Identifying the 'Season' Your Clients Are In

At a certain point every fall I step outside and realize, okay, this is why I live here.

The air is cool, the leaves are turning, and for a handful of days everything just feels right. Those are the days that bring me home — that remind me why I chose the Midwest, the changing seasons, the whole rhythm of it. I was born and bred in Columbus, so of course I’m an Ohio State fan. Football weekends, Thanksgiving pulling the family in, sweater weather before it gets too cold. I’ll admit I’ve given in to being an old fart and stopped going to the games in person, but the season still lands for me the same way it did when I was a kid.

What I like most about fall goes past the weather and the traditions, though. It makes me think about the seasons of life. We all cycle through them. Some are easier, some harder, some bring the days you wish would last forever. They’re all part of the deal.

Different Clients, Different Seasons, Different Financial Solutions

That’s the beat that lands differently when you spend your days with pre-retirees and retirees — the households we all serve.

Every one of those households is in a season. Reading which one they’re actually in is one of the most under-appreciated diagnostic moves in this work.

The client who’s still accumulating and treats a bad year like a temporary inconvenience is in a different season than the client who stopped contributing eighteen months ago and treats a bad year like a threat to the whole plan. The couple whose kids are grown and financially independent is in a different season than the couple raising a special-needs child who will need lifetime support. The 63-year-old sitting on a decade of retirement runway with no earned income is in the shortest, most valuable tax window of their entire financial life — and if we treat them like a client mid-accumulation, we miss the whole thing.

None of that shows up on the fact-find in a way that flags itself. You have to read it. The client who says “I want to keep working as long as I’m healthy” and the client who says “I want to walk away next August” are describing two different seasons even when the balance sheets look identical. The plan has to be built for the season the household is actually in, not the season the software assumes them into.

That’s the work of the fall for those of us doing it.

To-Dos During Q4

And speaking of fall — Q4 is a season for us too, and worth naming as one.

The calendar between now and December 31 is the harvest window on nearly every planning decision this year. Roth conversions have their last chair in the game. RMDs finalize for the households in that band. Year-end tax-loss moves, charitable stacking, gifting decisions, bracket-fill discipline — all of it has to close before the ball drops. Seminar season peaks. The client meetings we’re setting now are the ones where the households in the bridge years actually pull the trigger on what we’ve been modeling for them since June.

For the peers reading this — this is the season where the whole year’s planning either shows up or it doesn’t. It’s the difference between the households who look back on 2026 and say “we made every year-end move that was available to us” and the households who look back and say “we ran out of runway again.”

None of that requires heroic effort. It requires being awake to which season the household is in, and moving before the window closes.

Winter’s coming. That’s part of the deal. The dollars converted this quarter compound tax-free for the rest of the client’s life. The dollars not converted this quarter compound under whatever the future looks like — which none of us can price today.

For now, though, fall is here. I’m going to enjoy every one of those cool, crisp days that remind me why I love living in the Midwest. And I’m going to spend the ones in between doing the year-end work with clients who are counting on the season getting used the way it should.