Leaving Portland: Looming Regrets

Not sure I’m gonna make it to Saddle Mountain for the flowers this year. Might have to choose between that and Dog Mountain. I leave two weeks from Monday, and next week is my second Covid shot, and the week after that should be chaos, and pretty soon … yeah, I’m running out of time.

The list of people I’ve probably seen for the last time before I go is growing, too. Just said goodbye to two of them today, in fact. Some others might be coming by over the weekend, and if they don’t, well … see you in a year, maybe?

That’s not even to mention the ones I haven’t even reached out to.

I was gonna do all 60 hikes for the book, too — sixth time I have said that since I wrote the First Edition 21 years ago, and the sixth time I have failed to live up to it.

Definitely not gonna finish the photo scanning and family history research project. “Maybe in a year” on that one, too.

I was planning on at least a night or two of backpacking before I go, so I wouldn’t be re-learning everything in Wyoming. I could probably still get one night in, just to check the gear out. But I might not. Another case of setting a goal and then not meeting it.

And oh, yeah: work. We’re about a month from re-launching the business, and I think we were supposed to have the new website up (not done), new systems in place (ditto) and a new financial plan all set (no such luck.) I wonder why I didn’t start on that stuff earlier?

All I know is, at some point, about 17 days from right now, I will roll into a campsite on Day 1 of My New Life, having left so much of this one behind, along with so many people and possibilities and projects. The path into the future is paved with aspiration on a layer of regret. I want to apologize to everybody in town I didn’t see before I went, even the ones I haven’t seen in years, and the ones who haven’t reached out to me in all that time, either. I ball my fists at the frustration of things not getting done. I sigh at the idea of not seeing the flowers on Saddle or Dog until next May — or never again.

Part of me wants to stay up all night, every night, and on-task all day until I get everything just right: all the work done, all the people reached, all the trails hiked and the words written. Then I can go in peace.

Never works that way, does it? We just move forward, if we’re going to. We leave with our regrets and our disappointments, we hope people will understand, we believe the real relationships will last, we look for new dreams to dream, and we open ourselves to the new experiences.

I mean, what’s the alternative? For me, staying put just isn’t an option. Never led to long-term happiness, anyway. So I might as well go see the world, at least.

We think we might take the lessons of the past with us, but we also know that, when it comes time to leave the next place — and for some of us, it always comes time to leave — then we will do so with more regrets and disappointments, more tasks unfinished.

And then we’ll do what I’m about to do: Bow to the past, shrug, and lean into the future.