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First of all, let’s start with a few reasons why I may not be considered unemployable.

  • Let’s face it, it’s hard to call yourself unemployable when you’ve had a successful career based on a traditional (sort of) education.
  • I’ve spent the past 28 years working as a teacher, school administrator, and technology coordinator, all in the public school system.

My current career is an investment that has awarded me a lifetime MRR that is very adequate to live a modest life till I die (talk about true passive income). Everything else I earn now is gravy.  Also, I have had the opportunity to live a great lifestyle with my wife (of 31 years), have a nice house, raise 2 fantastic kids, and still get every summer and all of the holidays off from work.  We travel (before the pandemic), and don’t really need any necessities in life.

A big reason why I never left this world is the fear of the unknown. I like having a steady paycheque, a pension for life, medical and dental coverage, and the assurance that it would all be there for as long as I continue working.  I do a good job, and I have no real fear of losing it. That makes for stability.

So, why would I consider myself unemployable?

I’ve been fortunate to be able to do my job, and have quite a bit of freedom during my workday. I still need to get a lot of trivial things done, and a fair amount of what I do is dictated by powers above me. Sometimes this makes for the feeling of being trapped.

But, being in middle-level educational administration does award me a fair bit of freedom.  I have a passion for technology in education, and I have taken every opportunity to use this passion to build skills that I can use in my school and my classroom.

Coincidently, these skills have quite a bit of value in the freelance marketplace.  Although I have never really explored any big paydays from freelance, I have used my skills to help out local businesses and organizations when they need to establish a web presence.

As I wind down my current career and think about retirement, a couple of things pop into my mind.

  1. I can’t sit back and do nothing. I have an insatiable urge to create things and look for business possibilities.
  2. I want to earn the extra money that will allow me to do more than just live an adequate life.
  3. I’m too young to really retire. What would I do for the next 40 years?
  4. I don’t know if I can go to work for someone else.  I want the freedom to do my own thing.

I feel unemployable.