5 Ways to Handle the Stress of Being a Freelancer

Aly Keller is a full-time freelance copywriter and marketing consultant for healthcare organizations. When she’s not typing on one keyboard, she’s playing another as a local piano and children’s choir instructor.

Whether you’re a rideshare driver, Esty seller, copywriter, or a consultant, running your own business comes with a lot of freedom. It’s the perk that draws so many of us to the 1099 life. When you’re a freelancer, you’re allowed to choose who you work with. You’re free to pursue projects that interest and excite you, and you’re free to work when and where you choose.

As a freelancer myself, I also know that these freedoms come with their own weight. Self-employment lacks structure and stability. All your business’s successes are on you – and the means all your failures are, too. 

Here are a few strategies I’ve picked up over the years that help me stay sane,and genuinely happy, as I face the challenges of being my own boss: 

#1: Use To-do Lists 

While flexibility is often seen as the number one perk of self-employment, it can quickly become a freelancer’s greatest vice. As a freelancer, you are totally responsible for yourself.

Avoid the stress of being a freelancer by following these tips

That means it’s always tempting to start the workday late. It’s easy to get distracted by unnecessary tasks. And it’s overwhelming when you have big goals that you want to reach, but no idea where to start. 

When I first started working on a passion project of mine, I made a big list of all the steps I wanted to accomplish by the end of the year. I wrote down a few of my main to-do items: things like “build a website” and “design the product”  and just left it at that.

As the days ticked by, I felt more and more discouraged as my checklist sat on my desk entirely untouched. Even though I was always working, it felt like I wasn’t accomplishing anything. And guess what? By the end of the year, I hadn’t completed a single item on my list. 

Now, I set weekly, monthly, and yearly goals, but I break them into small, manageable tasks that I can tackle on a daily basis. This provides a visual representation of how I’m progressing towards my bigger goals. These mini to-do lists help me manage my anxiety, since with each ticked box, I feel more accomplished and productive and they reassure me that I am progressing. 

Try using lists to help with these common freelancer woes: 

  • Worried about a busy day ahead? Anxiety about to-do items can make it hard to fall asleep. Listing out specific tasks (and setting alarms for important deadlines) takes the pressure of remembering these items off your mind and makes it easier to relax. 

  • Need a more structured schedule? On Sunday evening, make a list of the things you want to accomplish each day in the upcoming week. Pre-assign those tasks to certain blocks of time. Be sure to include your hobbies, errands, and lunch breaks! 

  • Getting distracted throughout your day? You’re your own boss, so hold yourself accountable with a to-do list. When you know exactly what you need to accomplish each day, it’s easier to stick to important tasks when distractions come your way. 

  • Feeling discouraged? Make a list of all the things you’ve accomplished as a freelancer so far. Don’t leave out the little things, like designing business cards or networking with a potential client. You can even make a list of positive feedback or compliments you’ve received from your clients or coworkers in the past. Constructive lists that visualize your progress remind you of what you do well and motivate you to keep working hard. 

You’ll also want to stay on top of your business finances, since filing your 1099 taxes can be trickier than filing with the standard W-2. Learn more about tracking your expenses here.

#2: Give Yourself Some Credit 

When I was an undergraduate student completing a degree in piano performance, I learned all about anxiety. Nerves and pressure can drive us to work hard and perform our best, but too much worry and self-doubt is absolutely crippling. 

During my studies, I took a class from a performance psychologist. He often had us play music for one another and record how we felt our performances went. Afterwards, he would share our classmates’ feedback with us. I often found that while I harshly critiqued my own performances, my classmates’ comments were positive and encouraging. They often noticed so much in my music and playing that I never gave myself credit for. 

A psychologist once taught me to flip my negative thoughts into positive ones. For example:

[Competitor] has so many more clients than I do.
I am not good at freelancing!
vs. Wow, [Competitor] has found some
great strategies to grow her business.
I should reach out and learn more
about what has (and hasn’t) been working for her.
I only got a few things done today.
The whole day is wasted!
vs. Today wasn’t as productive as I’d hoped, but that’s okay!
What distractions made it difficult to work today?
How can I avoid those in the future?
What can I try to do better tomorrow?

This strategy allows self-criticism and anxiety to drive me in a positive, constructive way. It also encourages gratitude over comparison, which studies have proven helps build self-esteem! 

#3: Be Willing To Learn (And Fail) 

Daniel Jones, editor of The New York Times’s famous Modern Love column, gave this wonderful advice to aspiring writers: 

“You have to write badly to write well. And you have to sit with the bad writing and write more of it and then sit with that until eventually you start writing well… Write badly. It is productive. You just might not know it yet.” 

I often think of this advice when I’m in a freelance rut. When I don’t have enough clients, or I feel behind on work, or I wake up and don’t want to take on a certain project, I remind myself to “write badly.” Sometimes, we need to just show up and keep working. If we let them, our constraints can drive us to be creative and grow our business in new ways. 

I recently met with a good friend of mine who works as a freelance consultant. She had been struggling to find new clients because her time-intensive work was too expensive for the small businesses she wanted to help. After some consideration and experimentation, she designed a unique “DIY” program that allowed small businesses to consult with her while taking on the more time-consuming parts of the process themselves. This saves them money, allowing her to work with more clients in an entirely new way. 

Be willing to experiment and research. Be willing to fail. Evaluate your strengths and weaknesses, and always ask for help. 

#4: Learn To Say No

When you first begin freelancing, it is tempting to take on any paying project that comes your way. Truthfully, you may need to take on jobs you don’t love at first to build your clientele and establish credibility in your field.

When my husband and I were first starting our small business together, I reached out to an old friend who manages his own marketing firm. I provided our budget and asked if he could help launch our new business’s marketing plan. He politely replied, “I’m afraid I can’t help you here. I used to do smaller projects, but with my limited time and small team, I now only take on projects that pay twice your budget. I would be happy to refer you to someone who can help you.” 

As you grow in your freelance career, you’ll be able to learn what type of work you’re willing to take on. If you’re an Uber driver, this may mean avoiding early airport runs that, while lucrative, leave you too tired to work meaningfully later in the day. Don’t be afraid to say no to work that isn’t an effective use of your valuable time. 

#5: Clock Out 

A recent study by HoneyBook found that 92% of U.S. freelancers work on vacation. As a freelancer, your work shift lasts as long as you want it to. This can make it difficult to “clock out” at the end of the day. 

Give yourself permission to pursue hobbies, exercise, and yes – even take a vacation! Not only is taking breaks healthy (sitting for long periods of time can literally harm your well-being), it’s invigorating. I live near the beautiful Wasatch mountain range in central Utah. When I’m stuck on a certain problem, I’ll grab my dog and head for the hills. It is often on one of these refreshing hikes, far away from my desk, that I’ve stumbled upon my most creative solutions.

You are your business, so treat yourself with respect. Give yourself permission to rest, recover, and enjoy life. You’ll return to your work with a renewed creative energy. For more ideas on how to take meaningful work breaks, check out this article

Freelancing is intimidating, frustrating, and rewarding. Stay creative and “keep writing.” With gratitude, self-care, and a mean to-do list, you’ll be ready to tackle whatever challenges self-employment sends your way.

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