Opposing views
I found this Ray Dalio quote insightful:
Everyone fails. Anyone you see succeeding is only succeeding at the things you're paying attention to--I guarantee they are also failing at lots of other things. The people I respect most are those who fail well. I respect them even more than those who succeed. That is because failing is a painful experience while succeeding is a joyous one, so it requires much more character to fail, change, and then succeed than to just succeed. People who are just succeeding must not be pushing their limits. Of course the worst are those who fail and don't recognize it and don't change.
I shared it with two friends, both excellent Product Managers in MAANG, and here are their responses, on WhatsApp, without comment:
One
survivorship bias - that's why I think a lot of the glorification of successful entrepreneurs is unjustified
they deserve credit for the work, getting some things right etc.
but we over-index on the success (similar for arts, business etc as well)
Two
I like Dalio’s writings. Here is a note to self that I draft sometime back.
Failing well is perhaps the most overlooked life skill. In our pursuit of success, it is the quiet foundation of resilience and growth.
The fear of failure is, in my view, the biggest reason many talented people never reach their potential. This is the burden of unique talent: the more one can do, the more one expects from oneself — and the greater the fear of falling short. Failure is not just external — it strikes at identity. Like trauma, each failure leaves a scar. Over time those scars add up and can weigh heavier than the original loss. Pushing forward takes real courage.
Society adds to this. Today it often feels more important to show success than to be successful. Social pressure rewards the image of achievement and punishes open acknowledgment of failure. This drives many to hide behind the mask of success, leaving the real lessons of failure behind.
Some choose denial instead. They treat every outcome as a win. This may ease the pain, but it blocks growth. If failure does not exist, then neither do the lessons it carries.
The harder path — and the better one — is what Ray Dalio calls “failing well.” It means letting failure hurt without letting it define you, much like trauma. The pain is real, but it does not have to become your identity. To fail well is to look at the experience honestly, learn from it, and move forward stronger.
In our fixation on success, we forget that failing well may be the life skill that matters most — precisely because it is the one we so rarely learn and practice.
I’m fortunate to have good friends.
Published 23 Sep, 2025.
Last edited 3 weeks, 4 days ago.