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

What that frustration produced:

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 recognized my tendency to disappear into thinking and analyzing until I could no longer act. Seeing the pattern helped me develop tactics to break out of it and deliver.

I also learned to involve 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

Years later, I found the concept described precisely 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 weight was real. Relief at finding a way forward. Surprise that I hadn’t looked for this information earlier. Sadness at the wasted time. I accepted it as the price for a lesson I would use for years. There was still fear about the resources needed to meet my ambitions, but the renewed clarity made moving forward possible.

Inversion in practice

In many decisions since, I have used structured versions of the same instinct. Backcasting: imagining future success and working backward to identify the necessary steps. Premortems: imagining future failure and examining the causes before they happen. Devil’s advocate: arguing against my preferred option to find its weaknesses. Annie Duke describes these in “How to Decide” – each one is a form of inversion applied to a specific decision point.²

The concept had been an abstraction until I used it under pressure. That experience later shaped my approach to game theory in leadership – mapping both what to pursue and what to avoid.

Try inversion yourself

Looking at things in reverse is an effective way to move forward. Simple to explain, hard to remember when you need it most.

• Instead of asking “How can I succeed?”, ask “How could I fail spectacularly?”
• Instead of 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 put it: “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.”