By Ashlee Vieregger, JD, CFP®, CTFA, AEP®, Senior Lead Advisor & Shareholder, Foster Group
It’s early January and I’m already bored with the same old New Year’s resolutions, often some combination of eat better, exercise more, purge clutter, or try a new hobby. Been there, done that, and honestly, I’m lucky if it lasts until February.
Instead, let’s talk about money in 2026, especially with other women. No spreadsheets, no impulse purchase phone apps that look like a video game and promise to get our finances in order, no gimmicks.
As a financial advisor on the front lines of facilitating healthy money talk, here are my three tips for having a money conversation without feeling awkward, out of place, or intrusive. Invite a friend to coffee this month and give one of these conversation starters a try:
Ask for a story to make money talk personal.
What was the first job you ever had? How old were you? How much did you get paid? What did earning money for the first time feel like?
My first job? I worked at the local dry cleaners at age 15, where it was always sweltering (even in January!) because of the big steam presses used to iron out wrinkles. I was paid $5.25 an hour, barely more than minimum wage. At this job, I learned that I wanted to be a supervisor, because I saw my 17-year-old boss counting the cash register drawer at the end of the night and thought it was an important and interesting task. I also saw an ethical dilemma about money unfold in real time: when customers accidentally leave a couple dollars in their dirty pants pockets, what should a bunch of teenagers do with it? Integrity starts early — we stapled the cash to the customer’s invoice for them to pick up with their clean clothes.
Ask for a tactic to make money talk practical.
Tell me about how you evaluate a major purchase. How do you define “major” in dollars? What rules do you set for yourself or have together with a spouse? What exceptions have you made? Were you happy with your buy or did you have regrets?
My major purchase? Last fall, I spent months considering a big purchase, a new winter coat made of 100% wool with a price tag of several hundred dollars. At the time, I was wearing a $69 Black Friday special. Its polyester blend looked nice and professional but didn’t keep me warm when I was commuting or attending events. Once I’d sufficiently talked myself into the purchase, the first few coats I tried were disappointing: ill-fitting, an unflattering color, a scratchy fabric. Doubt crept in. When I finally found the one, I was relieved but also a little underwhelmed. The fit, color, and quality were excellent, but did it change my life? Not exactly. Of course I already knew that a really nice wool coat would not in fact solve all my minor gripes and daily frustrations. But I still love it and always wear it when it’s cold.
Ask for a reflection to make money talk purposeful.
Tell me about a big decision that seemed scary at the time. How did it affect your career and finances? How did it affect your family? What was the outcome? What did you learn?
My big decision? In college, I knew I wanted to go to law school. In law school, I knew I wanted to practice law. But in law practice, I was unfulfilled. I didn’t feel a personal connection to the work I was doing, which was mostly about sorting documents in preparation for trial. So after three years of law school, a bar exam, and two years into a fledgling legal career, I did a 180 and said yes to an entry-level role in financial advising. I had the life-changing opportunity to learn our business from a woman partner who ran her own practice. She taught me that being a great advisor isn’t just about financial acumen, data, and numbers — it’s about truly caring for people who are seeking confidence in an uncertain world. It’s about building relationships. Nearly 15 years later, I lead a team of advisors at Foster Group and we counsel multigenerational families on the financial journey of a lifetime. I’m a shareholder who participates in the success of our firm. And I’m a mentor to women advisors who are just starting their careers. Leaving the practice of law was still the biggest risk I’ve ever taken and I’ve never looked back.
Not a resolution, just a conversation.
When we’re done with coffee and our cups are empty, what do we do with the personal story, the practical tactic, the purposeful reflection? What’s our takeaway? What did we discover?
It’s surprisingly simple: we learn that money conversations are just ordinary discussions. On some level, we already know how to do this. We just need to practice. Talking about money doesn’t require a resolution, a plan, or a perfect outcome. It just requires dialogue. In 2026, let’s trade silence for conversation. One coffee. One question. One story at a time.
