The Most Expensive Investment

The great millennial crisis continues in this household.

Employed. Check.
Health. Check.
Wealth. Let’s call it... a work in progress.

Lately I feel like I’m on a merry-go-round that only plays one song: how do we make more money?

Not because we are broke. We are not. But affordability right now feels like a puzzle with moving pieces. Rent, childcare, groceries, utilities, taxes, travel, saving for retirement, contributing to a 529 plan, attempting to live a little along the way. Every decision starts to feel like a line item.

Some weeks it feels less like life and more like a spreadsheet.

And yes, context matters. We live in New York City. No one accidentally ends up here. Living here is a choice. A lifestyle. A tax bracket. A personality trait.

But here is the thing I always come back to. While the monetary taxes of living in New York are high, the non-monetary tax of living somewhere else would be even higher.

The energy. The ambition. The creative friction of this city. I would miss all of it.

Still, the millennial math problem remains. Save. Invest. Pay bills. Repeat. Try to get ahead while the cost of everything keeps inching upward.

And last weekend, while sitting in a ski lodge two hours north of the city, something clicked for me.

We enrolled our daughter in ski lessons.

Why skiing?

Honestly, it might be one of the bougiest sports we could have possibly chosen for a two-and-a-half-year-old.

Why skiing and not something simple like a recreational game of tag at the neighborhood park?

Tag is free. Snow pants, ski rentals, and the rest of the alpine costume department are not. And yet here we are, two parents mounting a chic Arctic expedition so our toddler can spend three hours learning how to stand upright on two tiny skis.

From the lodge window I watched her take the magic carpet up the bunny hill over and over again. Tiny skis. Oversized helmet. One instructor trying to keep a group of toddlers together like a flock of slightly confused ducklings.

Up the hill.
Slide down.
Repeat.

Every so often I would sneak outside and record a video like a proud stage parent at a recital.

But the thing that struck me most was her confidence.

She just went for it.

No hesitation. No fear. Just trust that she could figure it out.

I do not know if that confidence is something she was born with or if it comes from knowing we are nearby if something goes wrong. That is a parenting thought for another week.

What I realized in that lodge was something simpler: I would use whatever resources I have to give her opportunities like this.

Standing there with a lukewarm coffee and a view of the bunny hill, I had a mental shift.

The ski lessons were not an expense. They were an investment.

Call it a recategorization of the accounting line.

All week long I stress about resources. Saving. Investing. Earning more. Optimizing the balance sheet of life.

And yet watching my daughter spend three hours learning something new with a group of kids who started the morning as strangers and ended it laughing together on skis gave me a return I cannot measure in dollars.

Index funds. High-yield savings account. Those things are responsible. Necessary even.

But the emotional return on investment from watching your child discover confidence on a bunny hill?

That return compounds differently.

In that moment I realized something about the millennial affordability crisis that I had been missing.

Affordability is not just about what something costs.

It is about what something is worth.

And sometimes the best investments we make are the ones that do not look financially efficient on paper.

They look like ski lessons.

Or ballet lessons (where she just runs around in a tutu).

Or family trips.

Or any moment where we quietly give up our resources so someone we love can grow into who they are meant to become.

Millennials spend a lot of time worrying about whether we are getting ahead.

Are we saving enough?

Investing enough?

Making enough?

Retiring someday?

But maybe the better question is this.

What are we investing in while we are here?

Because yes, I want my savings account to grow. But I also want to look back someday and know that I invested heavily in the things that mattered most.

Time.

Opportunity.

Confidence.

Experiences that shape a life.

Which leads me to the question I kept coming back to on the drive home to Manhattan.

If we spend so much of our lives chasing more… are we remembering to invest in what matters most?

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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: A Little Fashion Fantasy

It will surprise absolutely no one that I have been watching Paris Fashion Week. Matthieu Blazy stepping into Chanel has been fascinating to watch. None of it is remotely affordable. Even if you had the money, it still lives in the category of fantasy. But sometimes fantasy is the point. Watching creative people reinvent something iconic is an investment of time I am happy to make because imagination has a funny way of unlocking creativity in the rest of us.

🎭 Fiction: The Long Investment

Meanwhile, oil prices spike every time the world gets a little tense and we all act surprised. And I cannot help but wonder when we are going to wake up and realize that the real investment in solar, wind, and new energy might be the kind where some of us never actually see the payoff. The kind we make anyway.

If this reflection resonated with you, forward it to three people in your life who are investing their time, energy, and resources into something bigger than themselves. Parenting, building a life, showing up for the people who matter. Because sometimes the best returns do not come from what we save, but from what we share.

Is this it?... - Chris