The Buck Stops Here

I recently read an article on Forbes.com written by Jane Park called, “Are Entrepreneurs Really The Happiest People On Earth?” Smart lady. I too am often at a loss to respond to the inevitable statement, “Oh you are so lucky to be working for yourself.” Aside from grinning and politely swallowing my sarcasm, I’m stuck for an answer that wouldn’t require me pulling out my business plan and a whiteboard.

Recently a rather large bump in the road made me question why on earth I ever decided to plunge into the role. But as Jane laments, it rarely is a plunge. It’s a process that starts with a tickle in the back of your brain that won’t go away. It’s kind of like starting out on a really exciting road trip you’ve meticulously laid out and bumping into a whole bunch of detours. But if you just keep going (and don’t run out of gas), the destination can turn out to be awesome! Besides, turning back is an option that is no longer on the table. Going back would be admitting defeat…and I don’t like losing!

Sorry, I digress. The question I wanted to discuss was, “Why did I want to work for myself?” Truth be told, I never did – I was just thoroughly bored with what I was doing, and didn’t feel I was making a difference in this world. I finally asked myself the questions so eloquently expressed by Peggy Lee, “Is that all there is? If not now, when?” It occurred to me that I had spent my entire working career honing my much-praised skills at being the best darn assistant you could ever want to employ. WTF! If I put that much effort into making others successful, what was stopping me from doing it for myself? I came up with two really good reasons why not.

First, I had no idea what to do. This starts a whole new conversation about what would make me happy? What was I good at? Where would I start? What did I want to be when I grow up? And the kicker – what would bring me personal joy AND wealth? The wealth part was pretty important since divorce and raising kids on my own had succeeded in pretty much wiping out whatever savings I ever had.

The second answer was easy: fear. Fear of failure, fear of not being smart enough, having my customers – whoever they may be – knowing much more than me and finding out I was a pretender, a charlatan. Taking full responsibility for everything I did and not being able to point my finger and saying, “I’m just the hired help! Blame him.”

Why couldn’t I be happy like most everyone else I knew? Work for the man, collect my pay cheque, take my annual vacation, save my money for retirement and in the end, be given a nice fat buyout package when the company was ready to unload me for someone half my age and half my salary. What the heck was wrong with me? And if not me, what was wrong with everyone else?

I believe that the little grey cells of entrepreneurs have issues. Jane calls it a mental illness. I’m inclined to agree. Be happy with what you have, don’t make waves, relax and be content. I could just never get it right. I can’t speak for others but I seem to take some masochistic pleasure in making waves, questioning authority, being outraged by injustice, and pushing the envelope. I have on many occasions heard that rational voice in my head say, “Wendy don’t say it! Don’t say it!” And then, POP, out it comes followed by a, “Damn, I told you not to say it!”

As I continue down my path towards my ultimate goal, you know, the joy and wealth thing, I’ll keep you posted as to how it’s going. I have to say that once I settled on what really gets my heart pumping, being self-employed really does have its blissful days. You get to hang with people that are interesting, smart, funny and respect your expertise and what you are offering them. You really are making a difference in their lives and this gratification alone makes it all worthwhile.

As one of my favorite movie lines opines, “Everything will be all right in the end. If it’s not all right, then it’s not the end.”

Tomorrow just may be the day when this leap of faith pays off.