Troubadour Strategies

I am about to embark on a summer tour of several places throughout the Pacific Northwest.

That got me thinking:

What does it mean to be a modern troubadour?

I think it means at least five things.

First, they write and perform original songs.

Second, those songs carry a message. That message might come in the form of a lengthy narrative such as “Visions of Johanna” by Bob Dylan or “The Wreck of the Edmund Fitzgerald” by Gordon Lightfoot. Or it might arrive in a more concise and accessible form like Joni Mitchell’s “Coyote” or “Luckenbach, Texas” as performed by Waylon Jennings and Willie Nelson. It doesn’t have to be heavy or intellectual, but it should connect with people and evoke something real.

Third, they wander. They travel. They are, in a sense, real-life rolling stones.

Fourth, they can perform alone. Many are singer-songwriters by necessity. But they also play with others when the opportunity arises. Whether it’s a small listening room, a coffee shop, a bar, a theater, or an arena, a stage is a stage.

And fifth, they are fiercely independent. They tend to live at least somewhat outside the mainstream, both in their lifestyles and in their philosophies.

When I look at that list, my reaction is simple:

Sign me up.

But there is one part that keeps grabbing my attention.

The traveling.

As I’ve mentioned in several recent posts, I’ve been thinking a lot about place lately while making my way from the Southeast back to the Pacific Northwest.

But, this is not a new question for me at all.

I remember taking a business writing course during college and creating a final project devoted entirely to deciding where I should live after graduation. I developed a fairly sophisticated analytical framework and compared cities against one another.

The finalists were Albuquerque and Seattle.

The winner?

Albuquerque.

And where did I eventually end up?

The Pacific Northwest, with a brief stay in Seattle proper along the way.

So much for analytical decision-making methods.

But the larger realization I had yesterday is that I have always been something of a rolling stone.

And for a long time, I was embarrassed by that.

Let me explain.

I started college at the local junior college and spent three years theoretically attending full-time. At the end of those three years, I had accumulated only about thirty credit hours and a GPA somewhere around 2.3.

A truly stellar performance.

Eventually, one of my friends talked some sense into me and convinced me to transfer to his college and become his roommate.

The result?

Fifteen credit hours completed.
A 3.7 GPA for the semester.
My first job as a waiter.
The discovery that tips were wonderful.
A path that later led to bartending, which I absolutely loved.

Then our rental house burned down and I lost nearly everything I owned.

Fortunately, we had already committed to participating in an exchange student program in Massachusetts that spring. We were attending school in Oklahoma at the time, so off we went.

That year changed my life.

Not only did I do the exchange in MASSACHUSETTS, but I spent the summer working a seasonal job in South Dakota.

After that, I transferred again and attended the University of South Dakota, partly because my roommate’s father happened to be the Dean of the Business School there.

I could keep going, because the pattern continued. But you get the idea.

Looking back, much of my life until around 2010 was a series of major moves every six months to two years.

For years, I felt Embarassed about all that movement.

I felt behind. Unsettled. Less established than other people.

I was also a couple years older than many traditional students, which seemed like a very big deal at the time.

Now that I’m older, I laugh at the fact that two or three years ever seemed significant.

But the more I thought about it yesterday, the more I realized something.

This longing for rootedness has often felt less like an authentic desire and more like a “should.”

I should settle down.
I should stay put.
I should feel attached to one place.
I should belong to a particular community.

And yet, when I look at the actual evidence of my life, a different story emerges.

Even though I have owned my current home for more than twenty years, I have never been particularly happy spending all my time there.

I have never become deeply integrated into the local community.

I routinely create reasons to leave for extended periods.

And now I find myself designing a life that intentionally includes regular travel, touring, exploration, and movement.

In other words, maybe I have been trying to fit myself into a story that was never really mine.

That doesn’t mean I don’t value rootedness.

I do.

But perhaps my version of rootedness looks different.

Perhaps it is not rooted in a single place.

Perhaps it is rooted in a calling.

Or in a creative practice.

Or in a set of values that travel with me wherever I happen to be.

I’m not entirely sure yet.

But I do know this:

Part of the discomfort I have felt around place comes from carrying a little shame about all the moving, wandering, and place-hopping I have done throughout my life.

And when I notice shame attached to something that has repeatedly brought me energy and meaning, that usually tells me there is something worth examining more closely.

So I think it may be time to rethink my relationship with place.

I don’t know exactly where that realization will lead.

But it feels important.

And as always, I’ll continue exploring it here on the Highway to Yeah.