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Sunday, September 28, 2025

Dear Hannah: LEarning (The Life and Legacy of Captain Kuykendall: A Balanced Reflection) (682 Words)



 

The Life and Legacy of Captain Kuykendall: A Balanced Reflection) (682 Words)

By Derrick Brown (Join Our Mailing List!)
 

Dear Hannah,


There is some “hero” in every villain.

There is some “villain” in every hero.

In your lifetime, you will see countless people hailed as heroes … or villains … before the full story has been told.

Captain Kuykendall is one of those figures.

His life and influence evoke passion, division, and powerful lessons.

What I will share today is not a “verdict” (an assignment of “innocence” or “guilt”) … rather, it is a framework for understanding … the strengths, the dangers, and the “wisdom earned through lessons LEarned (#WETLL)” … even when we may fundamentally disagree.


Who He Was (and Became)

Captain Kuykendall rose to national prominence at a young age. He founded Turning Point USA, organized youth campaigns, and became a recognizable voice in American conservative politics. He spoke boldly about liberty, traditional values, individual responsibility, and a return to what he portrayed as foundational principles of America. Many young people looked to him as a "standard bearer".

He was charismatic … he was able to inspire people who felt overlooked or left behind. He built a movement. He had access to power. He became a media figure, often adopting provocative stances to engage audiences. His speeches, media appearances, and digital presence reached beyond campuses and into broader public debates.


Strengths and Influence

  1. Energizing Youth

    The Captain showed that young people can care about big ideas. He made political engagement feel urgent, meaningful, and possible. That energy, when channeled well, can be a force for good … especially when the voices of young people have been marginalized.

  2. Clarity of Message

    One of his strengths was a clear set of values … even if you disagreed with them. He valued freedom, responsibility, and tradition. In a world of rhetorical noise, this kind of clarity is rare.

  3. Platform Building

    He built an organizational and media infrastructure … of schools, conferences, and campus chapters. These networks multiplied his reach and influence. That’s a lesson … ideas don’t live in vacuum … they need vessels to help them "travel" (organizations, media, movements).

Critiques and Warnings

  1. Polarization & Overreach

    His style often favored "confrontation" over "bridge building". In a divided society, that amplifies conflict. At times, nuance and listening became casualties of rhetorical zeal.

  2. Simplicity Over Complexity

    "Big" problems … like culture, inequality, and systemic bias … cannot always be solved with slogans or oversimplified frameworks. When complex issues are “oversimplified”, people get “steamrolled”, “hoodwinked”, and “bamboozled”.

  3. Identity and Power Dynamics

    As a young White man in conservative spaces, The Captain exploited privilege and narrative power. His critics argue that his platform sometimes sidelined voices of women, people of color, or marginalized communities. Here is a sobering truth … influence often accompanies unearned benefit … that is important to acknowledge.

  4. Legacy Over Substance

    Public movements can drift into “cults of personality”. When the man overshadows the mission, the cause becomes fragile. What happens when the founder falters? Systems ought to outlast one person.


Wisdom Earned Through Lessons LEarned (#WETLL)

  1. Love the idea, but question the presenter.

    Be attracted to good ideas, but do not worship people. Evaluate character, contradictions, context, subtext, and nuance.

  2. Value complexity.

    When someone offers "oversimplified" answers, selah (pause and think). Many of life’s hardest questions have “layered” answers.

  3. Use your voice.

    You don’t have to wait for permission to think, to speak, or to challenge. But when you speak, lead with empathy, humility, and curiosity.

  4. Hold space for grace.

    People make mistakes. Some damage can be repaired. Discern when to debate, when to forgive, when to walk away.

  5. Know that legacy is more than applause.

    The people whose lives change quietly decades later … because of wisdom earned through lessons LEarned (#WETLL) ... leave legacies that are more powerful than viral media moments.

Captain Kuykendall’s life and passing will be interpreted in many ways. Some will lionize him. Some will condemn him. But for you … my daughter … mi gente … I want you to carry a compass … clarity tempered with humility, passion bound with discretion, and a constant courage to narrate your own story rather than lean entirely on theirs.

That is a legacy worth seeking.

 
 
Love,

Daddy



Support Our Work - Buy Our Other Podcast Series (SEE BELOW)!
 
 


 
 
 
 
 
 
"Daddy's Home" (2018)

(The "Follow The Leader (changED - Volume 2)" Audio and Video Album / Mixtape is also available at TeachersPayTeachers.com) 

(The "changED (Volume 1)" Audio and Video Album / Mixtape is also available at TeachersPayTeachers.com) 



About Derrick Brown (Standup Storyteller)

 

 

I am Keisha's husband, and Hannah's father.

I am a “standup storyteller.”

I fuse rap, spoken word (poetry), oration (traditional public speaking), singing, and teaching into messages of hope, healing, and change that I write, direct, and produce to help people who help people.

Everything must change - and stay changED.

Tradition begins and ends with change.

Change begins with me and the renewing of my mind ... then continues through efforts to effect small-group discipleship (equipping others to equip others) with audiences that respect and embrace mentoring, mediation, and problem solving as tools of change.

I am the product of my mentoring relationships, peacemaking (and peacekeeping), and problem-solving ability.

My education began when I finished school.

After school, I enrolled in a lifelong curriculum that includes classes in ministry, entrepreneurship, stewardship, literacy, numeracy, language, self-identity, self-expression, and analysis / synthesis.

My projects execute a ministry that has evolved from wisdom earned through lessons learned.

I want to share this wisdom to build teams of "triple threat" fellows - mentors, mediators, and problem solvers.

We will collaborate in simple, powerful ways that allow us to help people who help people.

I now know that power is work done efficiently (with wise and skillful use of resources, interests, communication, and expertise).

Copyright © 2025 Derrick  Brown. All Rights Reserved.
 
 

 


 
 




Saturday, September 27, 2025

Dear Hannah: LEarning (Watershed Moments) (686 Words)



 

Watershed Moments (686 Words)

By Derrick Brown (Join Our Mailing List!)

 

There are “life” moments that do more than “mark time”.

They carve channels.

They redirect the current.

They become “watersheds”.

I have lived through several “watershed moments”.

Marriage.

The birth of my daughter.

The birth of #StandupStorytelling.

The creation of #TheSeeSayShow.

Each one raised the waterline … raised the “standard” … for what I deem a “turning point”.

These are not just “milestones” … they are “uprisings”.

My “education” has not been a neat sequence of classes, degrees, or credentials.

It is everything I remember after I have forgotten what I was supposed to have “learned”.

It is what I have LEarned … with a capital “L” … and a capital “E” … through life’s “crooked” paths.

Our present times do not define “what” or “who” we are.

Present times tell us “where we are” … and “where we are going”.

The life I have lived speaks for me … and tells me “who” I am.

 

Naming Who I Am (and Who I Am Not)

For years, I wore titles that felt accurate … and incomplete.

Teacher.

Researcher.

Professor.

Engineer.

Businessman.

Each of these roles carried respect.

Each demanded effort … and expertise.

Yet none spoke to the whole of who I am.

I am not a religious leader.

I am not just a teacher.

I am not just a researcher.

Nor just a professor.

Nor just an engineer.

Nor just a businessman.

I am a #StandupStoryteller.

I am an “autoethnographer”.

I am a “thought leader”.

Today, I grant myself renewed permission to “lean into” those names.

#StandupStorytelling is the art of fusing rap, spoken word, traditional oration, song, and teaching … into messages that generate hope, healing, and change.

“Autoethnography” is my way of testifying … not simply describing what happened to me … but showing how it felt … how it shaped me … and how it reflects broader systems.

“Thought leadership” is not about having followers.

It is about daring to define the conversation … even if it means standing alone … and waiting.


“Crooked” Paths

I have LEarned to trust “crooked” paths.

They do not travel the “straight lines” of ambition … nor the “fast lanes” of status.

They wind toward patience.

They bend toward peace.

Along the way, I have LEarned to clothe my heart … with humility, grace, gentleness, mercy and patience.

These garments are required when you live in tension.

They are protection.

They are preparation.

Because the “causes” of our times … “politics”, “evangelism”, “discipleship”, “multiculturalism”, “freedom”, “equality”, “education”, “reform”, “tradition” ... and political labels like “conservative”, “liberal”, “progressive”, and “independent” … can easily become “camouflage”.

Sometimes they each mask the real work of healing.

Sometimes they hide agendas … that hide deeper wounds … deception … delusion ... marginalization … and control.

“Watershed moments” force us to unmask disguises.

To look in the “mirror” … and through the “window” at once.

What am I clinging to?

What am I covering up?

What am I chasing?

What am I fleeing?

Where is this current carrying me?


Permission to “Become”

In my “last days” of teaching high school, I am convinced that the sustainable work is not in entering enough grades … avoiding unnecessary adult interactions … or fighting murmurs in the “classroom cauldron”.

The sustainable work is in telling stories.

Naming truths.

Planting seeds of dignity and humility … that can grow even in soil that resists them.

The “watershed moment” we have been waiting for … is here.

It does not ask me to abandon the past … but to claim all that it has taught me.

It asks me to see “crooked” paths not as “detours” … but as “design”.

It asks me to become … who and what I already am.

I am a #StandupStoryteller.

I am an “autoethnographer”.

I am a “thought leader”.

This is not arrogance.

It is acceptance.

It is obedience.

It is alignment with what the waters have been carving toward all along.


Closing the Circle

“Watershed moments” demand that we pause.

Mark the crossing.

Affirm by saying “The waterline has risen, and I will not flow the same again”.

This is one of those “watershed moments”.

Selah.





Support Our Work - Buy Our Other Podcast Series (SEE BELOW)!
 
 


 
 
 
 
 
 
"Daddy's Home" (2018)

(The "Follow The Leader (changED - Volume 2)" Audio and Video Album / Mixtape is also available at TeachersPayTeachers.com) 

(The "changED (Volume 1)" Audio and Video Album / Mixtape is also available at TeachersPayTeachers.com) 



About Derrick Brown (Standup Storyteller)

 

 

I am Keisha's husband, and Hannah's father.

I am a “standup storyteller.”

I fuse rap, spoken word (poetry), oration (traditional public speaking), singing, and teaching into messages of hope, healing, and change that I write, direct, and produce to help people who help people.

Everything must change - and stay changED.

Tradition begins and ends with change.

Change begins with me and the renewing of my mind ... then continues through efforts to effect small-group discipleship (equipping others to equip others) with audiences that respect and embrace mentoring, mediation, and problem solving as tools of change.

I am the product of my mentoring relationships, peacemaking (and peacekeeping), and problem-solving ability.

My education began when I finished school.

After school, I enrolled in a lifelong curriculum that includes classes in ministry, entrepreneurship, stewardship, literacy, numeracy, language, self-identity, self-expression, and analysis / synthesis.

My projects execute a ministry that has evolved from wisdom earned through lessons learned.

I want to share this wisdom to build teams of "triple threat" fellows - mentors, mediators, and problem solvers.

We will collaborate in simple, powerful ways that allow us to help people who help people.

I now know that power is work done efficiently (with wise and skillful use of resources, interests, communication, and expertise).

Copyright © 2025 Derrick  Brown. All Rights Reserved.
 
 

 


 
 




Tuesday, September 23, 2025

Dear Hannah: LEarning (Final Exams (At Chipotle)) (524 Words)



 

Final Exams (At Chipotle) (524 Words)

By Derrick Brown (Join Our Mailing List!)

When my daughter and I walked into Chipotle on a quiet Fall Break weekend, I did not expect to find myself grading “final exams.”

But there I was, standing in line for burritos, face-to-face with students whose classroom journeys still lived vividly in my memory.


Test One: The Cash Register

The first was ESG, a sharp-yet-slippery presence from last year’s most rambunctious geometry class.

In school, he was quick to name the “learned helplessness” he saw in others … but slow to name his own.

He smirked through lessons … sometimes aligning with other teachers’ softer approaches … undermining me when my demands for accountability felt too sharp.

Eventually, I drew boundaries.

He withdrew.

Slept more.

Copied work.

Scraped by.

But at Chipotle, he wasn’t smirking.

He was working.

After ringing up my order, he frowned.

“Mr. Brown… I think I overcharged you.”

He apologized once.

Then again.

And again.

His voice carried humility I rarely heard in class.

He fixed the mistake, handed me the corrected receipt.

I handed him a tip.

“Maybe the only thing I taught you,” I said, “was how to own and correct mistakes. If so, you just passed life’s test.”

We bumped elbows.

Closure in a small gesture.


Test Two: The Real “Final Exam”

On another Chipotle afternoon, I ran into CK, one of the brightest … yet most shortcut-seeking … students from my 2022–2023 co-taught geometry class.

That year, “Finalsgate” rocked the room: a covert attempt to “steal” the exam.

I pieced together the evidence and presented it to the class with humor, tough love, and forensic detail.

At the end of the “trial”, CK is there … eyes sheepishly dropping … the quiet “mea culpa” observed … even if the words never came.

I told them back then that it would have been less work to study than to cheat.

But students often do more work … to avoid work … than it takes to do the work itself.

Two years later, there was CK again, alongside JP from another class.

The register was down, so we all waited.

When her food was finally ready, she looked at me with warmth.

“Mr. Brown,” she said, reverently.

She honored my daughter, smiled, and told me she had enjoyed my class.

That was her real “final exam.”

Not the one she almost stole … but this moment of dignity, memory, and respect.

She passed.


The Curriculum That Lasts

As my daughter and I left, I realized both students had reminded me of the same truth … the exams that matter most rarely come with multiple choice answers.

They come years later, in the way a former student apologizes three times for a mistake at a register, or greets you with reverence after once trying to cut corners.

In both encounters, I saw how teaching is not just about equations or proofs.

It is about planting seeds of responsibility and resilience … even when the soil looks rocky.

Sometimes the fruit blooms later, in unexpected places … like a Chipotle line.

For me, those moments were sobering … and sustaining.

They reminded me why I endure the murmurs … the shortcuts … the “painwork” of teaching.

Because every so often, those seeds bloom.

And that is a final exam worth grading.




Support Our Work - Buy Our Other Podcast Series (SEE BELOW)!
 
 


 
 
 
 
 
 
"Daddy's Home" (2018)

(The "Follow The Leader (changED - Volume 2)" Audio and Video Album / Mixtape is also available at TeachersPayTeachers.com) 

(The "changED (Volume 1)" Audio and Video Album / Mixtape is also available at TeachersPayTeachers.com) 



About Derrick Brown (Standup Storyteller)

 

 

I am Keisha's husband, and Hannah's father.

I am a “standup storyteller.”

I fuse rap, spoken word (poetry), oration (traditional public speaking), singing, and teaching into messages of hope, healing, and change that I write, direct, and produce to help people who help people.

Everything must change - and stay changED.

Tradition begins and ends with change.

Change begins with me and the renewing of my mind ... then continues through efforts to effect small-group discipleship (equipping others to equip others) with audiences that respect and embrace mentoring, mediation, and problem solving as tools of change.

I am the product of my mentoring relationships, peacemaking (and peacekeeping), and problem-solving ability.

My education began when I finished school.

After school, I enrolled in a lifelong curriculum that includes classes in ministry, entrepreneurship, stewardship, literacy, numeracy, language, self-identity, self-expression, and analysis / synthesis.

My projects execute a ministry that has evolved from wisdom earned through lessons learned.

I want to share this wisdom to build teams of "triple threat" fellows - mentors, mediators, and problem solvers.

We will collaborate in simple, powerful ways that allow us to help people who help people.

I now know that power is work done efficiently (with wise and skillful use of resources, interests, communication, and expertise).

Copyright © 2025 Derrick  Brown. All Rights Reserved.
 
 

 


 
 



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