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Fast Company: Why “Just go freelance” is crappy advice

by | Nov 4, 2022

Working Freelance dual environments of employee working at desk.

Originally posted on Fast Company by Emily A. Hay and Alison Spitzer on November 4, 2022.


Reason number one: Many freelancers fail after the first year as a result of making avoidable mistakes.


Great resignations, reshuffles, and the ultimate reality of gender inequity in caregiving roles acted as tectonic plates of the pandemic, and the pressure forced a different landscape on the surface level: an eruption of freelance into a mainstream profession.

Today, freelance is one of the most powerful trends in the way we work.  According to a current study, there are 70.4 million freelancers in the U.S.  By 2028, this number will increase to 90.1 million, or 54% of the workforce, basically divided equally between genders.

On its surface, freelance fits the bill for disrupting the broken and outdated corporate structures and systems we’ve come to accept as gospel that consistently marginalize and penalize entire demographics. Once invisible segments of the workforce: namely women with caregiving résumé gaps, have a much more viable and professionally respectable option than, for example, selling leggings out of their living room as part of a multilevel marketing (MLM) scheme.

It doesn’t hurt that freelance is also bringing about better business results, including an increased ability to be nimble during times of uncertainty for the companies that participate in hiring these once “corporate America outsiders.” Per a Fiverr survey, the larger the business, the more money invested in freelance talent: 65% of businesses with 100-240 employees are turning to freelancers more now than they were before the pandemic.

It would appear to be solid guidance in today’s modern workforce to tell someone who wants the “3 Fs”—flexibility, fulfillment, and financial independence—to “just go freelance,” right?  The large numbers and data supports this direction and suggests that it could be perceived as safe, prudent advice. Anyone with some industry experience and a laptop can participate.  The groundswell of freelance focused companies like A.Team, Upwork, and We Are Rosie that make freelance work more attainable for skilled workers is proof that all you have to do is “just go freelance,” right?


Despite irrefutable data and industry growth indicators, telling someone who is unhappy in their current professional situation to “just go freelance,” is like telling them to summit Mt. Everest without oxygen: 5% of climbers have succeeded, so it can be done, but there will be avoidable hardship and a much higher chance of failure.



Not repeating our main street and corporate American history of exclusion is the key to freelance success. If you have taken a road trip, you know that every town in America once had a thriving main street, driven by local entrepreneurs, necessity, and loyally supported by their communities that have since been unapologetically forsaken, leaving no trace of the hope, pride, and promise that fueled their establishment in the first place. The leveling of main street America was a natural, unavoidable sacrifice of underlying societal progress. Highway infrastructure and automobiles paved the way for irreversible changes to our economic landscape.

By the 1950s and 60s, the new, safe, borderline conservative advice to aspiring professionals was to leave entrepreneurial aspirations behind with the limitations of small town brick and mortar in pursuit of the “opportunities” corporate America promised in bigger cities. As a collective, we had this pivotal moment to architect a more inclusive environment. We failed.

Now, we have the luxury of hindsight, and we know that while there were many so-called opportunities in corporate America, they generally were only afforded to one specific type of employee. If you didn’t or couldn’t conform, you were left behind in one way or another.

There is a serious lack of women at the top; with a mere 5% serving as CEOs in 2022, we find ourselves waving in the rearview mirror again, no love lost for another archaic work structure that rewards a very specific few. We are at another crossroads, and for the sake of our overall economic strength, we must proactively afford more professionals the ability to flourish.



Just as one should weigh the risks of attempting to ascend to 29,029 feet without essential supplies, the current trend of freelance must be truly understood in order for America’s efforts to redefine work to be realized. The growth numbers presented in celebration of the freelance movement are dangerously misleading. Three quarters of self-described freelancers in the U.S. are part-time, meaning the vast majority are using freelance as a side hustle to supplement a steadier source of income coupled with traditional benefits.

Furthermore, a recent study says the 70% of women considering self-employment are motivated to escape workplace discrimination and corporate glass ceilings will be met with a gig economy that overall faces even wider gender pay disparities around the world, which, even at the current rate of improvement, will take a staggering 132 years to reach full equality.

Freelancing is a $450-billion industry, yet gender pay research reveals that men earn 48% more than women as freelancers. Although there are more female freelancers than males, women comprise a much larger percentage of part-time work and less of full-time.

One of the primary reasons women are not as successful as their male counterparts in small business entrepreneurship is a lack of role models. Almost half of female founders cite being held back by a lack of available mentors, and furthermore, an absence of role models is a leading reason why women do not start their own business at all.

Without a path to follow, we are setting women up to fail. This could explain why the multilevel marketing model was so successful at attracting women over the past century. An acquaintance of some sort that was perceived to be achieving “success on their terms,” recruited them with a mentoring tone, selling a woefully misleading promise of the “3 Fs.” Believe it or not, in 2022, there are still well over six million Americans actively pursuing economic gain from one of 350 multilevel marketing companies in an industry valued at approximately 44.1 billion dollars in 2022.

We’ve learned the MLM business model is inherently flawed considering success is the exception and the majority of income gained is by recruiting underlings, not selling the product du jour. From tell-all documentaries to legitimately disgruntled anti-MLM-ers, this corrupt business model didn’t just deplete bank accounts, it has effectively left a limited view of what professional flexible options are available to women as 86% become mothers by the age of 44, and inherit two-thirds of what it takes to run a household and raise kids, regardless of whether she works outside the home.

Left in the rubble of these eruptions are a mass of bewildered MLM refugees, alone and still looking for a way to supplement or support their families. Countless women whose résumés boast business development skills, a proven background in customer service, and PR experience want to consider a professional option that will afford them the “3 Fs,” but today may never consider that they could start a freelance business with their existing degree and/or skill set as a foundation.



Unlike MLM, a freelance business does not require a massive up-front investment in products that may fill your garage; rather, a viable freelance business could grow tenfold with an investment in oneself as a training to get started.

This was the experience of SonSeri Kennedy, a military spouse with an MBA, and a 10-year résumé gap. When looking for workforce reentry in 2020, the future looked bleak until she stumbled upon a specialty upskilling program that included real world guidance for starting her own business, and a community of like-minded women.

“It was exciting . . . I felt empowered, I felt like I was actually a business owner as a freelance professional. It felt great knowing that I was working again. I no longer had a gap.”

Today, SonSeri has achieved the “3 Fs” freelancing in the high-demand field of social media marketing, something she would never have considered without the training and ongoing community support.

Despite freelance being mainstream, the on-ramp is overwhelmingly improvised, and the act of self-navigating the day-to-day landscape is still foreign for the majority of professional women. You cannot “major” in freelance, and internships do not exist. Concentrated, practical courses known as “microtrainings,” can serve as oxygen to freelancers by offering potentially career-saving tools to virtually anyone considering freelance, starting where they are. With the trend of questioning the value of higher education altogether, microtraining offers a solution that can most effectively fill the current void for proper career preparation.

Furthermore, “upskilling” is defined as “a workplace trend that facilitates continuous learning by providing training programs and development opportunities that expand an employee’s abilities and minimize skill gaps.”

According to a 2022 Rosie Report by We Are Rosie, one of the most important ways to achieve freelance success is to possess a specialty.  Microtraining and upskilling aren’t just for the benefit of those new to the industry; they provide a way for established freelancers to obtain specialized knowledge that can increase their project rates. In fact, research shows that 70% of full time freelancers participated in an upskilling training in the past six months. Upwork shares that the most in-demand specialty skills are web design, social media marketing, and customer service.

In addition to the need for guidance and training, freelancers need more safeguards against risk. More than half (58%) of freelancers have experienced non-payment from clients with little recourse, and most do not have retirement plans or affordable health insurance.

Companies like We Are Rosie, established to serve and support the marginalized, not only function as an intermediary tracking and paying freelancers, they also offer common traditional workplace benefits like healthcare and 401ks. No question, this work is filling a void, but the major benefits are only experienced by “Rosies” who officially receive work from one of their corporate clients.

What about the unknown percentage of freelancers who don’t find work? How long can they afford to hang in there and how much does their failure ultimately cost? The raw number of freelancers completing profiles on these sites may continue to increase, but without training and guidance first, there will be attrition, and sites like Upwork and We Are Rosie will remain less accessible to people like SonSeri.

Those experiencing internalized limitations based on past cultural norms of exclusion will be perpetuated unless further action is taken to prevent fallout, leading to another slow but predictable abandonment of a once-promising way to work.

Not all that long ago, entrepreneurial-minded professionals were the rule, not the exception. As a collective, we are moving toward an increasingly decentralized model as more resources of all kinds shift to Web3. We have an obligation to grow freelance in a human and inclusive manner. Many freelancers fail after the first year as a result of making avoidable mistakes, with only a third making it to their tenth year intact. Still, 87% of freelancers believe the best days of freelancing are ahead.

After all, “the hardest mountain to climb is the one within.”  We can’t simply tell people to “just go freelance” unless we also tell them to invest in training, align with like-minded, supportive communities, and join advocacy groups to strengthen industry rights before they start their journey to the summit as an individual, but never alone.