Sometimes I feel
I might touch eternity –
Lewis tells me that now
Is its closest point.

from Resonant Tension, Phillip Berry

In a note to me last year, my sister called me a “serial reflectionist.” Not long afterward, I started a post with the title above and stopped after the first paragraph. I decided that I needed a bit more reflection before engaging with my sister’s creative description. This morning, I noticed the draft post in a queue on my website and opened it to see where it was going and where it stopped. Interestingly, it is one of 16 unfinished drafts on the site. A curious thing about my approach to these posts is that I very much run on inspirations in the moment.

This is how I know I am not a professional writer – I do not write from discipline but from the things that are striking me at a point in time…usually the Sunday morning of my post. The other way I know? I do not have to make my living by writing. A reality for which I am very grateful.

Today, I am going to pull a few of my old drafts into this post and tackle them with intention as a committed reflectionist. I make no promises of cohesion, order, or profundity. However, I have never promised any of those. My hope is that something in them prompts the reflectionist within you.

In 2011, HBO released the first episode of Game of Thrones, a raw and often troubling journey through a fictional world blending elements of medieval fiefdoms and fantasy in a brutal storyline focused on the various character’s quest for power. Recently re-watching the very first episode, I found its raw brutality and sensuality as jarring as the first time I experienced it, but it was the grimness of the characters that stood out even more in this viewing. Recently walking through a tour of Orsini-Odescalchi Castle in Bracciano, Italy, I had visions of that grimness in harsh realities of its history.

Built in the 15th Century in the midst of city, family, and nation power struggles, loads of intrigue, and existential conflicts, in a rawness reminiscent of Game of Thrones, I realized that author, George Martin, had plenty of inspiration for his stories. No magic or dragons needed, the castle, rising high above the beautiful valley around Lake Bracciano, echoed with the stories of arranged marriages, secret notes, crazy looking medieval weapons, “murder holes,” and epic struggles among families with names like Medici, Borgia, and Orisini, not to mention kings like Charles the VIII. Some things never change.

Looking around today, not much has changed in the 600+ years since the castle was built. Rulers vie for territory. Nations threaten and war over resources, control, and pride. Intrigue abounds and we now have technology that the 15th Century Orsini would look upon as magic. We’ve gotten even better at intriguing and killing in the years in between. My mind is taken to the movie Terminator 2. A young John Connor asks if humanity is doomed; the Terminator, sent back from the future to try to save humanity, coldly responds: It’s in your nature to destroy yourselves. Will we ever learn?

Evil is such a strong, uncompromising word. History is rich with examples. Alas, history is unnecessary for the affirmation of evil’s dark presence among us. We know when we hear of it or when we see its ugly head reared in our midst. A quick search for stories or quotes on evil reveals a voluminous accounting of the dastardly, depraved, and the devastating. Headlines affirm these darker tendencies. Consider these quotations:

Stevenson’s story goes directly at man’s curious capacity for light and darkness in his tale of the good and upstanding Dr. Jekyll who slowly loses himself to his dark alter-ego, Mr. Hyde, through the creation of a potion to separate the good and evil parts of the human personality. The book draws a stark line between man’s good and evil natures, suggesting a hardwired dualism within each of us. Solzhenitsyn knew it well, writing of gulags and the brutal nature of marxism and power in Soviet-era Russia. He saw the evil that men do.

But Solzehitsyn also wrote that “beauty will save the world,” referring to the elevating power of the aesthetic, the moral, and ultimately what they reflect: the Sacred beauty of God. Taking some time to study virtue and man’s quest for deep and abiding happiness, we begin to realize that our great potential for evil stems from the deep sin of pride – a self-regard that puts us at the center of everything. Our needs. Our wants. Our demands. The will to power comes from this place and the story repeats itself again and again and again.

But we find that it is a hollow and finally unsatisfying place. Yes, the capacity for evil runs through the heart of every man, but we are blessed with the power to choose. Our great gift of free will gives us the power to do what is right and the person formed in the habit of making that choice is path to beatitude: complete joy and fulfillment of all desire.

Since we’re in the middle of graduation season, it seems fitting to return to a couple of drafts that tie into the transition from college to profession. These reflections come from 2016 and 2017 and center on entrepreneurship. I’m not sure why I did not post them at their respective times but such is the way of inspiration – not all inspiration is good or timely, and not all posts go where I want them to. There is so much more to be said about both but graduation speeches aren’t meant to be books and we’ll leave what’s unsaid as potential for a future post…or two.

I recently had the opportunity to experience commencement exercises at Hillsdale College.  Justice Clarence Thomas gave an inspiring keynote address which you can see in this full video of the afternoon.  There has been some wonderful commentary on Justice Thomas’ message but that is not what this post is about.

The Class President gave a strong speech connecting a liberal arts education with entrepreneurship.  “I’ve heard it said that entrepreneurship is living a few of years of your life like most people won’t so you can spend the rest of your life like most people can’t.”  He goes on to tell us that his liberal arts education has led him to the conclusion that he wants to be an entrepreneur.

For the last week or so, the speech has rolled around in my head as I considered a classical education, entrepreneurship, and the quotation he shared.  Yesterday, in a casual meeting over coffee, I was asked about my “Why?”  The context centered on my motivations relative to my companies.  As I answered the question, that graduation speech came back to me and I realized that his opening quotation on entrepreneurship did not reflect my experience at all.

For me, entrepreneurship is about the infinite game.  It is a marathon not a sprint.  The goal is to stay in the race.  Sure, there may come a time to sell and review options.  But entrepreneurship should be a way of life not a build it, sell it, and retire on the beach plan.  My father-in-law successfully built several companies and I can remember him telling people that he hadn’t had a job for 30 years.  His work was a way of life.  It was more of an endless project than some grand plan to build and sell, amass wealth, or maximize his accumulations.  He lived his ventures and in so doing, experienced a life full of adventures.

As I consider that speech so many years ago, I realize that I want to live like most people won’t but it has little to do with money or things.  For me, the entrepreneurial journey has been about building a life: a family, a team, companies, relationships, purpose, experiences, stories, resilience, expertise, perspective, independence, impact, and perhaps a little wisdom.  I could stop today and feel pretty good about each of those categories.  But that is not the point – there is no arrival.

To the young entrepreneur, if you feel called, I encourage you to pursue the path.  It is a journey worth taking and I’m confident that you will find success – however you may define it.  Your message regarding a liberal arts education is spot-on: I can think of nothing more valuable than leveraging the lessons of our greatest thinkers and learning how to think and communicate for yourself.  Those skills will serve you well along the way.  As for the details of your “why,” “what,” and “how,” you’ll figure it out for yourself.

Congratulations on your recent graduation from college!  These are heady times with the world wide open before you – the sky is truly the limit!  I wish you worthy challenges and the joys that accompany when you overcome them.

The temptation is great to seek a pathway, a set of plays that will result in the achievement of your dreams.  Alas, you have chosen a direction that does not lend itself well to a fixed recipe.  I suspect that is what has drawn you to this adventure but more on that later.  No, the direction you have charted is toward open water and there is little now visible to tell you which way to go.  Do not be discouraged by this!  For the faithful, the signs will appear and you will feel nudges indicating direction.  For now, the important thing is getting started.

Each of our journeys is as unique as we are as individuals.  Some choose a trade which often gives a clearer sense of direction in terms of what their working world will be.  Medical professions, law, accounting, engineering, and teaching are examples of more concrete paths with somewhat easier to identify outcomes.  Invest your time, take certain courses, pass certain tests and you will be a practitioner.  There are certainly bumps and surprises along the way but there are also clearer steps and clearer results should you complete the journey.  This is not what you’ve chosen.

To choose the path of the entrepreneur is to choose the unknown.  Like many things we seek, it is a movement toward a way of life.  Some may choose it because they think it will bring riches.  Some may choose it because of the sense of freedom it inspires.  Some may choose it for a perceived glamor and status that our society attributes to those who successfully navigate its difficulties.  Whatever motivates you, it is obvious you feel called.  Right now, your “why” isn’t particularly important.  Right now, deliberate movement is critical.

You see, true entrepreneurship is not a destination.  It is a journey.  It is a lifestyle.  To be an entrepreneur is to see things that others can’t and to do things that others won’t.  It is identifying risks, accepting the possibility of failure, and moving forward anyway.  To be an entrepreneur is to undertake the journey even though you know it might not work.  To build a life as an entrepreneur is to pick yourself up from those times it does not work and try again.

To begin is first to make a choice and then take a step.  Now is the time to take the step, whatever it may be.  Just remember that there are many more to come.  On this occasion, celebrate the choosing, identify that first step, and begin your journey.