If you looked at our family calendar between the last week of October and the first week of December, you’d probably assume someone in my house was running an events business. It starts with my youngest daughter’s birthday in late October, just a few days before November hits. A couple weeks later comes Thanksgiving, which is also the birthday week of my wife and my oldest daughter, as they were both born on that holiday in their respective years. The back half of November additionally brings the birthdays of my wife’s sister and my mother-in-law, and just as we’re finishing up the leftovers and thinking the season is about to wind down, my oldest son’s birthday shows up the first week of December. That’s six birthdays and one national holiday in about six weeks, which is a lot for any calendar (or any grocery/shopping list) to hold, but I wouldn’t trade a day of it for anything.
For a while I probably felt like this stretch was something to “get through,” kind of like a long drive or a busy week at work. With gifts to buy, meals to plan, travel to book, work to get done, and time off to request, there’s always a monthly statement waiting at the end that tells the whole story too, whether I want to hear it or not. But over the last few years I’ve started looking at it differently, mostly because of something that surprised me: I almost never feel anxious about the money going out the door in those weeks anymore, even though it’s probably more than any other stretch of the year (especially if you count Christmas only a few more weeks down the road). If a stranger handed me that same total on a statement with no context, I’d surely be demanding a full explanation of where it all went, but attached to six people I love and a table that’s full, I hardly think twice about it. So why is that?
I don’t think it has much to do with the amount. I think it comes down to how clearly I can answer the question of what the money is for. I wrote earlier this year about “knowing your why,” and the more I think about it, the more the calendar seems like one of the most honest places to find it. Ask most people to write down their values on a blank sheet of paper and I bet they’d stare at it for a minute before writing anything down (I know I did). But ask them which dates they protect, what events they rearrange almost anything for, and who they spend both time and money on without keeping score, and the answers start to flow pretty quickly.
When I started thinking of how this concept applies in other ways (like at work), I discovered that it’s a huge part of why I find our advisers’ approach to planning so compelling here. From what I’ve seen working alongside them, the conversations that go best rarely start with a number. They start with a person or a date: a daughter heading to college in a few years, a parent who needs more help than they used to, a retirement party someone has been picturing for a decade. Don’t get me wrong, the numbers matter a lot, but they matter because of those dates, and a plan that doesn’t know about them or incorporate them is really not a plan at all, because it would be a plan for a family that doesn’t exist. After all, when was the last time anyone got as excited about a quarterly statement in the mail as they do about a birthday card from a loved one?
Also, there’s something fitting about a holiday built around gratitude landing on my wife’s and daughter’s birthdays, because it keeps everything in proportion for me. Each year the table looks a little different, the kids are a little taller, and the stories get retold with a few more details than the year before. Somewhere in the middle of all that I find the question of what we’re working toward answers itself better than it ever does in a planning meeting. It also reminds me that the calendar doesn’t stand still. The birthdays that feel like a fun party right now will eventually turn into a countdown for another related event we have to be ready for, whether that’s a first car (makes me nervous just thinking about it), a college tuition bill, summer camp, or something none of us will even see coming. Do we ever really know which next big thing is actually next?
That’s what I keep coming back to as the year winds down. A lot can change between one Thanksgiving and the next: a new baby, a marriage, a new job, or a move (we know a little something about that). Sometimes a plan quietly keeps up with all of it, and sometimes it’s still describing the family you had a few years ago. Which one is yours right now?
If you want to find out, here’s something you could try this month. Pull up your calendar from now through the new year and read it like someone who had nothing else to go on except those dates and was trying to work out what matters to you. What would they guess, and would it match what you’d say yourself? Maybe it’ll confirm that your time and money are already pointed where you want them. Or maybe you’ll spot a tradition you keep out of habit, or a person you’ve been meaning to make more room for, and you’ll wonder why it took a calendar to show you.
And if something doesn’t quite line up, that’s usually where a good conversation starts. It doesn’t have to be a big one, and it doesn’t have to begin with a spreadsheet. It’s the kind of thing our advisers talk through with people all the time, and our door’s always open if you’d like some company while you sort it out.
As for me, I’m grateful for the six people who fill up my November and the start of my December, and for a team that understands the point of all this planning has always been the people. Happy Thanksgiving to you and yours.
