My 20-year-old son doesn’t shy away from asking about money. He’s been curious since he could talk, always the kid with a thousand questions. He wants to know about the mortgage, how much we owe, what I earn, and why I invest in angel deals, private companies, or public markets.

Recently, after haircuts and over breakfast at my favorite Waffle House in Lemay, MO, he even asked how much equity I hold in the bank I lead and what kind of investment it takes to sit on corporate boards.

At his age, I didn’t just not have those conversations, I didn’t have anyone to ask. Money felt abstract to me, like a concept that existed in other people’s worlds but didn’t fully connect to my own. The few times it came up were during life skills courses I took in foster care. Even then, it felt distant, like reading a manual for a tool I’d never held.

I recently came across a stat that floored me, over 60% of people avoid talking about money with family, friends, or their spouse. That hit home. I thought back to my fundraising days, theology school and working with clergy early in my career. It struck me that even clergy, people trained to guide others through life’s most personal and painful moments, often aren’t equipped to have honest conversations about money.

Why is that?

Money is as essential as air and water. It’s the infrastructure of our lives, the roads we drive on, the electricity that powers our homes, and the pipes that keep everything flowing. Yet, we treat it like a secret, something to avoid, even as it shapes nearly every part of life.

I’ve decided that won’t be the case in my house.

I regularly talk to my kids about what I call the Treasures and Traps of Money.

• Impulsive Spending – Letting emotions drive purchases instead of planning.
• Debt without Strategy – Borrowing without a plan or understanding the long-term cost.
• Comparison Culture – Measuring success by someone else’s life, leading to unnecessary spending.
• Short-Term Thinking – Prioritizing instant gratification over long-term growth, missing out on compounding wealth.

I remind them: Money isn’t something to hoard, it’s something to manage, grow, and share. It’s not about chasing more, it’s about making intentional choices that shape the life you want.

But none of that happens without conversation.

Why Don’t We Talk About It?

I believe we avoid money conversations because we often tie finances to self-worth. When things are good, we feel validated. When they’re not, we feel shame.

But here’s the truth: Money is not your identity, it’s a resource.

The more we learn to manage it, the less power it holds over us.

3 Simple Ways to Start Talking About Money (Without the Awkwardness):

1. Be Open About Your Journey – You don’t need all the answers. Sharing your wins and lessons makes the topic relatable and real.
2. Start Small – Ask questions within your network like, “What’s one thing you wish you learned about money earlier?” or “What’s a financial habit you’re proud of?”
3. Frame Money as a Tool, Not a Taboo – Money isn’t the goal; it’s a means to build security and create opportunities. Focus on what’s possible, not what’s limiting.

So, when was the last time you had an honest conversation about money?

Maybe today’s the day to start.

P.S.

It’s interesting, as The Accidental Banker, I’ve noticed that one of the biggest challenges small businesses face isn’t necessarily competition or market demand, it’s managing the money. Many of us didn’t have those money conversations growing up, and that often carries over when we start businesses. Accounting, cash flow, and financial planning can feel just as abstract as personal finance did when we were younger. The good news? It’s never too late to learn, and the best place to start is by talking about it.

#FinancialWellness #MoneyMindset #GenerationalWealth #FinancialLiteracy #LeadWithConfidence #theaccidentalbanker