This document provides 8 reasons to fail regularly: 1) To keep striving by pushing outside your comfort zone, 2) To stay innovative and learn from surprises, 3) To keep an open mind by challenging assumptions, 4) To stay humble by not becoming overconfident, 5) To build empathy for others who fail, 6) To build confidence in your ability to recover from failures, 7) To develop better skills for recovery so you can improve after future failures, 8) To become less afraid of failure by seeing it as an opportunity for growth. The document encourages analyzing failures, supporting others who fail, and learning from mistakes.

1. TO FAIL
REGULARLY
REASONS
8
https://www.flickr.com/photos/gidzy/

2. REASON 1
Fail regularly to ensure that
you keep striving
Failure occurs when you stretch / grow yourself, because you are out of
your comfort level. If you’re not failing, you’re likely not stretching.
Explicitly track (and record) your rate of personal failures. Ensure 1 meaty screw up
per quarter, or force yourself to move into personally uncharted waters.

3. REASON 2
Fail regularly so that you
continue to be surprised
Surprise is a key to innovation because it reveals opportunities. It also
stores valuable Return on Investment if you learn from it.
Seek out Failure and aggressively run retrospectives (post mortems). Celebrate what
you learn positively, widely, and publicly.

4. REASON 3
Fail regularly to keep an open
mind
We are biologically predisposed to calcify assumptions & shy from
cognitive dissonance. Shake things up before they can’t be dislodged.
Compose a list of 10 things that you believed 15 years ago, which you now know are
false, or at least, not quite right. Remember how sure you were.

5. REASON 4
Fail regularly so that you
remind the ego to stay
humble
The greatest danger of confidence is over confidence
Find and listen to the album “Nothing’s Shocking” by Jane’s Addiction. It has nothing to
do with this topic. It’s just a fraking good album.

6. REASON 5
Fail regularly so that you build
empathy for others who fail
Most people fear failure because of how they think others will see
them. It is peer pressure which makes us avoid what is innately good for
us.
Look around for someone who is currently failing and give them a shoulder to lean on.
No questions asked. No judgements made.

7. REASON 6
Fail regularly so that you build
confidence in your resilience
One of the reasons that it was so hard to shave my head bald for the
Children’s Cancer Foundation Hair for Hope program was the worry that
it wouldn’t come back. It did.
Compose a list of 3 big mistakes you’ve made in your life thus far. Appreciate that you
got through them and that they are not nearly so dire years later.

8. REASON 7
Fail regularly to build practical
recovery skills so that you get
up faster & stronger next time
‘nuff said
Go back to the retrospective you ran for Reason #2 and analyse the process after the
failure rather than before. Identify 1 thing to improve with recovery next round.

9. REASON 8
Fail regularly so that failure
becomes less scary &
embarrassing
Once you train your brain to see failure as an opportunity, it will
become one
Find someone who has failed (and who may feel privately ashamed) and let them know
personally that it’s no big deal.

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