WINNING PORTLAND? LOSE SOMEPLACE ELSE FIRST

Winning Portland, if you call it a win, is easy: grow a beard, wear plaid, work up an opinion on every beer you open.

If that sounds like a Portland dream, it is, but it doesn’t last.

Bikes, beer gardens, and weed shops are all good news from the outside looking in, but if those are the special features that bring you here, you won’t stick.

I’ve lived where it’s important to blend in, but couldn’t quite make the jump to permanent residency. That’s why winning Portland takes big city practice.

My first big city was Philadelphia. It’s strange to even think back to those days as a twenty year old in the Army expected to figure things out on my own.

Through the wisdom of military decisions, I’d gone from San Antonio, Texas to Fort Dix, New Jersey for a tryout on the All-Army wrestling team. After enough losing, the Army decided I’d be a better fit on a permanent temporary duty assignment.

A driver delivered me and my duffle bag of Army clothes from Dix to South Philadelphia, said good luck, and turned around.

I was still fuming from my performance on and off the mats during my tryout. It happens when you wash out, and it’s a great motivator to do better when you have the next chance.

Winning Philadelphia In 1975

After a few false starts I fell in with a bunch of locals who went to school together. Teachers, med school students, and older hippies were in my new circle.

I was the one with the hair high and tight.

One of the guys had started renovating a row house with the plan on living there while he worked on it, then moving to another, and building an empire.

Those people were educated and skilled and were winning Philadelphia in the time of Mayor Frank Rizzo.

They were my influencers and visionaries, but I wasn’t feeling it and returned to Oregon for continued education. Those guys were too smart and I needed to catch up.

But I must have had some kind of Philadelphia hangover in Eugene at the UofO.

Winning Brooklyn, New York, 1978

In Eugene I met a dynamo of a woman from Delaware, of all places. It’s a short drive to Philadelphia, but she and her family had more focus on the Big Apple.

I learned more about it after moving there.

I asked one of the older people why they lived where they did. It’s the sort of question asked by someone trying to find a place where they could feel like a winner.

Their answer: “We couldn’t imagine living any further from The City.”

“When is the last time you visited New York?”

“It’s been years, but the city vibe still reaches this far.”

With that in mind I made the jump to Brooklyn. I got dropped off at the local train station and showed up in mid-town Manhattan just in time for the regular subway rush hour.

If you’ve seen images of a guy strapped with a backpack, shoulder bags, and suitcases plowing through a thick crowd, then you saw my arrival.

Like Philadelphia, I had help and moral support. Also like Philly, I was a little burned up for losing ground far from home.

I didn’t stick.

Winning Portland, 1980

I left Brooklyn during an airline strike that raised ticket prices into the price gouging range; Greyhound still had it’s $100 ticket to anywhere deal.

Sooooo, I got off the bus in Old Town Portland, and my future. Just not the future anyone planned. I had help adjusting to Portland from a longtime resident.

She had opinions on Multmomah County vs Washington County.

We were driving around one day and she said, “Feel that bump. It’s a pothole. That means we’re in Washington County.”

She knew the lay of the land from the start.

We drove up and down Northwest Portland and I was shocked by the trees. It was May and it all looked bursting with life. It looked like a cleaned up Greenwich Village and I was immediately drawn.

After following my by now routine path of relationship fails, I moved to NW Portland near the intersection of 21st and Lovejoy to review what went wrong and what went right.

It wasn’t much of a mystery. In a combination of Peter Pan and failure to commit, I was a bad bet for long term relationships.

The over/under was around three months.

Winning Portland Northwest, 1981

The biggest moment of winning Portland moved into the neighborhood in 1981.

By then I had a better understanding of time and place. Through no fault of my own, I landed in the right place at the right time.

This new woman liked some of the same things I liked. We toured graveyards, walked to Old Town under the old Lovejoy ramp off the Broadway Bridge.

She bought a bike so we could ride together; we followed recipes from Moosewood Cookbook when we cooked together. It all felt so grown up, which is a feeling you look for if you need a win in life and love.

I heard the music, felt the warm breeze, and we got married five years later and been on a winning Portland streak ever since.

Winning Tigard, 2020

If you’re asking, and I’d be asking if I were you, what’s the point to a post like this? Who really gives good rip?

Let me tell you.

There’s a chance you’ve noticed a fair amount of uncertainty over the last year or so. Unparalleled uncertainty from the covid pandemic, to questioned election results, to learning how to cope.

My examples are for the coping part. Single people need a lift up. Young married people need to know they’re on the right track.

New parents deserve the reassurance that there is room for them and their baby in a changing world.

Most of all, those who are in the midst of deciding their futures together, and where it will take them, need to know there is hope, that the rest their lives will not be consumed with helplessly hoping.

Hit that link and sing along. Leave a comment only if you get a little misty.

Helplessly hoping her harlequin hovers nearby
Awaiting a word
Gasping at glimpses of gentle true spirit, he runs
Wishing he could fly
Only to trip at the sound of goodbye 

Wordlessly watching, he waits by the window and wonders
At the empty place inside
Heartlessly helping himself to her bad dreams, he worries
Did he hear a goodbye?
Or even hello? 

They are 1 person
They are 2 alone
They are 3 together
They are 4 each other 

Stand by the stairway, you’ll see something certain to tell you
Confusion has its cost
Love isn’t lying, it’s loose in a lady who lingers
Saying she is lost
And choking on hello