Digital marketing guide for small businesses
Digital marketing guide for small businesses
Entrepreneurship

What scares you the most as a freelancer? 19 freelancers share their stories

13 min read
What scares you the most

Being a freelancer often means very little stability. To thrive in this field, you need to get used to constant uncertainty about your income and your number of clients — at least, at the beginning of your career. It can be exhausting and detrimental to your productivity and, by extension, career.

But you should know that even experienced freelancers have been there. So, we thought they could share their stories on how they’ve overcome their biggest fears as independent workers.

We’ve asked a group of them the following question: “What scares you the most as a freelancer, and how do you deal with it?” Then we’ve sifted through dozens of answers and selected the most useful tips for you. 

Here they are.

Elna Cain

Elna Cain, expert freelance B2B writer for brands and SaaS.

“The one thing that still scares me is the inconsistent income months.”

As a freelance copywriter for over six years, the one thing that still scares me are the inconsistent income months. Every month, the income from my freelance business changes. Sometimes I hit five figures, and other times four figures. As a mom to twins, I not only support my twins but also my husband, and it’s up to me to land more freelance work, which sometimes means working more hours during the week and diversifying my income streams.

Milena Regos

Milena Regos is the Co-Founder of Unhustle, a speaker, an award-winning marketer, biohacker, and certified human potential coach.

“My fear is not getting into hustle mode.”

Every entrepreneur and freelancer deals with fear: fear of not making enough money, fear of not doing enough, fear of not being successful, fear of imposter syndrome, and fear of overcommitting. The fear is real. My fear is not getting into hustle mode when I’m creating a company called Unhustle, and yet doing enough to grow my community. 

When I experience fear, I get into my body, locate the fear, and sit with it for a while. I go outside and hike. I move. I take a cold shower. The fear is there to protect us. Instead of trying to ignore it or avoid it or overcome it, it’s a matter of sitting with the fear. At least, that’s what I learned from my mindfulness training.

Steve Morgan

Steve Morgan, a freelance SEO consultant for over seven years (since May 2013). 

“I often feel like I’ll either have too much work or not enough.”

The thing that often scares me the most about being a freelancer is simply the ability to juggle and balance my time in order to try and keep a healthy work-life balance. I often feel like I’ll either have too much work on, and therefore the money’s good but my time is pushed to the max, or vice versa. 

I try my best to handle this by being careful and selective about what (and how much) work I take on, however tempting the project or client may be. I’ve also been trying to invest more time into side-projects and other potential income streams (such as my book), so that I’m not entirely reliant on my freelancing work to bring in 100% of my income. Doing so results in less pressure if I do have a quiet spell on the freelancing front or I underestimate how much work I need.

Chelsea Bonner

Chelsea Bonner, a freelance Social Media Manager who previously held analyst and marketing roles at companies such as Nielsen and Edelman.

“My worst fear is waking up one day only to find that the work-life balance I worked so hard to create has disappeared.”

As a freelancer, you often spend time not only doing the client’s work but also prospecting for new clients in order to meet your income goals, which is something employees don’t have to do. What scares me most as a freelancer is taking on so many new projects or clients and spending tons of time prospecting that I eventually end up working just as much or more than I was at my 9-5 job. 

One of the biggest reasons why I quit my corporate 9-5 was so that I could create my own schedule and work less in order to have more time to do other hobbies and spend time with family and friends. My worst fear is waking up one day only to find that the work-life balance I worked so hard to create has disappeared. 

To deal with that fear, I do my best to track how much time I spend each day both on client work and on prospecting. I’ve also raised my prices so that I don’t need as many clients to meet my income goals, and therefore, I have a healthy balance of client work and free time.

David Cusick

David Cusick, Chief Strategy Officer at House Method, a resource for those looking to improve and maintain their homes.

“The most common fear I’ve seen is the fear of career stagnation.”

As both a former freelancer and a CSO who hires freelancers, the most common fear I’ve seen is the fear of career stagnation. When you work for a company there’s typically a higher-up who, for better or worse, will push you to take on larger, multi-person projects that push you out of your comfort zone.

As a freelancer, it can be tough to jockey for bigger assignments, ones that pay better and necessitate long-term interactions. Yet these are the ones that make up the cornerstones of your portfolio. As a freelancer you can often wonder about where you’ll find these opportunities, or if you’ll be the first person your client thinks of when they approach such a project.

Pauline Orr

Pauline Orr, a creative website developer who’s spent five years in the advertising industry.

“Being without health insurance is the scariest.”

Out of all the possible failures I can have as a freelancer, being without health insurance is the scariest. I can face financial hardships since I have a mindset built for this. However, it would only take one bad day to need health insurance, and if I did not have it, it would be financially devastating. 

To make sure I can always afford health insurance, I do two things. I prioritize constant creation to build my audience, products, and streams of revenue. I also prioritize having 1-2 stable contract jobs with regular work specifically to cover my monthly costs.

Kendra Bruning

Kendra Bruning, founder of GameCows, a website for board game enthusiasts. 

“My greatest fear as a freelancer is that I won’t be able to maintain a regular enough income to meet my financial obligations.”

I just started freelancing this year, and it’s been a bit of an adjustment. My greatest fear as a freelancer is that I won’t be able to maintain a regular enough income to meet my financial obligations. So much of my work is on temporary projects. The pay can be amazing, but it’s not always consistent. My first few months as a freelancer were feast or famine; I’d either be overwhelmed with work or scrambling to make ends meet.

I’ve since learned to embrace the ups and downs of freelance work. I squirrel away any extra income I obtain when work is good to help me through those times when things dry up. I’ve also started trying to obtain more long term and consistent work. It doesn’t always pay as well as brief projects, but knowing I’m guaranteed a paycheck gives me a sense of security.

Kristy Speciale

Kristy Speciale, founder of A Speciale Life and freelance writer of nearly two years.

“My biggest freelancing fear is losing consistent and long-term clients.”

Fear is present consistently as a freelancer. Personally, my biggest freelancing fear is losing consistent and long-term clients. While it’s always possible to get a few one-off jobs, the long-term jobs are the ones that pay the bills. There are some situations that freelancers have no control over. For instance, one of my long-term clients decided to revamp their entire website over the next few months, leaving me without that reliable work.

Dealing with this fear starts with learning how to develop long-term clients. It starts with a good proposal and excellent communication. When a freelancer has these skills down, the fear of losing the possibility of long-term is far less intense.

Janni Nilsson

Janni Nilsson, a full-time freelance writer and managing editor at Resumoo.

“The fear of not meeting expectations.”

The scariest thing about being a freelancer is the fear of not meeting expectations — both your own and those of your employer. It is easy to misinterpret emotions if employer/employee communication is not sufficiently clear, and the best way to combat both misunderstandings and fear of failure is to set up goals and to communicate openly with team members and management.

Michelle Bourbonniere

Michelle Bourbonniere, PhD, a freelance website editor and SEO specialist at Edited by Michelle.

“Losing the battle for life-work balance.”

Life-work balance is such an elusive beast sometimes. Losing my balance is what scares me most about freelancing. The promise of a work schedule which could ebb and flow with my family life is what drew me to freelancing in the first place. But when an enticing opportunity with a quick turnaround comes along, it’s sometimes hard to say no.

One powerful way of being able to say yes (while maintaining balance) is to always schedule in a couple extra days for each project, so that there’s enough wiggle room to be able to take on projects that matter, without sacrificing sleep!

Rick Patterson

Rick Patterson, founder of Poolonomics, a pool care blog.

“I’ve been freelancing for years now, and what scares me the most is that I’ll become obsolete and outgunned as more and more turn to freelancing.”

I think a lot of people this year are realizing that they don’t have to sit in an office to bring home the bacon. And as more people lose their jobs to current world events, resulting in economic depression, the freelancer pool will continue to grow rapidly. I have an extensive portfolio and diverse work experience, but there’s always going to be someone out there who is willing to undercut me.

I try to stay relevant as a freelancer by educating myself on shifting elements within my field. I learn to use new software, read about evolving trends in marketing, and work hard to prove to my clients that my exceptional services are worth it. I’m a big believer in lifelong growth, especially when it comes to my career.

Lewis Keegan

Lewis Keegan, founder and writer at Skillscouter, a resource to help people find the right course or MOOC for their needs and budget. 

“What scares me the most is the fact that some of my clients might not like my output.”

Of course, I always see to it that I put in my best work in everything that I do, but you can’t please everyone, and there is no exact way of knowing how to create an output that will surely be approved by your client’s taste. All you have to do is work hard and give your best to attain it.

Kate Diaz

Kate Diaz, an interior designer and owner/writer for Swanky Den, a home DIY, decor, and how-to website.  

“I always have this nagging feeling that clients will not choose me over those who have plenty of experience.”

When I was starting out as a freelancer, one of the biggest fears I had was that clients would not hire me because I don’t have enough experience. The industry is huge and full of individuals who have been freelancing for years, so I felt like I was a tiny fish swimming in the ocean. I always have this nagging feeling that clients will not choose me over those who have plenty of experience.

To overcome this, I’ve worked hard and built my portfolio with high-quality samples of my work. Aside from this, you can even ask friends if you can do some free work for them as I did just to build up my portfolio. If you don’t know anyone that needs free work, then you can charge your clients with an entry-level rate that you think is fair. As your experiences and value increase, you can easily increase your rate over time.

There is plenty of available work for new freelancers, and there are clients who are willing to hire newbies as well. Just be patient, keep working hard, and make sure to always produce high-quality work.

Edie Reads

Edie Reads, a nutritionist, proud mom, fitness coach, author, and editor-in-chief for Corrie Cooks.

“My biggest scare is the fear of the unknown.”

Freelancing is an uncertain gamble at best, especially when starting out. Even if you have researched thoroughly and consulted far and wide about your preferred niche, you are bound to worry if you made the right choice after a few unanswered pitches.

Granted, freelancing doesn’t come with the trappings of a ‘normal’ job like a funded 401k, guaranteed salary every end month, and other social benefits. It is often contractual with no guarantee, and the jobs are more often than not one-time projects with no possibility of renewal. You, therefore, are constantly anxious, worrying if you will land a new gig and how you will  approach it. And this fear is even greater if the shift to the freelancing world is abrupt and as a result of changes in circumstances like the loss of a job. The landing and picking off is harder when you are ill-prepared mentally.

Solution

Experience has taught me that clients will be less willing to seriously consider a relatively new freelancer, especially if your rates are too high. You have to invest a lot of time in selling your brand while charging considerate rates (slightly less than pro freelancers) at least until you build a rapport with a client, as well as a good reputation across your industry. At the very early stages of freelancing, you need to appreciate that a client’s recommendation or vouching for you is worth more than the project’s pay.

Beth McCallum

Beth McCallum, content creator at Oh So Spotless, a blog for people who love keeping everything clean. 

“What scares me most about freelancing is that any moment, everything could change.”

I’ve been freelance since 2014, but it’s been more constant for the past three years. What scares me most about freelancing is that any moment, everything could change. I’ve worked steadily for clients who have run out of money without giving me any notice and dropped me, causing me to lose days of work per week. With freelance work, you run the risk of losing work without much notice and without having a redundancy plan in place.

I deal with this by knowing that I’ve now built a good portfolio that can get me another awesome job pretty quickly. I have good experience, a versatile degree to my name and really awesome references. It also helps to have savings ready for long gaps between projects. Although there are many risks that come with freelance, there’s always something else waiting for you around the corner.

Brett Downes

Brett Downes, founder and SEO specialist at HaroHelpers

“Scared of not being paid is prolific in the freelance world.”

As much as it’s lucrative, it’s still very difficult to get paid in a reasonable amount of time. And chasing up payment always makes me feel super-awkward and uncomfortable.

My skills lay in SEO, content and analytics, not chasing companies and admin. As a verified company, there seems to be a subconscious trust and more respect, which is wrong on so many levels, but it is true nonetheless. Freelancers just aren’t treated with the same respect as companies.

Daniel Carter

Daniel Carter, an electric ride enthusiast and founder of ZippyElectrics, a gadget review blog.

“It really makes me nervous whenever I receive emails asking for changes and additional details.”

I still occasionally accept freelance projects and try to juggle them with my full-time job tasks. However, it really makes me nervous whenever I receive emails asking for changes and additional details. It messes with my schedule and plans. 

To address this, I use a proposal now that highlights the agreement and all the details of the service I am offering, as well as the limitations. I discuss the outcome they should expect from my service and the modifications within the scope of the agreement.

Aaron Simmons

Aaron Simmons, founder of Test Prep Genie, a blog covering ways to develop smarter study habits. 

“My greatest fear was not getting paid on time or not getting paid at all.”

When I was starting my freelance career, my greatest fear was not getting paid on time or not getting paid at all. This is a rational fear in this field as most deals are just being closed through word of mouth and trust. However, this poses risk to freelancers. So, I started setting an agreement between me and a client before closing a deal and accepting projects: partial payment before starting the project. This places you in the safe zone in case the worst-case scenario happens.

Bottom line: Before taking any project, be sure that you have an arrangement that secures you as a freelance worker, especially when it comes to payments.

Michael Hammelburger

Michael Hammelburger, founder of the Expense Reduction Group, an expense reduction consulting firm.

“Job security”

Most of our freelancers are typically afraid of one thing: job security. That’s the risk that you take when you’re pursuing a freelancing career though. The pandemic has increased the competition for freelancing gigs, with some 9-to-5 office-based employees switching to freelancing, too. 

If they have a client retention strategy, they’d be more secure in their future and career.

Conclusion

Forewarned is forearmed. Let’s recap tips to never let freelancers’s fears prevent you from thriving:

  • Have several sources of income.
  • Be patient: build up your portfolio first and have faith in your abilities.
  • Do your work well. Your reputation is what will help you in the long run.
  • Don’t charge too much at first.
  • Be smart about the payment: sign an agreement or charge a prepayment.
  • Schedule a little more time than you need to complete the task. You’ll need this time in case a new client approaches you.
  • Always schedule off time. Having rest is crucial for your productivity.
  • Discuss your clients’ expectations at the beginning of the process.
What scares you the most as a freelancer? 19 freelancers share their stories
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