A freelancer's struggle with imposter syndrome
Imposter syndrome can make it hard to sell your services when you can't even convince your own mind to believe in your abilities.
So you’re out there on your own. Making a go of things. Grinding that grind. Hustling that hustle. (Insert your favorite freelance turn of phrase here.) But no matter what you do, nagging at the back of your mind, is that stinkin’ little doubt demon imposter syndrome just waiting to derail your day.
I’m not talking about the push back we get from the “real world”, nor is it from the doubters thinking the only way to be happy and successful is to have a “real job”. No, I’m talking about that creeping self-doubt that comes from…imposter syndrome.
Definition of Imposter Syndrome
From everyone’s favorite expert source, Wikipedia (so take it with a grain of salt):
Impostor syndrome, also known as impostor phenomenon or impostorism, is a psychological experience of intellectual and professional fraudulence.[1] One source defines it as "the subjective experience of perceived self-doubt in one's abilities and accomplishments compared with others, despite evidence to suggest the contrary".[2]
Those who have it may doubt their skills, talents, or accomplishments. They may have a persistent internalized fear of being exposed as frauds.[3] Despite external evidence of their competence, those experiencing this phenomenon do not believe they deserve their success or luck. They may think that they are deceiving others because they feel as if they are not as intelligent as they outwardly portray themselves to be.[4]
Impostor syndrome is not a recognized psychiatric disorder and is not featured in the American Psychiatric Association's Diagnostic and Statistical Manual nor is it listed as a diagnosis in the International Classification of Diseases, Tenth Revision (ICD-10). Thus, clinicians lack information on the prevalence, comorbidities, and best practices for assessing and treating impostor syndrome.[5] However, outside the academic literature, impostor syndrome has become widely discussed, especially in the context of achievement in the workplace.
There’s something critical to take away from this definition of imposter syndrome once you get past the jargon and alarming “exposed as frauds” phrasing.
The definition never says you don’t have the abilities, only that you think you don’t.
So, if it isn’t talking about something that is true (a lack of ability) what the heck is it talking about?
The Creeping Beast of Imposter Syndrome
Unfortunately, many of us grew up in a world where the best way for some to get ahead was by stepping on the backs of others. In many cases creating doubt in their ability to execute, whether true or not, provided opportunities to step in and showcase their abilities for their own gain. This starts the proverbial slippery slope because, “what if they’re right and I can’t do it?”
The reinforcement cycle of doubting one’s skills, tackling something new and struggling often without success, and then believing the doubt undermines our confidence and conviction when it comes to achieving our tasks and goals. Beyond the obvious truth of the existence of imposter syndrome, the bigger question is, what do we do about it?
I experience imposter syndrome all the time.
Should I be writing? Do I know how to configure this thing? Other people are so much better at X, why would someone want to use/purchase/read my version? These and a myriad of other self-destructive questions rattle around in my head taking up the valuable mental cycles I need to be productive and successful. How do I combat them?
Step 1 - What is the worst thing that is likely to happen?
Often, we’ll hear, “What’s the worst that can happen?” as a way to rationalize our fears and push through. The problem arises with that very question. If we are already battling with imposter syndrome, we’ll be great at producing a plethora of world-ending scenarios all inevitable due to our “lack of ability”. This is why I turn the question to what is likely to happen, not what is possible. Anything is possible and as such it is impossible to prepare for every situation.
If you look at what lies ahead and prepare for the likely negative outcomes you won’t waste time preparing for unnecessary ones. Imposter syndrome can be mitigated through a sense of preparedness, but only when done with reason.
For example, when preparing a technology project, I run through scenarios of the project execution looking for failure points, so I have a better understanding of what to expect. When imposter syndrome creeps in I can frame it in my mind that, if things do go off the rails, I won’t be unprepared. No matter whether I feel like I’m ready or capable, I am and I am.
Step 2 - Be a student of history
When the creeping beast arises, make a note of what you were doubting and your concerns. Capture details about how things went, where there were struggles, and what you think you could have done to mitigate or prevent them. This in-the-moment capture is key because you aren’t trying to solve the problem; you are gathering data for future you to leverage.
After the passage of time has allowed you to become safely removed from the scenario, look over your notes and find out if your doubts (which you should have captured honestly) were founded or unfounded. If founded, what could you do in the future to prevent them from being true? If unfounded, as is likely the case, just the sheer acknowledgement of their false nature provides strength and foundation for battling the creeping beast in the future.
Step 3 - Acknowledge the source of the voice
If someone were to walk up to you while you were doing something and say, “You can’t do that. You don’t have the skills. You’re not smart enough. Why waste your time?” What would you do? Speaking for myself, the conversation would not end well or politely. So why do we put up with this from ourselves?
That inner doubt we hear, so often it is our words but someone else’s voice. We may hear a parent, a teacher, a manager, or someone else who held sway and influence over our lives. That voice has gravitas regardless of the message it carries. Unfortunately for so many of us, the message it carries is destructive and limiting.
Don’t accept the inner voice when it tries to tear you down. Don’t respond with, “you may be right” but rather “prove it, I dare you.” Challenge the beast. Make it back up it’s words. If you’re on the freelance path, which means you’re not afraid of a challenge, use that to your advantage and prove the beast wrong.
There is no quick fix.
No matter what advice I give, or anyone else gives for that matter, there is no quick fix to the problem that is imposter syndrome. The only thing you can do is tackle it head on, prove it wrong, and then tell it “I told you I could.”


There is no quick fix! Fantastic post.
You could argue that a health amount of imposter syndrome demonstrates a well-managed ego. If you always think you’re the shit, you may not have to deal with imposter syndrome but you’ll definitely have other problems.
Good stuff brother.