My manager retired this week. Twenty-eight years with the same company. Let that number sink in for a moment.
She was a tough woman, a retired Air Force Lieutenant Colonel, an absolute hard-ass when the mission demanded it, but a human shield for her team when the corporate avalanche started sliding. She was, in the absolute best sense of the phrase, the devil we knew.
The funny thing about devils you know is that you don’t fully appreciate them until they’re gone. After many years of working for her, I realized that people like that are becoming increasingly rare, not because younger workers lack character, but because the workplace itself has changed.
In an era where the average millennial is lucky to spend a tenth of that time at a single gig, nearly three decades of service isn’t just unusual. It’s monumental. Longevity like that is not something to casually dismiss. Sticking with one job for more than a generation isn’t exactly viewed as a badge of honor these days. It almost feels like an artifact from another civilization. But that’s a cultural debate for another time.
Lack of workplace longevity isn’t necessarily because younger workers are lazy or disloyal. Modern work culture is simply different. Companies restructure. Careers pivot. Loyalty has become transactional in both directions. Staying at one job for thirty years is no longer considered the gold standard of professional life that it once was.
Where I work, corporate longevity isn’t rewarded with the classic gold watch anymore. Instead, you get “perk points” for work anniversaries and unexpected project successes. To be fair, it’s not entirely unimpressive. The points can be spent at an online company store. It’s not exactly thrilling, though I’ll admit I used mine to score a snazzy tablet and a nice winter jacket, one that blissfully doesn’t make me look like I’m conducting a search and rescue mission while browsing the grocery store produce aisle.
But the real perk for an old salt at our company comes at retirement. They pay for you to go out to eat and you get to bring family and coworkers along on a very liberal budget.
And that’s where the story really begins.

Stepping Into Another World
I don’t think my boss picked the restaurant herself. I suspect her boss did. We ended up at one of those upscale establishments where dinner costs around a hundred dollars per plate before anyone starts ordering appetizers, drinks, sides or dessert.
This was not a “show up in cargo shorts and a baseball cap” kind of place. This was a “respect the establishment” venue. The kind of a restaurant where if you show up dressed like a bum, you won’t even make it through the front door, although one of my coworkers walked in wearing a kilt. He’s tall enough to have to file a flight plan and as thick around as any two men. Most people stay out of his way, also due to respect.
Now, before I settled down, my career required heavy travel. I have literally eaten my way across the North American continent (and a couple of others). I’ve tried everything, a lot. And while I won’t say the $85 steak on my plate was poor quality, I can honestly say I’ve had steaks a quarter of that price that tasted every bit as good.
In my travels, the absolute best dining experiences I’ve ever found were small hole-in-the-wall mom-and-pop joints, tucked between gas stations and laundromats, family restaurants that could outperform half the culinary world with one handwritten recipe card and a grandmother who refuses to measure ingredients. Those are the places that leverage love and a generational family tradition to offer an unparalleled experience. Food, not dining.
Some of the best meals I’ve ever eaten came from places where:
- the menus were laminated
- the booths squeaked
- the waitress called everyone “hon”
- the family kid scooped up empty plates from the tables
- the owner wandered table to table asking whether people liked the pie
Those places didn’t have dress codes. The waiters didn’t wear tailored uniforms. But they had something else. Heart. They were sincerely glad that you came.
These small out of the way diners stand in stark contrast to the high-end spots where the waitstaff wear identical uniforms, move with choreographed precision, where napkins appeared folded the instant someone stands up and staff glide by to sweep your table with a silver crumber between courses. Somewhere in the distance, I’m fairly certain I heard the sound of wealth being gently plated.
Yet, as I sat there watching the room, the food became secondary to the people-watching. Despite the burden of status, restaurants like the one we visited continue to thrive, too.

The Crowd in the Room
That fascinated me, because when I looked around the room, I didn’t see billionaires and their upscale millionaire buddies. I didn’t see celebrities or hedge fund managers or people stepping out of chauffeured cars while checking stock portfolios on their phones. The restaurant was packed, but as I looked around, I didn’t see a single person I could qualify as a “one-percenter”.
I saw ordinary people.
I saw couples who were probably celebrating anniversaries.
I saw families gathered around graduation dinners.
I saw someone who looked like they had just gotten promoted after twenty years at an ordinary office job.
I saw wrinkles.
Gray hair.
Off-the-rack clothing.
Suit jackets that had clearly lived full lives before arriving at this dining room.
Dresses that weren’t tailored to a perfect fit.
In other words, I saw everyday people deciding that this particular night mattered enough to elevate.
And maybe that’s why these places survive. Not because people need hundred dollar steaks, but because human beings need ceremony. That’s what these restaurants are really selling.
Ceremony.
They create a space where life’s milestones feel substantial. The lighting, the formality, the pacing, the care, the sense that the evening has been intentionally separated from ordinary life. All of it quietly tells you, “This moment matters.”
That has enormous emotional value, especially in a culture increasingly dominated by speed, convenience and disposable experiences.
Fast food feeds hunger. A great restaurant feeds memory. And memory is powerful.
People remember:
- where they celebrated engagements
- retirement dinners
- anniversaries
- graduations
- reconciliations
- promotions
- final goodbyes
The restaurant becomes attached to the emotional geography of their lives. That’s why these establishments survive housing crashes, recessions and even pandemics. Not because luxury is recession proof, but because meaning is resilient. They survive because they sell sanctuary and significance.
Even during hard times, people still reach moments where they need to pause and say, “This mattered. We should honor it.” The $100 price tag isn’t just paying for the food. It’s an admission fee to a temporary world of luxury that says, “You earned this.” And honestly, maybe we don’t do enough of this anymore.

The Architecture of a Milestone
We rush through milestones now. Promotions become LinkedIn posts. Birthdays become text messages. Retirement becomes a calendar event followed by another meeting invitation.
But humans are ritualistic creatures. We need markers. We need transitions. We need occasions where the ordinary rules soften long enough for us to acknowledge that something important has happened.
That dinner was one of those moments.
And underneath the expensive menu and polished silverware was something surprisingly simple, a group of people gathering to acknowledge that twenty-eight years of someone’s life mattered.
As the night wound down, my thoughts returned to my manager.
Work is not always perfect. No job is. Companies are not families, no matter what corporate branding departments say. But over nearly three decades, relationships form. For twenty-eight years, she navigated the corporate storms. Shared battles accumulate. Trust gets built slowly through difficult projects, stressful meetings and long stretches where people quietly have each other’s backs.
She had my back when it counted and at the end of the day, she was the devil I knew.
Stepping out of our everyday routine to put on nice clothes, sit across a white tablecloth and watch the waiters sweep away the crumbs was the perfect send-off. It wasn’t about the steak. It was about taking a collective breath to say that twenty-eight years of dedication mattered.
And perhaps there’s another truth hidden in all of this. Sometimes the greatest luxury is not the steak. It’s having enough people around the table to celebrate the journey with you.
I’ll miss my boss. She’s had my back for a long time. And the next time I find myself at a small mom-and-pop diner enjoying a perfect $20 meal, I’ll still look back at that upscale dining room with a lot of respect, not for the price tag, but for the milestones it honors.
Even when the devil you know is finally riding off into retirement.







































