What I Got Wrong About Helping People in 1994
I came into financial services in 1994 at Edward Jones with thirty-some years of life already behind me, including years as a minister in rural Missouri. I was not a fresh-faced kid who'd just discovered compound interest. I thought I understood people. I thought that was my edge. And in the ways that mattered most, I was right. But I was also carrying a blind spot big enough to drive a tractor through, and it took me years to see it clearly.
My blind spot was this: I believed that helping someone meant giving them the right answer. In ministry, you counsel someone through grief and you point them toward hope. There's a right word for the moment, and you've been trained to find it. I carried that instinct straight into my first client meetings. Someone would sit down across from me and describe their financial situation, and I'd be halfway to a solution before they'd finished their second sentence. I was listening for the facts, not for the person.
It wasn't until I left Edward Jones for a more entrepreneurial setting, and eventually founded my own fee-based firm in Springfield in the late 1990s, that the problem became impossible to ignore. When you work for yourself and your clients can walk out the door at any time, you get honest feedback fast. What I kept hearing, in different words from different people, was some version of this: I don't feel like you understand what I actually want. They weren't wrong.
The shift started with a question I began asking in client meetings, almost as an experiment. Instead of opening with numbers, I'd ask them to describe what their ideal retirement looked like. Not the account balance. Not the age they wanted to stop working. The actual picture. What would a Tuesday afternoon look like? Who would be in it? A dentist I worked with years later told me about a deep love for restoring old cars. That detail changed everything about how we built his plan. If I'd been in solution mode from minute one, I never would have heard it.
Here's what that taught me about the difference between information and understanding. Information is what someone tells you when they think they're supposed to give you data. Understanding is what surfaces when they feel safe enough to tell you what they actually want. The financial industry has spent decades training people to walk into an advisor's office with their guard up, expecting to be sold something. I started telling clients to leave their checkbook at home. Just bring your dreams, I'd say. That single instruction changed the temperature of every first meeting.
The other thing I got wrong early on was underestimating how much fear was sitting in the room. Not fear of markets. Fear of the unknown, of making an irreversible mistake, of a government agency showing up and telling them they'd done it wrong. Tax questions especially. When I began teaching retirement planning classes at the local university and later presenting to CPAs and other professionals, I saw the same frozen look over and over. People didn't just misunderstand tax strategy. They were afraid of the subject itself. My job wasn't to be smarter than the tax code. It was to make the tax code feel like something a person could actually use in their favor, because it is.
Thirty-three years in, I still think about that minister who moved to Springfield convinced he already knew how to help people. He was useful. But he was also a little too certain he knew what you needed before you told him. The version of me sitting across from clients today asks more questions and talks less in the first meeting. I've learned that the depth of the questions you ask says more about your commitment to a client than the sophistication of the strategies you eventually recommend. That's a lesson I wish I'd learned in 1994 instead of earning it the hard way over the decade that followed. But then again, the lessons you earn usually stick better than the ones you're handed.
If you want to understand how that listening-first philosophy shapes the actual planning work we do today at WealthCare, the about page lays it out. And if you're curious about the tax and retirement strategies we build around what clients actually tell us they want, I'd welcome the conversation. You can reach us here.