The other evening, Paula Lucas shared a dream on Facebook. Paula is longing to travel the country pulling one of those adorable teardrop trailers.

Since I got to know Paula at the recent Obstacle Buster Mastermind program, I knew that she has been building a lively business selling at outdoor markets. I heard opportunity knocking.

I jumped into the conversation and suggested she could travel and build her business at the same time. She had, of course, considered that possibility.

“Do you realize,” I asked, “that if you and your teardrop trailer are not just traveling, but also setting up shop at flea markets, it would make your travels a tax deductible business expense?”

I was pretty sure Paula would find that appealing. As do I. Tax deductible travel is one of my favorite self-employment perks.

We’ve all been somewhat conditioned to think that benefits are something that come as the result of having a job. Consequently, logic suggests that not having a job means not having benefits.

Nonsense. Self-employed people have all sorts of benefits—both the conventional sort plus many others that no employer ever offered.

In fact, an important part of planning a successful business is deciding just what benefits matter to you and making sure that you include them. As your business grows and prospers, you’ll want to review your personal set of benefits and make appropriate changes and additions.

It’s also emotionally healthy to remind yourself often of the benefits that are accruing because you’ve chosen to put yourself in charge.

Here are some favorites of other self-bossers:

° Napping. According to a reports on the national news, a few companies are instituting nap time and providing places for employees to snooze during the day. They defend this radical notion by citing increased productivity.

The Joyfully Jobless have known about this perk for years.

° Automobile savings. Unless you drive extensively for your business, you’ll probably enjoy much lower car expenses—including lower insurance premiums—than if you were spending hours in traffic everyday.

And, of course, cutting out a long commute also has stress reduction benefits.

° Improved health. While a growing number of studies now verify the health hazards of a stressful job, less publicity has been given to studies showing the link between satisfying self-employment and healthy longevity.

One long-term university study found that the single consistent longevity factor in those they studied was a lifetime of rewarding work.

And as anyone knows who has to rely on restaurant and fast food for nourishment, it’s much easier to eat wisely when you’re the cook.

° You don’t have to ask for permission—ever. You can schedule your work around your own particular rhythms and burn the midnight oil if that’s your style.

Or spend six months working intently followed by six months devoted to leisure.

° Tax deductions. There are numerous deductions available only to the self-employed—including ordinary expenses you’d be making anyway, but not subtracting from your tax bill if you held a job.

“The self-owned and operated business is the freest life in the world,” says Paul Hawken. It’s also loaded with wonderful benefits unknown to those who inhabit the world of 9-5.

What are your favorite perks?


When Elizabeth Barrett Browning wrote, “How do I love thee, let me count the ways,” she wasn’t talking about her life as a poet, but we’re borrowing that idea anyway.  Our list isn’t nearly as poetic as hers, but it’s every bit as passionate.

√ Control over time. Self-bossers are more likely to plan their work around their 

bio-rhythms, not a timeclock.

√ No supervisor. Being self-directed builds confidence and maturity.

√ Imagination stays fit. Our creative spirit is like a muscle and needs frequent workouts to keep it in top operating form. 

√ Office can be anywhere. We get to decide if we’ll work at the beach, in our RV or in our home office. 

√ Time for creative excursions. Knowing how important it is to gather ideas all the time, we work frequent jaunts into our schedule and let ourselves be inspired.

√ No rush hour traffic.

√ No fast food. Not only do we save money but eating healthy is easier when we have time to prepare good food.

√ A more balanced life. Smart self-bossers begin by figuring out what’s important to them and find ways to spend time on the top priorities which include not working too.

√ Lifelong learning. Having experienced jobs where continuous learning was not valued, we now design our own curriculum of formal and informal learning. 

√ Pet friendly office. Fluffy and Fido can be part of our staff.

√ Custom-tailored benefits. While we have familiar benefits like health insurance and vacation time, self-bossers might give themselves other benefits like weekly massages or exciting sabbaticals.

√ Constant personal growth. Our businesses call us to keep growing and discovering new talents and wisdom.

√ The coolest friends. Entrepreneurial souls tend to be fun and fascinating. Building a personal network of such friends is a joy.

√ No office politics.

√ Great tax deductions. Our tax system favors the very wealthy and self-bossers. 

√ No dress code. Whether you’re funky or conservative, your wardrobe won’t be decided by a memo.

√ A variety of work. We resist doing the same thing day in and day out and our businesses reflect our love of different activities.

√ Learn talent management. Self-discovery leads to finding our biggest assets and making the most of them.


√ Be a positive role model. When we follow our dreams, we set the best example for our kids and others who we don’t even know are taking inspiration from our lead.

√ Longevity. Yup, we’ll probably live longer and happier lives by honoring the promptings of our hearts.

√ Master crowd control. We can go to the movies on Tuesday afternoon or bank when there’s no line. Not only is this efficient, it eliminates a lot of stress.


√ Practical mental health. Do you think it’s healthier to spend time problem-solving or complaining? Entrepreneurship, by its very nature, enhances mental health.

√ Meet fascinating people. As our businesses take us out into the world, we begin to encounter new and interesting folks we’d have never met any other way.

√ Feed our adventurous spirit. What others call uncertainty, we see as a passport to a rich life that keeps our curiosity busy.

√ Learn personal responsibility. If our parents and schools didn’t teach us this vital lesson, our businesses certainly will.

√ Naps.

√ Unlimited financial potential.  We get to decide our money goals and create ways to reach them. What a lovely notion.

√ Harmony. Self-bossers are more likely to live in alignment with their deepest values.