Are You Part of the Threshold Generation?
"I bought $847 worth of online courses last night."
Michael stared into his coffee, embarrassed. We'd met at our usual spot—the diner where the coffee's terrible but the refills are endless.
"AI prompting, LinkedIn optimization, digital marketing..." He laughed, but it came out wrong. "Jenny found me at 2 AM, laptop open, notebooks everywhere. She asked what I was doing."
He looked up. "I told her I didn't know. Dan, I've been married 40 years, and that's the first time those three words terrified me."
The Letter
I knew what triggered this. The Medicare enrollment packet had arrived at Michael's house yesterday.
"It's just paper," he said. "But it felt like a referee's whistle. Like someone calling time on everything I've been."
Tom nodded from across the table. He'd joined us late, still in his work clothes even though he'd retired six months ago. "I still put on the tie some mornings," he admitted. "Then I remember there's nowhere to go."
We sat with that for a minute. Three guys in our sixties, successful careers behind us, and not one of us knew what to do with a Tuesday anymore.
The Thing Nobody Names
"You know what kills me?" Michael continued. "I've got forty years of experience. My LinkedIn looks like a resume hall of fame. But yesterday, my daughter called to explain how to use Apple Pay."
"Like we're already obsolete," Tom added.
"Not obsolete," I said. "Something worse. Irrelevant."
Michael winced. "That's the word I've been avoiding."
Here's what we figured out that morning: We're all part of something I've started calling the Threshold Generation. Not old, but no longer young. Too experienced to be dismissed, too proud to beg for relevance. Standing in a doorway between who we were and who we're supposed to become—except nobody told us what that is.
The Real Cost
"Want to know something pathetic?" Michael pulled out his phone, showed us his credit card statement. "Three thousand dollars in the last two months. Courses, coaching programs, masterminds—all promising to help me 'reinvent' myself."
"Did any of it help?" Tom asked.
"They're all designed for 35-year-olds who want to quit their corporate job and become influencers." Michael shook his head. "I don't want to be an influencer. I just want to know what the hell to do with the next twenty years."
Tom laughed—the bitter kind. "My wife and I had our first real fight in years last week. You know what it was about? We don't know how to be together without schedules. No kids' activities, no work events. Just... us. And we have no idea how to do that."
The Suggestions That Don't Help
"Everyone has answers," Michael said. "Take up golf—"
"I hate golf," Tom interrupted.
"Volunteer somewhere—"
"Doing what? Feeling like I'm on the bench?"
"Travel—"
"Running away doesn't answer the question."
"Spend time with the grandkids—"
Michael's voice got quiet. "I love my grandkids. But I'm not ready to be a supporting character in my own life."
We sat there, three grown men who'd run companies, raised families, built things—and none of us could figure out how to just be anymore.
The Moment Everything Shifted
Tom set down his coffee cup hard enough to make it clatter.
"Forty years," he said. "Forty years I was Tom-the-executive. Tom-the-provider. Tom-the-problem-solver. You know what I realized last week? I have no idea how to just be Tom."
Michael and I looked at each other. Same thought. Same fear.
"That's it," I said slowly. "That's what this is. We're standing on a threshold. Not retired, not working. Not old, not young. We're between everything we were and whatever comes next."
"And the map's blank," Michael added.
"Maybe that's not a bad thing," I said, surprising myself.
The Questions Worth Asking
Michael leaned back. "What if we stopped trying to have answers?"
"What do you mean?" Tom asked.
"I mean, what if this threshold—this uncomfortable, uncertain place—what if it's not a problem to solve? What if it's where something new happens?"
We spent the next hour not solving anything. Just asking better questions:
What if expertise isn't about having all the answers anymore?
What if wisdom is knowing which questions matter?
What if this blank map is freedom, not fear?
What if we stopped trying to be relevant to everyone and started being real with someone?
The Invitation
That coffee turned into a weekly thing. Not to network. Not to solve. Just to be three guys on the threshold, drawing our own maps.
Michael texted me yesterday: "Stopped buying courses. Started having conversations instead."
So here's my question for you:
Are you standing on this threshold too? Did a Medicare letter start it, or was it something else—a retirement party, a kid's wedding, a mirror moment when you didn't recognize the person looking back?
More importantly: What if you stopped trying to rush through this threshold? What if instead of seeing it as a hallway to somewhere else, you recognized it as the place where transformation actually happens?
What Comes Next
We're meeting again Friday. Same terrible coffee, same wobbly table. But something's different now. We've stopped trying to solve the "Now what?" and started exploring it together.
I'll share what we're discovering—the good, the messy, and the surprisingly liberating.
But right now, I want to hear from you. Are you part of this Threshold Generation? Standing between chapters, holding a blank map, wondering if everyone else got instructions you missed?
You didn't miss anything. Neither did we.
And maybe that's exactly where the next chapter begins.
Coming Friday: "The New Loneliness: What Happens When Three Guys Stop Pretending They Have It All Figured Out"
About Third Space: Where the Threshold Generation meets—not to network or solve, but to be real about the questions that wake us up at 3 AM. For those brave enough to admit the map is blank and curious enough to draw new roads together.