In between red and blue

When confidence fades

I was developing a B2B service for real estate owners—essentially a customer support ticketing system. The idea was to offer renters one channel to contact building managers for any issues or service requests, allowing them to track the status of their tickets. At that time, this was still a novelty. People were used to calling or sending emails, which caused delays, miscommunication, and repeated interactions for the same issues.

What started as a clear solution to an obvious problem gradually morphed into a crisis of confidence. I found myself trapped by perfectionism and a tendency to over-analyze everything—a clear sign of procrastination stemming from low confidence. Although I understood the problem and had developed a solution, I began comparing myself with similar services, which further eroded my confidence.

The symptoms were classic: endlessly tinkering with code to optimize performance, redesigning sketches while looking for “inspiration” from other market players, and compiling ever-growing lists of features that “must” be developed before the initial release. I wanted to leave everything behind and commit to abandoning the idea by proving it wouldn’t work, freeing myself to pursue other endeavors.

Flipping the script

I wanted to convince myself with logical reasoning and facts that continuing would only make me lose more time and money. In a way, I had been heavily influenced by the sunk cost fallacy while also trying to turn opportunity cost in my favor.

I began acting as a devil’s advocate, deliberately looking for ways to poke holes in everything I had created—market size, customer profiles, business models, cost and profit structures—everything I had researched and planned. I found articles and case studies on other businesses with similar ideas, searching for opposite facts to convince myself to walk away.

But something unexpected happened. The more time I spent trying to disprove my idea, the more I noticed additional opportunities to improve it. The bad, frustrating idea started to shine again, but with new qualities.

Unexpected discoveries

This emotional reaction to my frustration yielded several important lessons:

Looking at the problem from the opposite direction gave me insights I had never considered before. I realized I needed to actually pay attention to users—I had been operating under the assumption that I needed to figure everything out myself and protect the idea. By studying how other small developers billed and funded ongoing developments, I learned the importance of finding the first subscriber early and continuing development based on real feedback.

I gained awareness of my tendency to immerse myself in extended periods of thinking and analyzing, which eventually led to analysis paralysis. This helped me develop tactics to cope with these tendencies and push myself to deliver.

Most importantly, I learned the value of involving customers in the development process. This led me to take my first steps toward user experience design, talking with real estate managers and renters about their actual needs.

My plan to convince myself to abandon the project had failed miserably—in the best possible way. I published the service in 2008, and it generated substantial passive income for years.

The power of inversion

This experience connected deeply with the concept of inversion described by Shane Parrish in “The Great Mental Models”:

“There are two approaches to applying inversion in your life. Start by assuming that what you’re trying to prove is either true or false, then show what else would have to be true. Instead of aiming directly for your goal, think deeply about what you want to avoid and then see what options are left over.”¹

The emotional journey was significant. I felt highly relieved to find a way forward, surprised that I hadn’t thought to look for this information earlier, and saddened by the wasted time and effort. Yet I accepted this as the price for a hard-learned lesson. There was still fear about the resources needed to meet my ambitions, but the renewed clarity made moving forward possible.

How to use inversion thinking in your decision-making

In many decisions since, I remind myself of Charlie Munger’s wisdom about inversion. For important choices, I now deliberately use structured approaches like:

1. Backcasting - Imagining future success and looking backward to identify the necessary steps
2. Premortems - Imagining future failure and examining potential causes before they happen
3. Devil’s advocate - Deliberately arguing against my preferred option to find weaknesses

These exercises from Annie Duke’s “How to Decide” help me channel my analysis productively and conclude with clear decisions.²

The concept of looking at problems from the opposite side had been an abstraction before, but through practical application, I understood how to use it effectively. This experience later inspired my approach to game theory in leadership, identifying both the ultimate goal and what must be avoided to prevent blocking future movement.

Try inversion yourself

Looking at things upside down and in reverse is a surprisingly effective way to move forward. The concept is deceptively simple to explain, often difficult to remember in times of need, but remarkably powerful when applied. Thinking backward uncovers hidden insights and opportunities that might otherwise remain invisible.

• Instead of asking “How can I succeed?”, ask “How could I fail spectacularly?”
• Instead than focusing on what to do, consider what you should absolutely avoid
• When evaluating options, first eliminate what definitely won’t work
• For important decisions, imagine looking back a year later on a failure—what caused it?

As Charlie Munger wisely noted, “It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent.”