How to Decide If You Should Freelance

how to decide if you should freelance

When people ask what I do for work and I tell them that I’m a freelancer, the universal response is “the look.” You know, the soft but confused stare that says “Oh, how nice for you.” Or the quick cringe of horror that contorts one’s face while they offer a sympathetic pat on the shoulder: “Good for you. The economy hasn’t recovered since the recession. It’s tough out there.”

I’ve enjoyed being a freelancer for roughly a year now. Some people prefer the title consultant. The phrase entrepreneurial has been attributed to my personality. Honestly, I made a decision in 2018 to step off of a career path of expectations paved by others and I took a chance on the route less traveled by creating my own unique career path.

Myers-Briggs results consistently tell me that I am an ENTP. By definition, I am an innovator, an originator, an inventor, an explorer, and a visionary. This sounds glamourous, right? I think so! My mind brings up images of Indiana Jones. Have I felt like Indiana Jones in my career? No, more like George of the Jungle: a little confused about where I fit in and where I’m going. When I decided to become a freelance marketer, fortunately, I was in a stable position to tread these deep, murky waters. I knew that there would be risks. I was willing to confront these uncertainties with a smile for the sake of personal and professional growth.

While I would strongly (emphatically) encourage everyone to take the risk of freelancing at some point in their career, there are questions to ask yourself if this is truly an undertaking for you. Here are a few things to consider before you step off your current career path to become a freelancer:

1 - Why do you want to freelance?

I remember asking myself this question on the drive home from my first job in Sacramento in 2017. Before moving to California, I had enjoyed an almost 10-year marketing career in Boston where I had learned so much and experienced a lot of career growth. But I knew I wanted more in my career. Leading up to this conversation with myself in my car in Sacramento, I had recognized that I wasn’t meeting personal goals and that I was bored in my career. I had moved to California for personal and career growth and I wasn’t accomplishing either. I wanted the freedom to explore my new home state. Freelancing seemed like the solution. If this sounds like you, continue reading.

2 - How much of a self-starter are you?

Freelancing requires you to be an extreme self-starter. You may have started a club in college. But have you created your own network of clients from scratch, written contracts, defined client needs, created a project scope and strategy plan, and delivered on contract terms? Times this by juggling five clients at once. It’s a lot. And this needs to be done with little or no direction from a boss impatiently sending you emails with tasks to follow-up on. Personally, I love this work style. Is it for you?

3 - Are you comfortable with instability?

When things are good, they’re good. When they’re bad, you may find yourself knocking on’s door. The fluctuations in stability experienced when freelancing can have an impact on you. Your confidence might take a few hits. But, refer to the first question. If you truly feel that freelancing is what you need in your career, and you acknowledge the risks and uncertainties that accompany the freelance lifestyle, you will be ok.

A recent survey by Upwork survey shows that the freelance workforce in the U.S. has grown by 3.7 million workers in the past five years. More than 1 in 3 Americans freelanced in some way in 2018. This trend is on the rise. If you’re considering counting yourself amongst the growing ranks of untethered professionals, know the risks and benefits. Be confident in the path you create for your career.

This is a guest post by Jaimie Asakawa, member of the Communications Committee. Connect with her on LinkedIn to talk about the wonderful world of freelancing.