Your Flex Life

The 7 Stark Realities Of Entering the Gig Economy

Flexibility Is Key To Mastering The Freelance Life

BY Carly MilneSeptember 24, 2018

The notion of work is changing. Nowadays, even those of us with full-time jobs are more likely to decide our own hours, dress codes and other previously set-in-stone elements of office life. For those working the gig economy, the freedoms are even greater – and it can be equal parts awesome and stressful.

With almost half of working millennials (47%) reporting that they freelanced in 2017, we all have that friend who seems to exemplify the best parts of the self-employed life—getting up whenever, working from wherever, and defining their own work-life balance.

But what is the reality of truly going gig-to-gig?

After compiling some stats on the gig economy from, Fair spoke with three freelancing experts to get their secrets for success, including setting boundaries with your clients, creating and leveraging your own professional networks—and, of course, staying flexible.

1. Get Comfortable Working Without a Net

The first reality of freelancing: it’s pricier than you think. Paid time off, regular paychecks, group healthcare policies and other benefits? Kiss them all goodbye. In addition, gig work means incurring personal business costs that are almost 8 percent higher than they would be for a company with a full-time employee doing that same job.

“And individual healthcare has become more expensive since they eliminated the bare-bones policies,” says Kathy Kristof, editor of, an online resource that reviews over 200 money-making apps and sites for the gig economy.

So how can you soften the blow? Kristof recommends building a financial safety net before you take the leap into freelancing. “The greater the cushion the better because you’ll want to be prepared for clients who pay slowly or try not to pay at all,” Kristof says.

2. Not All Clients Are Created Equal

The dream is to work with clients who value your experience, pay you accordingly and on time, and help you to become better at your job. Unfortunately, not all companies are like this. Worse yet, some of them may even try to scam you out of earnings or credit.

How can you know who to trust? Besides resources like SideHusl, Kristof recommends using staffing agencies like Onward Search, Creative Circle and 24Seven Talent, who vet clients and ensure prompt payment on a weekly basis for a cut of your earnings.

For women, other reputable freelancing platforms in the marketplace include The Second Shift and Power to Fly, which can provide some key backup in the often solitary life of a freelancer.

3. Your Work Flow Is Up To You

Freelancer Workflow To keep the money rolling, it means you’ll have to be proactive

You’ve probably heard of the dreaded feast-or-famine aspect of freelancing. In fact, keeping the money rolling it means you’ll have to be proactive.

“Start with your own network; the quickest gigs will come from people you know,” says Sam Laliberte, Podcast Host and Freelancer of Freedom Lifestyle. Laliberte recommends reaching out to businesses you’d like to work with to let them know your skill set and availability, as well as finding ways to discover new clients while managing your current workload. But sometimes even your best efforts can’t fix a slow freelance market—which is where the aforementioned financial cushion comes in handy.

4. Learn How to Say No (And Mean It)

It can be tempting to take any offer that comes your way to build a portfolio, expand your client roster or just plain make some serious dough. But one blown assignment that you didn’t end up having time for can do far more harm than good.

As you become more seasoned, experts say, you’ll learn the value of making some tough decisions on who you work for—and when. After all, taking on gigs you’re not excited about doesn’t just zap you professionally and creatively; it robs clients of finding the right fit for their project. How can you avoid this scenario and still save face? Laliberte suggests partnering with other freelancers.

“It’s a great way to still say yes to business opportunities without having to execute on work that's not a fit for you,” she says.

5. Your Time vs. Your Client’s Time: The Struggle is Real

Freelance build your clientele Setting boundaries with your clients ensures your capability to deliver top-notch work

Freelancing isn’t a guaranteed antidote for what ails you as a full-timer. There will be days you work long hours. Or lose a weekend to a deadline. Or skip social events to finish a project. But managing such stresses is now much more within your control. In fact, setting boundaries is a healthy part of being a freelancer, and keeps you fresh and focused so you can deliver top-notch work. Luckily, technology is here to help you.

“I have a calendar function through HubSpot where I send a link to clients, and they can schedule their own meetings with me, but only during the times I have listed as available,” says Debra Boggs, Co-founder of D&S Professional Coaching.

Boggs also turns off the mail notification on her phone “because I get e-mails 24/7 from international clients and I need to be able to shut my mind off from my work.” Guess what? So do you.

6. You Have To Be a Great Communicator

From one job to the next, you’ll build a professional network that can help land you even more jobs—whether it’s through referrals or by putting together a killer portfolio, resumé and LinkedIn profile. But Boggs says it’s far more important to simply be a good communicator.

“The hardest thing for people working with freelancers is to find someone who does quality work and communicates quickly,” Boggs says. “If you’re a strong communicator and deliver what you say you will when you said you would, you'll do great. But many freelancers don't deliver on these basic principles and then don't do well.”

7. Six Figures Is Totally Possible

Millennials making six figures A common misperception is that all gig workers are broke. Not so, says a new study

There’s a perception that freelancers are essentially choosing time over money. However, a State of Independence In America study from MBO Partners found that more than one in five full-time independent contractors earn more than $100,000. Of course, notching six figures on your tax return as a freelancer takes hard work, hustle, and a self-made system of professional support. But the point is, you can get there. So get out there and do your business your way!

As flexible as your life.

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