Launched in March 2022, System Sunday educates innovative people about technology and systems thinking for smart living.
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My white-knuckle-grip wrenched at the collar of my blue tee shirt.
I remember pleading with myself…
“Ben, why do you keep fucking up?!”
The year was 2016—and I wasn’t fulfilling my potential.
There I was—in a 350-sq. ft. apartment in Washington, D.C.—living vicariously through fictional characters. (I had just finished watching the third episode of Mad Men in a row, my favorite distraction at the time.) When what I desired most…was a successful life of my own.
I decided I couldn’t and wouldn’t take it any longer.
So what did I do about it? I spent the next forty minutes reading the summary of Mad Men’s final season (…because who wouldn’t need to know what happened to Don Draper at McCann?).
Yeah. Maybe change would take a little longer than I thought.
I failed to mention that surrounding me—while lounging on my floor mattress—were stacks and stacks of unsold inventory. Three years earlier (at the age of 22), I had started a men’s skincare company. And it was failing.
Sidenote: I’m not against leisure…after your house is in order. Mine at the time? Even Marie Kondo wouldn’t have worked with me. End of sidenote.
The root issue: I had no routines, no systems. I was entirely reactive to the world around me.
I’d wake up and immediately check social media and the news. Then, I’d spend the rest of the workday hyper-focusing on inconsequential things. Like the company’s social media followers. Endlessly anxious, I’d find myself repeatedly rubbing the back of my neck (apparently to try to soothe myself?).
To make matters worse, I’d beat myself up emotionally for not being able to control my constant feeling of dread.
It didn’t help that I had racked up tens of thousands of dollars in credit card debt to start the business…and the interest was piling up. To pay rent, I’d managed to land a serving job at a Michelin-rated restaurant. (That often meant 14-hour double shifts on the weekends.)
Have you ever had that nightmare—the one where you’re trying to sprint for your life, but instead move impossibly slowly? It felt just like that.
Moreover, I’d become so painfully thin that, when a former college baseball teammate and I crossed paths at a bar, he didn’t even recognize me. I rationalized it by saying, “I’m sacrificing other things to focus on the startup.”
But here was the Rich Life1 I dreamed about at the time:
I wanted to live in a home that inspired me.
I wanted to buy anything I wanted at Whole Foods without financial regret.
And I wanted to, well, have non-free activities available to me…
Then I did a mature thing. I took an objective look at my startup, weighed the commercial viability against the money already sunk in it, and decided the smart thing to do was to walk away.
Shutting down the business was one of the hardest things I’ve ever done. Self-esteem, meet rock bottom.
Now, at a crossroads, I considered what I needed most. The answer was specialized skills and structure. So, I pivoted—and applied to business school.
Not surprisingly, I got rejected by many.
After the third “no,” a childhood friend suggested that I stay in my lane…and that maybe I would be happier lowering my expectations in life.
That conversation still motivates and haunts me to this day.
I threw a Hail Mary shortly after, including a sample kit of my former startup’s products with an application.
It connected. Cornell admitted me.
I was happy! For a few moments. Until I realized that business school would be very expensive.
On came the internal demons: What if—like the startup—you fail at this, too, Ben? Maybe it’d be safer to “stay in your lane…”
The stakes were high. But the toll of not taking action was higher. The cost of unfulfilled potential—THAT was a cost I could no longer bear.
Fast forward to 2017, my first year at Cornell MBA.
I remember the specific moment in Management Operations that changed my life. I was sitting towards the back of the room, fantasizing about beating my friend James in a dance battle (which, BTW, would never happen…).
Then, the professor shared that the biggest difference between a high-performing company and a struggling startup was their systems.
That piqued my attention.
“The reason,” he explained, “is that systems allow businesses to operate more efficiently, scale faster, and create more value in society.”
Right there and then—in my mind’s eye—I saw the reel of my entrepreneurial plane crash. With my failed startup, it was like I had built a plane with no landing gear, no destination, and perhaps worst of all, the pilot wasn’t trained on any kind of safety protocol.
Soon though, I felt an enormous weight come off my shoulders. I was capable of being successful in business! I just needed the right strategy. And here it was, with systems thinking.
But even better was the next thought I had: What if I applied systems thinking to my own life?
I began to wonder: If systems are the biggest difference between a startup and a thriving company, then couldn’t systems also be the biggest difference between successful and struggling individuals?
I became obsessed with this question and started reading everything I could on systems and success.
It was like I had swallowed the red pill in The Matrix…and began to see the true nature of reality.2
I discovered that with systems…
your life doesn’t have to be chaotic.
you’re not dependent on “luck.”
you can statistically raise your chances of living the exact life you choose.
That was all the clarity I needed. Inspired, I embarked on a quest to build my personal systems. From physical to digital. From daily to weekly. Across life categories: wealth, health, relationships, et al.
From then on, a calendar invite, “System Sunday,” became the time to build and optimize my systems. A Sunday morning date with myself…to work on myself.
Over time, during this weekly session, I refined my method for building life systems (the inspiration for the website you’re reading now). And the results have been nothing short of transformative. In a few short years, I have:
Graduated with high marks from Cornell MBA
Landed a job at a well-known consulting firm
Increased my salary 5x into multiple six-figures
Paid off credit card debt from the unsuccessful startup
Saved money and bought my dream home
Became a NASM Certified Personal Trainer
Started a daily writing practice (the seeds of System Sunday)
I’ve also attracted into my life an extraordinary girlfriend. In my opinion—the fact that we’re together is all the proof I need that this stuff works.
None of this is to brag, but just to say that through systems, I’m finally starting to realize my potential…and even more. That “more” came to me one day, standing on the deck of my dream home in Vermont, with my favorite person by my side, looking out over the long-range mountain views…
It was then I realized…that even more than material benefits, systems have given me the greatest gift of all:
Stick with me, because this is crucial.
You see, many of us ask, “What’s the meaning of life?”
However, I believe it’s not our job to ask…but to tell. In the game of life, people can find meaning however they choose.3 A better question to ask is: “What’s a game worth playing?”4
Here’s what I know to be true: dedicating your life to becoming better than you were yesterday—to becoming the best version of yourself—is a game worth playing. (And yes, it’s a game that puts you in an optimal position to help yourself and others).
Sure, being bragged about more by your friends and colleagues will feel great. But know this: with systems, you’ll discover the best feeling of all:
Competency-based-admiration. For yourself.
Personal system management is both the means and the end. And for those with an open mind, I’m here to share this life-changing purpose with you.
System Sunday is the resource I wish I had six years ago…at my breaking point in that beat-to-shit apartment…before I spent untold hours (and tens of thousands of dollars) discovering personal systems.
I don’t have all the answers—and probably never will. But I’m happy to share what I’ve learned so far on my journey.
You can get started by subscribing to the System Sunday newsletter. There I reveal the tech-enabled systems that are powering a new era of personal development (the ones that have made all the difference in my own life).
In the words of David Foster Wallace, “I wish you way more than luck.”5
Sam Carpenter, in Systems Mindset (Chapter 36), relates adopting the systems mindset to taking the “red pill,” a movie reference to The Matrix. In The Matrix, Neo (played by Keanu Reeves) is given the choice between swallowing a blue pill and remaining in an illusion or swallowing a red pill and seeing the true nature of reality.
Inspired by Ryan Holiday’s The Daily Stoic, Marks of a Good Life (October 20th):
“What’s the meaning of life? Why was I born? Most of us struggle with these questions—sometimes when we’re young, sometimes not until we’re older. Rarely do we find much in the way of direction. But that’s simply because we miss the point. As Viktor Frankl points out in Man’s Search for Meaning, it is not our question to ask. Instead, it is we who are being asked the question. It’s our lives that are the answer.”