Berna said it at the top of the conversation before we'd even gotten into the mechanics of savings goals or quarterly planning or any of it. She was talking about sinking funds — those separate little accounts you set aside for the car repair you know is coming, the medical bill that always shows up unannounced — and she said: if they're having a financially stable, boring moment, that is the time where you set up.
That sentence stopped me.
Not because it's complicated. Because it's so obvious that almost nobody does it. The boring moment — the month where nothing broke, the quarter where income was steady and no emergency landed on your doorstep — that's the moment most people treat as permission to breathe. To spend a little more. To stop paying attention because the balance is fine and the balance being fine feels like proof that you don't need to do anything right now.
Berna's whole argument, underneath the savings calculators and the accountability check-ins and the "never do math alone" mantra she came back to three or four times, was this: the boring moment is not a reward. It's an opening. And the people who treat it as an opening — who take the down chill moment and use it to set up future themselves — are the ones who don't panic when life lives.
That's the episode.
The year most people don't plan for until it's already here
We recorded this in December. 2025 was basically done. And Berna made the point that most people close their eyes somewhere around September and open them in January staring at their finances wondering, in her words, what goblin came in here and ruined everything.
I know that feeling, even if the scale is different than it used to be. My schedule for 2026 is already booked through April in some places — speaking engagements, events, the remodel on the house, a trip I'm planning for my wife and kids around their birthdays in March. That's not unusual for me at this point in my life. But it took years to get to a place where I plan that far ahead without it feeling abstract.
In sports, the planning horizon is a week. You're preparing for Sunday. Everything past Sunday is theoretical. And there's a version of that mindset that stays with athletes long after they stop playing — the sense that the present is where the urgency lives and the future will figure itself out. It doesn't. The future is just a long series of present moments that you either prepared for or didn't.
Berna's framework for people who find the full year overwhelming: use a quarter. Break it down to Q1. Sketch where the big financial moments are landing — the trip, the wedding, the medical thing you've been putting off, the tax bill from the year before. Just get it on paper. The year stops being a wall and starts being four smaller walls, and smaller walls are climbable.
Never do math alone — and the Avengers aren't optional
Berna has a phrase she uses with her co-founder: never do math alone. She said it like a warning. Like the math itself is fine but the aloneness is the danger.
I think she's right, and I think it applies further than most people are willing to admit.
My accountant, Ms. Lonnie, has been with me for over a decade. I had a call with her the morning of this recording. Not because there was a crisis — because that's how often we're in communication. Quarterly at minimum, monthly in practice, and the day something changes I'm on the phone. I've got Matt building spreadsheets for the rental property my wife and I were just looking at — which banks, what rates, what variables matter — and Todd in the mix for other pieces. These are not luxury additions to my financial life. They are the infrastructure without which I'd be making expensive decisions with incomplete information.
Berna made the point that if you're first-generation — if nobody in your family modeled what a financial team even looks like — you start with two people: an accountant and a financial planner. Not ten people. Two. Someone who sees the tax picture and someone who sees the whole picture. That's the foundation.
What I'd add: get them before you need them. I sat in cash for two years early in my career — 2010 to 2012 — because I didn't understand what I was being offered to invest in and I didn't yet have the right team to translate it for me. The market ran without me. The opportunity cost on that decision alone is a number I don't say out loud. I wasn't lazy. I wasn't reckless. I just didn't have the right infrastructure in place at the moment when I needed it most.
The financial Avengers aren't a nice-to-have. They're the reason you don't make the decision you'll spend a decade undoing.
PULL QUOTE: "Never do math alone. It's dangerous. No lifeguard on duty." — Berna Annette
The savings goal nobody builds until after the emergency
The practical center of this conversation was sinking funds, and I want to spend time on it because it's the piece most people skip.
A sinking fund is a separate savings account — or just a named bucket inside your savings — for a specific thing you know is coming but can't schedule. Car repairs. A home emergency. Medical stuff. Not the big retirement account. Not the vacation fund. The money that covers you when the raccoon gets in the wall — Berna's example, which I'm still thinking about — and you need to act without blowing up everything else you've been building.
Most people's financial plan has no sinking funds. It has a main account, maybe a savings account they're trying not to touch, and then a credit card for the emergencies. So when the emergency comes — and it always comes — they go to the card, the card charges 20%, and now they're paying interest on a problem they didn't create on a timeline they can't control.
The fix isn't dramatic. It's a boring month, used right. One month where you're not in crisis, you're not behind on anything, the balance is fine — and instead of treating that as a signal to relax, you move money into the car fund and the home fund and the medical fund and you do it automatically so you don't have to decide again next month.
Berna's word for this, the one I want to land: setup. You are not saving in the boring moment. You are setting up for future you. Future you has the same emergencies present you has. Future you just either has the infrastructure to handle them quietly or doesn't.
The pendulum, and finding the middle
Berna asked me at the end about my financial goals for 2025, and I told her something I haven't said publicly that much: I retired close to $10 million in debt this year.
Some context. My dad taught me early — be careful with debt. And so early in my career I bought almost everything in cash. That was its own kind of overcorrection, because there's a version of leverage that's healthy, that's how businesses grow and how real estate builds wealth. I understood that eventually and started using debt strategically. But I got close to over-indexed on the debt side. Not reckless — but close enough that 2025 became what I'd call a hammer year. Hammer it down. Reduce what doesn't need to be there. Debt-to-income back in range.
Berna put it better than I did: you swung the pendulum this way because Dad taught you, and this way because you had access to money, and now you're finding the middle. That's exactly right. The middle is where you can actually operate. Not allergic to leverage, not cavalier about it either. Using debt as a tool for growth and getting rid of debt that's just weight.
My wife was a huge part of working through that, and she'll probably have to listen to this podcast to hear me say it. So. There it is.
What actually to do before January gets here
Three things, in the order I'd actually do them:
- Sketch the year before December 31st. Not a budget. Not a spreadsheet. A sketch — on paper, in your phone notes, wherever — of the big financial moments you can already see coming. The wedding you're in. The medical appointment you've been putting off. The car that has 90,000 miles on it. The trip you promised yourself. Just get them visible. Once they're visible, they stop being surprises and start being line items. Berna's point about the quarters is useful here: you don't have to see the whole year. See Q1 clearly, have a rough shape for Q2, and revisit it then. The goal isn't a perfect plan. The goal is not opening your eyes in January wondering what happened.
- Find one boring month in Q1 and put it to work. Not the month after the holiday spending. Not the month you get the tax bill. The month where things settle — find it in advance, mark it, and move money into whatever sinking fund you don't have yet. The car fund if there's no car fund. The home fund if there's no home fund. Even a small number — $500, $1,000 — changes the psychology of the next emergency from how do I cover this to this is what the fund is for. That shift is worth more than the dollar amount.
- Call the tax professional before the fiscal year closes. Berna made this point and I'll make it again because she's right: December is one of the best times to catch your CPA, right after the second wave of tax season, and ask them one simple question — what do I need to know or lock down before December 31st? 401(k) contributions, rollovers, anything you've been meaning to sort out. If you've got overseas income or K-1s or multiple business entities, this call isn't optional. Ms. Lonnie has saved me from problems I didn't know I had because we had this conversation in November, not in April. The tax year ends whether you're paying attention or not.
The boring moment is coming. The question is what you do when it arrives.