Tip Season, Bonus Season, Soul-Searching Season

I’ve spent the last twenty years wondering whether this phenomenon is unique to me or if it’s just part of the human operating system: the moment Thanksgiving hits, time becomes soup. Days blur. Weeks accordion. It’s like the annual software update of COVID brain fog, but make it festive.

Some mornings I blink and wonder how it’s already December; other days stretch out like New York subway delays, suspended in existential molasses. It’s the seasonal paradox of adulthood: the days are long but the years are short, especially once you become a parent and start measuring time in snack cycles and nap windows.

December is when the mirror becomes a truth teller. You catch your reflection and think:

Damn it. I didn’t do x, y, or z. Again.

Another year gone. More joy, more heartbreak, more healed scars you forget to be proud of.

And yet, here we are. Again.

I’m currently toggling between gratitude and logistical overwhelm: Christmas gifts, holiday cards, travel plans, a Santa meet-and-greet, the Big Apple Circus, swim lessons, preschool commitments, and, not to be forgotten… a new job.

It’s the time of year when we're all collectively flooring the gas pedal, then immediately slamming the brakes. Everyone is moving fast, everyone is exhausted, and everyone is at risk of becoming someone else’s seasonal collateral damage.

Which brings me to one of New York’s most confounding holiday traditions…

I have fully accepted that tipping is the eighth borough. And during the holidays, it becomes its own economy.

We live in a full-service building, which in New York is code for: here is your cast of characters who will expect an envelope stuffed with cash. Door people (all men, and yet I cling to the gender-neutral optimism of “doorperson”), concierge, maintenance, porters, gym attendants, garage attendants, package attendants.

Then there’s the swim instructor. The preschool teachers. The nanny. Basically anyone who has ever come into contact with my daughter or an Amazon package.

Do many of these people deserve it? Yes. Do some of them absolutely not deserve what they think they deserve? Also yes. But here’s the secret I’ve learned, and I share it with the confidence of a man who has made many spreadsheets about this: treat holiday tipping like you’re allocating a bonus pool at work.

When you give people more, they treat you better.

This is not shade - this is anthropology.

Now that my daughter is two-and-a-half and blossoming into a fully articulated human with preferences, comedic timing, and a negotiation style reminiscent of a tiny executive producer, my tipping calculus has shifted. It’s less about how these people treat us and more about how they treat her. Does she smile? Does she feel seen? Is she greeted with warmth?

That will get you bumped up a tier in my personal bonus matrix.

And yet, filling out these cards - putting actual cash into actual envelopes - forces me to stop, inhale, and ask the uncomfortable question:

Not the literal bonus (though, hi, wouldn’t say no). But the metaphorical one.

This year I’ve watched our spending more carefully than ever. I’ve gone through a career transition. I’ve had days where belief in myself felt like a full-time job. I’ve had moments where the mountain I was climbing felt steep enough to qualify me for a REI sponsorship.

And still, I can say honestly that I deserve a bonus.

Not in cash, but in confidence. In grace. In acknowledging the invisible work of holding yourself together while reinventing your life.

The employees in our building do physically demanding work. The teachers and nanny do emotional labor that would break most grown adults in under an hour. My challenges are different — not bigger, just mine. Everyone’s battle is relative to their own capacity.

There is a quote that landed with me this week: you can’t shave the mirror.

Meaning: you can’t change the reflection by attacking the surface.

You change it by changing the source.

And somewhere in the middle of all that introspection, I found myself asking the question I circle every December like a holiday carousel: Is this it? Is this the year I finally give myself credit for surviving the plot twists I never auditioned for? Is this the moment I stop measuring my worth by the size of the bonus and start measuring it by the size of the growth?

This year, I finally stopped trying to fix the externals and turned inward toward my thoughts, beliefs, expectations. And that shift was my real bonus.

Even amidst the blur - the chaos, the envelopes, the constant Venmo-ing - something extraordinary is happening this year: it’s my first holiday season where my daughter truly gets it.

And it is magic.

She lights up when we turn on the Christmas tree. She shakes the snow globe like she’s summoning weather. She yells “Ho! Ho! Ho!” every time she sees a Santa — even if it’s a bodega Santa taped to a dirty window.

She stands in front of the TV fireplace and says, “Warm,” even though the heat in our apartment is aggressively inconsistent and deeply personal.

And since the very moment Santa rode down 34th Street in the Macy’s Thanksgiving Parade, every day has felt like a gift. Every day has felt like my bonus — the most abundant one of the year.

It makes me emotional, realizing we all once had this innocence. And how fiercely I want to protect hers.

Earlier this week, the Met announced that Beyoncé, Nicole Kidman, and Venus Williams will host the 2025 Met Gala. The theme: Costume Art. A celebration of the relationship between garments and the human body.

Let me be extremely clear with you: this is my Super Bowl.

If this newsletter existed last year, you would’ve heard me breaking down the theme, the designers, the carpet, the cultural significance, the silhouette politics - all of it.

And maybe it’s the season of tipping and budgeting and making the bonus pool stretch like Peloton instructors claim hamstrings do, but the Met Gala is my one night of unapologetic abundance.

An escape hatch into a world where “too much” is simply the starting point.

A reminder that even in a year measured in self-made bonuses and personal reinvention, there is still room for glamour, imagination, and spectacle. There is still room for moments that lift us above the chaos, even briefly.

I don’t yet know what I’m going to say about the Met Gala when the first Monday in May comes, but I know this: it represents something I’m holding onto more tightly this year.

The belief that beauty still matters. That joy still matters.

That even in the blur, there are things worth looking forward to.

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: Flying High

My relationship with airlines has always been… complicated. Turbulent, you might say. But last week, on my way back to NYC, we hit an unexpected high note. I walked up to the gate just in time to watch the status flip from “on time” to “cancelled” for what appeared to be absolutely no reason. Classic.

But then - miracle of miracles -the gate crew sprang into action. Within minutes, they’d scooped up a dozen of us early birds and slid us onto a flight taking off an hour earlier than the one we were supposed to be on. It was a fraction of hope in human form: proof that even during the holiday travel gauntlet, when patience is thin and expectations are thinner, someone can still make the skies feel a little bit friendly. A tiny reminder that sometimes things do work out… and occasionally, they work out early.

🎭 Fiction: Secret Santa (or anything of the like)

Secret Santa, White Elephant, Yankee Swap - pick your chaos branding - is my annual reminder that not all traditions are sacred. Somewhere along the way, the joy of giving turned into a high-stakes game of “Who bought the least terrible $25 gift?” This is the season of abundance and intention, not the season of pretending anyone wants a novelty mug that screams World’s Okayest Co-Worker. Hard pass.

If this week’s essay gave you even the tiniest bonus of joy or perspective, consider passing it on. Forward it to three people who might need a reminder that even in the blur, there’s magic worth noticing. Thanks for being here - your presence is the real end-of-year upgrade.

See you next Friday,
Chris

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