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Failure State – My MBA

Welcome to Failure State, a series exploring my (many) failures in life and what, if anything, I’ve learned from them.

I’ve been feeling a little fragile recently, a little bit like I’ve made too many messes in my life. Maybe not fragile. Maybe tenuous, or volatile, or prone to melancholy. Maybe fragile. Perhaps the lack of sleep only a sleeping newborn can provide is doing it. Perhaps it’s tied to my current lack of gainful employment. Perhaps it’s because I have no friends here in Delaware and no good way of making them. Perhaps perhaps perhaps. In reality, it’s all those things and more.

My hope with this series of posts is to work through some ventures in my life that I feel missed the mark. Maybe at the time I thought they were doing ok, but in retrospect they weren’t. And other times I knew I screwed the pooch in the moment.

Everyone has these experiences, but not a lot of people talk about them. Sure, everyone loves to discuss their successes, their triumphs, how they conquered their fears and won the day. But I want to digest the trials I lost. What could I have done differently? How could I have changed my thinking about a problem that might have instead lead me to success? How have my bad habits, my bad patterns of thinking about things, led me astray?

Join me over the next few months as I do some critical thinking about my life through my finger tips. This first entry will be pretty straight-forward as a way to ease us all in.


In waning hours of 2018, I was excited about what we were doing with the greenhouse business. It was tough, but I was learning a lot all the time. It soon became quite clear to me that there was still quite a bit I was completely clueless about when it came to the running, growth, and expansion of a business. How do you expand a business? How do you market a business? What the hell is a stock option?

Now, we certainly didn’t have any of that stuff on our plate with Verdant. We were busy enough trying to keep jobs going and making sure people were getting paid. But what about the future? There was going to be a future, right? (spoiler: not really) And, if there was to be a future, then this was stuff we should probably know about.

I decided to start looking at MBA programs. I wasn’t going to move anywhere for school, so close to home was ideal. I went a couple open houses for various programs. I spent months studying for the GMAT. I bought some books. I taught myself Statistics because I had never learned it before. I dug out my old Ti-82 calculator. I called up people to get recommendations. I filled out the applications. I took the test, and I did pretty well on it.

I was accepted to Santa Clara’s Leavey School of Business with a scholarship. Nice! Santa Clara worked great for me: it was close to work, close to home, and with the scholarship not unaffordable. I started the program in the summer of 2019.

I was excited! I had worked hard to get there and it felt good to be surrounded by smart people who wanted to learn. It was a feeling I missed in my greenhouse construction life. Sure, JJ and I were working and learning for Verdant, but intellectual curiosity was not a job requirement for most employees.

And the material was fun at the beginning. Certainly quite different than what I learned in film school nearly two decades earlier. It was great for a while!

Soon, however, I started to realize that I wasn’t actually learning about how to run a small business like the one we had with Verdant. Instead, we were learning how to be middle managers in large corporations of the type that cover Silicon Valley. A type I find to be particularly onerous, unfortunately. A huge focus was put on tech companies, how they are run, how they go public, and how they are eventually sold. And it makes perfect sense! Santa Clara in located right in the heart of Silicon Valley, so why not learn about how business is done there?

None of this is inherently bad, either, no matter how I feel about the funny-money “disruptors” who fuel the wild speculation of Silicon Valley and are more interested in extracting value at all cost than creating it. The ethics in the situation rely more on what you do with the knowledge than the knowledge itself. Not everyone who runs a technology company wants to pull together angel investments on a business model that cannot possibly run profitably but looks compelling on paper, put traditional forms of the industry they are disrupting out of business, make absurd amounts of money going public, and then sell it all off for it to collapse under its own weight once the angel investment is spent. But lots do. Too many do. And that’s not me.

Why, then, was I in the program? What was I looking to get out of it?

Was I going to leave my life to be a manager somewhere at Google/Facebook/Whatever? No, of course not. What I wanted from running a business was more autonomy, not less.

Was I going to start my career over? No way. At one point I was exploring some sort of lateral moves based on what I had already spent many years doing. The job counselor suggested I look into taking an entry-level position in the AV department somewhere. That was eye-opening. First, I understood in that moment that she had absolutely no clue about what my previous work was, even though I explained it. Second, she was incapable of giving useful advice. Third, a lateral move probably wasn’t likely. I guess eBay doesn’t really care about how much DaVinci Resolve experience I have?

Was I going to drink the Kool-aid and prostrate myself at the altar of that year’s Elon Musk so that I might imagine I could one day be another billionaire king, even though I don’t have the same South African diamond mining wealth? No, not in a million years. I’ve never been much of a joiner. In fact, I might be a bit too much of an iconoclast to exist in a big corporation. I could barely keep it cool in the ad industry.

So what was I doing in a place where the target was a life I didn’t want to lead? What, exactly, was I investing in? I wrestled with that. And, I am not sure that those feelings were enough for me to leave the program by themselves. As Sir Francis Drake wrote in a letter to Sir Francis Walsingham in 1587,

“There must be a begynnyng of any great matter, but the contenewing unto the end untyll it be thoroughly ffynyshed yeldes the trew glory.”

You might have heard the more popular version of that quote as it was adapted 1941’s Daily Prayer by Eric Milner-White and G.W. Briggs.

“O Lord God, when though givest to thy servants to endeavour any great matter, grant us also to know that it is not the beginning, but the continuing of the same unto the end, until it be thoroughly finished, which yieldeth the true glory”

You, dear reader, will know I am not a religious man. Yet I often think about these words when I am considering dropping a pursuit or not. They have become deeply ingrained in the way I think about things. It should be no surprise, then, that I would probably have continued through the MBA program except for one other, little thing that happened.

My third quarter began in January of 2020 on the eve of a world-stopping pandemic. We began the quarter as any other. We met in person. No one had a stash of masks in their car. You were weird if you were constantly sanitizing your hands. Do you remember those sweet, innocent days?

Just before the quarter’s end in March, all classes went online-only. Everyone struggled with the transition, as can be expected. And we all sort of thought it would just be a temporary thing and that we could hopefully resume in-person classes in the next quarter.

Oh how wrong we were!

The entirety of the next quarter was online. It made sense. Covid-19 was ripping through the world and creating all sorts of havoc, not to mention killing and incapacitating people all over the place. It was terrifying. All the protective measures—as restrictive as they were—were put into effect to keep people safe. That’s not up for debate. I understood why things had to be the way they were.

But that didn’t change that I did not click with the online class format. I’ve never been good at paying attention, not in class, not at home, not at work. It’s a miracle that I get anything done at all. A shiny thing off to the side? Oh hey neat! Attention shattered. Something to tinker with while I should be doing something else? Fun! What was I doing? Oh well, time for a coffee.

If I am to dig in and focus, I require that all distractions be removed or that I am being held liable by other people. The classroom environment was great for both of those requirements. I wouldn’t even bring a laptop; I was fully pen & paper only. Internet access in class? Prescription for total focus loss. Plus, I was surrounded by other people. They weren’t paying attention to me in the slightest, but I still would have felt weird slacking off in front of them.

With an online class, though, all that is out the window. Surrounded by no one. Constant internet access. Everything’s on the computer. The ability to turn off my Zoom camera and wander to the kitchen for a snack. Can we see how bad this was for me? And that’s just on my side. Never mind that regular technical issues got in the way from all angles. Or that the professors, no matter how knowledgable or proficient at teaching, had a hell of a time adjusting to this new format. Or that everything was slowed down at every step by the remoteness. Or that I felt totally disconnected from my classmates. It was a disaster for my learning. I don’t think I remember any of what we learned that last quarter, just how miserable the process was.

And then my scholarship ran out. I knew that was going to happen. It wasn’t a tragedy. But it did weigh into my feelings about continuing.

It was clear at that time that the rest of our MBA program was going to be online-only. We had four quarters left and the pandemic wasn’t slowing down. Was I going to go into 60 grand of student loan debt to learn material I was reasonably sure wasn’t going to play into my life? Was I going to struggle through four more quarters of online classes when I could barely manage to get through one, during which time I had learned absolutely zero? Was I going to invest the time and energy into a program that was not going to pay for itself through career opportunity? (Not to say that it doesn’t pay for other people, just that it wouldn’t have paid for me.)

Oh! And we were also asked to move out of the house we were renting because the owner needed to sell to pay for the full-time care of her mother in law. No hard feelings. She did was she needed to and was reasonable about allowing us time to get our shit in order. It was nevertheless a bummer. Our house search during these early pandemic days of the eviction moratorium was a nightmare. Our only real options were wildly inflated dumps up in the mountains that we couldn’t have afforded anyway since Sarah lost her restaurant job. That was when we were offered shelter here in Delaware and decided to move.

Add that to the list of questions. Was I now going to be doing an online MBA in California from Delaware with zero chance to go back even if in-person classes did resume? Would I add “timezone difference” to the list of things that made it basically impossible for me to pay attention during online classes?

No, I wasn’t.

In July of 2020, just before we packed up and moved across the country, three little embryos cooking away in Sarah’s belly, I sent Santa Clara notice that I was taking a leave of absence. I knew I wasn’t going to return, but I bought myself a year to change my mind. And that was the end of my MBA journey.

At this point, I have no intention of finishing. I don’t see the value in it for my life. When I need to learn about business again, I can buy a book. Or books. Many, many books with the money I didn’t spend. Sometimes I feel like I should have finished, but only because of that Drake’s Prayer mentality burned into my brain.

On the eve of the three year anniversary of that fateful e-mail, do I regret that I dropped out? Yeah, sometimes. A little. Maybe more than a little. Mostly because who knows where it could have led in a different life. Am I like 80% confident that I made the right choice? Yeah, I am. And sometimes 80% is all you can ask for.

I hope you’ve enjoyed reading this dive into one of my personal failures. As I wrote in the intro, this was an easy one. Next time, we’ll dive into a subject I feel much, much more conflicted about. Guilt! Shame! Regret! It will have it all. I’m not even sure which topic it will be yet, exactly, because that description fits most of them.

3 Comments

  1. Jess Jess June 6, 2023

    Failures are the best; because each one leads to something new.
    At least that’s my comforting thought.

    I can relate to this; I dropped out of my master with 10 credits left. It has lived on my resume as forever unfinished for the last decade+, and always will.

  2. Angela Angela June 13, 2023

    I made it through. I have lots of thoughts about it. It was good to read yours though you didn’t make it through. Mba, Covid, etc…life has taken many interesting twists and turns the last few years.

    • Joe Dillingham Joe Dillingham Post author | June 13, 2023

      Congrats! I am super curious to read your thoughts about the program. Has it been useful to you since finishing?

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