Allison Cheston, Career Connector


Career Connector Blog

Don’t Freelance Too Early in Your Career


I read a post citing research claiming that only 27% of Millenials prefer to work full-time than to freelance. Now granted, this survey was conducted by Upwork, a freelancers’ website, but even so, that figure disturbed me.

According to the author, the desire to freelance is fueled by the lack of job security in the market, and the difficulty young adults have had in finding jobs during the recession. Another factor is the ability of freelancers to work flexibly, a need consistently mentioned in studies of Gen Y’s, including my own research for my book. While these are all valid reasons to work freelance, I feel this is a disturbing trend. Here are my reasons why:

Working Freelance Doesn’t Expose You to Life in an Organization

One of the most important things you learn in early jobs is how to function within an organization, and there is a lot to learn. It takes years to fully understand how to operate politically, socially and effectively within a larger group. And there’s no rushing it—it just takes time. A successful career path starts in an environment where you are learning from others.

Working Freelance Means You Are a Jack of All Trades

When you work on your own, you usually have to do everything. The article mentions the printer breaking down, but that is the least of it. You may have to take on assignments to pay the bills that don’t play to your strengths at best, and have you spinning your wheels, at worst.

Working Freelance Can Be Lonely

Unless you are extremely organized and a self-starter, sometimes it’s hard to get out of your pajamas and get with other people. If you’re an extrovert, meaning you derive energy from others, your best ideas may come from working with others. And that’s not usually on the phone.

Working Freelance Doesn’t Give You Ready Access to Mentors

Again, you have to be very focused and driven to find mentors when you’re not in an organization. Mentoring relationships are usually developed fairly early in a career, and while your mentor doesn’t need to work with you, usually they once did. For more info on how mentors and sponsors help you build your career path, see Carla Harris’s remarks.

Working Freelance Doesn’t Impress Future Employers

It will be difficult for prospective employers to take you seriously if you have only freelanced. It will send a single that either you are not employable, you’re lazy or you have some other negative quality. Also, it is hard to show a specific career path when you’ve only worked for yourself.

This is a handful of reasons to get your thinking started. I’m not suggesting at all that freelancing isn’t a good idea at some point in a career, but I don’t believe in starting your career as a freelancer—wait until later, when you can add more value.