Springsteen caught me on the way to work


Hello Reader,

Welcome to the conversation.

I was driving to work last week with a Spotify playlist on shuffle when Bruce Springsteen's "Glory Days" came on.

In the first verse, Bruce runs into an old friend from high school, a guy who used to be the star pitcher. They grab a drink at a bar, and all his friend can talk about is back then. The best part of his life already happened, and he's still sitting in it.

It struck me as so sad. We all know someone like that. Sometimes they show up at reunions. Sometimes they show up at Thanksgiving.

And then I noticed I've been doing my own version.

When I moved to Georgia, I took a role that's a step back from where I've been, on purpose, while I figure out what's next. Most days I'm genuinely OK with it. But lately I've caught myself replaying my corporate years with a soft focus filter: the title, the paycheck, the team, the freedom to set my own direction. What the filter leaves out is how dead I felt inside for a lot of it.

“
Well, the time slips away...
Leaves you with nothing, mister, but boring stories of...glory days.
— Bruce Springsteen

From My Chair to Yours

When I sat with that, I noticed I wasn't really missing the job. I was missing two things it gave me.

The first is certainty. For most of my career, I knew what the next rung looked like and how success would be measured. Now I'm in the Messy Middle of figuring out what my coaching work wants to become, and some days the not-knowing weighs more than I expected. Certainty is easy to romanticize when you don't have it.

The second is freedom. As a self-employed coach, and before that as the leader of an organization, I decided how my days went. Now someone else sets my schedule. I chose this season deliberately, and I still feel what it costs me.

Both are true. I'm OK where I am, and I'm homesick for a few things I used to have.

The longing has something to say. When I catch myself reaching for the glory days, I've started asking what exactly I'm homesick for. Naming certainty and freedom gave the longing somewhere to go. Now I can look for small ways to bring a little of each into the life I have.

The Lens

Glory days thinking is tricky because it can sound like wisdom. "I had my time." "Those were the best years." It passes for acceptance, even gratitude. That's what makes it a form of Deflation. It feels like perspective while quietly concluding that the good part is over.

Remembering a season fondly can be a gift. The trouble starts when the past becomes a destination, a place we keep returning to rather than a source of information.

As a messenger, nostalgia points forward. It tells us we had something then that mattered, and we may need more of it now. Maybe it's freedom, or belonging, or the feeling of being good at something. That gives the longing a job.

As a destination, it pulls us backward. Hold on tightly enough to how things were, and the present starts to feel like a consolation prize. That's the trapdoor into Defeat.

The Messy Middle makes this especially easy to slip into. When the road ahead is unclear, the road behind looks well lit.

So the question I keep returning to is one I'll offer you too: what would need to be true for your best years to be now, in this season, with what you have?

Reflection

  • This week, I invite you to name 10 things in your current life that you love. They can be as big or as small as they come. One of them might be "I'm reading Joanna's newsletter." (I'll take it.) Let whatever shows up, show up.
  • If 10 feels like a stretch, notice that too, gently.
  • And if you catch yourself drifting toward your own glory days, here's one more question to sit with: what exactly am I homesick for, and is there a small way to bring some of it into this season?

Until we see each other again, I hope you have a powerful day.

-Joanna

Joanna Douglas
Trusted Guide for Deeper Growth and Life Transitions Founder of Enneagram Ensight

Joanna Douglas

I've spent years helping others navigate the gap between achievement and aliveness and right now, I'm navigating it myself. This newsletter is where that happens in real time: honest writing about the messy middle, the questions worth sitting with, and what it looks like to let life lead when certainty takes a leave of absence. If you're somewhere between who you were and who you're becoming, pull up a chair. Oh, yeah - I am an ICF Certified Coach, a Certified Enneagram Professional, focus on leadership development with a customized path to Emotional Intelligence through the wisdom of the Enneagram and I created the Depletion to Fulfillment framework.

Read more from Joanna Douglas
A red heart shape drawn with light against a solid black background

Hello Reader, Welcome to the conversation. I moved back to Georgia not long ago, after seven years in Texas, and it didn't take long to hear it again. Bless your heart. That same sing-song lilt from all the years I lived here before. For a second I just stood there, because I couldn't tell if it was kindness or if it was aimed at me. I've been noticing phrases like that lately. Not just the Southern ones. The everyday ones. "You're fine," said before I've even finished apologizing for...

The interior of a vintage car with raindrops on the windshield

Hello Reader, Welcome to the conversation. The band Dire Straits has a song called "The Bug," later covered by Mary Chapin Carpenter, built on an image most of us understand without explanation. Some days you're the windshield, moving fast, and whatever you hit barely registers. Other days you're the thing that gets flattened. For most of my life, I believed I could stay the windshield if I worked hard enough at it. Staying in control, appearing powerful, keeping the upper hand. It kept a lot...

Hello Reader, Welcome to the conversation. Ted Lasso is fifty-something years old, a professional soccer coach, and by his own admission, has no business being on a dating app. Keeley helps him set up his Bantr profile, and true to form, he has wise and funny things to say during the process. Everything goes fine until the profile asks for three words to describe himself. He gains an insight that he might lean on the loquacious side and has trouble narrowing down to three single words. Later,...