Why I Love and Miss Teaching

From 2004 to 2006, I taught high school.  The courses I taught were

• Business Law - Contract, Tort, Criminal, Personal, and Agency Law
• Interactive Multimedia Design - Image, Video, Audio, Print Editing
• Business Software - MS Office Suite, Word, Excel, Access, PowerPoint
• Entrepreneurship - Students won second in state competition
• Web Design - Everything about web design

What I Loved About Teaching

The first lesson in Business Law I had planned for 3 months: origins of law.  I discussed ethics, morals, religion.  Students looked in awe as I crafted my argument.  It was a magnificent lesson.  At the end of the day, a student said, "You made me think."  When hearing that, my inspiration to achieve soared.

As a teacher I learned my passion: challenge people with what they need to hear.  Paint them a picture of their future, and push them toward it.  Tell them they can achieve it, give them a path, and hold them accountable to that goal.  I continue to employ this skill/passion as often as someone will listen.

What I Loathed About Teaching and/or Non-Essential Tasks

Each dislike I had for the education system derived from one problem: lacking constancy of purpose.  As a teacher, I claimed to be "stamping out ignorance in East-Central Alabama."  Often, I felt I was preparing students to conquer the world.  Occasionally, the thought crept in my mind, "the education system drives our economy by allowing parents to go to work for a full 8 hours per day," which turned me into a $32,000 babysitter.

Schools adopted bloated mission statements stating the duality of purpose.  Optimizing schools as knowledge centers and nurseries results in schools performing neither optimally.

Documentation causes paralises.  The shear act of documentation is a classical management style which does equate to good teaching.  In Sebastian Junger's War, he describes great garrison soliders as poor infantry fighters and great infantry fighters as poor garrison soldiers.  Essentially, you want to fight with a "hell raiser."  Good documenters are poor teachers; good teachers are poor documenters.  Since I considered my job to "provide the most holistic education possible to my students," I often turned in documentation at 11pm on the due date.

Since 1930, the education system has instituted 80 major initiatives (assuming 1 per year), yet has not removed a single one.  Education systems should prioritize their initiatives; then, formally retire items outside the top five.  Teachers receiving tasks, reading mission statements, or policies will find too many tasks to effectively provide.

What I Learned

Teaching young people at school is a unique environment: I was responsible for students who did not necessarily need to be there, or want to be there.  My "carrot" was an environment to grow and learn.  My "stick" was failing.  I believed the average grade was a 75, and students receiving an 'A' were exceptional.  The stick was as a sales commission: directly tied to performance.

Due to my belief in the values of Theory Y management, "the stick" was rarely used.  I learned students wanted to learn.  I learned students wanted attention for performing outstanding work.  I learned students are complicated human beings: the 96% of their time outside my class affects my class.  Positive progress in my class can affect the other 96% of their time.  Students want to feel people are supporting their growth.  Someone is watching and waiting for them to achieve.

As convicted as I am with Theory Y, I learned it is tougher.  Organizational culture drive performance and unspoken rules.  However, once students agree, they support the system for growth.  Students eventually support each other and push growth.

Part of "the stick" was behavior correction.  As young people are apt to do, they wanted to assert their place in my class.  I prided myself on knowing what was "good", "okay," and "wrong" actions.  The "good" I praised, the "okay" I kept a check on, and the wrong I fixed quickly with a sharp rebuke.  I learned to discipline a student whom I genuinely liked.  I eventually considered discipline a core component of helping these young people grow.

Lastly, I learned to love public speaking.  As I stand in front of people I feel the room, watch their responses, and tailor my message.  Given bodily responses, I can determine who is interested, who would like another method of explanation, and who would never accept my message.   I learned to speak with authority, and accept questions on the fly.   Even if every prop I had planned is failing, I learned improv.  One day, electricity was halted; we discussed the philosophy behind our work.

Why I Quit Teaching


In the end, I quit.  I have various excuses, but none satisfy me:

• My wife wanted to stay at home with the future kids, which she couldn't do on a teacher salary.
• My next step was to get my MBA.
• I was burned out on teaching 8 hours per day, and documenting the other 2 hours per day.

My passion for teaching waxed and waned as often as I felt the grass was greener in the business world. Lot's of folks around me seemed to put bugs in my ear about my potential outside the classroom.  In 2004, going the public school teaching route with a degree in Business Management looked like my career had crashed on take-off:

• My professor/mentor, Dr. Hamilton, looked visually disgusted when thinking of my decision.
• While I was walking with a student, he said, "Mr. Winslett, I would expect you would be doing something more."
• My father, assuming I should feel sinful for what he was about to tell me, said, "You know you are being paid with tax money right."
• Even today, my quick description of the decision to take the teacher job is "They were the first organization to say 'we will pay you to spend your days here.'"

While I was teaching, most everyone was shocked I was teaching: except me.  However, the eventual push of my perceived under-performance was too much: I jumped off a hedge fund to complete my MBA.


Completed Circle


My passions for work are: business, technology, and education.  Now, at GradesFirst, I am realizing each.  For me, business is a team of individuals accomplishing one goal via many motives.  When I see technology, I see good business practices.  Education is the largest of the three: it is where the world changes.  Business is the local team; technology is the method; and education is the output.  We at GradesFirst produce change in people's lives.