Writing The Lobster League: A Roadmap to Clearer Financial Decisions

For most of my career as a financial advisor, I’ve been just as interested in how people make financial decisions as I have in the decisions themselves. That curiosity ultimately led me to write The Lobster League, a short parable designed to help people see the hidden psychological forces shaping their financial choices and, more importantly, how to make clearer, more intentional decisions.

This book isn’t meant to turn readers into experts in behavioral finance, but instead, to bring awareness to our everyday actions. It’s about understanding why smart, well-intentioned people often feel stuck, conflicted, or uncertain when it comes to money. I want to share the story behind The Lobster League, why I wrote it, how the process unfolded, and what I hope readers take away from it.

Years Ago, I Noticed Gaps in How We Make Financial Decisions

Early in my career, I observed something that confused me. When I focused heavily on risks, fees, and downside scenarios, people were often more inclined to move forward. When I focused on benefits or clearly explained why a particular strategy made sense, I sometimes received more pushback. And when conversations centered on long-term goals, people often became overwhelmed or paralyzed.

As far back as the 1990s, I began noticing a consistent disconnect between what people said they wanted to accomplish, what was being recommended to them, and what they actually did. Those experiences made me step back and ask a simple but powerful question: why is there such a consistent gap between intention and action when it comes to money?

That question eventually led me to behavioral finance and behavioral economics. I began to see that financial decisions are rarely just about numbers. They’re deeply influenced by emotion, fear, social pressure, and mental shortcuts that operate quietly in the background. Quiet, subtle influences that many people don’t even know exist.

The dot-com bubble was a vivid real-world example of this. Companies were trading at huge, unfounded valuations simply based on social momentum. Investors weren’t carefully analyzing fundamentals. Instead, they were responding to herding behavior and confirmation bias. Watching that unfold globally reinforced what I was seeing in everyday client conversations.

I Kept Track of Examples of This Disconnect

Around 2013, I began writing down examples of the cognitive biases I saw repeating themselves over and over again. These patterns showed up regardless of age, gender, or level of wealth. Clients would have vastly different circumstances but rely on the same mental shortcuts.

At the same time, the financial services industry was placing greater emphasis on understanding behavior. Advisors were being trained not just in technical expertise, but in how the brain influences financial decision-making. That shift validated what I had been observing for years.

One book that helped crystallize this perspective for me was Thinking, Fast and Slow by Daniel Kahneman. His description of two modes of thinking, one fast and emotional, the other slow and logical, mirrored what I saw play out in financial decisions every day.

What Made Me Finally Put Pen to Paper

The outline of the book probably started about a decade ago in some form or another, some written, some in my head. After more than 30 years of working closely with people and their finances, I reflected on my experiences and realized I had a message that everyone could learn from.

The brain is incredibly efficient, but that efficiency comes at a cost. We oversimplify complex decisions, rely on mental shortcuts, and let fear or optimism take the wheel without realizing it. Everyone does this. It’s the fundamental way the brain works, and there’s no getting around that, so it’s crucial for people to understand the power that these forces have in affecting their decisions and therefore the quality of their lives. If we’re unaware of these forces, they can quietly steer our decisions away from what we truly want.

I gained clarity about the format of the book while preparing a 30-minute talk on the most important lessons I had learned as a financial advisor. I reviewed every area of my work, from investing to insurance to estate planning, and asked myself what information would be most impactful for people long term. The answer kept coming back to decision-making itself.

I feel this is the most impactful area I can speak on out of everything that I'm an expert in, and I wanted to share knowledge that I hope lasts beyond my time on this earth.

Why a Parable?

I wanted The Lobster League to feel different. I wanted to design the book in a way that was an easy, enjoyable, entertaining read while also teaching invaluable lessons and conveying what I believe to be some of the most important knowledge and experience I have.

I have read many books that explain financial concepts clearly and accurately, but they’re not always enjoyable to read. A parable allows people to see themselves in the story without feeling lectured. When you observe characters making decisions, it becomes easier to recognize similar cognitive patterns in your own life and the lives of people around you.

I was also inspired by books like The Energy Bus by Jon Gordon, which uses storytelling to convey meaningful lessons in an accessible way. My goal was to create something that could be read shortly, understood easily, and still leave a lasting impression.

The Writing and Publishing Process

The writing process took about 2-2 ½ years from initial draft to completion. Early versions of the book included more than two dozen scenarios I commonly see in real life. Over time, I refined and simplified.

The structure evolved significantly. The original draft used one-on-one conversations between several different individuals and the main character, who was inspired by a wonderful, caring, and honest late aunt of mine, as a vehicle to get my points across. But when I was partway through the draft, I realized during a small group discussion at my church that an intimate group setting created the kind of openness and honesty I wanted to capture.

At the same time, it became clear that the main character needed to be an expert who could help unpack what was happening beneath the surface. That is how Alan, a financial advisor, came to be the central figure. Making those changes required rewriting a large portion of the book, but it ultimately made the message stronger. I could’ve added another 7-10 important concepts I had in mind, but my priority was keeping the book easy, fun, and able to be read in one sitting, rather than being lengthy and potentially a grind to get through like some technical books.

Publishing itself was a learning experience. Writing the book was a challenge, but getting it printed and published was another hurdle I didn’t expect. You need people to edit, typeset, design a cover, format the cover to the right size, format the typeset to the right size, pick the font type, and choose the font size. These things took more effort than I had any clue about. I’m happy I reached out to a publisher and didn’t fully self-publish. The one part that came easily was the cover, thanks to the wonderful creativity of my dear friends Lewis and Kathy Cahill.

The Lobster League’s Main Takeaways

The goal of The Lobster League isn’t to make people experts in these concepts of behavioral finance or even learn the terminology. The idea is to plant a seed of curiosity and introspection, and introduce people to the forces that influence their financial decisions.

I want readers to be aware of biases, notice them in other people, and then apply the lessons from the book to their own lives in order to be more introspective. I want them to pause and ask why they’re making a particular decision. You have to be cognizant of when the prehistoric brain steps in and takes over logic, because it’s so quick and subtle.

After 30 years, and out of all the different topics I could write on, this is the most important information I could give back and help people be aware of. I feel this topic is very important to share widely, and could help many live more fulfilled lives. If someone reads the book and thinks, “this is what this expert felt mattered the most for me to know,” then I have accomplished what I set out to do.

Rational Finance: A Strategy for Clearer Decision-Making

My experiences observing decision-making are what led to the development of our Rational Finance approach at PFW Advisors. It focuses on aligning people's desires, fears, and goals with their financial decisions, and closing the disconnect between what they say they want and what they actually want.

In my practice, I want clients to understand the “why” behind their choices. “Why am I investing? Why am I not investing? What am I accomplishing or not accomplishing with these decisions?” Those questions go back to what you really want out of life and what you want to avoid. What you want or don’t want should be the first part of your decision-making process. When decisions are rooted in clarity around values, fears, and goals, they become far more aligned and sustainable.

If you are interested in gaining a new perspective on financial decisions, not just what to do, but why you do it, I hope you will read The Lobster League. My aim is simple: to help people think more clearly, act more intentionally, and ultimately live more fulfilled lives.

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