The Real Challenge of Freelancing

Serena is a life coach and therapist. She works from her home outside Tucson, Arizona, with her two cats and her Labrador. Working about 5–6 hours per day, she earns ample income while reserving enough time to enjoy hikes in the natural park (a 15 minute drive from her home) and to spend evenings with her spouse. She loves to travel, too, and while the timezones can make things tricky, she generally has no issue working from places as far flung as Mexico City, Portugal, and Thailand — where she can actually save money by visiting. In years past, she has traveled as many as 6 months out of the year, all without a hitch in her growing business.

Daniel is a recent graduate from a top college with a degree in English. He moved to Los Angeles to become a television writer. PA (production assistant) spots come and go, lasting only 6 weeks at a time, and they aren’t exactly lucrative. He might take a 9 to 5 if he could find one, but as it is he cobbles together an income from a number of sources, including driving his car for Uber and Lyft, working odd jobs on TaskRabbit when he gets tired of being in his car all day, helping some of his parents’ friends with their computers, and tutoring high schoolers in English and history.

Both Serena and Daniel are working freelance. And both are, according to many reports, the future of work. Yet their lives could hardly be more different.

Which future are we facing?

Articles covering the freelance industry exaggerate the realities facing freelance for clickbait or product promotion. On the one hand, many voices depict a life that offers simultaneously the pursuit of one’s passion and the relaxation of retirement. Do what you love — from the beach! Tim Ferris is perhaps the most famous of these voices, thanks to his seductive promise of a 4 hour work week. And yet other venues describe freelancing as a never ending and tenuous hustle, a frenetic dance from gig to gig with none of the traditional support systems of employment. These voices have even coined a term, the precariat, to describe this new working class, a motley crew of victims of seemingly Gilded Age-style, pre-Labor Movement exploitation.

The truth is a mosaic of these qualities. Where the first notion is too rosy, overlooking many of the pitfalls of self-employment, the second exaggerates the insecurity by positing unrealistic worst case scenarios.

And I should know. For one, after a decade in the work force, I have not once worked as an employee — only as an independent contractor. That experience includes work for non-profits, for agencies, and for myself. Second, I have made the rare steps from subcontractor in an agency to independent freelancer to founder and manager of my own agency staffed by (happy) freelancers. In other words, I have experience at every level of freelancing; even now, I freelance for my own company.

So here are a few myth busters:

  • Myth: The schedule is always at your will. This is only partly true. In most industries, clients expect their freelancers to work certain hours. Tutors have to be free in after school hours and Sunday, for example; personal trainers tend to work before and after the work day. If you’re a freelance programmer or designer, odds are you have to overlap with your clients’ work schedules at least a few hours per day. Even drivers aim to work during busy periods.
  • Myth: The payment is unreliable. In broad strokes, we live in a growing economy, and most freelancers who are more than decent at their jobs can find enough work to support them. And that’s before even considering that, if need be, there are platforms like Uber that will eagerly put freelancers to work. While payments are uneven, while certainly late and missing payments are a big problem, and while invoicing and collecting is a pain for everyone, it’s not fair to say payment as such is unreliable.
  • Myth: There is no security and no benefits. While true, this deficiency is generally made up for by the increased wages paid to freelancers vs. similar professionals under employment, and by the growing availability of insurance and retirement services for freelancers. Put otherwise, the health insurance and other benefits offered by employers are often de facto taken out of the employees’ paychecks, just not in a manner to make the expense transparent. That said, as the Affordable Care Act sees its premiums rise and as it faces repealing, the accessibility of health insurance to freelancers is subject to change.

So what is the true plight of the freelancer? The hard part of working for yourself isn’t surviving — it’s thriving. In a word, it’s the hard, awkward work of not only running a business, but building a career. Let’s consider:

  • Fact: You will not get a regular paycheck with taxes and so forth handled for you. You will have to figure out how to get paid, and then make sure your clients follow through. And if you’re successful, you will have to do this a lot.
  • Fact: You will not get annual pay bumps, much less promotions, unless you work for them yourself. That means raising your rate (which is hard), hustling for more clients (which is harder), or scaling your business (which is hardest).

Who normally handles these things? Your boss. Thus the bad parts about freelancing, like the good, stem from the fact that there is no boss: no boss to set your salary, to cut your check every two weeks, and to boost those checks every year. Even worse, there is no boss to replace.

The question isn’t what perks do freelancers have or do not have; it’s how can they build a career, a life?

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