The Cure-All for Entrepreneur Imposter Syndrome

It involves saving positive feedback to an inbox folder called “CUTE.”

 minute read

Liz Hammond

Imposter syndrome is a form of self-doubt that affects creatives, intellectuals, and humans of all walks of life. I would venture to guess that everyone from Albert Einstein to Meryl Streep and Elon Musk have felt a touch of imposter syndrome at some point in their lives. It’s human nature to underestimate our abilities and to be our own worst critics. While it doesn’t discriminate, I would argue that imposter syndrome is felt most intensely by entrepreneurs. The humans that have said no to the bounds of the 9-5 grind and put themselves and their talents on the line every day (myself included) come up against intense self-doubt on the regular. 

As a self-employed individual, we don’t have the backing of a large company when we’re pitching ourselves, negotiating payment or navigating feedback. Going at it alone raises the stakes and makes every rejection (and win) feel completely personal. It’s almost impossible for self-doubt not to wreak havoc when a proposal you’ve put your heart and soul into for hours is passed on, or a client starts ghosting your emails. There’s also the initial guts required to take the leap into self-employment and put yourself out there. Imposter syndrome has a field day when you share some of your work with the world, or when you start reaching out to potential clients you’d love to work with. I can’t tell you the amount of times I’ve thought to myself “Who the hell do I think I am?!” as an entrepreneur. It’s a constant battle for many of us, but I’ve gathered some of my go-to tips to help you overcome imposter syndrome when it rears its ugly head. 

1. Believe Your Reviews 

 Does anyone remember the Sex and the City episode when Carrie fixates on the one tiny negative comment in her New York Times Machiko Kakutani review? Instead of celebrating the otherwise rave review, she went into a tailspin over a single sentence. Even if you haven’t seen the episode, there’s a learning in this. We have a tendency to focus on the negative and brush past the evidence that we do in fact know what we’re doing (heck, I’d venture to say we’re even amazing at it). Whenever a project goes smoothly or I receive positive feedback from a client, I try to take a pause and savor that shit. This is the medicine for self-doubt, and it’s important to stock up on it when you can.

 2. Bank the Wins 

I believe so strongly in the magic of compliments that it goes beyond savoring them – I have to save them for a rainy day. My friend did this endearingly brilliant thing where she would save all nice feedback from managers or work wins in an email folder aptly titled “CUTE”. She would look back at these affirmations of self-worth when she was having a hard day or was hit with imposter syndrome. I copied this and find it beyond reassuring to peruse my rave reviews when I start to doubt myself. 

 3. Cut the Comparison 

You’ve probably read on a bumper sticker or Pinterest that comparison is the thief of joy. Cheesy as it might sound, the dangers of comparison are real – especially to an entrepreneur deep in the throes of insecurity. Although it can be beyond tempting, resist the urge to compare yourself to other entrepreneurs, people in your industry or strangers on the internet. No matter how polished or perfect that they may appear, they too are undoubtedly faced with imposter syndrome from time-to-time. 

4. Surround Yourself with Cheerleaders 

Just like furniture, doing a little feng shui with the people and energy around you can shift your perspective when you need it most. When I’m feeling unsure about my abilities or worth as a freelance writer, I try to surround myself with people that get it (aka other entrepreneurs), or the friends who are generous with reminders that I am indeed awesome. Even if this person is your mom, being around your cheerleaders helps squash imposter syndrome in no time.  

5. Fake It ‘Til You Make It 

If I were to write an entrepreneur’s handbook, this tip would be at the forefront. So much of what I do as a self-employed individual is saying yes and figuring it out later. A client doesn’t have to know it’s my first time doing something, or that I’m battling self-doubt if I show up with confidence. This doesn’t mean taking on a project you have zero expertise in or refusing to take feedback, but entering into the entrepreneurial arena does require a bit of diving in headfirst and hoping for the best. The more you fake it, the sooner you’ll start to feel authentically confident and your results will speak for themselves. 

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