Michael Rispoli

August 28, 2025

The worst kind of failure looks like success

"I'd rather be cancelled than irrelevant..." I said to my co-founder Justin in frustration. We had been at the social media game for our software business with barely any success for over a year. Posting every day, newsletters, podcasts, videos, nothing seemed to be resonating with the audience.

Software has two particular kinds of failure, catastrophic and intermittent. Catastrophic failures great for software engineers. Why? Because they are easy to debug. A change gets pushed, the app or feature is bricked. Failure happens the same way every time for everyone. You know exactly where to look and how to begin fixing it. Contrast this with the classic intermittent bug. These are the bugs that happen for one person, intermittently, and are impossible to reproduce with consistency. The classic works on my machine bug. It's impossible to know how many people are experiencing it and what the far reaching effects are. But most of the time, the software works fine, so we live with it.

What Justin and I were experiencing in marketing wasn't a catastrophic failure though. Impressions were increasing gradually, we'd get a few more likes and followers ever week, but this wasn't translating into leads and sales like we wanted. We had enough success to tell ourselves if we just kept at this long enough it would work but not a clear enough failure to make the change in direction we needed. This is what failure in disguise looks like and it's the worst kind of failure you can experience.

Failure in disguise distracts you from changing to a direction that would produce the results you want. It gives you just enough signal to stay on the cursed path. AI driven coding can do this as well. You prompt the machine and  it produces results that are almost perfect. So you issue another prompt and then another and another. You end up stuck at that almost success place for an hour but can't see if you blew it all up and tried again you'd have the result you wanted in ten minutes.

It sounds a lot like the sunk cost fallacy, except you don't feel like you're sinking costs. You're uncertain if this is as good as it gets. It's the almost good relationship you stay in for too long.

It's the I love you but I'm not in love with you. 

It's internal bleeding. 

It's going down like the Hindenburg.

It's should I stay or should I go now.

It's failure disguised as success and what you want is to drop out of the sky like a lead zeppelin. Why?

So you know it's time to pivot.

Best,

Michael Rispoli
Co-founder and CTO at Cause of a Kind