How to Survive (and Thrive) While Freelancing With Imposter Syndrome: Part Two

Elizabeth M. Jones
6 min readJan 28, 2020

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Freelancing can be tough, and imposter syndrome makes it even more difficult. Read on to find out how imposter syndrome rears its head for three freelancers and why it is that freelancers are vulnerable to it.

Welcome to part two of my four-part series on surviving and thriving in the face of freelancing with imposter syndrome! In the last post, we covered what imposter syndrome is and the different personas it takes on; in this post, we’ll cover how that dastardly imposter syndrome distorts the headspace of freelancers and just why it is that we’re prone to grappling with it.

And don’t forget to stay tuned for the next installment in the series, where we’ll dive deep into ways freelancers can combat imposter syndrome, including perspectives from freelancers just like you and I who’ve dealt with it firsthand. If you want to receive the next post right in your inbox, follow me on Medium.

Ways imposter syndrome tricks freelancers

Imposter syndrome can be succinctly described using the same words Gollum used to describe the hobbits in The Lord of the Rings: It’s wicked, tricksy, and false. It pulls the wool over our eyes and makes us question whether we have what it takes to make it as a freelancer at all. Some of the ways it does this are by triggering feelings of jealousy, preventing us from trusting in ourselves, and causing us to doubt our abilities. Let’s take a closer look at each of these games imposter syndrome plays with us.

It triggers feelings of jealousy

I’ll be the first to admit that sometimes when someone on my social media feeds celebrates their newest accomplishment, it makes me squirm a bit as I compare myself to them and my wins to theirs. Every time I end up feeling as though I come up short, and instead of feeling proud and excited to have such a successful and supportive network, I feel small and frustrated by my own lack of sterling success. I’m not alone (and neither are you!); many freelancers I spoke to felt inadequate when other people share the news of a big win.

“Imposter Syndrome always shows up for me when it comes to my business. As soon as I get a brilliant idea and start the execution process, I start getting the feeling of “this won’t work” or “you aren’t qualified to do something this great. If I see someone in my industry having success, even if it’s a win I don’t particularly care for, my inner critic says “See. They are better than you.” I know that I’m genuinely happy to see others’ progress but that IS is real!”

Maleeka T. Holloway, award-winning publicist and owner of The Official Maleeka Group (The OMG)

It keeps us from trusting ourselves

Imposter syndrome has a knack for finding ways to make us think we don’t have the answers we need. When it seems like everyone around you is an expert and you’re not, it’s so incredibly easy to fall victim to the trap of doubting yourself. It’s normal to want feedback on your work and to get a second opinion when a concept seems fuzzy or foreign to you, but if you’re constantly looking for validation of your expertise and abilities, imposter syndrome likely has its claws in you.

“I’ll seek out the advice of others far earlier, rather than having a go myself, and perhaps compromise too often on something I think is right, but will take the advice of others to be better informed than my own thinking.”

Matthew Knight, Chief Freelance Officer at Leapers

It makes us second-guess our capabilities

Show of hands — how many of you have ever been writing an email, blog post, or tweet, hesitated halfway through, and then deleted the entire thing, opting to stay silent instead of sharing your valuable perspective? Ah, I see a lot of hands in the audience. In fact, I’m willing to wager that all of you have silenced yourselves at one point or another when your insight, reply, or pitch could have been brilliant. It’s an ugly reality, but if your thinking is muddled by imposter syndrome, it’s almost certain that you’ve censored yourself when the world would be made better and brighter by your voice.

“Whether I’m about to respond to a tweet or I’m sending a proposal to a prospective client, something in me says, ‘You’re not as good as everyone else. Now, freak out, forget to breathe, and quit before everyone in the world finds out what an embarrassment you are.’”

Karonica Paige, freelance copywriter

Why are freelancers prone to it?

Imposter syndrome exists in every industry and at every education and experience level, but freelancers seem to bear the brunt of the psychological phenomenon. When I mentioned on Twitter my idea for this blog post, freelancers came out of the woodwork to offer their perspective, showing me that there’s a real problem with it in our community.

Why are freelancers prone to imposter syndrome, though? There are a few reasons that those of us working in such a nontraditional fashion fight it: A lack of transparency among freelancers, the sometimes cutthroat competition, the harsh reality of ghosting, and the isolation of working for yourself by yourself much of the time. I’ll touch on each of these points in greater detail below.

Lack of transparency

There’s a strange swirling fog of secrecy that envelopes freelancing as if it were one of H.P. Lovecraft’s Elder Gods instead of a form of self-employment. This is clear simply from the sheer number of resources and information other freelancers offer behind paywalls. You can purchase a lot of what’s not freely available, like templates and references, but there’s a lot that freelancers are reluctant to share with one another, even for a price. There’s a pretty good reason for it, too…

Cutthroat competition

…there are a lot of freelancers out there in every field imaginable, and while the demand is equal to the supply, it still leaves a lot of us feeling as though there’s a scarcity of clients. This goes hand-in-hand with the lack of transparency we deal with; freelancers may feel compelled to keep their knowledge to themselves to give themselves a leg up on the competition. It’s not necessarily a bad thing, rather it’s more so a necessity of working for yourself.

I’d like to add that, while there is a lot of competing for the same clients, there are also all kinds of welcoming and inviting freelance communities on every platform imaginable. We want to welcome new freelancers; we just don’t want to share our rates or our best tricks for writing a killer pitch email. And a lot of this is because if rates were transparent to our competitors, it could lead to a fast race to the bottom in terms of pricing for all of us.

Ghosting

The struggle against ghosting is one of the most valiant and noble fights a freelancer could take part in. When a client ghosts you, whether it’s ignoring your brilliant proposal or disappearing off the face of the planet when it comes time to make a payment, it is a direct line to a manifestation of imposter syndrome. After all, what could make you feel worse (in terms of working) than someone not valuing you enough to respond to (or pay) you?

If you’re already feeling less-than for any number of reasons, it’s a no-brainer that someone blatantly ignoring you and disregarding you would make you feel as if you and your work have no value.

Working solo

I work out of my home, and so do a lot of you. There’s a lot of advice out there on getting out of the house and going to a library, coffee shop, or renting a desk at a co-working space, but that’s not always an option for any number of reasons. If you can’t get out and you’re stuck staring at a less-than-personable screen for several hours a day, imposter syndrome can easily take advantage of the situation and creep into your cranium.

It’s not simply because we work remotely that we feel isolated, either. Working on your own, managing your own projects, and taking on all of the administrative duties can make you feel as if you’re stretched too thin and that you really don’t know what you’re doing in the first place. When you don’t see others struggling with their invoicing or banging their head against the keyboard like you do (just me?), you can really easily slip into the mindset that you’re just a fraud chugging along until you get caught.

Now that we’ve uncovered what imposter syndrome is, how it manifests and impacts freelancers, and why freelancers are particularly susceptible to falling into its trap, we’re going to take a close look at how freelancers are taking stands against it in the next installment. But for now, share your story of freelancing with imposter syndrome in the comments below, or contact me here to share your story directly with me. And to get notified of the next post as soon as it’s live, follow me.

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Elizabeth M. Jones

Hi there! I’m Elizabeth, a freelance digital marketing copywriter hailing from Maryland. You can find out more about me here: elizabethmjoneswrites.com