$pent Millennial

Dear Reader,

Consider this my holiday newsletter.

I have always loved the tradition of the holiday card. The glossy family photos. The perfectly staged dogs. The coordinated sweaters. But my favorite has always been the letter tucked inside — the multi-page, single-spaced humble brag update that somehow manages to sound both casual and wildly impressive.

You know the ones. The children who are thriving (one learned Mandarin, another captained a travel team, a third founded a nonprofit). The promotions that were “unexpected.” The vacations that were “much needed.” The subtle flexes disguised as gratitude. I read every single one with genuine joy… and just a little awe.

Despite this deep admiration — and despite many years of good intentions — I have never actually sent one myself. I’ve accepted that this is unlikely to change.

So please accept this as my real, honest, brutally transparent holiday newsletter.

This year began on solid footing — the kind of footing that would absolutely be mentioned in a holiday letter. Personally and professionally, things were going well. Boxes were checked. Savings were growing. Plans were forming. If this were a traditional newsletter, this is where I’d reassure you that everything was “falling into place.”

Behind the scenes, of course, there was also the small matter of a new administration taking office — a detail that didn’t exactly fit neatly into the glossy update format. Still, we pressed on, carrying a quiet undercurrent of fear, anxiety, and sadness while outwardly maintaining calendars, meetings, and productivity.

As the year progressed — as these letters so often say — it brought its share of challenges.

Many navigated uncertainty, loss, and instability. While day-to-day life largely continued as usual, everything felt just a bit more precarious. Business as usual, but with a persistent sense that the ground could shift at any moment.

In lighter news, Jesse and I spent part of the year “practicing” for homeownership by unseriously open-house hopping. This involved touring homes, marveling at how unrealistically (and offensively) overpriced they were, then returning home to enthusiastically run — and re-run — our numbers. A hobby. A pastime. A mildly masochistic form of recreation.

Still, friendly realtors fed our fantasy, encouraging us to make offers well over what we were financially positioned for, reassuring us that renters could be “easily” removed, and casually sharing stories of “motivated” sellers facing job loss or urgent circumstances. 

While we were never planning to put in offers, understanding our own financial limitations and the broader economic forecast much more realistically than any realtor – or even lender– would care for us to, it was a powerful reminder of how often opportunity is framed through the lens of someone else’s hardship — a detail not usually included in holiday letters, but hard to ignore nonetheless.

On the professional front, stability prevailed — a true newsletter highlight. Jobs remained intact. Financial goals continued to move forward. Resources were set aside to give and support others where possible. From the outside, things were going strong.

And yet — as many of these letters fail to mention — All was not as it seemed. I felt a growing pull beneath the surface. The mission mattered. The work itself was meaningful. But a slow, persistent sense of misalignment crept in. Culture and values didn’t quite line up. I focused on the positives. I waited. I hoped it would resolve itself.

Spoiler: it did not.

Eventually, that tug became impossible to ignore, leading me to make the difficult decision to step away. Yes, “in this economy” — a choice that came with uncertainty, emotional weight, and a necessary reckoning with mental health and priorities. 

Not exactly a highlight reel moment, but an important- and honest- reckoning nonetheless.

So, despite my desire to be as humbly impressive as the next gal,  I close out the year not with a tidy conclusion, but in a season of reassessing and rebuilding — asking more honest questions about what I want my work and life to look like, and what I’m no longer willing to trade for the appearance of having it all figured out.

Which, I suppose, feels perfectly appropriate for this particular newsletter.

As the year comes to a close, I remain deeply grateful — for stability, partnership, growth, and the awareness that none of it is guaranteed.

Wishing you and yours rest, warmth, and gentleness this holiday season. May your newsletters be impressive, your realities be supported, and the year ahead bring alignment with what actually matters.

With sincerity (and no matching sweaters),

Everett