Thoughts on the Second Career

As I noted the other day, I expect posting frequency on the blog to go up soon. About this time last year I started serious planning on my “what’s next?” project — that being my long-term look at how I want to make the shift into the second career. I see a time where I’m not going to want to work in Silicon Valley and hack high tech 24×7 (gasp), but I certainly have no plans on retiring.

The elevator speech: I want to earn a respectable income from my home office in Astoria, Oregon without telecommuting.

Yes, you could potentially contract and consult from there (although if I were going to do that game, I’d do it from Ashland or Medford — like, it sometimes seems, half the population of those towns) but that’s not the point. At some point, I know I want to get out of the Silicon Valley rat race and do something else. The question is — what?

I want to emphasize something: this is a long term (3-5 years) thing; in fact for about the last 15 years I’ve been keeping (with more or less intensity) a 3-5 year plan. That’s the first lesson in something like this: planning is good, because it helps you map a path, but it should also be flexible because as you do the planning, you’ll change your mind, new situations come up, the unexpected happens. For me, the planning on the second career wasn’t so much about implementation, but on understanding where I wanted to end up and to influence decisions now that will make it happen someday. And occasionally, after a really bad day at the office, as a way to keep my sense of humor and sanity. Well, okay. My sense of humor.

Now, the day for that second career is closer. I’ve known for a few years roughly what I wanted to aim at here. Various decisions I’ve made over the last couple of years have been driven by this long-term planning. My move of the blog from Typepad back here to was because I knew I wanted total control over my online environment, and I wanted it under my own domain name for branding purposes. I chose WordPress because I really like that tool as a platform for it’s flexibility and the community ecosystem that exists around it (my second choice, even thought I’ve occasionally described it as sportfishing off of an aircraft carrier, is Drupal, and the drupal community has done a really nice job of cleaning up issues that bothered me back when they couldn’t even run the Drupal site on the Drupal 6 release).

Another decision I made was shutting down the “Two for Elbowing” blog on hockey and de-emphasizing my hockey writing. I did that for a few reasons; originally, that blog was supposed to be for both myself and Laurie to write about hockey (“two for… get it? heh. heh.). Laurie’s life took her in other directions and it turned into a solo gig (although the hockey world is missing out on a damn good hockey geek, and I’m not talking about me); as a solo, I much preferred putting all of my writing into one place (the branding thing) again. Also, think about my long-term goal: moving to Astoria. Building an income around writing about hockey and the Sharks and moving to Astoria conflict. Just a bit. Besides, there are plenty of good hockey writers out there now, and if I was 25 (instead of 50+), I might take a run at doing something like what Rich Hammond is doing with the Kings. Instead, I made a decision to enjoy hockey, not sweat about what to write about it — and I only write when I want to. This is a feature, not a bug.

I’m firmly convinced that what Hammond and the Kings are doing is the future model for journalism in pro sports as the newspaper business continues to evolve and implode. NHL teams that haven’t figured this out yet should take a close look and find a good beat guy to bring on board and nurture. The Sharks could do a lot worse than hiring Dave Pollak and bringing him in-house, for instance. Having been writing about hockey online since before the Sharks existed, I do sometimes wish that the online environment that exists today had existed 15 years ago, but it didn’t. Sometimes timing is everything, and understanding that is a key aspect of designing success into your plans.

To succeed in ANY career path, not just a second career, it’s important to know what NOT to do, what not to sidetrack yourself on, what not to invest time and money in. That may be even more important than knowing what to do, in fact, because that’s how you stay focused and moving in the direction you want to end up.

In any event, this is the first in a series of articles on the idea of a second career and my thoughts and plans. I’m hoping this becomes a conversation, not a lecture; I’m doing this in public both because I hope you find it interesting and learn from it to help refine your own plans and ideas — and because I hope you will help me improve my own ideas and fix the flaws in my thinking and make my own second career success happen as well. I hope you find this interesting and useful; I know I’ll learn from your feedback and comments and end up the better for it. Together, everyone wins — and how can that be bad?

So, onward. The future starts today.


Footnote on Astoria: For those not familiar with Astoria, it’s about 2 hours from Portland on the coast, and it’s a very nice, small, homey town, but has some really nice places like the restaurant Baked Alaska and Cellar on 10th that make it more than a small rural town — and it’s well located to a lot of great photographic opportunities). It might not be Astoria (I’m really falling more and more in like with Morro Bay, for instance, and I love the northern Oregon Coast so it could be anywhere from Astoria to Newport…), but that’s a nice placeholder for what I’d like to do.

Small, inviting, not urban, on the coast, lower cost of living but with some nice amenties and close to civilization when I want it. The kind of place most Silicon Valley Geeks seem to wish they lived, unless they’re the hard core urban type. I’m not, but Vancouver tempts me to convert…