The idea that as a team we should be constantly looking at ways to improve our local areas. E.g. this project could be improved by doing Y. However, for the large scale (the company and the project) we believe that it will succeeded and be better. It’s better to ask how will this work rather than how can this fail 1.
Internally, we’re always thinking about what’s broken, which problems could lie around the corner, and where the unaddressed risks lie. But an important aspect of Stripe culture is macro optimism. We believe that Stripe will be far better in the future than it is today. When considering ideas, we think “how might it work?” is more interesting than “why will it fail?” We believe we’re yet to see most of the impact of the internet. And we think that ambitious, energetic, and deliberate efforts directed towards progress are surprisingly effective in improving the state of the world around us.