Financial Planning

At the end of the first article in this series, I suggested that the first step in understanding your money script is simply noticing when it appears. That idea sounds straightforward on the surface, but in practice, money scripts rarely announce themselves in a clear or obvious way.

Nobody walks into my office and says, “My tendency toward money vigilance is creating an emotional barrier to retirement spending.” That would definitely make the meeting efficient and frankly, a little unsettling, but it is not usually how these conversations begin. Instead, someone says they need to keep another $500,000 in cash, or that they want to work one more year, or that the family vacation feels too expensive even though the financial plan comfortably supports it. They may explain that they cannot sell a concentrated investment because it has always done well, or that they need to help an adult child one more time.

Lizy and I have a very simple pattern when it comes to home projects.

We usually start with something reasonable. A contained idea. A project that feels like it should fit neatly into a category called “adult decisions we can handle easily.”

Right now, that project is our downstairs bathroom.

At first, it stayed in its lane. We talked about finishes, layout, and what it would take to make the space feel more current and functional. It felt focused and straightforward. Then, as home projects tend to do, the conversation widened.

At the end of the first article in this series, I suggested that the first step in understanding your money script is simply noticing when it appears. That idea sounds straightforward on the surface, but in practice, money scripts rarely announce themselves in a clear or obvious way.

Nobody walks into my office and says, “My tendency toward money vigilance is creating an emotional barrier to retirement spending.” That would definitely make the meeting efficient and frankly, a little unsettling, but it is not usually how these conversations begin. Instead, someone says they need to keep another $500,000 in cash, or that they want to work one more year, or that the family vacation feels too expensive even though the financial plan comfortably supports it. They may explain that they cannot sell a concentrated investment because it has always done well, or that they need to help an adult child one more time.

A few years ago, I started with a couple who had done almost everything right.

They had built successful careers, saved consistently, avoided unnecessary debt, and accumulated a portfolio that most people would consider more than enough for a comfortable retirement. When we reviewed their financial plan, the numbers were clear: they could retire whenever they wanted.

One spouse leaned back in their chair and said, “So… we’re done? We can actually do this?”

We would have loved to stay where we were. It was familiar, comfortable, and already felt like home. But once we started looking honestly at the space, the layout, and everything that comes with adding a child to the equation, it became pretty clear that making it work long term was going to be difficult. Babies may be small, but they come with an impressive amount of furniture, equipment, laundry, and general logistical chaos.

There is a point in nearly every retirement planning conversation when someone reaches an inflection point.

For years, the questions are comfortably theoretical. Am I saving enough? Should I contribute more to my 401(k)? At what age could I reasonably retire? Retirement sits somewhere in the distance, safely tucked behind several more performance reviews, tax returns, and company holiday parties.

Then one day, the question bubbles up because something at work happens, our health changes, or we’re just flat out ready for a change.

“Could I actually give notice?”