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Michelle Nickolaisen

If you’re coming from a traditional job, freelancing can be tough — always leaving you wondering if you’re good enough. It’s not an uncommon problem, at all, and these questions can help you overcome it.



We’ve been told we need day jobs and that we need to be in an office with a boss and coworkers and a salary to be productive members of society. So when we deviate from “the norm,” it’s easy for a sense of panic to set in. Even for people who have a solid foundation for their new freelance career.

When people decide to take chances in life — be it moving to a new city, or moving in with a significant other, or switching majors — self-doubt will almost inevitably sink it. Mix in a major lifestyle change that impacts your finances and daily schedule? Forget it, it would be almost impossible not to feel a little terrified. So if you’re struggling with self-doubt as you embark on this new journey, remember: we’ve all gone through it!

Think of it this way: What if Bill Gates gave into any self-doubt he had about dropping out of college? What if Elvis Presley listened to his middle school music teacher who told him that he wasn’t a good singer? Heck, what if Nelson Mandela gave up on the anti-apartheid movement during his imprisonment? Where would we be if Harry Potter stopped trying to find the Chamber of Secrets? They’re just four people who shaped the course of modern society and who could have easily given up.

Having said that, you don’t have to just resign yourself to the prison of negative thoughts because “everyone has them.” There are tricks to curb your own self-doubt so you can go back to kicking ass and taking names. So when you find yourself listening to that voice that keeps telling you that you’re going to fail, here’s a checklist you can run through in your mind:


Question One: Are you comparing your accomplishments to people you know?

If the answer is yes, remember that everyone has a different path — personally and professionally. Someone else’s accomplishments don’t make yours any less qualified.


Question Two: Are you worrying about what people think of your new career?

If the answer is yes, guess what? Most are actually too focused on their own careers. For the rest of them, you can always share this study commissioned by the Freelancer’s Union and cite your 53 million brothers and sisters (in the U.S. alone!).


Question Three: Are you talking to yourself the way you would talk to a friend or relative?

If the answer is no, this can be a great exercise as you wade through uncertain times in your freelance career. Start talking to yourself the way you would talk to your best friend if she was dealing with self-doubt — and give yourself the same advice you’d give said bestie. Many find gratitude journals helpful for this sort of thing.


Question Four: How are you viewing the obstacles before you?

How you frame the challenges you experience in life will determine how you encounter, interact and resolve them. One ancient school of philosophy — the Stoics — viewed obstacles as both a natural and neutral part of life. Neither good nor bad. In fact, obstacles were viewed not as impediments but opportunities. Here’s a modern take on the idea.


Question Five: Where are you getting your support from?

One of the rougher things about transitioning to freelance work is that you don’t necessarily have a built-in support network. Even assuming that your real-life friends and family are supportive and well-intentioned, not having anyone around who understands the day-to-day reality of freelancing can get lonely. Make sure you’re actively seeking out freelance communities both in person and online (like Domino!) so that you can share your concerns, struggles, doubts — and successes! — with peers that understand what you’re going through.



Ultimately, getting over self-doubt is a matter of reframing how you think about your circumstances and the roadblocks that may come your way. This can seem easier said than done, so when you find yourself really struggling with your thoughts, try to get some distance on them — whether that’s via writing them down in a journal or sharing them with your community to get outside input.

No matter how your career shapes up, never let your ‘what ifs’ and ‘I don’t knows’ take away from the things you want to accomplish. You went freelance for a reason — don’t let self-doubt make you forget why you’re on this journey. Got that? Now go make your world.

This article was originally contributed by Mattie Quinn, who is a freelance writer based in Washington, D.C.