Straight into freelancing?

Like this post? Please share it!

straight freelancingI have Google alerts set for a few variations on the words freelancing and freelance, as a pulse check on what’s happening in the industry. Over the past few months, I’ve seen a trend of opinions that gives me pause: The idea that millennials can and should go straight into freelancing, no traditional job experience required.

I’m as much of a proponent of entrepreneurship and self employment as anyone I know. Having been at it for 16 years as of this month, I can’t think of anything I’d rather do. The underlying fact is, however, that I doubt I would have survived at it without a solid decade of working at small, medium, and large companies before going solo.

Among many other things, those traditional jobs:

  • enabled me to improve my skills by being mentored, critiqued, and edited by people with far more business and life experience
  • created durable, lasting business connections in a variety of industries
  • taught me how successful businesses and managers operate, and why it all comes down to sales and profitability
  • provided insights on what my clients would need and the problems they wrestled with

It’s important to note that it wasn’t just about improving my writing and editing abilities—it was a matter of interacting daily with people who were highly skilled in diverse areas such as finance, production, marketing, graphic design, human resources, and so on. I also had the opportunity to hire, work with, and observe freelancers of all stripes, which was educational in its own right.

Risky Business

Frankly, I think the advice to go straight into freelancing without any prior business experience—or its positioning as an easy way to make money—is risky, and fostered by those who have a vested interest in cheap labor. (I’m looking at you, content mills, and even the popular bidding sites.) Sara Horowitz, author of The Freelancers Bible (reviewed here) and founder of the Freelancers Union, put a happy spin on it in a recent article in Fast Company, “Why Millennials Understand the Future of Work Better than Anyone Else.” As much as I respect Sara, I think her premise is flawed. A freelance career isn’t fostered by a million loose social media connections; it depends on strong, intimate business connections.

I suspect that there are two related mitigating factors: 1) the tough job market, and 2) the number of millennials who live at home: at latest count, about 26% of the 18-to-34 population. Most of us probably could have freelanced till we were 34 if we didn’t have to pay any bills or put food on the table. I’m not saying that to slam the younger generation, or to denigrate those who choose part-time freelance work, or to sound like the cranky old uncle who walked uphill both ways to school.

I’m saying it as a businessperson. I’m saying it as someone who believes you can expect more from freelancing than a way to get by—if that’s what you want to achieve. It takes work, time, experience, and real networks, and there are no shortcuts. It’s my opinion, but I believe there’s a benefit to doing that kind of apprenticeship on someone else’s dime before going out on your own.

Perhaps I am overestimating the value of traditional jobs in laying the groundwork for an entrepreneurial career. Maybe I am underestimating the business acumen, tenacity, or cash-rich networks of freshly minted college graduates. If that sounds like you, and you want to set me straight in the comments, please do.

Free Marketing Q&A

Want to further your freelance education? Join Lori Widmer and Dr. Freelance for a free webinar session, “Everything You Ever Wanted To Know About Freelance Marketing…but Were Afraid To Ask,” on September 14. 

Like this post? Please share it!

Like What You've Read? Subscribe to Dr. Freelance

* indicates required


  1. says

    Because I have shoes as old as some Millennials, I am probably not the best person to comment. 😉 With 30-plus years in the corporate world, to say freelancing was my imitation of a late bloomer is putting it mildly.

    I am a firm believer in everything happens for a reason. I have shared with friends that if I had a do-over, I would have gone into freelancing in 1999 when I accepted my employer’s severance as part of their being acquired by another company. Instead, I worked another eight years in corporate. The most immediate employer was an international consulting firm.

    The flip side is I learned invaluable consulting experience from that firm. I credit that experience with much of the success I have had as a business owner. I also spent 20 years in management. While I MUCH prefer working for my current boss ;-), the management experience (as well as sales & service) has helped me in the critical skill of networking and managing business relationships.

    I am quite certain there are those who could be successful in making the leap to freelancing; however, like you, Jake, I suspect those are the exceptions. The mentoring you receive along the way and the structure are truly great tools for owning your own business.

  2. Jake Poinier says

    Thank you for a thoughtful comment and for the social media shares, Cathy. There’s no perfect amount of corporate grunt work required to be successful at freelancing, but for the vast majority of new grads, I can’t imagine doing it with zero real-world experience. Being hired by a company or professional is a whole different ballgame from being edited or critiqued by a college professor.

  3. says

    Great article, Jake. I couldn’t agree more. I didn’t start my freelance editing career until age 42, after over two decades in the media, arts, and corporate world. I was just mentoring a college student this morning who was interested in a freelance editing career. Near the top of my advice was to get some life experience and business experience first, before launching into a freelance editing business. The editing is the easy part. The business aspects can be very, very tough at times. While there are always exceptions, I don’t think a lot of 22-year-olds, straight out of college, are cut out for the tough road of entrepreneurship, especially the financial struggle at the beginning. That said, I wouldn’t trade my freelance life for anything. Despite the difficulties and long hours, I still love it as much as when I started.

  4. Jake Poinier says

    Thank you for the comment, Arlene. You’ve provoked me to wonder how old the average freelancer is when they make the leap, and whether the success rate is correlated to length of corporate experience. My intuition would be that there is. I’ve been considering reviving/revamping Freelance Forecast, so maybe I’ll try to take it on.

    Having grown up the son of an entrepreneur, I knew how tough it was. Even in my first job, my dad told me, “Eventually, you’re going to have to work for yourself,” but like you, the corporate experience I got was invaluable as a foundation.

    And thank you for sharing the article elsewhere—always appreciated!