Cyberhobo as Weekday Warrior

October 25, 2008 in Weekday Warrior

My outdoor values were being heavily suppressed when I lost my fashionable dot com software engineering job in 2001. I bravely set out on my own as a freelance developer. This allowed me more and more outdoor time as my contracts shriveled up along with the tech sector economy. I didn’t think of it as such, but this was my first attempt at being a Weekday Warrior. I took long mountain bike rides into the Denver front range in between short bouts of intensive coding. When I could no longer afford rent, I created a web site at, likening myself to a depression-era traveling worker whose profession happened to be software engineering.

It was not yet my time. I managed some traveling, but was mostly supported by my family along the way. Eventually I found myself lurking at my dad’s house, in limbo, unable to find work. When a job as a government contractor came my way, I returned to life as a Weekend Warrior, and not for the last time. My outdoor values continued to grow, though, and I never stopped updating my cyberhobo web site.

I’m now four months into another attempt at establishing myself as a Weekday Warrior. I’m freelancing again, and have a growing base of good clients. I choose my hours, and spend a respectable of amount of high-quality time outdoors. But I’m not yet making a living. My wife is currently a Weekend Warrior. As fortune would have it, she’s found the best full time job of her life here in Santa Fe, New Mexico. We find ourselves in a mixed marriage of sorts, uncertain which way to proceed. We are certain of the importance of the outdoors in our life, and our intention to keep pursuing it.

So even though I’m not yet a self-reliant Weekday Warrior, I have taken note of a couple of tactics that helped me get this far.

  • Establish a network through free labor. Independent, part-time workers all need some kind of network of clients or customers. I attempted a few entrepreneurial projects, and the one that ended up bringing me clients is an open-source product that I developed myself and make freely available to anyone. This is an old pattern of “paying your dues”, but I really had to see it work to believe it.
  • Be persistent. Some of my projects failed. Many ideas came and went. I had to keep my day job longer than I hoped. I got tired, and often felt I was making no progress. I still feel that way sometimes. But whenever I feel the least bit inspired, I plug away at whatever project seems to hold the most promise at the time.
  • Seek renewal outdoors. I can’t quite force it to happen, but sometimes I return from the outdoors completely refreshed and ready for anything. The more I go out, the more reliable a source of energy and vitality it is.

These are some of my lessons learned so far. My greatest liability is probably my tendency toward social isolation. The more people I can meet that share my values, the more opportunities I’ll have. I hope to meet Weekday Warriors more successful than I, and get them to share their secrets with us here…

1 response to Cyberhobo as Weekday Warrior

  1. I can totally relate to this article. I am also trying to find a good balance between getting outside and affording a living, and I can’t agree with you more on “be persistent.”

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