Breaking Through Impostor Syndrome: A Letter to the Doubting Entrepreneur

This is a letter to the imposter… Yes, you.

Do you consider yourself an imposter? Does it sting a little to think about?

Don’t you believe that you can do this? That you can be a successful entrepreneur? Do you remember why you started?

What makes you an imposter? Huh, really?

Think about it… Everything you’ve done in life you’ve started without the evidence of future success – right?

Think about your favorite thing to do. Did you really know how to do that thing when you came out of the womb?

I don’t know why or how this happened, but I think I’ve felt like an imposter for most of my life. Maybe you have too?

I don’t know about you, but I tend to get imposter syndrome when it comes to learning new things. From becoming a freelance writer to learning how to climb, from learning how to code to digital marketing.

But I’m getting over it. I’ve been working hard at changing my thoughts and my approach to everything I do since mid-2019.

Getting over impostor syndrome (much like everything else in life) is about the journey. Not the destination. You’re never going to arrive. It’s a practice.

What is Imposter Syndrome?

Impostor syndrome is “a psychological phenomenon in which people are unable to internalize their accomplishments.” Nearly 70% of people experience Imposter Syndrome at some point in their life.

In a 1978 study that named the phenomenon, psychologists found that despite having adequate external evidence of accomplishments, participants with Imposter Syndrome were still convinced that they didn’t deserve the success they had. The study focused on women specifically because it was originally assumed that only women experienced Impostor Syndrome.

What does Impostor Syndrome look like?

Impostor Syndrome typically manifests as a persistent, internalized fear of being exposed as a fraud and doubting accomplishments. Valerie Young outlines some common feelings in her book. Here’s how those feelings might manifest in you.

1. Perfectionism

You might be a perfectionist if you set extremely high expectations for yourself. Even if you meet almost all of their goals, you feel like a failure. Every minor error leads you to doubt their competence. You rarely, if ever, give yourself credit for your accomplishments.

2. Experts

You feel like you need to know everything you could possibly know about a project or skill before you can start doing it. You look for ways to continue learning about a skill or a project like taking courses, getting certifications, or reading books. You might even research a topic your entire life without ever trying what you learned in your research.

3. Struggle

You’re a “natural genius” in a certain area, but you believe you have to struggle, work hard, or feel discomfort in order to accomplish something. When you don’t struggle or work hard for something, you feel like you’re not deserving of that thing (often money). You use it as proof that you’re an imposter.

4. Superhuman

You’ll push yourself to work harder than anyone around you to prove that you’re not an impostor. You need to succeed on a high level in every aspect of life (work, family, relationships, at the gym) and you feel stressed when you’re not accomplished on a high level. 

Is Imposter Syndrome really just a lack of confidence?

Not exactly. Imposter Syndrome is noted as a reaction to circumstances or situations. Perfectionism, comparison, fear of failure, and self-sabotage are widely known as the main fuel for the syndrome fire.

It’s believed that Imposter Syndrome is a self-perpetuating cycle. Those feeling the effects of Imposter Syndrome may experience debilitating stress, anxiety, low self-confidence, shame, and even depression.

No one knows why so many of us feel Imposter Syndrome. Some psychologists believe that It stems from anxiety or neuroticism, while others wonder if it stems from family, institutionalized discrimination, teachers, or some other part of their upbringing. Some psychologists will ask, “Was there someone in your life whose opinion you felt was important that you felt you could never do well enough for?”

If you’ve ever felt like…

  • your grades were never good enough
  • your tuning or rhythm was never quite right
  • your writing was always heavily critiqued
  • your sibling outshone you.

You probably started getting imposter syndrome when your brain was developing.

How to overcome Impostor Syndrome

I’m not a licensed professional. I’m not your therapist. This is not professional advice. But I can tell you what’s helped me overcome my Impostor Syndrome. Here are seven ways to work with your brain.

1. Reframe

Observe the feelings of Imposter Syndrome and put them in perspective. Try not to engage the thought.

When you notice Impostor thoughts creeping in, ask yourself… 

  • “Does this thought help or hinder me?”
  • “Is this thought true?”
  • “Is there a way to get around it?”

Often the easiest way to get over feelings of being an imposter is by taking action. I know that’s so scary, but it truly is the best way that I’ve found.

Don’t get me wrong, 80% of the time I’m too afraid to do this. But when I do, I feel phenomenal and competent. If you’re not ready for this, try one of the exercises below. They’re a softer introduction to overcoming your thoughts.

2. Give yourself credit

Make some lists of things that:

  • you’re good at
  • you’ve accomplished
  • make you unique
  • you love to do
  • argue your feelings of being an imposter

Don’t feel like you have to be the best at something to write it down! If you can’t think of anything, ask someone you know!

My roommate made me feel so seen and valid when I asked her, and she told me things I never would’ve given myself credit for. I also keep a file full of screenshots. Every time a client gives me a compliment or good feedback, I add a screenshot to the file.

3. Talk to yourself

I know this sounds awkward and silly. Trust me, though, it works. Just try it. Tell yourself the things you want to hear, look yourself in the eye, and say them with confidence. Here are some of my favorites.

  • “You can do anything you put your mind to, get out of your head and just do it.”
  • “You are capable.”
  • “You are not an imposter.”
  • “You are a ______”
  • “No one’s thinking that about you. It’s okay.”

4. Talk to someone else

Talking to a business coach, therapist, or peers who are experiencing the same thing can help you feel better. For me, knowing that I’m not alone is so helpful. It makes it seem possible to overcome these feelings. As Mr. Rodgers says, “If you can mention it, you can manage it.”

5. Replace your thoughts

Okay, this one is definitely easier said than done. I spent the past six years “replacing” my thoughts.

I actually printed out this chart and hung it by my desk as a reminder. This took me about four years to get the hang of. And sometimes, when I’m burnt out, especially, I falter. That’s okay! What matters is that it’s always there to come back to.

Instead of…



Am I good enough?

How can I get better?

Why don’t you feel good enough?

What if I fail?

Failure is learning.

My brain doesn’t have any concrete evidence that I will succeed so I need to create some.

What if people judge me?

What’s the cost of not trying?

If you start now with determination, where could you be one year from now?

How can I catch up to them?

How can I improve from last week?

Don’t compare yourself to other people doing what you’re doing. They’re not you!

6. Make a friend

Get in touch with someone you look up to in the field you’re feeling like an imposter in. You could contact them on LinkedIn or another social media platform or even email! Ask if they’d be willing to do a short virtual coffee date, 15-30mins, or meet them in person if they’re local to you.

Make it easy for them to schedule it with a tool like Once you get to the coffee date, don’t be afraid to be honest with them!

7. Ask for help

Changing your thoughts is actually super hard. But changing your thoughts will change your life, your business, and yourself. By doing thought work, I’ve made breakthroughs in my business, found better ways to cope, changed my work/life boundaries, and even started to get past my own imposter syndrome.

I began changing my thoughts by hiring a business coach and going to talk therapy. Hiring a coach was honestly the biggest catalyst for me. I received the sessions with my first coach as a gift. I never would’ve spent money on that. Now I work with a coach for 3 months at the beginning of every year.

Are you experiencing Impostor Syndrome?

From one impostor to another, I hope this article helps you scratch the surface of your own Impostor Syndrome. You can work with your brain instead of against it to move past the fears that block you.

I’d love to hear from you! Do you experience Impostor Syndrome? If so, what’s it like for you?

Rachel has been a freelance writer for 6 years and a business coach for 4. She grew up in a family of entrepreneurs and carries the torch for the next generation. When she’s not writing, she spends her time adventuring in the outdoors, doing arts and crafts, and snuggling with her cat, Bonnie.

Find her on LinkedIn and her website.