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How to become a solopreneur

Do you want more freedom in your career? It may be time to think outside the cubicle.


As employees, we’ve all been struck by wanderlust—the feeling of being shackled to our desks when the weather outside is gorgeous. As we curse our long commutes or roll our eyes at the latest bureaucratic snafu, we can’t help but think, “If I were my own boss, I wouldn’t have these problems.” Or, “If only I could work from home and have a more flexible schedule.” 


Thinking outside the cubicle

It’s no wonder more than one in three U.S. workers—an estimated 53.7 million Americans—now think outside the cubicle. That’s the number of freelance business owners, independent contractors, moonlighters, temporary employees and “diversified portfolio” workers with different income streams in the U.S. today. According to a recent study. This study, conducted by the independent research firm Edelman Berland and commissioned by the Freelancers Union and Upwork, also reveals approximately 700,000 more workers joined the ranks of freelancers between 2014 and 2015. “Freelancing is the new normal,” says Sara Horowitz, founder and executive director of Freelancers Union. 

A greater demand for flexible work hours drives the trend. The study shows the majority of workers freelance by choice—with 50 percent reporting they wouldn’t trade freelancing for a traditional 9-to-5 job, even for better pay. In fact, 60 percent of freelancers discovered higher earnings after saying so long to 9-to-5. Of those who earned more, 78 percent said they accomplished the feat within a year or less. 

Today, several factors make becoming your own boss a more attainable goal than ever before.

The new commute

First, it’s now affordable to tout your skills (or wares) on a website and connect with potential clients around the globe via social media.

“Videoconferencing in particular has been a real game changer for people who want to work independently because you literally can work from anywhere,” says Katy Tynan, professional speaker and author of Free Agent: The Independent Professional’s Roadmap to Self-Employment Success. “Companies have also latched on to the idea that they can look for talent outside the 20-mile radius of the city they’re in,” she says.

Through low-cost, high-bandwidth Internet access, remote team members can collaborate on multimedia projects, videos, documents and spreadsheets from a variety of locations. 

Going the way of the Edsel

These high-tech changes in how we work make the 40-hour workweek look, well, antiquated. About a century ago, Henry Ford cemented the 40-hour workweek as a labor norm, and some think the tradition should go the way of Ford’s Edsel.  Recent research reveals the 9-to-5 routine is a poor fit for the natural sleep/wake cycle of many workers.

Till Roenneberg, PhD, a researcher with the Institute of Medical Psychology at the University of Munich coined the term “social jetlag” to describe the mental fog that results when you skimp on sleep or set your alarm clock an hour or two earlier to get to work. Other sleep experts, such as Kevin Wright, PhD, a researcher with the Sleep and Chronobiology Laboratory at the University of Colorado at Boulder, use the term “sleep inertia” to describe the grogginess or gradual awakening of our brain each morning. It’s easy to see why members of the chronically fatigued workforce are considering taking the leap to self-employment. 

Look before you leap

If you have a salaried position or were recently laid off, how can you decide if now is the right time to pursue self-employment? 

“One of the common mistakes that people make is jumping into freelancing all at once,” says Caitlin Pearce, Freelancers Union director of member engagement. “We always advise that you do it gradually. A hard and fast rule is make sure you have between three and six months’ living expenses before you quit your job. You should definitely have enough clients to keep you going.” To build up your client list, you’ll need to moonlight on projects outside your normal work schedule. 

Next, take an honest look at what tasks you enjoy. Keep in mind that once you’re self-employed you’ll have to handle all aspects of the business—from secretarial and accounting duties to chasing overdue payments like a bill collector.

“The people I know who are really successful like the variety self-employment brings,” Tynan says. “The people who are less successful are the people who really, really love the work they do, but don’t like the rest of it. These are people who typically prefer to be employees.” 

Once you've built a list of long-term clients and work keeps rolling in, never stop marketing.

“Allocate at least a couple of days per month to business building—to find new leads, get to know folks in your industry, find mentors and industry groups to keep you on top of trends, and to develop yourself and your skills,” Pearce says. 

Expect to devote long hours to your enterprise, but keep your eye on the prize, says Barbara Winter, author of Making a Living Without a Job: Winning Ways for Creating Work That You Love. She says, “If you don’t follow your dream, what will be missing from the world?”