The question everyone always asks almost immediately when you first meet them is “What do you do?” or “Where do you work?”. After this, I often try to deflect the conversation to something else – or try to make a silly comment to the effect of “I’m Unemployed”. Sometimes, when I’m pressed, I will admit that I’m Self Employed or that I own my business. I have pondered this more than once though; why is it so hard to say I’m self-employed?

Some context here. Calwell has existed in some form or another for ten years now. Some of the first work I did for clients related to the Year 2000 bug that had everyone freaked out (for the record, I didn’t expect a problem). Many companies had earned a great deal of money from all the fear and uncertainty surrounding the year 2000 and here I was starting out at the end of all this. I have never been known to take the easy path.

Hard was exactly how things were. I would live in a family member’s garage for the first year while I worked to find enough clients to support myself. When you start a company with no investment – you’re probably creating allot more work than you expected. After a few years the work would pay off for Calwell as much of the development work be put into production and Calwell’s client list would grow.

Clearly, I’ve paid my dues. So, why is it so hard to say “Self Employed”? I have thought that the words are just hard to say. They don’t exactly roll of your tongue. Try it – say those two words in a conversation and see if it doesn’t just halt with a sweeping THUD. You don’t exactly have your choice of pronouns here either – “I’m self-employed” sounds just as crappy with or without needing to add ownership. Maybe there is a better way to say it? Something cooler like “Freelancing! I love it” or “I do network engineering consulting services”. That last one sounds like I’m a rocket scientist.

The other word, one that I have never uttered, is the “E” word. To call myself an Entrepreneur would be overstating what I do on a fundamental level. While I may be the very definition of an entrepreneur based on assuming ALL of the risks:

Wikipedia: An entrepreneur is a person who has possession of a new enterprise, venture or idea and assumes significant accountability for the inherent risks and the outcome.

Calwell is not new, and nor is it much of an idea. More than those things though; I tend to see Entrepreneurs as “Business Engineers”. These are the guys that are creating businesses and designing businesses from nothing. In my case, I’m more of a “Keep a business from dying” kind of guy. There are parts of a certain spirit that defines me as an entrepreneur, I would never define myself as one.

What is it then? Is this some sort of psychological defect (I’m sure some would say I have many!) that keeps me from proudly proclaiming what I have rightfully earned? Could I have a problem accepting that I have created a business with my sweat and kept it operating for more than ten years? Could there be a mental roadblock that, for some reason, keeps me humble and modest right to the last-minute? There must be this auto-humble translator in my head that keeps me from owning “self-employed”.

Psychologically, there may be another reason for not wanting to be so proud of my business ownership. Most souls out there tend to be in a 9 to 5 job that they may not exactly love. For me to stand up and proclaim my self employ-edness in front of them may come off as slightly arrogant, condescending and rude. I would rather not.

I urge you to submit some ideas here; Continue the conversation. Is there a cooler, more hip way of telling others that you work for yourself? For the self-employed among you – are you finding it difficult to tell others about your personal independence?