On Becoming Self-Employed

I’m trying to figure out where I fit in the employed — self-employed — unemployed landscape. Technically I’m still employed in that I will continue to have a paycheck for approximately three more months and I am still working on some “special projects” for my employer. However, it really feels as though I am unemployed, since I received the news (see previous post) that my position is being eliminated at the college.

As I write this I am working on plans to see if I can make a living being self-employed. I’ve been self-employed previously and I really believe that it feels more like being unemployed than employed. Not because you don’t work when you’re self-employed (usually, quite to the contrary), but because you do not have the security of the trappings that come along with those remaining good jobs that are out there – particularly those significant employer contributions to insurance and retirement costs as well as managing all that income tax crapola that requires special attention.

Although some of the advice is questionable, I am re-reading “Before You Quit Your Job” by R. Kiyosaki (you know, the Rich Dad guy) to get my mind around reviving my entrepreneurial spirit. More relevant to me have been several posts by Harold Jarche, including Freelancers Unite, Freelance Lessons, To be, or not to be a consultant, and So You Want to Be an E-learning Consultant.

I’m also faced with a bit of a dilemma. Although I would love to go down the entrepreneurial path, I do have concerns about my ability to put 3 kids through college in addition to all that other stuff like keeping a roof over their heads and food on their table. So I’m also sprucing up my job application materials with the thought of applying for several of the jobs that are recently posted or about to be posted around the region. Right now it feels like figuring out my next ten years is a bit of a full-time job itself.

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