Rebecca, thanks for joining us, excited to have you contributing your stories and insights. One of the toughest things about progressing in your career is that there are almost always unexpected problems that come up – problems that you often can’t read about in advance, can’t prepare for, etc. Have you had such and experience and if so, can you tell us the story of one of those unexpected problems you’ve encountered?

I’ll give you a real answer—not a polished one.

One of the most unexpected problems I’ve faced wasn’t a market event, and it wasn’t a bad investment. It was a breakdown in trust with a client when I thought everything was going fine.

That’s the part that catches you off guard. You think you’re doing good work, you think the strategy is sound, and then suddenly the client feels unsupported, confused, or even frustrated—and you didn’t see it coming soon enough.

I remember a situation where I had built out what I genuinely believed was a strong plan. It had tax strategy, long-term positioning, protection—everything I would have done for my own family. And then something went sideways in execution. Communication wasn’t as tight as it should have been, pieces were handed off, timelines stretched, and the client started to feel like they were being managed instead of cared for.

And when that feedback hit, it didn’t feel like “oh, we just need to tweak something.”
It felt personal.

Because when you take pride in your work, and especially when your work is tied to people’s money and their lives, that kind of disconnect stings. There’s a moment where your instinct is to defend—explain the strategy, justify the decisions, point to everything that is working.

But that’s the wrong move.

What I had to do instead—and this was the lesson—was stop explaining and start listening. Really listening, not just waiting for my turn to respond. I had to step back and ask, “Where did the experience break down for them?” not “Where was I right?”

From there, the resolution wasn’t complicated, but it required ownership. I tightened communication, pulled things back under my direct oversight, simplified how we were presenting information, and made sure they felt the consistency they should have had from the beginning.

And here’s the part people don’t always say out loud—sometimes you don’t get to fix it perfectly. Sometimes the best you can do is show up, take responsibility, and do better moving forward.

What that experience changed for me is how I think about my role. It’s not just about building a technically correct plan. It’s about making sure the client feels clarity and confidence the entire way through.

Because you can be right on paper and still fail the relationship.

And in this business, the relationship is the business.