My wife and I live in New Jersey, in a nice location that we both like. We have friends that we love and jobs that we enjoy. We do volunteer work that makes us happy and is very fulfilling.
But we're sick of New Jersey weather -- and traffic, but mostly it's the weather. The summertime heat and humidity is insane, and seemingly getting worse. It's becoming spring and fall heat and humidity, and it's preventing us from doing all the fun outdoor things we like to do. I feel like we live in Florida -- albeit without Florida Man, but still... Florida. Fuck. Florida is one of five states that I have never visited and it's the only one I don't want to visit.
Plus, last year we got enchanted with a whole other place: Bend, Oregon. Bend is a high-desert town on the eastern edge of the Cascade mountains. Most of what you think of as "shitty, gloomy Portland rain" falls on the western side of said mountains. The eastern side is relatively dry. Unlike Portland -- where, literally, the suicide rate is higher because of the weather -- Bend gets a lot of days of sunshine per year (they will tell you 300, which strikes me as a bit hyperbolic, but, still, it's pretty great whatever the real number is). Bend is just big enough to have a lot going on, and still small enough that it's not overrun. It's one of those magical freaking locations where you really can be at Whole Foods one minute, or drinking a delicious whiskey in a delicious-whiskey bar, or eating at a hipster restaurant that would make Philly proud, and hiking a mountain fifteen minutes later. (Not that I advise hiking after whiskey consumption). It has all the standard conveniences of Everywheretown, America -- you know Costco, etc. -- but with nature right next door, and all around. Did I mention the weather is awesome? Did I mention the humidity is low? Did I mention how completely fucking sick of humidity I am? Oh yeah, and even on the uber-practical end of things, the housing prices are similar to where we live now; it'd be close to a swap situation, monetarily.
But Oregon is a long way away from New Jersey. We don't know anyone near Bend. Moving there requires a leap of faith in our ability -- at about age 60 when I think we'd make the retirement-based jump -- to make new friends in a very new place.
Moving so far away scares the crap out of me (perhaps unreasonably) from a loneliness perspective. However, my wife and I are pretty social creatures, prone to volunteering and joining fun activities and groups. So we really ought to be good. There'll just be a weird transition when we will be leaning on each other pretty hard when we first arrive in town.
But when I really think about it, assuming that we are both in good health five or six years from now (when this plan would be taking effect), just living out our days in this flat humidity-choked rain forest of a mid-Atlantic state is the most depressing thought of all. There's also something that the Butthole Surfers taught us years ago: "It's better to regret something you have done than to regret something you haven't done." (Yeah, I know... it's not always true, but work with me here).
And believe me when I say that I am haunted by the fact that either form of regret is possible. But there's a difference: if we don't make the move, the "haven't done" one will always be there, like a nagging finger poking me in the side until I die that says, "You know you love the mountain west. What the fuck are you doing staying out east your WHOLE FREAKING LIFE?" On the other hand the "something you have done" regret? If this is a good move, it may never show up at all.
If this were anyone else facing this type of question, I know what my advice would be. Now all I have to do is follow it myself.