How I Overcame My Biggest Freelancer Fears

Three successful self-employed professionals share how they worked through the most common freelance trepidations.

How I Overcame My Biggest Freelancer Fears
[Photo: Tim Trad via Unsplash]

No two freelance experiences are alike, and freelancers are unique individuals with different strengths and experiences. If two freelancers are given the exact same brief for the same job and client, they’ll most likely turn in different work. But there is usually one thing most freelancers have in common: the fear they carry related to their career.


The term “freelance fear” was first brought to my attention by a London-based advertising creative. Before she held her current position, she was a freelance copywriter for years. I’ve been a freelance writer for a decade, so we compared experiences.  We discovered that despite our different situations, we share the same fears: getting paid on time, how to say “no” to a client, how to charge a fair amount for your work and services, and more.

So I spoke with a number of successful freelancers across varying industries and disciplines to find out how they’ve overcome these fears.

Overcoming The Fear Of Rejection

Without a doubt, the biggest fear of freelancers I’ve spoken with is the fear of rejection. No one likes to be told that they aren’t the right fit for something, and this is all the more true when their livelihood depends on it. But the way to overcome this fear is knowing and accepting that it will happen from time to time, no matter how good you are.

“Rejection is like anything else in life: The more it happens, the less it scares you,” says David Holmes, a freelance writer and video producer whose work has appeared at the Daily Beast, the Guardian, Fast Company, ProPublica, and the New Yorker. “Sure, rejection is never a good feeling, but it’s important when a pitch is rejected that you don’t let yourself get discouraged from pitching again to that employer or others.

“That’s because employers turn down pitches for countless reasons, and most of them have nothing to do with your talents or abilities. Maybe payroll tore through the company’s freelance budget too quickly this month; or maybe half the editors are sick or on vacation and they lack the resources at the moment to give your assignment the attention it deserves; or maybe the person you’re pitching just doesn’t get it.

“In any case, a freelancer is only as good as her last pitch, so there’s no use delaying your efforts to get back out there as quickly as possible, no matter how bummed out you are by a rejection.”


That’s something Amy Jordan, a freelance content marketer, agrees with. And if you do get rejected, “Know that no one wins every pitch; don’t take it to heart, learn what you can, and focus your energy on positive things like improving your pitch or services rather than worrying that you aren’t good enough,” she says.

Overcoming The Fear That You Don’t Have The Experience To Begin Freelancing

Another widely held freelance fear won’t even get you to the stage of the fear of being rejected if you can’t overcome it. That’s the fear that most want-to-be freelancers have: they don’t have the experience to go into business for themselves.

“[The worry of] not having enough experience is the sum of two fears,” says Rakesh Krishnan, freelance digital product designer. “First, the fear of not finding clients, and second, the fear of not doing a good job when you find one.

“I mitigated the former by being more aware of the market I was going to serve. I went through the job postings on freelance platforms and found that there are clients at various levels: from hobbyist individuals to multinational conglomerates, which meant there was a place for freelancers at various levels. That showed that there would be at least a few who require my services,” he says.

“I overcame the latter by being confident in myself. Confidence doesn’t come easily, you have to build it. The only way for beginners to develop self-confidence is to make themselves good at their chosen area of expertise. In my case it was design. I read books and developed a strong foundation of the core concepts of design. In addition, I continuously kept in touch with the latest happenings in design and tech. This is how I transitioned from web design to mobile design, which later became a staple of my work.”

Overcoming The Fear That You Won’t Be Able To Pay Your Bills 

Even when you’ve built up a successful freelancing career, that doesn’t mean it’s clear sailing from here on out. Ask any freelancer and they’ll tell you it’s easy to constantly worry about being paid on time. Unlike with traditional employees, there are no federal laws that dictate that a client must pay a freelancer within a certain timeframe.


If a freelancer isn’t good at budgeting and hasn’t set aside an emergency fund, this could mean being left high and dry when it comes time to pay rent. While being paid on time isn’t entirely within your control, Jordan says there are several proactive steps you can take to get paid on time.

“First things first, you need to have some savings or have clients lined up before jumping in full-time,” she says. “It can be tough to drum up business when you have no reviews or record of your previous work, so allowing yourself a financial buffer is a good idea. Second, you have a few options to reduce this risk; you can either take a deposit up front before doing work (if your clients are happy to do this), or if you have ongoing contracts, you can stop doing work if bills go unpaid, until they are.”

Even with those steps, she says it’s important to realize that not all clients always pay on time–even if they have in the past. “It’s a fact that for whatever reason, backups in accounting or just forgetfulness, you sometimes won’t get paid on time. Knowing that can help you guard against the issues it may cause. I combat the potential risk by holding some wages in my business account every month so I know if someone’s late, I won’t have the wolves at my door!” says Jordan.

Overcoming The Fear Of Turning Down Work

Another universal fear a freelancer has is saying “no” to a client. After all, you don’t want to turn down a job, only to see them go to someone else to fulfill it, and then continue to use that person for all future jobs, leaving you cut off. But understanding that saying “no” to a client can sometimes be the best thing you can do is paramount to overcoming this fear, according to Matt Goolding, a freelance writer and digital consultant and the founder of KYO digital marketing collective.

“I went through a period of always saying yes in early 2016, and I got very close to burnout. It’s this memory that sticks in my mind, and ensures that I won’t push for unmanageable levels of work ever again,” he says. “I overcame this fear by taking a more optimistic outlook. If I do consistently good work, good clients will find me at the right time. It’s this simple shift in expectations that has allowed me to spot opportunities that are best avoided, and to wait for the right businesses, led by the right people.”

Holmes couldn’t agree more. “Last year, two outlets approached me at around the same time with two long-form assignments that each demanded a ton of background research and reporting. Despite the fact that the two deadlines were only a couple days apart and fast approaching, I said yes to both assignments in the hopes of a big payday and of seeing my name printed in a publication I’d long admired,” he says. “It won’t shock you to learn that by the time I completed the first assignment, I only had two days left to write the second–an impossible task, considering the number of sources I needed to schedule calls with. As you might guess, the publication was less than pleased. But I did learn a valuable lesson: Publications won’t blacklist you for saying no to them. But they will blacklist you for blowing a major assignment.”


Overcoming The Fear About Asking To Be Paid What You Are Worth

This final fear has become more prominent as an increasing number of freelancers enter the workforce. More freelancers in any given field mean people are more likely to compete for a job based on price. While it’s easy to get sucked into a race to the bottom as far as pricing goes, virtually every freelancer I spoke with said not to be afraid to charge what you are worth. After all, most clients would rather pay more for good work from one freelancer than have to pay a second freelancer to fix the shoddy work of a cheaper first.

“When it comes to putting a price on your own services, the worst that can happen is someone says, ‘No, I won’t pay that,’” says Holmes. But he also notes that sometimes you may want to consider taking a lower fee counteroffer anyway. “Such assignments may be personally or professionally worthwhile if the project is important to you, or if it forges a relationship with a person or company you admire, or if you stand to greatly expand your audience or notoriety by accepting it.”

“All in all, you shouldn’t be afraid to negotiate the best possible price for your work. That said, it helps to look at the big picture,” he says. “One week you might spend five whole workdays on two pieces that net you just $150 apiece. But the next week you might stumble upon a sponsored post series that can net you up to $800 a pop for articles you can crank out in a couple hours. In other words, the lower-paying gigs tend to balance out with gigs that pay you far more than you deserve,” he says.

Don’t know what you are worth–or what you need to charge to live the lifestyle you want? Freelance designer Mark Hendriks created this nifty calculator called Your Rate that helps you decide how much you should charge per hour based on how much you want to make and work per year.

About the author

Michael Grothaus is a novelist, journalist, and former screenwriter. His debut novel EPIPHANY JONES is out now from Orenda Books. You can read more about him at