The reality of freelancing overwhelm — and how technology helps
Illustrations by Sergey Isakov
by Tammy Danan
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Freelancing is almost always depicted as the be-all and end-all answer to achieving work-life balance. Whether you want to work and travel, get things done from the comfort of your own home, or set your own hours, freelancing is often hailed as the solution. But building the kind of freelancing business a person needs in order to secure financial stability comes with a lot of challenges, including being overwhelmed by the amount of work it takes to be successful.
It happens to the best freelancers, even those who have found a system that works for them and longstanding, enjoyable clients. That’s because there are a lot of moving parts involved in building and running a freelance business. Overwhelm, and the stress that comes with it, are one of the biggest issues freelancers have to contend with and nearly inevitable — and we need to talk about it more.
“There’s no PTO. No slowing down. That is really taxing,” shares Kaleigh Moore, a writer who has been full-time freelancing for a decade. “Where I'm at now is making me realize it's time for a break… I'm feeling extremely burned out.” Moore is not the only one. Fellow freelance journalist Kaitlyn Arford says, “I think that all the unsung parts of freelancing become overwhelming fast — the unending admin of invoicing, staying organized, marketing, and being on top of communication.”
Being a freelancer means wearing multiple hats. You are in charge of finding clients, doing the work, creating invoices, making sure those invoices are paid on time, and building your personal brand on social media. Juggling all these tasks without an efficient system is one of the most common causes of overwhelm. You may find yourself unable to do all that needs to get done in a day. “Automation is your best bet to combat that kind of overwhelm,” Arford says.
Sergey Isakov
How to avoid freelance overwhelm
Mindset is everything when you dive into freelancing. It’s important to prepare yourself mentally and emotionally so you don’t wind up unpleasantly, perhaps even disastrously, surprised down the road. Inner work exercises can help you develop tools for when things like stress, anxiety, and overwhelm enter the picture.
Journaling: It’s important to give your thoughts and emotions a safe space. Write them down so they don’t live in your head. Bottling them up inside isn’t going to help. It might feel like a solution in the short term, but those feelings will eventually find their way out. The healthiest thing to do is to provide space for those feelings as they come up for you. One of the ways you can achieve that is by getting your thoughts out of your head and onto a sheet of paper (or notepad on your phone).
Breathwork: Another inner work activity you might consider trying is breathwork, which can help to improve focus and encourage calm for those who can safely practice it. You can start with the simplest exercise: breathing in for eight seconds, holding it in for another eight, and slowly breathing out for eight seconds. Do it a few times and see if it helps you to relax your mind.
Turn to music: Dopamine, which helps to generate feel-good, fuzzy feelings, is best friends with music. Happy tunes increase levels of dopamine, which helps improve mood. So when overwhelm starts to creep its way in, hit play on some favorite music (or even a random Spotify playlist).
Freelancing tips: optimizing technology
Sergey Isakov
For Arford, technology is an important tool in her business. “You have to have some kind of system in place to handle both sides of your freelance business — the client side and the business side,” she says. “Create a spreadsheet that tracks your assignments or use another tool that works for you. I recommend using zcal or Calendly to book meetings and Passionfroot to book sponsorships.” Arford notes, “If you don't implement some kind of system, you are always going to be behind and overwhelmed.”
Digital resources have so much to offer when it comes to combating overwhelm. Beyond the tools that you can use to automate tasks, here are other ways you can maximize tech:
Facebook groups
When you are in the right Facebook group, it feels like a virtual support group. There are so many freelance-related Facebook groups out there, so find the ones full of supportive people who are generous with their knowledge and not too focused on selling their services. If you don’t know where to begin, try searching for groups on Facebook with the term freelance and check out the groups that are populated, active, and seem to have a positive approach to how they do things.
Slack groups similar to Facebook groups
Slack groups tend to appeal to those seeking connection over niche interests. Peak Freelance and Superpath are two of the many great Slack groups out there. These are great places to express your worries, ask questions, and find people who understand what being a freelancer is like. If you’re still starting out as a freelancer, these groups will also make you feel less lonely.
Listen to podcasts
Freelance to Founder, The Freelance Friday Podcast, and The Writer’s Co-Op are all podcasts to get you through the grind. These podcasts will help you slow down, breathe, and be reminded that it’s really just a matter of understanding your feelings and developing a system that works for you. Even the best freelancers and entrepreneurs have overwhelming days too.
YouTube Videos
YouTube is a massive resource for freelancers and creatives to find inspiration and solutions for overwhelm. Channels like Marie Forleo, Matt D’Avella, Chase Jarvis, and Creative Mornings are full of videos for creatives and entrepreneurs at all levels. If you need help feeling grounded on days when overwhelm is at its highest, The Green Renaissance is full of humbling interviews about life and inspiring change.
“Feeling overwhelmed always increases the level of stress I feel. And that stress makes it much harder to focus on getting anything done. It's hard to think your way out when you're in the weeds,” says Arford. Freelancing is just like any other career, any other business — it’s not pretty and easy all the time.
“The business side of things — figuring out taxes, retirement investing, invoicing, accounting, bookkeeping… these things are so unsexy and easy to get wrong, “ says Moore. “You really have to dedicate time to get it right or outsource it.” Apart from outsourcing, figuring out a system that fits you is an effective way to deal with overwhelm. Maximize technology, find your people on social media, and connect with fellow creatives and freelancers. As Arford puts it, “Every freelancer needs to have a community around them.” And technology has made it easier than ever to find yourself a community.