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Itching to be your own boss? Examine your motives first

Lead Yourself First! Breakthrough Strategies to Live the Life You Want by Michelle Ray.

Red Carpet Publications

Excerpted from the book Lead Yourself First! Breakthrough Strategies to Live the Life You Want by Michelle Ray. Copyright © 2013. Reprinted with permission of Red Carpet Publications.

When deciding whether self-employment is right for you, it is important to understand the challenges associated with being your own boss. We've all heard sayings like "the only place where success comes before work is in the dictionary." Although it is an overused cliché, the fact remains that many small businesses and solopreneurs fail because they mistakenly believe that self-employment provides a glamorous lifestyle. In my experience, nothing could be further from the truth.

Working in my family's retail business as a teenager certainly opened my eyes to the meaning of hard work. I watched my parents endure the trials and tribulations of staffing issues, robberies, days where there were no customers, several recessions, and, ultimately, liquidating their business to stave off bankruptcy.

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But that experience alone wasn't enough to prepare me for my own journey. While I gained invaluable insight into business operations, merchandising, selling, customer service, and employee/management challenges, having entrepreneurial roots did not give me the rite of passage to financial freedom. It took considerable time for me to see my business as an enterprise.

My first step to self-employment was values-based: the primary motivator was lack of fulfillment. I could have remained gainfully employed if I wanted to merely survive and make enough money to pay my rent and living expenses. But I wanted more. My decision to start my first speaking business was based primarily on lifestyle considerations, coupled with the belief that if it were a truly viable enterprise that allowed me to do what I loved, it could afford me a way of life that would be immensely gratifying. At the core, I believed in myself enough to take the risk.

If you are contemplating leaving your job or starting a new venture, your capacity to be brutally honest regarding your expectations is a good place to start. The first step requires honing an unfamiliar kind of mental toughness that will force you to personally dig deep and assess your own reality. Do you feel resentment about your current situation? How is that resentment playing out in your partnership, your family, your life? You have to be willing and ready to do this for yourself; you have to let go of fear, step into the unknown, and be prepared for all the bumps along the way.


When it comes to making choices such as pursuing a new vocation or business, your most important asset is mindfulness. It is all about practicing"Me" management – being able to effectively manage yourself. The process begins by connecting with what truly feels right to you. Can you discern your own truth and are you able to follow through on your own values and beliefs by putting them into action, rather than rhetoric?

There were many lessons that I learned in the early years of being an independent contractor. When I first started out, there was one client who gave me a lot of work. I was so excited to have that kind of stability. But then, I began to realize that there was an expectation that my calendar was an open book and therefore I could be called, at a moment's notice, to work for however many days the contract required. In fact, it was indeed an "open" contract, which meant that although there were no guarantees regarding how much work I would be given, the assumption was that I was available for my contractor and no one else.

I became attached to their value system and made myself completely available to them. The more I continued to say "yes," the more I sacrificed opportunities for new work with other prospective clients in order to grow my business. This played havoc with my own personal time because I found it difficult to turn work down.

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I realized that I was attached to what is called a "scarcity mindset." I so desperately wanted to be a successful solopreneur that I made myself completely available to this one client at the expense of all else. Unfortunately, I did not understand this concept or the degree to which I had allowed this to be my code for living over a considerable period of time.

Dr. Stephen R. Covey, author of The Seven Habits of Highly Effective People wrote: "People with a scarcity mentality tend to see everything in terms of win-lose. There is only so much; and if someone else has it, that means there will be less for me. The more principle-centered we become, the more we develop an abundance mentality, the more we are genuinely happy for the successes, well-being, achievements and good fortune of other people. We believe their success adds to . . . rather than detracts from . . . our lives."

Many of us buy into what is perceived as "the norm": job = security; money = happiness; title = success. As a result, we experience an inner conflict as the real "me" is trying to find the way. Experience is truly the greatest teacher. As an independent contractor, my first client afforded me a deeper, richer learning – developing an inner-knowing around my own work habits and life priorities. As a result, I was able to define the core values that remain central to my business and personal life and, more significantly, to give them meaningful application.

If you are truly considering embarking on becoming an independent contractor and joining the self-employment world, it is important to examine your motives behind doing so and making sure that you understand the realities of this lifestyle. In order to succeed, you need to be ready for the thrill of the ride – it is sometimes exhilarating and sometimes terrifying. Make sure that you are flexible enough to change course if your plans don't quite work out. And always be mindful of your values.

The more clarity you gain around your values and beliefs, the more effective "me" management becomes and the happier you will be with your new boss – YOU !

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