Overcoming Self-Defeating Behaviors – Leadership Freak

Overcoming Self-Defeating Behaviors

You do things for good reasons that have bad endings. Some work long hours till they lose their family while telling themselves they’re working for their family, for example.

The worst self-defeating behavior is persisting in self-defeating behaviors.

Self-defeating behaviors are like tires with holes. It doesn’t matter how many times you pump them up.

Self-defeating behaviors corrode success. Image of a rusted jalopy.

3 reasons self-defeating behaviors persist:

#1. Misguided self-reflection.

Everyone thinks about their life. Very few engage in structured self-reflection. Self-reflection isn’t thinking about frustrating people. It’s noticing things you do that allow frustration to persist.

Dumb self-reflection ends with blame instead of responsibility.

Today’s challenge:

Write about this in a journal for a week. The life I live is the one I’m building. What specifically am I doing that makes my day better? Worse?

The above is an example of structured self-reflection. Take it to the next level by completing this sentence. The one thing I will do today to make life better is __________. Or eliminate a self-defeating behavior. The one thing I won’t do today is _________.

#2. Stupid works for a while.

You can eat unhealthy food for a day with few negative consequences. Eat it every day and it will kill you.

You get away with…

  1. Rudeness until people speak up.
  2. Working long hours until stress catches you.
  3. Pushing people instead of inspiring people until they leave.

Stupid persists when you don’t ponder the path. Every path has an end.

Today’s challenge:

Make a list of behaviors you persistently do and ask, “Where does this behavior take me?”

Learning is painful for arrogance and joyful for humility. image of a students desk.

#3. Correction stings.

Someone suggested you change, and you defended yourself instead of leaning in.

Smart leaders seek correction. Stupid leaders resist.

Today’s challenge:

Seek correction. Ask, “What am I doing that doesn’t serve my goals?”

What are some common self-defeating behaviors?

Why do self-defeating behaviors persist?

Still curious:

The #1 Self-Defeating Behavior That Brings Leaders Down

10 Self-Defeating Behaviors You Need to Let Go

Our book, The Vagrant enables leaders to spot self-defeating behaviors and offers strategies for structured self-reflection.

Click here to purchase: https://amzn.to/47G98jP

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Wisdom from Charlie Munger – Leadership Freak

Wisdom from Charlie Munger

Charlie Munger died November 28, 2023. He was the right-hand man of Warren Buffet for 60 years.

Gain wisdom by avoiding stupidity. Image of a sheep.

If you want to gain wisdom:

“I sought good judgment mostly by collecting instances of bad judgment, then pondering ways to avoid such outcomes.”

You can gain wisdom by studying stupidity and doing your best to avoid it.

Charlie expanded his search for stupidity beyond investing. “After all, why should I search for some tiny, unimportant, hard-to-find new stupidity in my own field when some large, important, easy-to- find stupidity was just over the fence in the other fellow’s professional territory?”

On incentives:

“Never, ever, think about something else when you should be thinking about the power of incentives.”

Know what motivates people to action and stick with it. Hint: It isn’t reason.

Benjamin Franklin put it this way, “If you would persuade, appeal to interest and not to reason.”

The hard things leaders do make them glorious. Image of a tree reflecting on water under a night sky.

On grannie’s rule:

“Granny’s Rule, to be specific, is the requirement that children eat their carrots before they get dessert. And the business version requires that executives force themselves daily to first do their unpleasant and necessary tasks before rewarding themselves by proceeding to their pleasant tasks.”

On liking and loving:

“… (We) like and love being liked and loved.”

Don’t expect devotion from people you don’t like. Do you like the people on your team? More importantly, do they know you like them?

On doubt:

“The brain of man is programmed with a tendency to quickly remove doubt by reaching some decision.”

You rush to decisions because living with doubt is painful. If you can tolerate doubt you are likely to make better decisions.

Random quotes:

“… bad behavior is intensely habit-forming when it is rewarded.”

“…Repeat behavior that works…”

All quotes are from, “Revised Psychology of Human Misjudgment,“ by Charlie Munger.

What bit of wisdom will you take with you today?

What Charlie Munger quote can you add?

Still curious:

Between Stupidity and Wisdom

How to Stumble Toward Wisdom and Find Success

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How to Avoid the 3 Biggest Mistakes Leaders Don’t Need to Make

How to Avoid the 3 Biggest Mistakes Leaders Don’t Need to Make

Mistakes are inevitable, but some are avoidable.

The worst mistakes are the ones you didn’t need to make.

The worst mistakes are the ones you don't need to make. Image of a man tripping with a sword.

The 3 biggest mistakes leaders don’t need to make:

#1. Certainty when you’re ignorant.

You amplify ignorance when you screw up after pretending you knew. Don’t hide ignorance. Use it as motivation to learn.

When you’re unsure, say, “We evaluated the options and sought input. We’re moving forward.” Don’t give the impression you know when you’re ignorant.

Hiding ignorance exposes arrogance. Fools know. Wisdom learns.

When you embrace ignorance, you learn. When you feign knowledge, you fail.

The mistakes leaders make are deadly because they harm others. Image of a cat with its paw covering its eyes.

#2. Bravado when you’re worried.

Bravado only fools simpletons.

You look like a poser when you beat your chest during turbulence. Leadership confidence is about people, agility, and a commitment to learn.

“We can work through this together,” is better than, “I got this.”

“We will learn as we go,” is better than, “I have the answer.”

#3. Openness when you’re rigid.

You deflate energy when you ask, “What do you think?” after you made up your mind.

Seek input, but don’t let people think you’ll do what they suggest. Explain that you’re seeking options with an “S”. After the first suggestion say, “And what other possibilities come to mind?”


5 things to do when you screw up:

  1. Lean in, not away.
  2. Take responsibility. Don’t blame.
  3. Commit to learn.
  4. Take corrective action.
  5. Demonstrate commitment to improve.

5 essential practices for all leaders:

  1. Humility.
  2. Authenticity.
  3. Vulnerability.
  4. Self-reflection.
  5. Courage to act.

What’s on your list of mistakes leaders don’t need to make?

Still curious:

How Humble Leadership Really Works

The Top 4 Mistakes Busy Leaders Make

I believe our book, The Vagrant: The Inner Journey of Leadership, enables leaders to avoid mistakes that don’t need to be made. I invite you to purchase it.

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Feedback: Do These 3 Things Before You Say a Word

Feedback: Do These 3 Things Before You Say a Word

The heart of feedback has nothing to do with correct phrasing, strategies, or techniques.

The heart of feedback is being human. People aren’t cogs and gears; they’re flesh and bones. They respond to input as individuals based on past experiences, values, and personal goals.

Show up to row-with before you give one word of feedback. Image of two women rowing.

Image by ahsing888 from Pixabay

Before you speak a word of feedback:

#1. Get right with yourself.

Reflect on yourself. Don’t spew on others.

  1. How are you feeling? Emotion colors communication. Stressed leaders speak aggressively. Optimistic leaders speak hopefully.
  2. How do you evaluate yourself? When you’re disappointed with yourself, you tend toward disappointment with others.
  3. What are your intentions? You have more experience and skill. You know what people need to do. What do you intend people to feel when the conversation is over? Encouraged or discouraged? Confident or insecure? Confused or clear? Dwelling on past performance or focused on where they are going?

#2. Put your fixer to bed.

The desire to fix people is normal. But you can’t fix anyone. People fix themselves. You can speed their journey, but everyone chooses their own path forward.

Determine if you need to tell, explore, correct, or instruct. Do all four with openness.

Forget about having all the answers.

People who know are…

  1. Overconfident.
  2. Opinionated.
  3. Closed minded.
  4. Dismissive.

Choose how you show up before you show up. Image of a person looking across a bridge.

#3. Choose how you show up.

Choose environments that support the goals of the conversation. When your goal is a conversation, how does the environment support the goal?

It’s nearly impossible to resist the power of architecture and environment.

Choose the lens you use on yourself. Are you there for others or for yourself? The quickest way to lower stress is to seek to advantage others. Tell people you are in it for them. You seek their best interest.

Show up to row-with before you give one word of feedback.

How can leaders prepare themselves to have performance enhancing conversations?

Still curious:

After Giving Tough Feedback Good Bosses Do 5 Things

17 Things to Never do when Giving Corrective Feedback

Humility and self-reflection strengthen leaders for the battle. Click here to check out, The Vagrant: The Inner Journey of Leadership. It’s a wonderful tool for leaders facing challenges.

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5 Things That Should Increase Happiness but Usually Don’t

5 Things That Should Increase Happiness but Usually Don’t

Employee happiness is declining even though autonomy, pay, and time off are increasing.

Many large companies increased investment in employees by 20% through the COVID years. At the same time the number of people who dread work has risen by 11% since 2020. (WSJ)

The number one factor in happiness is social connection. Image of a cat and dog facing down.

Image by Gisela Merkuur from Pixabay

5 Things that should increase happiness but usually don’t:

  1. Less stress leads to boredom, not happiness.
  2. Minimum effort doesn’t elevate mood. People who do as little as possible end up resentful.
  3. Raises and promotions give temporary bumps in mood. The pursuit of advancement means you’re always looking for the next thing. (Hedonic Treadmill)
  4. Working at home means you can’t escape work. Team members feel unsupported and disconnected.
  5. Self-care makes people self-centered when it is the goal of life.

Choose happiness: happiness is experienced directly but pursued indirectly. Image of a happy seal.

4 ways to improve well-being:

#1. Talk to people.

The #1 factor in personal happiness is social connection. That’s why working from home has a dark side.

  1. Talk to people face-to-face.
  2. Learn about people.
  3. Show concern for people.
  4. Tell people about yourself.

Even introverts are happier when they force themselves to talk to people.

#2. Be otherish.

The “get” life impoverishes. The “give” life enriches.

Well-being is more about giving yourself than finding yourself. Find yourself so you can give yourself away.

Self-care is necessary to be otherish because serving requires energy.

“You don’t become happy by pursuing happiness. You become happy by living a life that means something.” Harold S. Kushner

#3. Enjoy small stuff.

The hedonic treadmill sucks happiness out of life because hopes for more belittle what you have. Enjoy the taste of coffee. A walk isn’t a chore, it’s a delight.

Presence is paying attention to what you’re doing now.

#4. Don’t worry about happiness so much.

The aggressive pursuit of positive emotion makes people miserable. Those who most value positive emotion experience it the least.

What improves well-being?

What do we believe increases well-being but doesn’t?

Still curious:

How to Find Happiness in Leadership

A Surprising Thing You Can Do for Yourself

The Good Life: Lessons from the World’s Longest Scientific Study of Happiness

Humility and self-reflection strengthen leaders for the battle. Click here to check out, The Vagrant: The Inner Journey of Leadership. It’s a wonderful tool for leaders facing challenges.

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Navigating the Mental Minefield: A Guide for Leaders

What are the cognitive challenges leaders at the highest levels face?

Leadership, especially at the C-level, is a journey of high-stakes decisions and complex challenges. The intensity of this role often exposes leaders to cognitive biases—subtle yet profound thinking errors that can misguide decisions and strategies. While these biases can affect anyone, thinking mistakes made by leaders often have a more severe impact.

Understanding and mitigating these biases is key. In this article, I’ll explain five of the most common cognitive biases that affect C-level executives, illustrate them with real-world examples, and offer pragmatic strategies to counteract their effects.

Confirmation Bias: The Echo Chamber Effect

The Trap: Leaders often gravitate toward information that aligns with their pre-existing beliefs, inadvertently overlooking contradictory and important evidence.

In Practice: A CEO convinced that remote work hampers productivity may only acknowledge studies supporting this view, while ignoring evidence to the contrary.


Pursue Contradictory Evidence: Actively seek out information that challenges your beliefs.
Embrace Diverse Opinions: Consult individuals with different perspectives, including team members and external advisors.
Separate Beliefs from Identity: Understand that being proven wrong is an opportunity for growth, not a personal failure.

Overconfidence: The Illusion of Certainty

The Trap: Executives often overestimate their knowledge and predictive abilities, overlooking potential uncertainties and risks.

In Practice: A CFO might confidently project revenue figures while neglecting market uncertainties and potential disruptions.


Conduct Reality Checks: Regularly compare predictions with actual outcomes to ground your expectations.
Explore Multiple Scenarios: Conduct sensitivity analyses to understand different possible outcomes.
Solicit External Insights: Engage experts and team members to provide fresh perspectives and challenge assumptions.

Sunk Cost Fallacy: The Costly Commitment

The Trap: Leaders sometimes persist with initiatives due to past investments, regardless of current or future viability.

In Practice: A CEO might insist on continuing an unprofitable venture simply because substantial resources have already been invested.


Implement Regular Audits: Continuously assess the return on investment of ongoing projects.
Be Ready to Pivot: Embrace the courage to discontinue projects when necessary.
Focus on Future Gains: Shift attention from sunk costs to potential opportunities that could arise from reallocating resources.

Groupthink: The Consensus Conundrum

The Trap: The desire for group harmony can lead to unchallenged decision-making and potentially flawed outcomes.

In Practice: Executives in a board meeting might hastily agree to a strategy to avoid conflict, neglecting a thorough risk assessment.


Assign a Devil’s Advocate: This individual will critically question group decisions.
Promote Anonymous Input: Use anonymity to encourage genuine opinions.
Foster Healthy Debate: Cultivate an environment where diverse viewpoints are valued and encouraged.

Halo Effect: The Deceptive Glow

The Trap: An overall positive impression of an individual or organization can overshadow objective assessment of their true capabilities.

In Practice: Business books often use successful companies as examples of “what to do” ignoring whether the company did those things to become successful or because once they were successful they decided to do those things.


Adopt Objective Evaluation Metrics: Utilize clear, measurable criteria for performance assessment.
Invite Independent Reviews: Consider external evaluations…

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16 Ways to Give Constructive Feedback Like a Human

16 Ways to Give Constructive Feedback Like a Human

Constructive feedback is a gift few leaders enjoy giving. Done carelessly it quenches enthusiasm.

Before feedback people struggle. After constructive feedback people feel confident.

Successful feedback sharpens someone’s axe.

Constructive feedback is a gift. Image of a person offering a rose as a gift.

16 ways to give constructive feedback:

  1. Build trusting relationships. Don’t show up to hammer people and saunter back to your easy chair like you’ve done something spectacular. Do people believe you care about them?
  2. Speak to career goals. When you don’t know their goals, the first step is to learn them.
  3. Always seek to advantage others. There is no exception to this rule.
  4. Use the lens of career goals when explaining negative behaviors. “Interrupting people in meetings doesn’t improve your communication skills.”
  5. Encourage more than correct.
  6. Build on strengths.
  7. Focus on one concern. Old habits are like gum on your shoe. We change slowly.
  8. Express issues in one or two sentences. The more you talk the worse it is. “I notice (fill in the blank with specific behaviors.)
  9. Give examples. “When you….”
  10. Relax. You’re here to help.
  11. Speak directly and with kindness.
  12. Provide adequate time and privacy.
  13. Avoid but. “You’re doing a great job, BUT…” Don’t dilute affirmation with correction.
  14. Don’t interpret intentions or motivations. Ask about them. “What are you trying to accomplish when you…?”
  15. Collaborate on solutions and develop a path forward. Spend more time talking about solutions than problems.
  16. Follow-up with progress reports.

Feedback that works begins with positive intention. Image of a person helping someone over a wall.

4 tips:

Optimism is essential when giving constructive feedback.

Avoid giving feedback until you believe growth is possible.

If growth isn’t possible, redesign their job or manage them out.

Sit on the same side of the table, when possible.

What have you learned about giving constructive feedback?

What do leaders do wrong when giving feedback?

Still curious:

Feedback: Solving the Most Common Failure in Leadership

3 Ways to Give Feedback that Works

Humility and self-reflection strengthen leaders for the battle. Click here to check out, The Vagrant: The Inner Journey of Leadership. It’s a wonderful tool for leaders facing challenges.

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How Gratitude Shapes Identity – Leadership Freak

How Gratitude Shapes Identity

“Gratitude is not only the greatest of virtues, but the parent of all the others.” Cicero

An ungrateful leader is a staggering contradiction in terms.

Ingrates are unworthy of leadership.

Gratitude is not only the greatest of virtues, but the parent of all the others. Image of Cicero.

Ingratitude shapes identity:

It’s difficult to imagine a virtuous ingrate.

Ingrates tend toward isolation, anger, and resentment. Relationships with ingrates are strained because a relationship with someone who doesn’t appreciate you is difficult to sustain.

No one aspires to be an ingrate.

No one admires an ingrate.

Can you imagine a happy ingrate?

Image of honey overflowing on a spoon.

Gratitude shapes identity:

One of our neighbors is renovating a house up the road. I stopped by to chat and asked if he might have a few empty spackle buckets. He said, “No, but I have three buckets you can have.”

He explained that he buys buckets from a laundromat for two dollars each. I reached for my wallet and said, “I’m not going to take your buckets, but I’ll pay for them.” We had a short discussion that ended with, “I’m not going to take your buckets.”

I enjoy being the giver and resist being the receiver. When you resist gifts, gratitude shrivels because gratefulness begins with receiving.

Our neighbor grabbed the buckets as I left and put them in the back of my truck. Now I have the three humbling-buckets in my garage.

Where pride feels resistance, humility feels thankful.

I plan to return the favor, but if I thought he gave me the buckets to create obligation, I would feel manipulated.

Gratitude humbles because you become a recipient of benefit.

Lack of thankfulness signals naïve self-sufficiency. If you question the power of gratitude to shape identity reflect on the shaping power of ingratitude.

Gratitude expands your soul and enriches those around you.

The ability to receive is essential to successful leadership.

Project: Practice being a grateful recipient today.

How does gratitude/ingratitude shape identity?

Still curious:

The Secret to Magnificent Success

The Simple Shift that Supercharges the Power of Gratitude

Author’s note: I learned how gratitude shapes identity from Robert Emmons, a world recognized gratitude researcher.

Humility and self-reflection strengthen leaders for the battle. Click here to check out, The Vagrant: The Inner Journey of Leadership. It’s a wonderful tool for leaders facing challenges.

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Thanksgiving Lessons from a Bone Turkey

Thanksgiving Lessons from a Bone Turkey

We were poor college students, over 1,600 miles from home, when my wife and I celebrated our first Thanksgiving. It was 1976. Our first anniversary wouldn’t arrive for three weeks.

I’ll never forget how proud we felt to host Dave Tricky, a fellow student, and his girlfriend for our first Thanksgiving as a married couple. Yes, that’s his real name, but this Thanksgiving the trick was on me.

We were almost ‘real’ adults. My bride was 19. I was 20.

Image by PublicDomainPictures from Pixabay

We moved our tiny kitchen table uncomfortably close to the front door to accommodate the crowd of four.

After the blessing, I ceremoniously stood, blade in hand, ready to carve the bird. It was one of life’s great moments. I was the ‘man’ of the house. But my manliness soon withered.

The knife point struck bone, not turkey. I poked around with the blade. The whole turkey was bone.  I purchased a BONE TURKEY!

Dave and his girlfriend probably stopped at a fast-food joint on their way back to campus. If not for the drumsticks and wings, our first Thanksgiving was a vegetarian delight.

In defeat, after our guests left, I carried the bone-bird to our closet of a kitchen to scavenge the remains. We could use even sparse leftovers. When I flipped the bird over, two succulent turkey breasts mocked me.

We cooked the bird upside down!

What I learned from a bone turkey:

  1. Humble yourself before a turkey humbles you.
  2. Practice gratitude. You have more than you know.
  3. A shift in perspective has power to change everything. During difficulty, gratitude is a shift in perspective.

One day, if you keep learning, you’ll laugh at how ignorant you used to be.

Happy Thanksgiving.

Author’s note: I often repost this story when Thanksgiving Day comes to America. By the way, it’s also Thanksgiving in Brazil.

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Gratitude When You Don’t Feel It

Gratitude When You Don’t Feel It

Feelings aren’t the final authority on noble behaviors.

You do the right thing when you feel like doing the wrong thing all the time. For example, you want to share a piece of your mind you can’t afford to lose, but you don’t. That’s maturity, not hypocrisy.

Gratitude is a practice.

Express gratitude when you don’t feel it as long as you believe it’s the right thing to do.

The tragedy of ungratefulness is gratitude is free. Quote

4 ways to practice gratitude when you don’t feel it.

#1. Think about obstacles you have overcome.

The world’s leading expert on gratitude, Robert Emmons, says, “Remembering failures, sorrows, and other painful experiences is more beneficial to gratitude than recalling only the successes.”

Faking positivity hinders gratitude. Don’t forget the bad, remember how far you’ve come.

#2. Simplify a gratitude journal.

When I struggle to come up with five things to write in my gratitude journal it makes me ungrateful.

Don’t write five things in a gratitude journal, write one. If you want to challenge yourself, write one thing in the morning and one thing in the evening.

#3. Ask others about gratitude.

When you don’t feel grateful, ask others what they are grateful for. Better yet, ask, “Who are you grateful to?”

#4. Express gratitude.

Unexpressed gratitude is ungratefulness.

  1. Lower your expectations. Notice little things.
  2. Say, “I appreciate you.”
  3. Say, “I notice xyz. Thank you for doing that.”

What suggestions do you have for expressing gratitude when you don’t feel it?

Still curious:

7 Powerful Ways to Elevate Leadership with Gratitude

The Five Freedoms of Gratitude

A Little Gratitude Goes a Long Way

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