“No one is perfect…that’s why pencils have erasers.” – The Simpsons

The worries and doubts of an entrepreneur are a dime a dozen.

Do you worry about being able to raise the amount that you’re asking for, and with the terms you want? Do you panic that you’ll fall short on the promises you made to your investors? Or, do you worry if your team sees you as their leader? The list goes on …

You may be suffering from “Imposter Syndrome.”

Sounds scary. Not to worry though. Imposter Syndrome, as we’ll talk about below, is a temporary state, which means it can be reversed.

In this post we’ll identify your Imposter Syndrome, and more importantly, provide you with tactics to overcome it. Specifically, we’ll teach you how to measure your baseline level, followed by evidence-based tactics to help you curb your feelings of Imposter Syndrome.

The tactics you’ll learn about are based in dialectics, an ancient system of thinking that has gained recent traction in the behavioral and brain sciences. Part of this will be challenging some of your “hard wired” distortions of how the brain and body work, altering the autopilot function buried deep within you.

You can rest assured knowing that our team of PhD psychologists and serial entrepreneurs have combed through the literature, giving you only the best advice that you can count on.

What is Imposter Syndrome?

Imposter Syndrome is a phenomenon where you have trouble internalizing, and realizing, your successes. Instead of seeing the “wins” as a product of your own personal hard work/talent, you attribute them to some outside source, like luck or opportune timing.

And you fear that it’s only a matter of time that you’ll be found out and people will realize the truth behind your chance successes. Your cover will be blown and others will finally see you as you really are: a fraud, a fake, an imposter.

At its worst, the symptoms of Imposter Syndrome can be quite distressing. Dysfunctional thoughts can impact your ability to do your job. You may find yourself feeling doubt in your ability to perform; wondering if your have the capacity to make the “right” decisions; questioning whether or not you are capable of overcoming the obstacles that come your way.

Imposter syndrome is a biological phenomenon. A brain network within our memory system can influence imposter syndrome. It’s called working memory. Working memory is like the brain’s whiteboard. It “writes” cues for you to keep on track of different tasks and goals, especially in busy environments with lots of things going on.

The upside of working memory is that it keeps you on task during times of distraction, and it cues your memory, which recruits the other parts of the brain that are needed.

The downside is that just as useful tasks get “written” down on the whiteboard, so do unhelpful and dysfunctional cues. These negative cues then overcrowd the mental whiteboard, forcing our thoughts, feelings, and behaviors to be about our negative self-image.

Why does Imposter Syndrome plague Entrepreneurs, in particular?

Entrepreneurs are particularly susceptible to Imposter Syndrome.

The combined personality traits of high achievement and perfectionism make an entrepreneur. But it’s these two things that, unfortunately, also lead to Imposter Syndrome.

The tricky paradox of Imposter Syndrome can also be thought of like this:

1. The very things that makes you an entrepreneur are the same things that makes you feel like you shouldn’t be an entrepreneur (i.e., you’re faking it).

And …

2. The more success you have as an entrepreneur, the worse your Imposter Syndrome gets because the successes are mere luck rather than coming from you.

How these experiences and feelings happen isn’t so straightforward. And as a result, it requires solutions that are equally not-so-straightforward. A paradoxical problem requires a paradoxical fix.

Enter dialectical thinking.

3 dialectical thinking tactics to overcome your Imposter Syndrome

The basic concept of dialectical thinking is that something is better understood the more you understand its polar opposite. And, it’s at this point in the understanding that the opposites themselves begin to dissolve – a coming together of two extremes as a final synthesis. The dialectic is said to be resolved.

It’s an ancient system of thought that helps us make sense of the paradoxes that exist around us. The Taoist’s tradition of the Yin and Yang is one ancient example of a dialectic.

Now modern neuroscience and psychology are finding that the brain perceives and organizes experiences in the form of dialectics. This is especially true for things that are complex and counterintuitive.

It’s for this reason that applying a dialectical thinking framework is a highly effective way for overcoming Imposter Syndrome. Remember, a paradoxical problem requires a paradoxical fix.

So, let’s start. Before we dive in to the tactics, the first step is to get your baseline measure. You can take the test here. Be honest in your responses. When you’re done, come back here.

Review your results below based on your Total Score:

40 or less→ few Impostor characteristics and experiences

between 41 and 60 → moderate imposter experiences

between 61 and 80 → frequent Impostor experiences

higher than 80 → often and intense imposter experiences

The higher the score, the more frequently and intensely the Impostor Syndrome can impact our ability to function and perform.

How do you feel about where you landed on your score? According to decades of research on how we think when we are feeling low, it’s likely that you will find yourself on one of two sides.

Side A: “I don’t feel like an imposter but I have a high score.”

This is normal. We are not very good at judging ourselves inaccurately. This is called the Above Average Effect (Van Yperen and Buunk, in 1991). It means we’re biased to believe that we are all above average or “better” than most.

Side B: “I feel like an imposter but I don’t have a high score”

This is also normal. This simply validates the idea that the feelings of Imposter Syndrome come and go.

And regardless of which side we fall on, we can all benefit from the tactics below.

Dialectic lesson # 1: shared experience VERSUS isolated experience

We often feel as though our experience of Imposter Syndrome is something that’s happening only to us. The truth is, Imposter Syndrome is a commonly shared experience among the entrepreneurial community (we all feel it sometimes). You may have read or heard of this general concept before. It’s called common humanity. It says that our negative experiences are actually quite commonplace and happen to everyone, not just us.

The following dialectic exercise is a way for you to think about your own negative experiences of Imposter Syndrome and to prime your thinking of a common humanity.

Step 1: Think about a time that you were feeling like an imposter (i.e., experiencing self-doubt). Focus in on the time, place, and context. Now, record the thoughts (the voice in your head) out loud on your phone in first person (or dictation software if you happen to have that handy). Get the transcribed recording ready in text format.

Step 2: Think about a different situation when you were feeling like an imposter. This time, focus your thoughts and make use of the word “they/him/her” rather than “I”. Make sure you are speaking in the third person. Again, get the transcribed recording ready in text format.

Step 3: Think about a time when another person came to you with concerns of self-doubt. Do as you did with the previous two steps, but instead say out loud what you would have said (or what you actually said) to them. As before, get the transcribed recording ready in text format.

Step 4: Go to this free linguistic translator tool. Copy the text from Step 1 into the textbox and follow the instructions to analyse your results. Record your results from the following linguistic dimensions:

Self-references (I, me, my)

Social words

Positive emotions

Negative emotions

Step 5: Do the same analyses in the translator but from the transcribed speech in Steps 2 and 3.

Step 6: Note the differences in self-references, social words, positive and negative emotions. Your first person speech will be higher in self-references and negative emotions, and lower in social words and positive emotions. What you should aim to see is that your third-person and other-person speeches are closer matched.

After you do this exercise, keep it in memory. At any moment you begin to feel the twinge of Imposter Syndrome, check in with your internal speech style. Are you internalizing your feelings in the first-person and making your experience seem more isolated than it actually is?

When we view our failures from a shared experience perspective, we are engaging in a social comparison that will make us feel better. We are less likely to feel like an outsider. We begin to realize that such feelings are quite normal, even banal. And when something feels normal, tension reduces.

Understanding your feelings by situating them into a shared experience is how the synthesis between the opposing forces happens. It’s at this point the dialectic is resolved.

Dialectic lesson # 2: Matter over mind VERSUS mind over matter

Our thoughts influence our emotions, which in turn, influence our bodies (expressed in body language, facial expressions, postures, gesturing, and the like). You often hear this reflected in the saying “mind over matter.”

The process works in the other direction as well. Much the same way, our bodies influence our emotions which influence our thoughts. Think of this as “matter over mind.”

Similar to the first set of exercises, knowing the two (seemingly) opposite processes will help you resolve the dialectic of Imposter Syndrome. We’ve developed this next tactic to get you there faster (and more effectively).

Step 1: identify compassionate body language in others. Think back to when you were a child. What did people do to help make you feel better? How did these people soothe you? How did they show you physical compassion?

Similarly, think about others in your life who you rate as highly empathic and understanding. These are the people who make you feel at ease just by being around them. For both your past childhood memories and the high empathizers you know, think about the compassionate body language in terms of their:

Posture

Facial expressions

Hand gestures

Gentle touch (e.g., hugs)

Step 2: Identify and compare your own body language. Think about yourself, specifically in times when you are at your busiest and feeling a lot of self doubt and worry.

More often than not, it’s not the thoughts that need to be challenged, but what’s happening in your body and physical responses.

Is your posture tight to the body and hunched?

tight to the body and hunched? Is your facial expression showing tension in the forehead?

showing tension in the forehead? Are you hands clenched into fists?

clenched into fists? Are you moving aggressively (i.e., typing hard, stomping as you walk)?

The matter over mind is a set of Pavlovian operations. Human beings function as a series of stimuli and responses.

We see food, we salivate. We clench our hands, we promote worry in our minds. We close off our body language, we close off our ability to think clearly. We stand erect at a podium, we feel confident and in charge.

Research has shown that bodily sensations, such as facial expressions, act as direct input to our emotional experience. Therefore, altering the body can alter the mind. Remember, matter over mind.

The goal then is to engage in the movements you noticed in the high empathizers of Step 1.

Step 3: The next step is to actually apply compassionate body language to yourself.

Literally give yourself a hug. And if you don’t want to seem weird around others, you can do the following:

Gently stroke your arm in a warm and soothing way (with intention)

Mimic hand holding – reach out to your other hand as if it was someone you cared for; use the same gentle grasp, and cultivate that same sense of satisfaction

Think of the the way that compassionate touch is displayed between two people. Imagine how you would hold your partner or child’s hand (even your furry pal! In fact, petting our pets reduces blood pressure and heart rates). It’s very different than the way you link your fingers in a meeting, or make fists when you are worried, or press down on your legs when you’re tense.

Compassionate touch releases oxytocin in the brain – the “love hormone”. Oxytocin is responsible for producing feeling of safety and connectedness, two states that get depleted when your Imposter Syndrome flares up.

Dialectic lesson # 3: identification VERSUS overidentification

Here overidentification is the norm and default. Once again, you need to understand its opposite to get the whole dialectic picture – to reach a synthesis and eventual resolution. Take the following steps (note: you will need one RED and one GREEN marker/pen).

Step 1. Pay attention to the feelings you’re “labeling” in your head. Write them down in your notebook.

Step 2. Code these feelings based on the questions below. Be an impartial judge and as unbiased as you can. If you are having trouble getting past your subjective view, ask someone else to get their objective opinion. They don’t live inside your head.

Is this feeling irrational? Yes = RED No = GREEN

Is this feeling harsh, mean or critical? Yes = RED No = GREEN

Is this feeling self sabotaging? Yes = RED No = GREEN

Is this feeling operating as a crutch? Yes = RED No = GREEN

Is this feeling helping you to procrastinate? Yes = RED No = GREEN



(be sure to notice the order of yes versus no coding for the next two).

Is this feeling helpful? Yes = GREEN No = RED

Is this feeling DIRECTLY related to this current situation? Yes = GREEN No = RED



It doesn’t matter how many are red versus green, but whether or not they are red versus green.

RED = overidentified and GREEN = identified

Our thoughts can lead to challenging feelings (or emotional thoughts). These feelings can end up with too much power, and too much weight – this is overidentification. The simple labeling of a thought as overidentified is effective in removing its power. So you can proceed to the next step with all of the RED thoughts.

Step 3. Take the overidentified thought and circle the words that are particularly triggering for you. These will differ for each person, but it could be something like: fail, fraud, stupid, incompetent, meeting, leader, inventory, etc.). Rank each trigger’s intensity from 1-10 (1 = no intensity, 10 = extreme intensity).

Choose the one with the highest intensity rating.

Literally say this word out loud. Yes out loud, and repeat the word for 45 seconds. (time yourself)

“Fail, fail, fail, fail, fail, fail, fail…fail.”

According to a concept called Cognitive Defusion, through this repetition, the word itself will eventually lose any associations it has with the actual meaning. It becomes a meaningless sound and will lose its power over you.

Recap and wrap-up

Imposter syndrome is a common and puzzling phenomenon in entrepreneurs. It’s an ironic outcome of being a high-achiever and a perfectionist that leads you to feeling, on the one hand like confident founder, and on the other, like an imposter unworthy of success.

Immersing yourself in dialectic thinking is an effective strategy for overcoming the paradox of Imposter Syndrome. To better understand your experiences, you need to see where your mind is at now – and reveal its opposite. Spend time in this opposite place. Experiencing both is how the dialectic is resolved. It’s how to overcome your Imposter Syndrome.

Remember the three dialectical exercises and implement them at any point that you’re feeling like an imposter:

Shared Experience VERSUS Isolated Experience. Matter over mind VERSUS Mind over matter Identification VERSUS Overidentification

Now go get your dialectical thinking on!

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