5 Lessons from a Lifetime of Mistake-Making

The real value of mistake-making is turning toward the future with less baggage.

The future is built by both endings and beginnings. Wisdom gained from mistakes is about endings. It’s useful only as it makes space to try new things.

The danger of mistake-making is giving up.


5 lessons from a lifetime of mistake-making:

#1. Fear of making mistakes is a little dog with a big bark. Most mistakes aren’t as bad as we fear. In some cases, it feels good to get them out of the way.

If you’re really worried about the impact of potential mistakes:

  1. Talk to higher ups.
  2. Discuss the worse that could happen with your team.
  3. Create contingency plans.
  4. Take a small step and see what happens. (Essential)

The real issue with mistakes is repeating them.

#2. Most people aren’t as comfortable with ambiguity as I am. I’m OK to let things play out and see what happens. Some interpret this as lack of concern. For me, it’s an adventure.

When others don’t enjoy ambiguity:

  1. Touch base frequently.
  2. Share information freely.
  3. Reconnect with purpose and vision, but pull everyone back to the present.

#3. Silence, when things aren’t going well, almost always makes things worse. Burying your head in the sand is a good way to get blindsided by a train.

#4. Turn the lights to bright when dimming them feels safer. Sometimes the leader’s role is stating the unspoken obvious. Healthy intervention is more about giving people permission to address awkward issues than it is fixing them.

Where do the lights need to be turned up?

#5. There is a downside to helping. Quick interventions often result in resistance, dependency, or lack of initiative. Give people space to work through their own issues.

  1. This doesn’t seem to be working.
  2. What would you like to do about it?
  3. How can I help?

What has mistake-making taught you?