The Working Sabbatical

3 minute read

Well, it must be official, I’ve told my parents. I’m effectively on a sabbatical, the nature of which hasn’t completely been defined but the purpose of which is to find something I can wake up every single morning and not hate. Perhaps the bar is set too low. Actually, the purpose is to expand my abilities in both code and words over the course of the next 4 months. The genesis of the sabbatical came about on a random Monday at the library when I realized that some day, if I continued on my current path, I was going to wake up having done nothing I really enjoyed for the large part of my working life.

This happened about 2 months ago and over the following 6 weeks, I formulated a plan for the exploration process of my future career(s). That plan is twofold. The first part of it is to concentrate on my writing. My writing has largely languished in recent years and certainly could be considered no better than sporadic. I am also getting back into writing fiction where “getting back” equates to the years since high school. For most of my life, people have told me that I was a good writer and somewhere along the way, it actually sunk in that maybe that was true. I don’t want to wake up one day and wonder what I might have been able to produce. I have always enjoyed writing but I have not been dedicated to my writing. I’m looking forward to developing that dedication and hopefully a sense of craft as well.

The second part of the plan is to dive deeply into Ruby and Rails by building an admittedly ambitious website to help me manage all my semi-illicit gambling pools from one location. I realized when I started learning Ruby and Rails that I had no interest in doing Microsoft development any more, at least not as the means of my living. That is not to say I won’t ever again. If I’m being honest, I’d give this little exploration process about a 20% chance of success so it’s not out of the question that I return to the corporate world. But for now, I’m diving deeper into the Ruby world starting with a website at (which currently just redirects here) and following with the previously mentioned project. This is an ambitious undertaking but one that I’d really love to tackle for a variety of reasons, not the least of which is how much time it takes me every year managing my office pools. I want to build it in Ruby and Rails because the philosophy of that community seems to more closely mirror my own.

So I’m jobless. Though I prefer to call it self-employed, not that there is any chance of money coming in over the next month or so, it just sounds better. I’ll be posting here in some regularity I expect, including a weekly update on progress. I think there has to be some accountability even if it’s just to myself or it will be too easy to have the four months quickly disappear with little to show. So the published goals for this week are to have in showable state, a story completed in rough draft and a blog post per day written either here or on my sports blog, You Need More Sports. The anonymous Internet will be my product owner and I expect him (her?) to hold me accountable.

Those with long memories will remember that I’ve done this once. In late 2007, I quit a perfectly good job and took 2 months off. That was more of a true sabbatical with few plans other than to take 2 months off and then find a job. There is no job plan at the end of this tunnel. This is a journey of self-discovery and learning, one that I hope leads to an entirely different viewpoint if not career.

For those of you who have always said I was a good writer and/or a good developer, thanks. You said it enough that I began to believe it. I couldn’t have possibly had the courage to do this without that support. Of course, if this fails, it will be all your fault.