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Going Solo: The Rise of the Gig Economy

Going Solo: The Rise of the Gig Economy

Hal Conick

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The gig economy was born in the wake of the Great Recession; since then, full-time freelancing has risen in popularity. With many now predicting that most of the workforce will be full-time freelance in the next decade, marketers and marketing managers alike must plan for their future.

In 2016, after spending years as the head of marketing departments, Mike Volkin quit his job. He felt liberated to be out of the office, especially his office chair. “Humans weren’t designed to just sit in a cubicle for eight hours a day and just work,” he says, now leaving work once a day to play tennis under the California sun.

After quitting his traditional job, Volkin started working as a freelancer and entrepreneur; he now runs his agency, 800lb Marketing, and works as a fractional CMO for many small and midsize companies. As a fractional CMO—essentially a freelance marketing executive and strategist—Volkin hires freelancers and staffers, holds weekly meetings and sets the company’s marketing strategy. “I’ll get a department up and running and headed in the right direction,” Volkin says. He never becomes the CMO of any single company and doesn’t want to; he’s able to work with different companies on a contract-to-contract basis, paying for his own health insurance, setting his own schedule and making a good living—he says that he makes $10,000 or more most months.

Though Volkin’s role as a roving CMO is unique, he’s part of a growing trend of full-time freelancers in the job market. According to the 2018 Freelancing in America report by Upwork, Freelancers Union and Edelman, 28% of full-time workers are now freelancers, up from 17% in 2014. This number will rise, according to multiple studies—Robert Half International reports that 34% of the economy will be freelancers by 2023; another report by Upwork goes even further, saying that the majority of the workforce will be freelance by 2027.


“I think that’s conservative, actually,” says Volkin, who also works as an entrepreneur coach. Volkin says that he’s had more inquiries from coaching clients about going full-time freelance in the past year than in the previous five years combined. He estimates that 20% of those inquiries have been from marketers.

Thus far, the trend of working and striving for full-time freelance trends younger. Prudential’s 2018 Gig Economy Impact by Generation surveyed millennial-aged workers and found that 62% believe traditional full-time employment will disappear in the next three decades, with freelancers making up 75% of the job force. The report also surveyed older generations—Generation X and baby boomers—who tend to work as full-time freelancers due to circumstance rather than by choice like millennials. The younger generation, the report finds, possesses a greater comfort level with taking career risks and views freelance work as a step toward realizing long-term goals.

Jeremiah Owyang, founding partner of research firm Kaleido Insights and a technology analyst, says that the U.S. economy has always had freelancers, gig-workers and consultants (the terms are mostly interchangeable). But since the Great Recession in 2008, Owyang says that it’s easier to both become a freelancer and hire one. Online freelance platforms such as Elance (now Upwork) and—in addition to gig giants such as Uber and Airbnb—were all founded in 2008 or 2009, giving unemployed workers new ways to make money. It marked the birth of what’s often referred to as the “gig economy.”

In 2014, marketing managers began employing more freelancers, Owyang says. According to a 2017 report from Upwork, 58% of marketing managers use freelancers to help scale projects and fill staffing shortages.

The move to freelancing full time can be scary for marketers used to regular paychecks and a benefits package, just as hiring an outside creative can be frightening for marketing managers who want to protect their intellectual property and brand voice. But while the relationship between marketing and freelance is new and growing, curious marketers can learn from those who have blazed a trail in the early days of marketing’s gig economy.

Is Freelancing for Me?

After a three-year stint in various marketing roles at HubSpot, Sarah Goliger left to work at a startup. It didn’t work out, but the timing did. “My now-husband was also at a startup at the time; that didn’t work out either,” Goliger says. “We both found ourselves with a blank slate.”

Goliger and her husband traveled to Southeast Asia for five weeks, came home and immediately started working as full-time freelancers in their respective niches. Now, Goliger works as a digital marketing consultant and a life coach, often getting referrals from her former HubSpot colleagues. Freedom has been Goliger’s favorite part of her freelance work. “There’s so much opportunity to create whatever kind of lifestyle you want,” she says. “I think it’s a much faster way to grow, compared to a full-time role.”

For those in their prime working years, feelings of freedom and growth are often stated as reasons they’re drawn to full-time freelancing. The 2018 Freelancing in America survey asked full-time freelancers and non-freelancers whether their work “provides upward mobility”—72% of freelancers agreed, compared with 53% of non-freelancers. The difference may be the result of freelancers more actively educating themselves—70% of full-time freelancers updated their career skills in the past six months, the report found, compared with 49% of non-freelancers.

When workers were asked whether their job “provides appropriate pay for my skill-level,” 77% of freelancers agreed, compared with 62% of non-freelancers. In addition, the report says that the number of high-earning freelancers—those who earn $75,000 annually or more—is up 15 points since 2014.

“I think that the millennial generation especially is really excited about the opportunity to work remotely and to get a lot of travel,” Goliger says. The Freelancing in America report echoes this, reporting that 42% of people ages 18 to 34 freelance full time, compared with 29% of people ages 45 to 54. “These are becoming really big priorities for our generation. I think that the more people realize that this is an option and figure out how to make freelance work, more people will take advantage.”

But not everyone likes this kind of self-created freedom at work—some people aren’t cut out for the constant grind of working for themselves, for having an uncertain schedule and not knowing when, exactly, their next check will come. Volkin says that when he’s coaching entrepreneurs, he’ll ask two questions to see if they’re “freelancers at heart”:

  • “Do you require the structure of knowing where your next paycheck is going to come from?” Volkin says that freelancers may make $10,000 one month and $2,000 the next—some people can plan for that, others get freaked out. Case in point: The Freelancing in America report finds that 63% of freelancers feel anxious because of the unpredictable nature of their work.
  • “Do you like to go to an office every day?” If someone dislikes going into an office, Volkin says that they’d likely have the determination to work on their own.

Working alone is one of the biggest changes Goliger experienced when she started freelancing full time. She’s not alone: 56% of freelancers say their work makes them feel isolated, according to the Freelancing in America report. Most of Goliger’s jobs have been remote, save for a couple of companies that have asked her to come in to build a closer relationship, and she only has a couple other friends who also work as full-time freelancers in marketing.

“The social aspect is definitely the big one for me—not having people to bounce ideas off or grab coffee with,” Goliger says. “But I think the flipside of that is that you’re able to be as efficient as you want. You can say, ‘I work from home, so I have all these distractions around me,’ or you can say, ‘I work for myself and I don’t have team members popping by my desk to interrupt with questions.’ … It creates a very different workflow where when you need to get work done, you do. And when you don’t, you don’t.”

A Strong Network Makes the Transition Easier

A good network makes the often-solitary nature of freelance a bit less lonely. Jennifer Perna worked in sales for about 25 years; by the end, in her role as vice president of sales for Blue Plate, she managed 32 people and was constantly networking. Now, in her second year as principal and owner of Fulton Market Consulting—Perna’s consulting business for sales and management in the catering, events and hospitality industry—she only manages herself, but has cultivated and relied on her network to fill gaps in her knowledge. Perna has found an accountant, a lawyer, business insurance and other skill positions through her network.

“Part of owning your own business is being humble, asking questions and not being embarrassed,” Perna says. “When people are [moving into freelance], I always help them out. I say, ‘OK, let me save a year of your life here and tell you what I learned in my first two years.’”

Just as competitive lawyers will send referrals to one another when they have a full case load, Goliger says that she’ll refer work to others when she’s too busy. Perna says that she’ll ask for help and give help to competition. “I was always a considerate professional and a good friend of my competitors,” Perna says. “It’s paid off, because you never know who in the local market will end up being someone you need in the future.”

Zach Weismann turned potential competitors into collaborators when he founded a group called MAG Impact Collective, a membership agency of consultants across the U.S. who work in marketing, strategy and design. The group of independent consultants will team up on pitches and projects, bringing in others from the group when the client needs certain specialties. The group, founded in 2018, has already pitched and won projects with brands such as Google, Chobani and Exxon.

“Work gets lonely,” Weismann says. “I think that we need collaboration and we need teaming up. We’re looking at things like pooling resources where we can invest in a project manager or a business development person together or even share simple things like accounting software where you get five licenses. Why should everybody have to pay for that on their own just because they’re part of the gig economy?”

Downsides to Full-Time Freelance

Many outsiders look at full-time freelance and worry about finding work, but as Matt Umbro wrote on MarketingLand in 2017, having too much work is often a bigger problem for creatives who survive on their reputation.

“People hire freelancers because they don’t want to pay agency prices, but they expect agency-quality work,” he writes.

Umbro says that this leads to freelancers who have fewer hours to complete projects and less time to communicate with clients. They sometimes find themselves needing to do unpaid work to complete projects. “If you choose to do freelance work, understand that your personal brand is at stake,” Umbro writes. “You don’t have your agency as a shield.”

When working as a freelancer, you are your own agency, your own business. As Umbro writes, each project puts your name and reputation on the line—fall short enough and word will spread, whether through word-of-mouth or online reviews. Every freelancer interviewed for this story mentioned that this means they are, to some extent, always thinking about work. Freelancers are expected to quickly respond to emails, answer calls and turn in great work on each project. Some people excel at this, while others wish they could return to the security of a cubicle.

Despite the downsides, those who seem to be made for freelancing appreciate the benefits. The Freelancing in America report found that 51% of freelancers say that no amount of money could get them to work a traditional full-time job. As Perna put it: “What’s the worst thing that can happen? I have to get a job.”

About Hiring Freelancers

When Volkin hires freelancers, he’ll test them. The test won’t be on any skill, nor will it be apparent to the freelancer, but he’ll watch how they communicate in the first exchanges—how quickly do they respond? Are they open and honest? Can they have a good relationship? But Volkin says that it’s just as important for marketing managers to communicate well—they must know what they want from a project from the start and set parameters. Doing so early will save time and avoid miscommunication.

“SEO, for example, is a task you have to break down … because there are many different types,” he says. “Also: What’s your timeline? What’s your budget? All that stuff has to be clearly outlined from the beginning.”

Managers can also look at freelancers’ ratings and reviews on platforms such as Upwork, Crowdspring and 99designs. If one freelancer has a series of critiques on his communication, for example, Volkin says that it may be best to avoid that freelancer. Outside of these rating systems, Owyang says that companies often internally pass around names of well-liked freelancers they trust to do good work for other parts of the organization.

But for marketing managers who have yet to employ freelancers, Owyang says that it’s best to start small. Many creative agencies, for example, farm out ideas for a campaign on freelance platforms, then hone the ideas in-house before bringing the fleshed-out ideas to a client, who likely never knew that freelancers were involved. “That happens a lot,” he says. “The crowd can provide far more variability and more creative offerings. We will only see this grow.”

Volkin says that he often finds these outside voices more valuable than perspectives within the company. “A lot of the employers within a company are too close to their product or service,” he says. “People outside the company that are just familiar with the basics provide some really good insight into how the company is perceived.”

The biggest fear marketing mangers have in hiring outsiders is protecting intellectual property, Owyang says. “If you have some people working on a secret project, there’s always the risk that they’ll spill the beans or they’re working for a competitor,” he says. Owyang says that Lexus worked with an agency that only allowed freelancers to work on-site on a computer not connected to the internet when working on a campaign for a new car model. “There are secret pictures of the new cars that, if those leaked to car blogs, would ruin the launch.”

How to Succeed as a Freelancer

When Goliger first started freelancing full time, she branded herself as a full-stack marketer. Very quickly, she developed a niche in paid advertising, similar to her last role at HubSpot.

“It just so happened that [paid advertising] is a really great spot to focus as a freelancer because if a company is running [a paid campaign], it means that they have a budget, which is a good sign for me, and it also means that it’s high risk for them because they want to get it right,” she says. “They don’t want to be wasting all that budget on ads that aren’t working well.”

Freelancers often debate whether they should be generalists or specialists, but Goliger says that she believes that having the skills of a generalist while focusing on a marketing niche is best. “You’re able to talk about that channel specifically, your experience and the results that you’ve delivered,” she says.

Volkin found his niche as a marketing strategist. When he hires freelancers, he doesn’t look for generalists, but the niche he needs for a company or project. For a marketer to find a niche, Volkin says that they must start by defining their goals. These goals must go beyond freelance and into what they want from life—some may want to make six figures, others may just want a bit of money but a lot of freedom. Once freelancers find their niche, Owyang says that their work must be well-reviewed, they must start building a portfolio and should have repeat customers they can rely on for some semblance of consistency. “You should really strive for the best customer ratings you can get,” he says. “You [should] build up that solid reputation to be the one that everybody wants to hire.”

Perna, who stressed the benefits of a strong network, says that the most important things for any full-time freelancer are focus and discipline. “If someone shows interest in wanting my services, I follow up with them,” she says. “But that’s what I love about it: You’re working for yourself. But it’s a different kind of work—it’s a very rewarding kind of work because you have to be extremely disciplined.”

For those who find their niche, can work well alone and don’t mind waiting for the next check, Perna says that the rewards of working for yourself can be immense.

“I really did love my previous job; I loved every part of it,” she says. “I was there almost nine years and I wanted to give my team growth opportunities. But I hit a point [where] I wanted growth for myself. I wanted to try something new and that’s what I did. And I have loved every minute of it.”

Hal Conick is a freelance writer for the AMA’s magazines and e-newsletters. He can be reached at or on Twitter at @HalConick.