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“It’s not the note you play that’s the wrong note; it’s the note you play afterwards that makes it right or wrong.” -Miles Davis

“We don’t make mistakes, just happy little accidents.” -Bob Ross

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In financial life planning, success isn’t about perfection—it’s about responding skillfully when the conversation veers off script.

Jazz pianist Herbie Hancock often tells the story of playing a completely wrong chord behind Miles Davis during a live performance. He was certain he’d ruined the song; maybe the entire show. But Miles didn’t react with panic or judgment. He simply paused, listened, and responded in a way that made Herbie’s “mistake” feel like it was exactly what they planned.

Herbie judged the mistake. Miles accepted it.

It reminds me of watching Bob Ross as a kid. Bob would never said “oops.” But he would sometimes smile and say, “Maybe we’ll put a little tree right here…” And sure enough, it looked exactly like what he wanted it to look like.

From the outside, you’d never know anything had gone wrong.

Unpredictable Client Conversations

No matter how well we prepare, we can’t fully control what unfolds in client meetings.

Sometimes, clients bring up something unexpected, something we didn’t include in the agenda. Other times, we might ask a question in a way we wish we could take back. Maybe we default to a closed-ended question. Maybe we miss an opportunity for reflection. Maybe we say something that feels a little off.

But once it’s said, it’s said.

And that moment is now part of the conversation. No amount of second-guessing changes what’s already happened.

This is where we can take inspiration from Miles and Bob. They didn’t fix mistakes. They integrated them. They worked with what was on the canvas. They responded to what actually happened, not what they wished had happened.

We can do the same in client conversations. Whether a moment felt awkward, imperfect, or just unscripted, the question becomes: What do I do now, given what’s on the table?

In this short “Sketchboard Series” video, I explore how lessons from Bob Ross and Miles Davis can help us respond skillfully when client conversations don’t go as planned.

Accepting, Adapting, and Moving Forward

Improvisers live by the principle of “Yes, and…”

They don’t fight the moment. They accept it and then build on it.

This doesn’t mean we pretend every moment is perfect. It means we treat whatever happened as real and valid. We don’t interrupt the scene by trying to deny it. We accept it and then respond in a way that moves things forward.

Whether we asked a clunky question, fumbled a reflection, or introduced a new framework awkwardly, we can choose the next best step.

Being hard on ourselves is common, especially when we’re learning new skills, like motivational interviewing, reflective listening, or life planning facilitation. But mistakes are inevitable. What matters is how we respond.

Mistakes don’t have to define the conversation. In fact, they can deepen it if we meet them with grace, curiosity, and skillful adaptation.

In this short video, I explain how accepting mistakes—like dropping your phone or asking a clunky question—can become a planning skill. It’s not about perfection; it’s about responding skillfully to what happens.

Want to Learn More?

Money Quotient trains financial professionals in the True Wealth process and helps them implement the concepts into their practices. The first step is to learn about the Fundamentals of True Wealth Planning.

References and Influences

Dalai Lama & Howard Cutler: The Art of Happiness

Gillihan, Seth: Mindful Cognitive Behavioral Therapy

Hanh, Thich Nhat: No Mud, No Lotus

Hanh, Thich Nhat: You Are Here

Hanson, Rick: Hardwiring Happiness

Hanson, Rick & Forrest Hanson: Resilient

Hanson, Rick & Richard Mendius: Buddha’s Brain

Harris, Dan: 10% Happier

Harris, Sam: Waking Up