. No one can fully ‘know what they’re doing’ when charting new territories.

Aaron tells us a little more about this:

“When I’m doing something new, for example, I’m working on some new content. I believe what I’m hypothesising is likely true, but I don’t have the facts.”

“Between confidence in my understanding and fact, I think there is space for imposter syndrome to creep in.”

Aaron talks about this topic with Elliot, an experienced User Experience Design Director. Watch the clips from their interview below 👇

Elliott reiterates many of the same points that Aaron has been feeling about imposter syndrome. He also raises a study which discovered the Dunning-Kruger Effect which could explain why imposter syndrome is so prevalent in high achievers.

What is the Dunning-Kruger Effect?

Dunning-Kruger Effect Diagram

As you can see from the diagram, this theory proposes that those who have little to no experience in something have high confidence that they know about it, or could do something they haven’t tried.

For example, have you ever had a conversation with someone who has less experience in something than you, but they appear to be unfalteringly confident talking about the subject - even if they're wrong?

Or maybe you’ve seen someone do something on telly and you’ve said “I reckon I could do that better than them” about a task or activity you’ve never done before in your life?

Essentially, this is because as a novice, you don’t yet have an understanding of all that the subject or activity entails. In other words, you don’t know what you don’t know yet.

This theory also has an opposite end of the scale. One that helps to explain why some high achievers may underestimate themselves.

The Dunning-Kruger Effect suggests that as you start to learn about a subject, and more importantly, can recognise how much more you have to learn, your confidence in your ability and knowledge falls.

Essentially, imposter syndrome - or more generally, anxiety and doubt - are natural by-products of growth.

That is, until you have become an absolute expert on the subject, when your confidence begins to rise again.

Why is this important to understand imposter syndrome?

Well, as individuals climb the career ladder, they’re able to understand and acknowledge how much there is to know. They’re better suited to assess their own abilities.

There is also an argument to say that high achievers may put more demanding expectations on themselves - the reason for this is that they’re often driven to perform.

In industries that are always changing, such as marketing, B2B sales and many more, there are no limits to how much you can know. Your knowledge changes or increases as the industry changes.

Even those at the ‘top of their game’ will have to continue to develop, grow and potentially take risks to stay successful.

Why don’t high achievers talk about imposter syndrome?

Okay, so we know imposter syndrome exists.

And we know it’s often experienced by people in well-respected roles.


Why’s no one talking about it?

First of all, there’s a natural bias to sharing good news over bad. Consider social media: most people share the highlight reel of their life, rather than the moments when they’re feeling low or doing menial tasks.

The same likely applies in reality.

Aaron has a theory:

“Vulnerability in these types of roles, like a C-suite member, even a politician - they’re not really allowed to be vulnerable. It scares people.”

“So instead they only share part of themselves - the part where they’re confident. The other parts they keep hidden. A ‘fake it til you make it’ kind of deal.”

“Then all your colleagues around you are doing the same thing, so you don’t ever realise that lots of people are feeling the same way. This only exacerbates the problem.”

“It leads to individuals who are already in high-pressure jobs then carrying around this extra emotional backpack.”

They call the role of the CEO ‘the loneliest job’ because no other employee sits above or on the same level as them in any organisation.

No one else within that organisation can really sympathise with the responsibility of the role, and everyone underneath might feel scared if the leader of the company even whispers that they might feel doubt.

After all, CEOs are just normal people, humans with emotions and fears - just like the rest of us.

They may fear that if they reveal any sense of wavering or doubt, their skill and livelihood could be called into question.

Aaron says:

“We’ve built this fairytale that people high up in businesses don’t feel fear. But the consequence of this is that they then can’t be themselves at work. Which in turn can result in holding the business back.”

“I think in a sense, the pandemic helped us to move forwards a bit in this mindset. It forced a lot of habit changes with remote work.”

“A lot of people went through a process of re-examination. People asked themselves: what do I really want from my job? Plus it offered an opportunity to open up a bit more about what the challenges of life were.”

“Even beyond the pandemic, there is a reason why levels of anxiety have been rising. There are just so many more ways to feel overwhelmed. More places to be contacted, more pressure, more judgement, more decisions to be made.”

“This will only continue to get worse. So we need to balance that out with emotional health.”

“If we don’t change the expectations of people high-up in organisations, allow them to show more vulnerability, they will just burn out more quickly. People need to be allowed to be people.”

This mindset change isn’t something that will happen overnight. There are a lot of deeply ingrained habits that need to be rewritten in order for change to occur.

But we can start to slowly work towards a destination that offers high achievers the space to be open and creates a healthier workplace in general.

How can we improve things?

It all starts with communication and awareness.

We need to allow others and ourselves to be more vulnerable with one another.

By this we don’t mean suddenly opening up the floodgates and sharing each and every one of our deepest, darkest fears - that could be equally unproductive to saying nothing at all.

As a collective, we need to find a balance in navigating the grey areas.

Aaron shares what he thinks the first step in this could be:

“I believe leaders are going to have to start putting themselves online more. It used to be a ‘nice to have’ but I think it’s going to become a ‘must have’.”

“I think those who aren’t sharing more openly online will be left behind by the ones who are - and it’s especially important if you want to attract and retain a high-value workforce.”

“The important part of this though is that they have to be a person online. Connect with other people on topics they can relate to.”

This is something we can already see a lot of people doing on LinkedIn.

For example, our very own Alice de Courcy, CMO at Cognism, posted recently about her 3 year anniversary in the position.


She shares that she originally turned the role down because she didn’t think she would succeed. She doubted her own skill, experience and ability to mould herself into the right person to lead Cognism marketing.

Luckily, she changed her mind and has confidently guided our marketing activity, having an influential impact on revenue.

But arguably more importantly, she is sharing her fears entering the role, how she was worried she wouldn’t be capable of fulfilling the requirements, even though she had proved herself to be more than deserving of the opportunity.

Other aspiring CMOs, or individuals holding high-up positions in organisations who are feeling the same way, may feel a little lighter knowing that these insecurities are normal.

In turn, they may take up the baton, sharing their own experiences of imposter syndrome with others in their network.

And there goes the positive domino effect that hopefully 🤞 over time leads to a more accepting environment where high achievers can lighten their emotional backpacks.

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