From Worst-in-class to Best-in-Class: Perseverance, Humility, and the Entrepreneurial Journey

Entrepreneurship is hard. The bigger your ambition, the harder it is. The harder it is, the more inevitable it is that you’ll fail along the way. The difference between companies that thrive and companies that die is not in whether they fail along the way; it’s whether they persevere through that failure. But perseverance alone is not enough: we also need the humility to face the weaknesses that cause those failures.

Failure isn’t the opposite of success; it’s imperative to it. If we let it, failure can humble us enough to start listening.

People have earnestly said to me, “It looks like Asana’s road to success has been such smooth sailing.” Ha. When Asana first launched its iOS app, it had a 1.5-star rating in the App Store. Some of the reviews are still seared into my memory: “Frankly, horrible.” "Terrible, TERRIBLE app.” “If I could give it a zero..." "Worst app I've ever used.” And my personal favorite: “Makes me want to stab my eyes out."

Yup. Smoooth sailing.

It didn’t feel good to read those, but we also felt genuinely grateful for the honest feedback. When people tell us what isn’t working, if we really listen, it clues us into what we can change. Criticism points the way to success. Failure is an opportunity to transmute something clumsy and ineffective into something intuitive and powerful.

We stuck with it but in a new direction. User complaints about the app’s speed helped us recognize we’d made poor engineering choices, so we rewrote the entire app from scratch. Usability complaints gave us insight into redesigning the interface. 

It’s been only four years since “frankly, horrible,” but 124 versions later, Asana’s app has a 4.7-star rating in the App Store, with reviews like, "Life Changer. I've never had a single program make such a positive effect on my company” and "I have used the app for 5 years now, and it just keeps getting better.” Recently, Apple named Asana the App of the Day out of over two million apps.

Perseverance was critical, but insufficient on its own. We could have charged ahead on making an app that made users want to stab their eyes out, but we would have persevered to failure. Just as critical was having the humility to see that our customers were right about all the ways the app wasn’t good enough.

This is at the heart of the entrepreneurial journey (and perhaps the human journey): We can (and often do) start off worst-in-class at something, but if we have the humility to recognize what we’re doing poorly, and we can bypass our egos to look our problems in the eye, we’ll find the keys to our success staring back. From there, we persevere - one day, one task at a time, improving, iterating, and polishing, until we find ourselves graduated from worst-in-class to best-in-class.

Read more from Justin Rosenstein and his global collaboration initiative One Project.