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Expert Source: Business coach Barbara Winter, author of Making a Living Without a Job,  focuses on creating and sustaining the mindset you need to succeed at self-employment.

Self-employment is a dream come true for independent types, in large part because it can be deeply fulfilling to create your own business, set your own schedule, and define your own goals. The process can also be extremely stressful. The exciting sense of self-direction can quickly turn to obsessive angst, since success or failure seems to rest entirely on your shoulders. Then there’s the variable income, the fear of taking time off, the frequent loneliness . . . and the list goes on.

Despite these challenges, self-employed people report significantly higher job satisfaction than their other-employed peers, a 2009 Pew Research Center report found. So if self-employment can be that good even with its challenges, imagine how much better it can be if you learn to manage them well.

Here are suggestions for how to make the most of self-employment from business coach and self-employment advocate Barbara Winter, author of Making a Living Without a Job.

Barriers to Overcome

  • Anxiety about unpredictability. Life as an employee is relatively predictable, Winter points out, which bores a lot of people. “But unpredictability is a fact of self-employment.”
  • Anxiety about responsibility. “As a self-employed person, I’m 100 percent responsible for decisions,” says Winter. “I can’t blame anybody else when I screw up, and that’s stressful.”
  • Self-doubt. The self-employed are particularly vulnerable to those head-slapping moments of wondering, “What in the world made me think I could do this?”
  • Freedom overdose. Early on, the freedom can be intoxicating. Winter calls it the “Wow, I can go to Starbucks anytime I want” reaction. But unless you get yourself on a schedule, she says, you’ll end up “sitting in the Starbucks with no customers.”
  • Variable income. For most self-employed people and freelancers, the biweekly paycheck is replaced by uncertainty about when, and from where, the next check will be coming.
  • Overwork. The self-employed can also be tempted to work all the time, assuming that any time away from the business is money or opportunity lost.

Strategies for Success

  • Embrace the chance to change old beliefs. Self-employment is more than just a way to make money, says Winter. “I tell my clients that self-employment, with all its problems, is a great opportunity for personal growth. It’s a chance to challenge many of the beliefs that hold us back in life.”
  • Expect emotional ups and downs. Understand that self-employment isn’t all freedom and joy. “Accepting that there are going to be hard times as well as good times is crucial,” says Winter.
  • Be patient. No business takes off overnight, Winter points out. “It can take a couple of years with your business to understand how it actually works, what your business cycles are like, and how to make smarter decisions going forward.”
  • Ease into self-employment. Winter suggests that if you’re not quite ready to quit your job, start developing elements of your new business. Work a few hours as a consultant, or sell some ideas or designs. Consider your job a means to lay down a financial basis for your new venture.
  • Be open to part-time work. This is especially important in the initial phase of self-employment, says Winter, while you’re establishing your business relationships and cash flow. “Having this income stream . . . creates a different mindset from the one that says, ‘I have to have this job, and I have to have it forever.’”
  • Understand the value of time off. If time off seems like an indulgence, Winter recommends shifting that point of view. Not taking it can hurt you. You are the major asset in your business,” she says, “and if you don’t take care of yourself, if you’re working below par, then business can’t proceed as it should.”
  • Set boundaries around ongoing activities. Perennial responsibilities like marketing can take up every spare moment if you let them. Winter suggests setting clear boundaries around the time you spend on ongoing tasks like networking, social media, and so on. “You could make Wednesday marketing day,” she says, “and give yourself over to that intensely for eight hours, rather than worrying about it all the time.”
  • Know your biorhythms. Are you a morning person or a night owl? Do you have a noontime or early-afternoon slump? Winter suggests getting to know these bodily tendencies and scheduling work accordingly — perhaps handling simple tasks during your slumps and tackling more challenging business when your energy is highest.
  • Find your own work-life balance. “One of the things I love about self-employment,” says Winter, “is that there’s no one way to do it. Some people like to work nonstop for a certain intense period, then sit on the beach for three months. Others need a steadier, more regular schedule. It depends on your needs and your rhythms.”
  • Know your limits. Be aware of the signs that you’re overdoing it — like tightness in your shoulders, a constant urge to cry, or snappish reactions. When they show up, says Winter, taking a break is practically mandatory.
  • Form a “council” of self-employment advisers. Consult with more-seasoned self-employed people. They can help you navigate the snafus that may be new to you. You can also establish a barter circle, exchanging services like promotional writing for help with invoicing. “But,” warns Winter, “the trade needs to be even, and that can be a bit of a challenge.”
Photo by: John Kuczala

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