Portland is enjoying a smoky Indian Summer, and it’s a situation in which I truly wouldn’t mind being caught in the rain on my way home.
I’ve ducked out of the heat in the Side Street Bar- not-quite-dive off of Belmont. I’d intended to drop copies of my books off with a local secondhand bookstore. Apparently my knack for salesmanship doesn’t extended farther than pastry, so I figured by handing a few autographed copies over bookstores I could at least get a little marketing done for the cost of the books. This is Portland, after all- we love “local” everything, including authors.
Hiding from the sun isn’t my thing, even on a sweaty Sunday. As busy as the bake shop has been, I find myself “working for the weekend” and trying to get as much low-pressure living into 48 hours as possible. Sometimes that means going afield and exploring a new part of the city- sometimes it means going down the street to a pub where no one knows me, having a couple beers, and putting down a couple words.
Sometimes peace of mind looks like mountain-top retreats and hammocks on beaches, and sometimes it a couple cold pints in a bar playing classic blues on a hot day. It’s a matter of personality and perspective really.
I used to say that I got truly restless when I lost weight and suddenly had a lot more energy. I couldn’t just crash out on the couch all day- I HAD to go out. I had to see, to do, to walk, move and find. I also used to blame it on being a fan of Anthony Bourdain, but the time line doesn’t quite jive. Tony made me want to try, talk, travel, and tell stories- but I can’t blame him for my inability to just sit at home on a dull day anymore.
Where does the urge to go out and wander around come from? From the need to feel free, and the knowledge you can.

The idea of Freedom is an appropriately wild, amorphous thing. The word, of course, has a knack for taking one whatever meaning your political cult of a choice has chosen for it. The current most popular one is “the ability to do as you like without consequences.” Physics, psychology, logic, and mathematics would like a word.
For me personally, I think I’ve developed a notion of personal freedom meaning “the ability to do as I like based on the potential consequences.” Professionally, I’ve come to thinking that Freedom means I get to suffer the consequences I choose to, rather than those that others choose for me.
Freedom inevitably comes with consequences. It inevitably comes with responsibility. To think otherwise is ignorance and adolescence.
You can all enjoy the political kerfuffle from that statement, but from a professional standpoint, freedom means ownership of yourself, your decisions, and your consequences regardless of what they are.
“There is such a thing as terrible freedom.”
– Joseph Fink, “Alice Isn’t Dead” (podcast and novel)
When you decide you want to go off on your own in anything, you get a ton of freedom- and any mistake you make can only land in your lap. Move out of your parents house? You need to pay rent and look after your own space. Start a new business? Its success or failure is yours to deal with- as is whether either result is bad or good.
On an order of magnitude lesser scale, when I go out wandering on my days off or go on a trip, I’m free to do whatever- and whether or not its a good time is up to me. There’s a low-stakes kind of adventure in that. If I find a new place that sucks, well… that sucks. But I know there’s another place in town that sucks.
Alternatively, if I find a new place that turns out to be amazing, it’s like discovering a new artist or a buried treasure.
Maybe that’s what wanderlust is- when you crave freedom AND risk all at once. Entrepreneurship comes from the same thing, and it can be a hell of a drug.
After failing hard the first time, why else would I be trying again?
Stay Classy,
