Learning to fail and failing to learn
In the world of startups, it’s good to fail.
Not only is it good, but it’s also something that most founders are (and should be) be proud of. Growing up in India, this wasn’t a common notion, so I thought I’d write a bit more about how my perspective has evolved over time on the topic of failing.
The education system and culture in most countries don’t encourage you to fail. Passing and doing things right becomes synonymous with ‘success’ and failing comes with a series of negative connotations. We get trained to avoid failure and the negative consequences that come with it.
However, I now strongly believe that failure is a sign of progress, learning, and a necessary step to find success in our endeavours.
Shifting perspective
After working on multiple startups over the last 6 years — my perspective on failure has shifted from that of avoidance to one full of excitement.
Failure is celebrated in the startup world because it’s often a pre-requisite to finding success. The faster you fail with a new idea, the faster you can move on to the next iteration of the same (or different idea). The more you fail, the more reps you’re putting in and the more you learn each time. The more reps you put in, the bigger your surface area to find success. Most startups go through tons of iterations (failures) before they land on a product or solution that finally clicks. In fact, the velocity at which startups fail with new experiments is a strong indicator of their ability to find success.
Failing is a form of progress. Let’s say you’re learning how to throw a dart. You’re much more likely to get a bull’s eye by trying and failing 1000 times than trying to get it 100% right on your first try. By getting in those reps, we learn what not to do when throwing a dart, which then helps us practice and reinforce the positive actions that do increase our chances of being on target. 🎯
Failing is required for learning. I learned this through chess – the more I fail at at chess games and lose, the more opportunities I have to reflect on what led to the loss and how I could improve in the next game. When OpenAI was training AI models to play complex games like Dota 2, they found success by letting the AI ‘self-play’ — i.e., letting it play games against itself and having it learn through failure. The AI lost the game enough times to then develop an understanding of the small steps it can take to increase the probability of wining the game. Eventually (and relatively quickly), this AI proceeded to beat the world’s best Dota 2 teams swiftly.
Failure is positive. This is where I most often feel the difference in perspectives — when talking to people about failures. Conventionally, failure is looked at as something that could have been avoided. “If only I did X, then I wouldn’t have failed at Y.” It’s seen as the cost of missing an alternative opportunity, path, or outcome. However, failure is not the cost of missing out on opportunities, it’s the cost of learning and making progress.
Whatever you are pursuing, the more you fail at it and learn from it, the more you will find success in it.
I’ve learned of at least two types of failure so far — ones which you quickly ignore/move past and ones that you intentionally learn from. The latter is required to apply the positive benefits of failing. When experiencing failure, breaking down why it happened + reflecting on what might have caused it is an incredibly powerful tool to make progress.
Failing in public
Failing in public is inspired by the Twitter movement to ‘build in public’. It started with indie founders building their own startup, business or product 'publicly’ on Twitter — by sharing the ups and downs of their journey as they go through it. In practice, this often involves talking and writing about failure as you launch ideas, test things, and learn what works or doesn’t work. Back in July 2021, I built DesignBake in public and wrote transparently about the process for the first few months. This helped me get my first customers, meet interesting people, and document my own journey in building a side project.
By failing and learning in public, I’ve been able to exercise my ‘failure’ muscle — I now feel confident, excited, and even proud to share the failures I’ve experienced and grown from.
I hope we can all talk about failure more openly and confidently — because it will give more people around us the confidence to try and take the leap with their ambitions.
Meanwhile, I’m looking forward to failing at my next chess game and startup iteration.