Impostor syndrome as a freelancer

Feeling Under Qualified to Run Your Business? You’ve Gotta Get Rid of That Impostor Syndrome

Jessie Authentic Business 2 Comments

It starts with our teachers. A+, F, somewhere in between—where do you rank on the scoreboard? How valuable are you abilities?

And then, it’s the bosses. “Nice work” or “We need you to do better.” It might not be nearly as clear of a grading system, but it’s enough to go off of.

The average American worker is used to operating in a system of hierarchy, where you have those above you and below you, and you have a pretty good idea of where you stand in your job.

But then you go off and start a business. There’s no one keeping score anymore.

One of the keys to succeeding as a freelancer or entrepreneur is to get comfortable with operating independently. Time management and client communication can be learned. But the hardest part of operating independently? Giving value to your own work.

Battling impostor syndrome

In 1978, two American psychologists by the names of Pauline Clance and Suzanne Imes coined the term “Imposter Phenomenon,” commonly called impostor syndrome, as a way to describe the feeling that you don’t deserve to be where you are in your career. You feel like a fraud, that at any moment someone’s going to realize that you don’t actually belong and you don’t know what you’re doing.

“Impostor phenomenon occurs among high achievers who are unable to internalize and accept their success,” writes Kristen Weir for the American Psychological Association, “They often attribute their accomplishments to luck rather than to ability, and fear that others will eventually unmask them as a fraud.”

I’ve dealt with impostor syndrome on and off throughout my career, but never has it been more palpable than when I launched my freelancing business.

My first week of freelancing was a dream. Suddenly being home, possibility at my fingertips, excitement about what’s to come.

But then week #2 hit, and things got scary.

Who was I to tell businesses I can help them write better website copy? What gave me the right to tell them how to improve their conversion rates?

Or worse, what if after I said I could help, the copy went live and fell flat? I’d ruin my reputation! Why should anyone pay me?

This is, of course, leaving out the fact that I’ve been writing professionally for my whole career, that I study conversion techniques in my free time, and that I’ve already demonstrated my chops with multiple companies. What if I’m just faking the whole thing? What if they find out??

It can be a paralyzing feeling. Which is especially terrible if, you know, you just quit your job and need to move quickly to start generating an income.

The gatekeepers are gone

In the good ol’ days, there was a set order to how you succeeded in your field. Artists wooed galleries. Software developers worked their way up from entry-level positions. Novelists found book agents to help them get their work published.

And then came the internet and things began to change. Now, artists can sell directly to their fans through social media and sites like Society6. Developers can find work as freelancers, giving them far more mobility in their jobs. Novelists can self-publish through Amazon.

In many fields, the systems that gave our work lives a definitive order are gone. This is a good thing in many ways. It means that people groups who have previously been restricted from certain fields (women and minorities) have a lot more power to connect directly with an active audience without having to go through the traditional gatekeepers.

But it also means that there’s far less guidance in our professional lives.

Impostor syndrome’s always been around, but I think it’s becoming even more pronounced in our current economy. Left unchecked, impostor syndrome can eat up your self confidence, erode your motivation, and leave you with fruitless anxiety. It can also stagnate your business. Which sucks.

SO, here are a few techniques mindset shifts that have been instrumental in my own life in retaking my confidence as a professional and kicking impostor syndrome butt.

1) Start teaching what you know

You don’t have to go chase down an adjunct professor job at the local college (though you totally could). The focus here is to get that knowledge that you have stored up in your brain out.

If you’re part of a trade organization, do they have a mentorship program?

Can you give a lunch and learn presentation at a local business?

Can you start a blog?

Heck, can you make a few YouTube videos?

Helping folks further down the mountain is a great way to see just how far you’ve come. You know more than you think you do. Which brings me to our next point…

2) What seems obvious to you is revolutionary to others

I was floored by this blog post by Derek Sivers:

“Any creator of anything knows this feeling:
You experience someone else’s innovative work. It’s beautiful, brilliant, breath-taking. You’re stunned. […] You think, “I never would have thought of that. How do they even come up with that? It’s genius!”
Afterwards, you think, “My ideas are so obvious. I’ll never be as inventive as that.”

He goes on:

“But I continue to do my work. I tell my little tales. I share my point of view. Nothing spectacular. Just my ordinary thoughts.
One day someone emailed me and said, “I never would have thought of that. How did you even come up with that? It’s genius!”
Of course I disagreed, and explained why it was nothing special.
But afterwards, I realized something surprisingly profound:
Everybody’s ideas seem obvious to them.”

As a specialist, you spend your days immersed in your realm of knowledge. But your customers probably know very little about your area of expertise. This doesn’t mean that you should ever take advantage of them, but here’s the deal: Your clients hire you because they can’t do the job themselves. You bring a value to their company that they can’t provide. Remember that.

Anna Kendrick conquers impostor syndrome too

3) Everyone’s learning it as they go

Some people feel like they need to wait until they know the answers to every question before they can consider themselves an expert, or even a professional.

But even the most experienced person in your field is still learning new ways of doing their work better.

Spending time researching answers to your clients’ questions or how to do specific services they’re requesting does NOT mean you’re failing at your job. It is your job.

You can’t know the answers to everything. Regular research means you’re staying up with best practices and doing your due diligence in creating long-lasting copy, code, designs—whatever it might be.

Of course, if you’re spending all your time researching, it’s probably a sign that you need to specialize your services a bit more. You’re probably taking a wide scope of jobs that require specialized knowledge in many different areas, and you could focus your messaging to find clients more within a defined range.

But you know your work, you know your industry. Each client brings a fresh set of problems to solve, and it’s your responsibility to handle them in an informed, educated way. Studying your specialty is a sign of growth, not a sign of falling behind.

4) Get outside perspective

While your customers aren’t your boss, their feedback can be extremely helpful in dealing with impostor syndrome. I’m not telling you to go looking to them for emotional support. Instead, keep track of the positive things they say about your work.

How to Kick Impostor Syndrome | Jessie Lewis


I save all happy client emails and testimonials in a folder I named “Encouragement.” The folder also includes positive emails from former bosses and mentors. It’s a helpful collection to turn to when I need a reminder that I really am doing great work.

If you have a mentor or experienced peer, they can also be an important source of guidance in a boss-free career. I meet with other freelancers in my city fairly regularly, and I had the opportunity to chat with one of them who I’ve partnered with for certain projects. She knows my work well. When I told her that I was dealing with those impostor feelz, she was quick to remind me of my past work and reassure me that I know what I’m doing. It was so impactful to hear that, and I sincerely hope I get to do the same for someone else!

You’re not alone

Impostor syndrome is a very, very common phenomenon. Chances are, a good handful of people you know are experiencing it. So keep the conversation going! Be honest about your fears, and you’ll soon find that we’re all in this boat together.

Love ‘n’ stuff,


Photo by Nicole Mason on Unsplash


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