Staying regular
Tips for never missing another money meeting with your partner.
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For more than two years, Heather and I had been remarkably consistent about our quarterly money check‑ins. We’d been carving out time every three months to open our spreadsheets, review the numbers, and see what’s working and not working in our financial lives.
But this quarter, we started slipping again. Blame it on what Heather and so many others are calling Maycember—the stretch of May when dance recitals collide with school performances which overlap with work deadlines and sign-ups for next year’s extracurricular activities. (In fact, Heather just did an excellent job diving into the logistical and financial chaos of Maycember for SheKnows.) Anyway, the point is how easy it is to fall off the wagon. So, for this week’s newsletter, I want to help you make your money rituals stick no matter what season you’re in.
First, block the time on every calendar. Don’t rely on just a phone alarm. Put your quarterly money check‑ins on your shared family calendar, your work calendars, and even set a couple of phone alarms for one a week before and the morning of. Treat your money meetings like any other appointment you can’t miss—like the dermatologist who has four openings in an entire calendar year! Choose a slot when you both know external commitments will be light enough to follow through. Then, lock it in as a recurring event. Seeing the same appointment everywhere and being reminded of it on a more frequent basis makes it much harder to push it aside.
Pair the meeting with something you actually like to do. You might want to meet at your favorite coffee shop and grab a pastry or walk around the neighborhood. You could even relax at a park with a blanket and some cold drinks. Heather and I usually like to walk or grab a cocktail. The key here is to link your financial conversations with quality time you enjoy, so your brain starts to associate it with connection and not existential dread.
If you’re having trouble sticking to the money conversations on your own, introduce external support to hold yourselves accountable. If you don’t already work with a financial advisor, consider hiring one. When you do, you’re not just paying for expertise but you’re making a commitment and putting some skin in the game and stick to it. I’m obviously biased in this department, but many advisors who provide comprehensive financial planning meet with clients two to four times a year. There’s your built-in accountability, assuming you show up for your meetings.
If paying an advisor is not an option, turn to community resources and free online events to keep you on track. Look for webinars from your local credit union, bank, or trusted financial platforms. Treat each session as part of your regular money meetings. Once you’ve registered and blocked off the time on your calendars, you’ll be far more motivated to attend and incorporate those insights in your own conversations around money. You might also consider subscribing to the same financial podcast together, so you have fresh ideas for when you sit down at your meeting. And if you’re not sharing this newsletter with your partner…what are we even doing here?!
You can also insert a little play into the process. This doesn’t need to be a full-blown gamification of your finances, but a little challenge could make things interesting. For example, you could try to guess the single biggest money‑saving move or unexpected expense from the past quarter and whoever identifies it can pick the venue for the next meeting (or NOT have to pick the venue for the next meeting, if this was Heather’s game). Or you could track a financial goal in one of those temperature charts and update it every quarter. NGL, seeing something physical move closer to your targets is actually exciting.
Keep focused on progress, not perfection. It’s easy to fixate on what isn’t perfect. You might say, “damn, we missed our savings target by a few hundred dollars,” but that mindset kills motivation. Instead, celebrate what went right. Maybe you chipped away at credit‑card debt even if you didn’t eliminate it, or you boosted your emergency fund by a small but meaningful amount. Acknowledge those wins before diving into what needs more work. Positive framing makes you both more inclined to keep tackling this hard work.
Regular money meetings aren’t just about spreadsheets and data. They’re about staying connected to each other’s intentions, challenges, and hopes for the future.
When you carve out that time, you’re saying “we’re a team,” even when life is pulling you in a hundred directions. Regular conversations build trust, spark new ideas, and remind you why you started doing this life together in the first place.
So, the next time Maycember or any unexpected whirlwind in your life rolls around, remember these tools. You’ll not only keep your financial life on track, but you’ll strengthen your partnership, too.
What do you and your partner do to stay accountable? Let us know.
My friend and colleague, Colin Overweg, invited us to YouTube’s Creator Collective event in NYC. We got to interact with a room full of amazing content creators at the beautiful Edition Hotel in Times Square. Heather even got a little star struck meeting one of her favorite online personalities, Murray Hill Boy. Unfortunately, I had to tell my kids I wasn’t able to find Mr. Beast. However, we did take this wonderful pic!
TJA in the news
For CNBC, I shared my thoughts on the dangers of using options as part of your investment strategy. And for Investopedia, I weighed in on why overprotecting your wealth (being too conservative) can be a costly mistake.
Shameless plugs
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The content shared in The Joint Account does not constitute financial, legal, or any other professional advice. Readers should consult with their respective professionals for specific advice tailored to their situation.
I am retired so I am coming from a different angle. May has and will always be an expensive month. Between the ending of a school year, class trips, proms, senior day, Memorial Day, graduation and summer camps you can almost forget a budget. There is also, if you can afford it, vacation, specialized summer camps, internships, special events etc. so budgeting gets hit fast.
Do I have any recommendations? First lots of us growing up did not have summer vacations. It was only when I got older did I get vacations. This year my family will be gathering on the east coast for a celebration and family get together. Because I live very far away I will not be able to go. Plane ride, rent car, and rent place to stay. I might be able to bunk up with family, but I really need quiet time, my husband’s and dogs. Too much money, not to mention food. So I will sit this get together out.
It’s okay not to do things everyone else does. It’s ok to go to the library, an afternoon movie, grill some hamburgers and hot dogs outside. Remember marketing and advertising is meant to make you feel like you are missing out on life events. Given the current economy, household, food bills, it is fine to say, “no thanks.”
Love this take on financial consistency.
I've found quarterly meetings are ambitious—monthly 15-minute check-ins actually stick better for most couples. For me and my wife the mental shift from "budget meeting" to "future planning session" also transforms the energy completely.