For When Imposter Syndrome Creeps In

Thinking about starting a freelance career? You’re not alone. Today more people than ever before are choosing freelancing careers, both out of necessity and flexibility. 

The inevitable self-doubt that comes with working for yourself can make it all the more daunting.

I’ve been working as a freelance writer since I was 17. And while working for myself can be fun, it’s not just sitting in front of a laptop with clients lining up to hire you, contrary to what most people believe.

Building a business is hard, and the inevitable self-doubt that comes with working for yourself can make it all the more daunting. 

It can make you wonder, especially if you’re just starting, how exactly do freelancers find success and mitigate self-doubt along the way?

Understand the Business Aspects of Freelancing

Before you start freelancing, do your homework; self-doubt often pops up when we’re entering new and unfamiliar industries. The internet is an ocean of information; take advantage of the many articles, videos, and podcasts available. Know which freelancing path you want to take and where you can develop your skills. These education platforms and websites, for example, offer classes for just about every skill set.

Depending on the freelance path you choose, here are some business aspects to consider:

While I’m an advocate of “no need to spend to get your first client”—I started my freelance career without a website or a professional email—you’ll also want to consider any potential expenses specific to your business. Do you need business cards for networking? A logo for your social media page? A domain name to sell your product or services? Keep all that in mind!

Understand The Roots Of Your Self-Doubt 

Some months, work can be unreliable, and I don’t always hit my income goal. During these moments, I find myself plagued with self-doubt or wondering if I truly know what I’m doing. But even the most successful freelancers and entrepreneurs doubt themselves every now and then. 

Reminding myself why I do what I do helps me move forward despite my doubts.

I’ve found that the best way to pull myself out of this mindset is to keep working and doing what I can, even if it’s the bare minimum.

Reminding myself why I do what I do, especially during the months when work is slow or new clients aren’t calling, helps me move forward despite my doubts.

While self-doubt is not something we can get rid of entirely, we can take steps to better understand its origins, as it often develops after a negative experience or even a traumatic event. If we failed at a project before, we might feel unsure about our future abilities.

The first step to moving through doubt is acknowledging it and recognizing that it’s there. Have an honest conversation with yourself, and try answering a few questions. For example, “Why do I doubt myself so much?” or “What negative experience did this feeling come from?” 

The level of imposter syndrome I experienced earlier in my career has mostly eroded away—while I still have moments today, I feel far more confident in my abilities than I did before, thanks to this introspection.

Talk About It With Fellow Freelancers

With any business, it’s helpful to find your people to celebrate wins and discuss challenges with. I’ve found it necessary to have a safe space to talk with others about the human aspect of working for yourself—e.g., trying, failing, feeling lost and uncertain, somehow making things work, all the nuances of freelancing.

Having healthy conversations about self-doubt helps you realize you’re not alone.

Having healthy conversations about self-doubt helps you realize you’re not alone. It’s so easy to shut down the seemingly unnecessary thoughts and feelings, assuming it only ruins our focus. But talking about it will help you process them in a healthier way.

Facebook groups are great places to start for finding a freelance community. You can also join membership communities, SXSW conferences online and in-person, and community meetups.

Do It & Do It Scared

Fear and self-doubt go hand in hand. And they’re not the enemy. You can either run from things that scare you (like leaving your 9-to-5 and becoming a full-time freelancer), or you can use your fear as a beacon.

You can either run from things that scare you, or you can use your fear as a beacon.

When I first started freelancing, I was always scared I’d never have enough clients, so I’d accept low rates for my work. But when I reframed my situation and used the fear of not having enough clients as a beacon, I saw what I was actually scared of: not hitting my monthly income goal.

This shift from a scarcity mindset to an abundance mindset helped me focus my energy on trying to get as many clients as I can, honing my skills, knowing my worth, and charging more for my writing. Now, I can meet my financial goals, and I’m constantly reminded that my skills and work are worth paying for.

Trust Your Process & Progress

I’ve been working as a freelance journalist on-and-off for seven years, and I’ve made many mistakes along the way. Even today, my mind constantly runs on faulty logic when I receive a rejection email for a writing or brand collaboration pitch.

You may not want to hear this, but one big lesson I’ve learned while freelancing is that it’s best to expect failure from time to time. Because it will happen; it’s inevitable. And when we expect these failures, they become less of a surprise and more of an opportunity. 

Focus not only on failure but on areas where you can learn and grow.

As a freelancer, it’s essential to trust your process and your progress. Focus not only on failure but on areas where you can learn and grow.

Similarly, if you’re moving slower than others, or if you’re not hustling as much, that’s okay. This is your journey! The question, “Is this the right next move?” can be daunting. And when you’re riddled with self-doubt, that’s a question you’re too familiar with. 

Remember that the answer doesn’t only have to be yes or no. The answer can be, “I don’t know but let’s see.” Give yourself the space to progress at your own pace and the grace to trust your process.

Remember Your Past Successes

Finally, celebrate your successes—no matter how small. Take note of your journey as a freelancer, and recognize every milestone along the way.

I like to track this by writing down every success story in a journal. You can also keep screenshots of positive comments from editors, content managers, and strangers who appreciate your work. I save these files in a folder called “Pep Talk” for when my imposter syndrome is especially loud. It helps to flip through journal entries and review these screenshots as a reminder that I am succeeding as a freelancer.

Take note of your journey as a freelancer, and recognize every milestone along the way.

Are you a freelancer? Share your tips for dealing with self-doubt in the comments below.


Tammy Danan is a freelance storyteller based in the Philippines. She reports on environmental and social issues. She also covers creative pursuits, freelance mindset, and sustainability and how they intersect with our everyday life. Her words have appeared in Wethos, Zapier, Shutterstock, ZEKE Magazine,, and others. Follow her on Instagram.