To freelance or not to freelance? That is the question.

Russell Holm
The Kalo Blog
Published in
4 min readSep 18, 2017

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There are an estimated 53 million freelancers in America today, and by 2020, some estimates predict that 50% of the U.S. workforce will be freelancers. Whether it’s a profession like journalism, which has historically relied a lot on freelancers, or a field just beginning to embrace them, there is no shortage of opportunity for people who are interested in striking out on their own.

The majority of freelancers in the U.S. started by choice versus necessity, drawn to the freedom and flexibility that the lifestyle can offer. Full-time jobs aren’t for everyone, just as freelancing isn’t for everyone. If you’re wondering whether self-employment is right for you, here are 5 things to consider.

1. Is there a market for your skills?

Freelancing is a skill-based enterprise. You have skills, an organization needs those skills on a temporary basis, and a match is made. However, some skills are more conducive to freelancing than others. According to Kalo’s data, the top freelancer, most in-demand jobs include writing and editing, photography, design and videography. The work is usually completed on a project-by-project basis, it calls upon a specific skill, and it doesn’t necessarily require in-person teamwork, so these professions are well-suited for the freelance economy.

However, if your area of expertise is product management, that’s typically a role that gets fulfilled in-house. Success requires knowing your team and how it works day in and day out. It doesn’t really make sense to hire someone from the outside for that type of job. Before embarking on a freelance career, make sure there is a market for what you do. Browse around on freelance marketplaces and ask around your network to see if people are hiring.

2. Autonomy vs. stability

As a freelancer, you get to set your own hours and work from where you want, which can sound like a dream come true. For someone used to working a traditional office job, the idea of waking up with no-one to answer to but yourself (and your clients) can feel exhilarating. If autonomy is one of your top priorities, freelancing is good path.

However, there can be downsides to all that freedom. If you are someone who craves stability and/or who finds uncertainty to be stressful, freelancing may not be for you. A full-time job comes with a steady paycheck and key benefits, like health insurance. As a freelancer, chances are you will face work droughts and encounter clients who don’t pay on time. You have to be prepared to weather the ups and down. For someone who is the sole income earner in their household or who has a family to take care of (health insurance for kids isn’t cheap), a full-time job provides a valuable safety net.

3. Structure (or lack thereof)

Full-time jobs provide structure. Not only is there a place to go, but most companies have hierarchies and workflows in place that help determine the shape of your days. The same is not true of freelancing, which can be a double-edged sword. When you wake up in the morning, the shape of your day is up to you, and some people find it difficult to stay on-track in what can feel like a vacuum. When deciding whether or not to freelance, think honestly about your work habits. How are you most productive? Succeeding as a freelancer requires a healthy dose of self-motivation.

4. Co-Workers

Freelancers generally work on their own, which can get lonely. Even if they do regular check-ins and client calls, that’s not the same as going to an office everyday and seeing coworkers who you can talk to and joke around with. If you are someone who thrives on collaboration and needs a hefty dose of social interaction to be happy, a full-time job better fulfills those needs. That said, coworking spaces are cropping up around the country in hordes. There are plenty of ways for freelancers to establish a sense of community, it just takes a little more effort.

5. What are your career goals?

There are certain professions where people can seamlessly go back-and-forth between freelance and staff, but not all. For someone who has leadership ambitions and wants to climb the corporate ladder, stepping out of the full-time workforce could potentially hinder that. In contrast, a graphic designer may find that freelancing gives them the opportunity to work on cool projects and build a strong portfolio, perhaps more so than being on on-staff.

What’s a “pro” about freelancing for one person may be a “con” for another, and vice versa. There are no clear answers, but at the end of the day, if your gut is telling you to be your own boss, go for it — just think carefully before you take the leap.

About Kalo

Kalo is the world’s leading freelancer management platform. We empower the most creative companies, including Google, Airbnb, Popsugar, The Economist, and many others, to easily manage and scale their freelance workforce. Learn more at Kalohq.com

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