Fear of risk can thwart office workers dreaming of self-employment


While I was congratulating myself on staying employed during the pandemic, moving up in my company from worker to team lead and then supervisor, some of my friends were leapfrogging salary rungs by job-hopping. Others were starting their own businesses.

Because I played it safe, I work in an office five days a week for far less money than others. I drag myself to work every day and envy my self-employed friends their ability to work from home.

I’ve never been a risk taker, and my partner wants me to stay fully employed so we can keep the life and health insurance benefits we have. She reminds me it’s not the right time to make job changes given all the layoffs and “last hired, first fired.”

I’m 41 and have always done “the right thing.” I’ve been stewing on this problem for a year and a half because starting a business at this age feels like jumping off a cliff. But I really want to have my own business and work from home. Would it be a mistake for me to try? Is it a myth that my friends are as happy as they say they are?


If you drag yourself to work daily, it’s time to plan a new career future.


What holds you back is risk. When you face the choice between letting things stay as they are and the higher risk/greater reward alternative, you often imagine what might go wrong and let potential consequences stop you. By doing so, you take a greater risk, as the real risk lies in underestimating your abilities and selling yourself out. What happens when you fear risk too much to move forward? Fear erodes confidence and amplifies worry. When you allow fear into your brain, it not only moves in, it owns you.

Further, you don’t need to jump off the job cliff; instead, develop a solid foundation for your life as a self-employed individual, so you can create a soft landing. Explore the health and life insurance options available to self-employed people. Assess the skills and talents you have that might enable you to create viable self-employment. The Small Business Development Center,, can provide you with assistance, counseling and training to help you start and grow a business.

Here’s the reality of self-employment: recently surveyed 1,000 self-employed and 1,000 employed U.S. workers. They discovered that four in 10 self-employed people felt happy they chose self-employment. In contrast, one in every three employed people described themselves as unhappy or very unhappy with their current employment.

Forty-five percent of the 1,000 self-employed respondents felt satisfied with their work-life balance. Seventeen percent would “not change” their employment status “for anything.” In contrast, 95% of the 1,000 employed respondents would change to self-employment so they can gain a better work-life balance and increased job security. Self-employed respondents also reported far higher levels of job satisfaction and lower stress. One in 10 self-employed respondents reported zero stress levels at work.

There are downsides. Small businesses can fail. Self-employed people earn less, on average, than do their traditionally employed counterparts. One out of every three self-employed individuals felt dissatisfied with their current income.

If you don’t feel prepared to launch a small business, you have two options. You’ve proven yourself to your current employer through your years of hard work. Talk with your manager about allowing you to work remotely for at least part of the workweek — they may offer you that concession to keep you.

Alternatively, you can investigate the opportunities for higher salaries and remote work advertised on, LinkedIn and ZipRecruiter. Before you switch jobs, however, investigate the employer to make sure it can fare well in an uncertain economy.

In short, don’t waste the next year and a half regretting the risks you don’t take. As Wayne Gretzky once said, “You miss 100 percent of the shots you don’t take.” Educate yourself on the risks and opportunities you might encounter if you start a small business. Assess the likelihood of every potential negative, and plan what you’ll do if the worst happens. By doing so, you shift the odds for success in your favor. If you want more help along this line, check out the detailed strategies in “Courage Is Your Partner,” Chapter 4 of my book “Navigating Conflict.”

Finally, stop evaluating yourself against others and instead measure yourself using the dual yardsticks “What do I want?” and “What am I doing to get it?”

Lynne Curry | Alaska Workplace

Lynne Curry writes a weekly column on workplace issues. She is author of “Navigating Conflict,” “Managing for Accountability,” “Beating the Workplace Bully" and “Solutions,” and Submit questions at or follow her on, or @lynnecurry10 on X/Twitter.