You’re Probably Working on a Doomed Project

And That’s Okay

Years ago, I worked for a boss who was substantially more senior than me. I was in my early 30s and he was in his late 50s. He’d been around, worked at lots of companies, and had become wise in the ways of corporations and technology.

We were working on a doomed project at the time. Everyone on our team knew it. The tech didn’t work, sales couldn’t sell what did work, and office politics were tearing the team apart. The constant topic of conversation in hushed 1:1 meetings was how long the business would keep funding what seemed to obviously be a losing bet.

This situation was pretty challenging for me. I’ve always struggled with internalizing failure. From a very young age, if something went wrong, I assumed it was because of something I had done. When things went right, I assumed it was due to someone else or something else. Neurotic? Yes. Difficult to rewire my brain? Also yes. 

This tendency to internalize failure had inevitably spilled over into my career. Here I was, almost a decade into my career, and it felt like none of my products had been super successful. I had begun to wonder if perhaps I was the weak link.

The Revelation

But over lunch one day, I decided to ask my boss about success in his own career. “How many times have you worked on a team that functioned well, with technology that worked, in a market that actually wanted what you were building?”

He paused, introspected, and then in a nonchalant way said “twice.” He then took another bite of his lunch as if this answer was to be expected and didn’t warrant further discussion.

I was shocked. This guy’s LinkedIn page looked like a who’s who list of the best-known tech companies of all time. And he hadn’t just been a random employee at these places: he had worked on some really important products and technologies. And here he was admitting that in 35+ years across dozens of companies, product launches, teams, managers, and tech stacks, the stars had only ever really aligned for him twice.

That lunch was a sobering reality check. Up to that point, I had assumed my undignified tenure in the tech industry was abnormal. I was sure that everyone else was working with cutting-edge tech, supportive and highly-skilled coworkers, in a fast-growing vertical. 

A Reality Check

But if you step back, that definitionally can’t be the case. Companies don’t pay people to work on solved problems where things are already going well. They pay people to solve new problems, and solving new problems is highly prone to failure. If there was no risk, you wouldn’t be paid. 

So, if your project is failing and your team is dysfunctional and the market doesn’t want what you’re building, just remember: what you’re experiencing is the norm. And it’s almost certainly not your fault. Hopefully, this realization will even make you more effective. Whereas previously every little dysfunction and failure might have been painful to behold, you can now simply expect them. And, when something goes right, a launch is marginally successful, or a coworker acts like an adult, you can think “wow, that exceeds my expectations!”