A New Job Didn’t Fix Everything... and That’s the Point

This week’s Is This It? comes to you from a hotel desk in Chicago. Not because I’m reinventing myself as a Midwest gay dad (please, the fashion alone), but because I started a new job on Monday and onboarding is hosted here.

Before anyone spirals: no, we’re not relocating. This is a cameo. A limited series with no renewal clause.

But here’s the truth: getting a job didn’t magically resolve the mid-life messiness that led me to write this newsletter in the first place. Employment solves the logistics, not the existentialism. The deeper questions? They packed themselves in my carry-on.

And honestly… that’s comforting.

I had a whole concept for this week’s edition - light, clever, maybe even a tangent about airport snacks.

But then, on Day 2, onboarding served up an activity that shifted everything:

Part 1:
Explain the job you were hired to do, then explain why you were chosen.

Part 2:
Pick 10 personal values → narrow to 5 → land on your top 3.

Deviously simple. Shockingly emotional. And exactly the kind of introspection that hits differently when you’ve spent months writing your way through the messy in-between.

I didn’t expect Part 1 to be easy, but it was.

After months of unemployment-fueled self-reflection, I’ve become skilled at identifying both:

So sharing why I belonged here felt… earned.

Hearing others at the table felt even more powerful. Every week, I fling my reflections into the digital abyss and wonder:

Is anyone else navigating a mid-life reinvention while changing diapers and asking ChatGPT “am I too old for this?”

Turns out: yes. Many. They were sitting right next to me.

And then came the value selection.

I live for an exercise like this. My top three?

Not groundbreaking on the surface—but deeply clarifying when said aloud.

Well-Being: The Foundation I Wish I’d Prioritized Sooner

Some chose Family. Some chose Community. And listen, those matter enormously to me. But if I’m not well—physically, mentally, emotionally—how can I show up for anyone else?

At 39, everything hits harder: a back spasm, a career cliff dive, a toddler tantrum in public. Well-being isn’t optional; it’s structural.

Determination: The Muscle Behind the Reinvention

Many selected Achievement or Accomplishment. But to me, determination is what makes those possible.

It’s the reason I’m still standing after the last 20 editions of this newsletter chronicled my personal unraveling → rebuilding → reimagining.

Joy: The Value I Didn’t Expect to Choose—But Needed Most

Only one person chose Hope. But when I shared why I chose Joy, the room shifted.

Joy is the flicker that keeps you going. Joy is “what could go right?” Joy is asking the question Is this it? and believing there might still be something beautiful (or at least mildly hilarious) around the corner.

This exercise may not have been designed to be spiritual—but I let it be. And what it revealed was simple:

I am exactly where I need to be.

Not because the job fixes my life, but because I am different now. And I like the person I’m bringing into this new chapter.

In the last hour of onboarding, it struck me:

This is only my second employer in nearly two decades.

I don’t regret the first; it shaped me profoundly. But I was on autopilot. Comfortable. Drained. Detached but high-functioning, like a Roomba that keeps vacuuming long after the battery should’ve died.

It took being shoved into the black hole of unemployment to wake up. To question everything. To see myself clearly again. And now, I’m determined not to slip into that old pattern of unintentional living.

Let’s soften the existential crisis with some geography.

Chicago is lovely. The lights on Michigan Ave. The tourists paying $280 for a winter coat they’ll never wear again. The politeness - almost Olympic level of “I’m sorry” per capita.

But walking around, taking it in, something hit me:

It’s too clean.

Which made me long - viscerally - for New York.

New York is a mirror: chaotic, gritty, self-aware, delusionally confident, and somehow thriving under conditions other cities would classify as a humanitarian crisis. Literally. Need proof? Subways during a rainstorm. 

If you’re a gay man, it’s also the Hunger Games of wellness. Everyone looks like they’ve been training for a Calvin Klein casting call that hasn’t existed since 2012.

Chicago is charming. New York is home.Full stop.

Maybe not. Maybe it’s the beginning of asking better questions.

Because this week taught me something unexpected:

The point isn’t for the question to disappear. The point is to stay awake. To stay aligned. To stay curious enough to notice when you drift.

And sitting in that Chicago conference room, scribbling down my values, I felt it:

A little joy. A lot of determination. And - for the first time in a while - well-being rising back up to meet me.

The weekly section where I will call out a fraction: something that felt like progress this week (like a fraction forward) and a fiction: something that turned out to be a distraction or illusion.

🎯 Fraction: The Chanel fashion show in the New York City subway. BRAVO. Whimsical, progressive, deliciously chaotic in that “only in New York” way. Karl would’ve clutched his pearls; the rest of us clutched our oat-milk lattes. It felt daring for the brand, relevant for the moment, and honestly, a breath of fresh air in a city that at the same exact moment was being pummeled by rain so aggressively I started googling ark-building instructions.

For one glittering moment underground, fashion, magic, and MTA delays became the same thing. A fraction forward for culture, hope, and the belief that beauty can exist next to a damp subway rat.

🎭 Fiction: Those back-of-the-head ear muffs absolutely not. Chicago reminded me (in 27-degree wind) that they still exist, and New York reminded me (in the rain) that men still wear them. And I’m sorry but… no. Absolutely not. Under no circumstances should these devices - which look like rejected props from a 2002 Sharper Image catalog - be allowed in polite society.

There are so many more stylish ways to stay warm. Scarves! Beanies! A hood pulled up with just the right amount of nonchalant drama! But the behind-the-head ear muff? It’s giving regional manager at a suburban ice rink. It’s giving divorce dad at the ski lodge who says “sport” unironically. It gives me the ick.

Banned in the fictional universe where I make the rules and frankly, it’s a platform I’m willing to run on.

A quick round-up of clips, headlines or stories, and cultural crumbs that made me pause and ask… is this it?

💸 Hollywood’s Nostalgia Cash Grab Continues
Men In Black is getting a reboot… because apparently reviving old franchises is still cheaper than writing something original. Between Bad Boys 5, Rush Hour 4, and now this, it’s clear that Hollywood’s real creative engine is “IP we found in the garage.”

✈️ Rosalía’s Frequent Flyer Status Is Higher Than My Self-Esteem
She’s hitting 17 countries on this tour. Seventeen. I’m exhausted just typing that. Capitalism says: monetize every continent. My knees say: please sit down, girl.

🎬 Oracle Money Buys Another Creative Soul
Jon M. Chu just inked a first-look deal with Paramount courtesy of Oracle’s bottomless pockets. At this point, Silicon Valley isn’t just eating Hollywood’s lunch… it’s buying the restaurant.

📱 How Much Does It Cost to Leave Apple for Meta?
Apparently… a lot. Like, “more zeros than I’ve ever seen on a W-2” a lot. This story reads like capitalism’s version of a custody battle: who gets the engineers, who gets the designers? and at what price does love—er, talent—transfer?

🛒 Goodwill, But Make It Venture-Backed
Goodwill is rebranding with tech-platform energy and Gen Z gloss. The thrift store of our childhood is now giving “sustainable luxury startup,” and honestly… I’m not mad. Capitalism stays capitalism, but at least this version comes with better lighting.

As I wrapped up my week in Chicago - values scribbled on paper, confidence slowly recalibrating, and a renewed sense of direction taking shape - I kept coming back to something I felt in that onboarding room: we’re all just trying to figure it out, one honest question at a time.

If this week’s edition reminded you that your own reinvention is allowed to be messy, hopeful, determined, or even a little joyful… share it with three friends who might need that reminder too.

Because whether we’re in a conference room in Chicago, a stroller-pushing sprint across NYC, or standing at the edge of the next big unknown - none of us are doing this alone.

Until next week,
Chris

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