Breaking Free from Employment

When I first heard Elvis's voice I just knew that I wasn't going to work for anybody and nobody was gonna be my boss. Hearing him for the first time was like busting out of jail.
~ Bob Dylan

How did you decide to become self-employed? Did you grow up in a family of entrepreneurs or did a dramatic event occur that turned you in another professional direction?

My moment happened last April.

I had worked for four and a half years at a small business and loved it, despite having some severely unhealthy dynamics at play in the office. The work engaged my creativity, challenged me, and provided unending variety and nourishing interactions with customers and vendors. It also brought me a great deal of satisfying achievement: in three short years as sales manager, and then operations manager, I doubled the company's sales.

Record-breaking month after record-breaking month, I watched my boss, the owner, grow more and more wealthy.

"Hmmm..." I thought, "I've been doing sales and marketing for more than a decade and everywhere I go, I make other people lots of money. What's wrong with this picture?" It became clear to me that if I wanted to be the one who benefitted from my talents, I'd have to be making much better commissions or be the person who ultimately owned the whole organization.

I spoke to my boss about her plans for passing on ownership of the company and she assured me that she wanted to sell it to me. In 5-10 years.

No good.

So I began looking into other businesses to buy and applying for commission-based sales jobs. Finally, after nearly a year of searching, I found a sales position I was excited to try. I gave notice to the boss and mentioned in my letter of resignation that I'd appreciate her keeping me in mind when she was ready to sell the company.

"I'm ready now," she said. "Let's do it. I really want you to have it."

We had our attorneys draft terms and I hired a team of advisors to investigate the legal and financial issues of the company. I withdrew from the sales job, explaining the surprising turn of events to the new company. Then, for two and a half months, I performed due diligence: getting the company's first ever accurate inventory count; reviewing the tax records and month-by-month financials; creating balance sheets, P&Ls, and pro forma cash flow projections for the next five years. I wrote a business plan, met with representatives from the SBA, and obtained two independent valuations on the company. I rounded up money—more than I ever thought I could ever get. With bank approval and the nod from my attorney and advisors, I made her a cash offer for what the SBA and my accountant had concurred was the full value of the company.

In the end, negotiations failed. The deal was off and I was out of a job. I picked up the phone to call the sales manager at the new company who had hired me, confident that she would still take me on if I asked.

But I couldn't do it.

I realized, with my hand on the phone, that I absolutely, undeniably never, ever wanted to work for another person again. The process of crafting my business plan and securing a large sum of money, being coached by advisors and encouraged by mentors...it all changed me. I had greater understanding of what others could do for me, and most importantly, what I could do for myself. And to be that close to holding it all in my hands...I couldn't walk away and not have it. I had to try again.

That was my moment.

What was yours?