Wisdom from Wizard Academy

Last week I had an email conversation with someone that made me stand up in my office and go outside to take a walk in the cold. I did it primarily to calm down, but also to give myself time to think before I started replying. 

I’m not proud of that moment, but it’s necessary to tell you about it. It’s how the rest of this story makes sense. As I walked and started breathing normally again, a phrase my dad often says to me popped into my head.

“Never attribute to malice what can be explained by stupidity.” 

That phrase is referring to “Hanlon’s Razor”, an idea put forward by Robert J Hanlon. It came from a submission he made to a book that was compiling various approaches to reality that mirrored Murphy’s Law. It’s not entirely original, but it has a good flow to it. As a musician, I appreciate that. 

It was restated by Douglas W Hubbard as ““Never attribute to malice or stupidity that which can be explained by moderately rational individuals following incentives in a complex system of interactions.”  It is a much wordier version of the same thing, but avoids calling people stupid. I shared that one just in case you need a worksafe quote to use at your next meeting. 

When I got back to my desk, instead of responding, I asked a question. The answer to that question completely altered our entire email exchange. We both realized we had been talking about totally different things with completely different contexts. I’m amazed we got as far as we did before it became obvious. We can be so myopic when it comes to our own little storylines. 

So my thought today, as I write to you, is the same thought I have on an almost monthly basis. Possibly weekly.

When something offends you, never assume that was the intent. When someone does something stupid or hurtful, take a breath and ask yourself if there’s any possible explanation other than, “This person is a selfish/hurtful a$$hole/idiot.”  

It’s more likely you are dealing with a simpler situation. It’s more likely it becomes clear as soon as you ask a few context questions. Everyone is stupid sometimes. But no one goes around intending to be stupid. 

It’s more gracious and far less stressful than walking around with a chip on your shoulder. And it is kind.

Daniel Whittington – Chancellor

PS. Just for fun, it reminds me of this Key and Peele sketch. Enjoy a laugh. 

In January of 2020, I took over as Chancellor of Wizard Academy. In March of 2020, I celebrated by closing the campus due to a worldwide pandemic. 

My first fear was that I was going to be standing at the helm as Wizard Academy sank beneath the waves. Thank God, a handful of major donors stepped up and donated very real amounts of money to keep us open, keep our staff employed, and give us time to figure out a plan. I’m still immensely grateful for that moment. 

But I was grateful for another reason. It also gave me a chance to address another very real fear I had leading Wizard Academy. How do we stay relevant as a business school in a world where the business tools, strategies, and resources change almost weekly? Are Magical Worlds, DaVinci, Portals still relevant as the date of their first appearance gets further away in the rearview mirror? 

During the pandemic, we continued our monthly “Ask the Wizards” and helped guide our alumni by answering their business questions each month. Everyone was navigating the constantly changing landscape. Everyone was in survival mode. 

But the reality that surfaced during those Zoom calls calmed my fears in a way I never expected. Yes, the world was changing dramatically. Businesses that were supposedly “bulletproof” were going bankrupt. Other industries were exploding far beyond anything we’d ever seen. New ideas were surfacing, new resources were offered, and everyone had theories about why it was happening, how to stay on top, and what was next. 

But in the monthly calls, the opposite was happening. In spite of how dramatically things changed, the questions we got each month were the same ones we’ve been answering in classes at Wizard Academy for 20 years. The core curriculum of Wizard Academy became more relevant than ever. And it saved a lot of our alumni from closing their doors.

I came out of that pandemic with a renewed sense of purpose and a solid understanding of Wizard Academy’s place in the world. I’m hoping it’s a helpful reminder to you in 2025. 

The fundamentals of human communication and marketing remain true regardless of era, business category, or size of the company. 

You don’t stay relevant by figuring out how to ride the ever-changing currents. You stay relevant by being anchored on solid ground in the midst of the flood. 

Find your North Star. Choose your non-negotiables. Define your destination. Don’t forget to celebrate. 

Daniel Whittington – Chancellor

PS. Magical Worlds is the core curriculum piece that built Wizard Academy. It’s the guiding class by which all others are measured. The next one is in February and we’d love to see you there. 

“If you make small steps of progress every single day, the destination is inevitable.”

Those words were spoken to me by Roy Williams when I first got to Wizard Academy in 2013. I don’t remember what I was doing exactly. I do remember that it was a large project that felt impossible at the moment. I was bemoaning the lack of progress and talking about how the end felt miles away. He said the words while waving a hand slightly in my direction. Like he was shooing away worries fluttering around my head. 

He followed it with another sentence I’ve never forgotten. 

“You can accomplish almost anything if you remove arbitrary deadlines and relentlessly pursue the destination.”

These phrases roll around in my head these days as we stumble into 2025 with a lot of whispering question marks. 

If something is important enough, then dropping a deadline on it is pointless. Either you’re going to do it or you’re not. Maybe a deadline can give you a sense of urgency. I’ve heard that’s helpful for some. But if you reach the deadline without achieving it, do you plan on giving up?

I was about 15 years into pursuing a full-time music career when someone in my life uttered the words, “So, exactly how long do you plan on doing this?”. Looking back it was one of the first true death bells of that relationship.

I should have paid more attention to that moment. I should have held that question up against my heart to see if it fit. Instead I listened, and marked a deadline in my head. And then, in 2013 I walked away.

I don’t really have regrets. 

Life is choices followed by consequences. When I left that pursuit, I walked into the arms of Wizard Academy. It changed my life forever in beautiful and immeasurable ways.

I’m older now. In the last few years, I’ve had more wisdom whispered into my ear than angry words. Standing in the entry door of a New Year, I’m more concerned with figuring out what is important than creating arbitrary goals. 

I want to hold things up against my heart until I find the ones that fit. I want to name my destination and then carve pathways towards it. Even incremental ones.  I want my hopes and dreams to be inevitable.

Maybe New Year’s Eve in 2026 will be less about coming up with new agenda’s and more about looking backwards and celebrating how far I’ve come. 

So here’s to you and incremental steps. May your dreams be inevitable.

Daniel Whittington – Chancellor

“Good magic isn’t cool. It can’t be cool. Cool is divisive. Cool is exclusionary. Cool does not sit next to the new kid at lunch, and good magic is all about sitting next to the new kid at lunch.” – Nate Staniforth,  “Here is Real Magic”

I was walking the campus last week with a few people who hadn’t heard of Wizard Academy until moments before they stepped through the threshold of the Wizard’s Tower. 

We roamed the stairways and halls, gazed at old oil paintings of Don Quixote, sampled a a cool glass of whisky from the Vault, and rang the bells in the railing of the mezzanine Library. As we stared over the edge of the roof towards the Hill Country horizon, one of them said, “Man, if you could just show the world how cool this place is, you’d have to fight people off with a stick. you’d have people lined up at the gates trying to get into a class.” 

My first reaction wasn’t, “Yeah, you’re right! If only more people in the world knew more about us!”. It was, “Oh HELL no.” I didn’t speak, but I felt those words well up viscerally from my bones until I had to clench my jaw to keep them inside. Instead, I said, “Yeah…”, and then I changed the subject. 

I’ve had that reaction before, and I’ve been thinking more about it this week after that conversation. Shouldn’t I want the world to hear about us? As Chancellor, shouldn’t I want the markers of success that come from having to turn people away because so many are knocking at the door? I really don’t think so. But why?

This morning, my father, Brad Whittington, posted the quote above from one of my favorite non-fiction books. Immediately, it crystallized. 

For eleven years, I’ve told people that the death of Wizard Academy would be if we became “cool”. Cool people are hung up on image and posturing. Cool people follow shiny objects and change their passions with the weather. Cool people are afraid to be goofy and dorky. Cool people are terrified to fail. 

That is the exact opposite of our brand of crazy. We do the work. We wade into the mix. We commit to unreasonable dreams, and we don’t give a crap about what other people think. We know that failure is temporary (as is success). We don’t worry about being cool. We worry about being kind. We are trying to find how we contribute to a better world for our businesses, our employees, and our customers.  

True success is measured by the people who stand with you. True success is how you impact the people in your world, not how you are perceived by the people outside your world. 

Happy Christmas to all my fellow uncool people, from your home in Texas. There will always be room for more uncool people at our table. 

Daniel Whittington – Chancellor

“You are our brand of crazy!”

That phrase gets thrown around a lot at Wizard Academy. Sometimes we’re talking about a person.  Sometimes we’re talking about an idea, ad copy, or a business approach. 

There are a lot of filters in place for Wizard Academy. It doesn’t take much to ruin the vibe in a small and tight-knit community. Just one person walking into a class more concerned with selling than learning. One person who views networking as a notch on a belt instead of relationship and connection. 

You have to do weird things to keep out the wrong sort of people. So we call ourselves Wizard Academy. We talk about Broca’s area in marketing terms and we throw around lingo like “third gravitating bodies” and “Write like Monet” or, “Man that’s just frosted Frank.” 

We also don’t advertise to the generic business community at large.
If you found us, the odds that you’re our kind of person are already astonishingly high.

There’s also a beautiful benefit of being your most weird self with no apologies and no qualifiers. 

The people who show up at Wizard Academy have something in common. It’s not their business category or their job description. It’s that they feel like outsiders. They see the world in a way that is hard to explain to others. They feel the need to constantly translate themselves to other people to seem a little less “weird”. 

When you arrive at Wizard Academy for the first time, you discover there’s an entire room full of people just like you! You may have different opinions, different approaches to the world, and different goals. But you’re all just a little on the outside of how “normal people” do things. 

Which makes you “Our brand of crazy.”

When you experience that, you immediately understand why so many people call going to Wizard Academy, “coming back home”. 

We feel the same way when you walk into the room.
We are looking forward to seeing you soon. 

Daniel Whittington – Chancellor

PS. The next chance you’ll have to gather for no reason except to hang out with other crazy people, is the Wizard Academy reunion one week from today. If you’re joining, head over and register so we make sure we order enough food!.

“When I step onto this campus, it feels like I can finally take deep breaths.”
“When I step onto this campus, it feels like coming home.”
“When I step onto campus, I feel a sense of peace wash over me.”

These are words I hear at least once during every class we hold at Wizard Academy. This week, as we wrap up Magical Worlds, the thought that lingers with me is, “Why?”

What is it about this place that makes people feel as though they’ve escaped from the real world for a brief moment of respite and inspiration?

I believe the land itself is part of the answer.

Wizard Academy sits on ancient holy ground. The original humans to walk these paths recognized it as special, a place set apart from war and conflict, from ordinary villages or encampments. They sensed something here that, even in our more “modern” age, remains true.

There are elements of this earth that carry knowledge we are either too old or too young to fully understand.

We attempt to capture this in terms like “intuition,” “feelings,” or “feng shui,” but you might as well call it “magic.” We can touch fragments of that knowledge, but we can never fully grasp it.

Yet there is a deep truth in the resonance that rolls through our bones. It’s the origin of all the mythology that surrounds elements and the physical earth. We are all part of a song—not just one, but a myriad of songs woven together like harmonies in an orchestra.

And this land vibrates with those songs. I recognized it the moment I first set foot here, my soul resonating like a tuning fork as I walked the trails to the Wizard’s Tower. That’s why I’m still here. In the eleven years I’ve served the students on this campus, the feeling hasn’t diminished. No matter my mood, the conflicts in my life, or the burdens I carry, when I walk the foothills of Wizard Academy, something in my bones says, “It’s going to be okay. You’re part of something greater.”

That’s what makes this such a remarkable place to learn and teach. At Wizard Academy, it’s easy to find deeper meanings and answer life’s biggest questions. They are threaded through these hills like veins of gold.

If you’ve ever felt the same as you made your way to Engelbrecht House or climbed the hill to the Tower for class, you’re not alone.

We all feel it.

It’s why we keep coming home.

Daniel Whittington – Chancellor

A few weeks ago, I picked up an old friend from the airport. I knew I hadn’t seen him in awhile, and I knew I missed him. I was excited to spend an uninterrupted afternoon together before we got sucked into the business that brought him to town. It wasn’t until he walked through the sliding doors towards my car that I felt a wave of “Nostalove”. Don’t blame me if that word makes you feel weird. I read about it on the internet and, according to Google, all the cool kids are saying it. I picture a fragrant college freshman with fake dreads and a Bob Marley poster wearing tie-dye. Sure, the phonetics are funky, but the meaning is exactly right. Nostalove is a strong combination of remembering and nostalgia mixed with affection and joy.Life gets busy. And the older I get, the more the people I love are scattered across to the ends of the earth. We remain tied together only with texts, phone calls, and random social media comments. That is not enough. I desperately need face-to-face interaction with the people I truly know and love. I need to share the same space and breathe the same air. I need to watch the smile roll across their face and hear the sound of their belly laugh. Nothing on the internet can equal the magic of in-person connection between like-minded human beings with affection in their hearts. That afternoon was a tapestry of laughter, empathetic anger, joy, discovery, remembering, and whiskey. It reminded me of who I am. Go find your people. If you need to get in a car or on a plane, it’s worth it. Yes, money is a real thing, and life is expensive. You can get more money.The only thing we’re truly running out of is time. Daniel Whittington – Chancellor

Recently I was talking to someone I hadn’t seen in twenty years. They remained actively involved in a worldview that I had left behind somewhere in my mid-twenties. This person’s world hadn’t changed much since then. Mine had fundamentally altered in both color and shape.

Surprisingly quickly, a few things were stated as assumed facts that caused a visceral reaction in my bones. I realized I was about to have a fundamental and possibly aggressive disagreement with someone I hadn’t seen in two decades. 

They didn’t intend malice or have any desire to fight or argue. They just assumed that I was still the person they remembered from twenty years ago. They were simply making small talk with what they thought was common ground. 

Two things occurred to me. 

Our current era is an US VERSUS THEM era. That’s the water we’re swimming in. All the instincts of our culture are shouting. 

“Pick sides!
Find your enemies!
Burn things to the ground!” 

I don’t want to be a part of that world.

I want to be someone who listens, sees, and tries to understand. I want to find the human behind the opinions. It’s really hard. And I’m not always good at it. 

I had a chance to be kind, or a chance to turn our conversation into a micro version of our current culture war. 

And there was almost nothing to gain. I didn’t plan on staying in this person’s life to see it through to the end. I had no relationship skin in the game. That’s called an opinion hit-and-run. The odds of it having any value is so close to zero that the number is irrelevant. 

The second thought I had came later, and it landed like bricks.

Everything this person was saying was exactly what I used to say. Almost word for word. Effectively, I was about to have an argument with myself from 20 years ago. 

I remember that time in my life. I remember how certain I was of so many things. I remember the hubris of “knowing” that threaded through all my words and beliefs. 

I’m not that person anymore. I doubt more than I know. I’m constantly learning ways that I’m wrong. I’m constantly caught off guard by my ignorance and assumptions. It makes me less certain about anything other than relationships and people. 

Keep in mind, that doesn’t stop me from having opinions. I definitely have opinions. I’m a professional opinion-haver. But I also eat my words so frequently that it might as well be my part-time job. Hopefully this reminder is as helpful to you as it is to me.  

Hold your opinions lightly.  Especially when your theoretical opinions run up against very real human beings. 

Daniel Whittington – Chancellor

A weakness of ambitious and creative humans is their seeming inability to be worthless. Even our hobbies are labeled and tracked on score cards and fantasy leagues. When it comes time to finally relax, your phone and brain maintain a constant bell ringing of “things you can’t forget to do”. 

Sitting in community and enjoying interesting conversations about fascinating topics is a lost art. 

“We are awash in numbers. Data is everywhere. Unquantifiable arenas like history, literature, religion and the arts are receding from public life, replaced by technology, statistics and math. Even the most elemental form of communication, the story, is being pushed aside by the list.” –  Bruce Feiler, The New York Times May 16, 2014

We’re working to put a stop to that with a revival of Gatherings of the Worthless Bastards. 

What does it mean to be Worthless?

My friend, Tom Grimes said it best, “It can involve engaging conversations or it can be a big swath of quiet as you take in the world and simply watch. It always involves laughter. It always involves exploring but it never requires an agenda. It’s adults at play. Everyone is on the same level … all bastards, no titles, no prima donnas, no one has rank, no one is in charge.   It really just needs two things … a few friends and a little time. Time to not DO ANYTHING … at least not do work or anything related to work.

There are only three rules for being worthless:

1. If you have a good story, tell it!
   Funny stories of personal experience are encouraged. Discussions often wander in and out of the arts: Music, Film, Literature, Painting, Photography, Good Food, Drink, Sculpture, Gardening, Poetry, History, Psychology, Culture, Travel, “Seen any good movies lately?” or we may tumble into talking about an interesting discovery in science. The conversation can go anywhere. You’re free to talk about anything that fascinates you, intrigues you or impresses you, except:
2. There is to be no discussion of business, politics, sports or work.
3. These are not counseling sessions.
   Leave your problems at home. Leave your business cards at home. Leave your plans and goals and objectives at home. Bring only your curiosity and a desire to unwind.

We’re going to start hosting them again at Wizard Academy. 

Our first one is Friday, September 6th at 4pm and we’ll gather at the Wizard’s Tower. 

This is us sounding the siren. If you want to incorporate a bit of intentional worthlessness in your life by hosting your own gathering, let us know. We’ll post your dates on our site. We only ask that you host it somewhere anyone can join, and that you hold it on a predictable schedule. 

Click here to let us know and announce your first one. 

Daniel Whittington – Chancellor

“Be careful of the company you keep, because you become like them.” 

That is practically a truism. But you can’t say that without also saying this. Sometimes the company you keep fundamentally changes you in the opposite direction.

What happens when you stumble into a workplace where the worldview is foreign or even aggressively opposed to who you are? What about when circumstances force you to choose a path that is not what you wanted?

Your desperation to survive and protect yourself can also transform you, sometimes into someone you don’t want to be or someone you have a hard time recognizing.

I’m an independent and stubborn person. I tend to aggressively fight against being pulled into “sameness” in a group. I would argue that’s my default setting.

In high school and through my early 20s, I was heavily involved in religious communities. I saw myself as a true believer at the time. I was all in. But I was also not willing to abandon who I was and what I thought about the world. Because of that, I was often seen as a problem. I regularly got into trouble or was lectured and reprimanded. More than once, new rules were made because of something I had just done.

I worked various jobs to support a music career, but I always held tight to my identity as a musician regardless of what paid the bills. I might wait tables, but I wasn’t a waiter. I might bartend, but I wasn’t a bartender. I might work at a large marketing company in the customer service department, but that was incidental.

I was a musician.

Everything else was something I was forced to do in order to play music. That attitude meant I often did the bare minimum to accomplish what was needed and get out the door to my real life. Now that I’m older, I’m realizing how much that prevented real growth and understanding.

I arrived at Wizard Academy in July 2013 and crashed into a world of business thinkers and doers. People tossed around business terminology, authors, and “Thought Leader” celebrity names like popcorn in a crowded theater. In some ways, it was like entering a foreign country.

At first, I took a sort of pride in that. I thought being an outsider was my strength. Actually, I still do. But somewhere around the two-year mark, I started reading some of those authors and listening to those thinkers, and I discovered what I was missing.

There is an element of being an outsider that lets you see things clearly. But there’s also an element of being deeply connected or involved that allows you to understand and gain nuances not available to the outsider.

As of this month, I’ve been at Wizard Academy for 11 years. I’ve been the Chancellor for almost 5. I’m not sure what that means exactly, but I think I’m in the middle of a journey as I write this newsletter. It feels simultaneously like I’m a road-weary traveler and like I still have so far to go and so much to learn.

This is more of a confession than advice. But I would like to tell you something, as we sip whiskey in the shadow that the tower casts across the woods. 

Pay attention to the moment.

Don’t become defined by your reactions. Take time to see yourself truly and choose your path with intention.

When you find yourself in a moment or a space that is not of your choosing, slow down, take a look around, and see what there is to learn.

Daniel Whittington – Chancellor

How you live in scarcity is the true marker of your company culture. 

Wizard Academy is a business school, but the first thing we built was a wedding chapel.

Whimsy was a big part of it, because life isn’t worth living without a golden vein of whimsy threaded through it. But it was also born from the desire to give from first fruits and provide something magical for those who couldn’t otherwise afford it. Roy and Pennie have two firm beliefs that drove the creation of the chapel. The first is the importance of commitment and all that marriage symbolizes. The second is that you shouldn’t have to be rich to have your wedding in a gorgeous location. 

Never put off doing kind and generous things until there’s plenty of money. Inevitably, you’ll discover that there’s no such thing as enough. Budgets have a way of sucking up available cash flow like a teenager in a grocery store. 

I’ve been thinking about this in relation to taking care of employees and staff. Recently, quite a few business owners I know have been instituting staff resources and support that should have existed long before. Almost all of them see it as vital, but are not 100% certain they can afford it. 

What I keep telling them is they can’t afford not to. 

In the beginning of a startup, every single dollar is spoken for three times over. You’re not worried about prioritizing people’s emotional well-being as much as you’re hoping you’ll still be able to pay them next week. But that’s a dangerous paradigm. If you put off the health and mental support of your staff, you’ll burn through people like gasoline-soaked paper and fireworks. 

Name your priorities. 
Establish healthy boundaries and take care of your people. 
The well-being of your employees should be as inflexible as rent and utilities. 

You’ll watch your people go from coworkers to teammates. An inspired and healthy team will lead you straight to the treasure troves you need to be successful without sacrificing your people. 

Make the right call before the money, not after. 

Daniel Whittington –  Chancellor