March 15, 2021

Exploring Failure

A regular TBOA listener observed that Rochelle and I don’t talk about failure much, which can make it feel like everyone is succeeding all the time.

Here’s our response:


Talking Points

How to think about your business as an experiment and failures as practice.

The value of postmortems to understand - and rebound from - failure.

How to put failure in service to your story, your audience and the change you want to make in the world.

Reframing failures (after you’ve worked through the emotions around them) and the role of resilience.

Why being willing to fail is part of the mindset of an authority.

Quotable Quotes

“My philosophy (on failure) for years has been that everything is practice for the next time.” - JS

“When you have a big failure…you’ve got to go through that experience of feeling the pain, feeling the crap and then you come out the other side.” - RM

“What’s the worst that could possibly happen - what’s really at risk?” - JS

“Most of our failures are not nearly so public as they feel to us.” - RM

“Have lots of little failures instead of betting the farm on one big thing.” - JS

“It’s about getting comfortable that all those external things - your job, your bank account, what people think of you - if they all go away, you’ll still be OK.” - RM

“If you have a catastrophic failure, you can’t come back and play again tomorrow - you’re more or less forced into a pivot.” - JS

“You have to find the right support from the right people in the right places. We all know who NOT to go to.” - RM

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