This is a blog post that I'd much prefer not having to write, but I've learned some lessons that could be very helpful to others. I'll first describe what I did, and then, what I should have done.
In late January of this year, I ended a multi-year consulting project. Much of my role in the project was done in the fall of 2013, and to be fair, I was expecting my client to end my contract as early as October. They were a great client to work with, but I had been thinking about what my next move would be for more than a year. I worked almost my entire career on the West Coast, and I really wanted to get back there if I could. Given the cost of living in Silicon Valley, I decided to look at Portland as the place to move; I started my career working for HP in Corvallis, Oregon, 90 miles south of Portland.
When my project ended in January, I had a lot of money set aside to pay income taxes; more than enough to pay for the move and several months of rent and utilities. However, I decided that it would be very risky for me to pick up and move to Portland without having a job lined up. In addition, I was convinced that I could find a new job or project in the Chicago area within a month or two. So, I stayed here, applied to jobs and took calls from recruiters. Unfortunately, from February to today, I've had exactly one job opening that resulted in onsite interviews, and the client ended up hiring none of the candidates, including me. I burned through the tax money to the point that it was insufficient to pay for a move, so I was stuck here. I ended up selling some of my belongings, and then my car, in a last-ditch attempt to move, but that fell through.
Now, I've got three job prospects, two in the Chicago area and one on the West Coast, and I'm hoping that one of them turns into a real job. I've also been working on a crowdfunded Internet of Things project since May. However, in hindsight, when my project ended in late January, I should have immediately booked a flight to Portland to find an apartment, and then moved. Moving without a firm job offer or contract in hand seemed like the much riskier option at the time, but in reality it would have been no worse than the situation I'm in right now. In fact, given that Portland has a far superior public transit system than the far northwest suburb of Chicago in which I live, it would have been better because there's an excellent chance that I could have sold my car if I'd needed to without having to buy a replacement.
The lesson is that you should look at the worst-case scenario for all the options available to you, not just what you believe to be the most likely scenario. In my case, I compared the worst-case for Portland with the most likely case for Chicago. If I had compared the worst-case for both locations, I would have moved immediately. Given my background and experience, I have a much better fit with the companies and markets along the West Coast than I do with Chicago. I could have lived in Portland and either worked full-time for a technology company there or consulted for firms from Seattle to San Diego.
Staying in Chicago, which I believed to be less risky, turned out to be the much riskier option. I made the mistake because I didn't judge both risks equally. Keep that in mind when you're making a major business or personal decision.