How to Stumble Toward Wisdom and Find Success

We stumble toward wisdom all our lives, but some die a fool’s death.

Wisdom thrives regardless of circumstances.


The danger of stupidity is it works at first.

How to stumble toward wisdom:

The influence of wise leaders helps us stumble toward wisdom.

Wisdom is social before it’s intellectual.

I’ve noticed three things about wise leaders.

#1. Enjoyment:

The most surprising thing I notice about wise leaders is enjoyment. Nagging sadness and recurring anger speak to foolishness.

Wise leaders choose enjoyment that doesn’t include regret.

Fools choose happiness that eventually produces misery. Think of enjoyment produced by over-work, too much alcohol, or advantaging yourself at the expense of others.

The danger of stupidity is it works at first.

3 ways to stumble toward enjoyment:

  1. Think less about the future and more about the present.
  2. Don’t compare today with the past.
  3. Reflect on stories, both yours and theirs.

The secret to enjoyment is being present.

Vision for the future beats you down when it’s more than a compass.

#2. Liking:

Wise leaders like people. Haters are fools.

Wisdom sees opportunity where fools see threat.

3 ways to stumble toward liking:

  1. Focus on liking, not being liked. The need to be liked leads to enjoyment with regret.
  2. Accept frailty. Everyone has weakness and frailty. Your job is to maximize strength and compensate for weakness. (Some people should be managed out.)
  3. Spend more time encouraging high performers. Most leaders spend too much time trying to fix low performers. (A savior complex brings enjoyment with regret.)
Duck and ducklings

The path to success is the pursuit of wisdom.

#3. Gentleness:

The wisest leaders I know are also the gentlest. Bravado is bullshit.

Harshness produces results with regret.

3 ways to stumble toward gentleness:

  1. Think of words as hammers.
  2. Listen and speak as if everyone around you is an 8-year-old kid.
  3. Practice curiosity.

Gentleness in you enables boldness in others, but never think of gentleness as weakness. Be tough and gentle.

The path to success is the pursuit of wisdom.

What do you notice about wise leaders? Foolish leaders?

Bonus material:

How to be a SAGE without being a Snob | Leadership Freak