Whether you are beginning a new venture, taking a promotion with new responsibility, or retiring from work, starting a family, or seeing your children leave home, getting married or divorced, looking for a mate or breaking up, you know that change is difficult.
If you are going through any life change, or planning one, you understand the pain of uncertainty, of circumstances being less than ideal. That pain is doubled by the fact that you know you cannot change many of those circumstances — the state of the world, the behavior of other people, and so on.
Few people anticipate that one or more of the major transitions in their lives will take place during difficult and uncertain circumstances in the world, beyond their control. Yet nearly every one of us will encounter this reality, and most of us many times. Even a superficial reading of history is enough to remind us that life is change, and with change, there is always uncertainty.
Each of us would like to imagine that we would finish education during a time of abundant opportunity and economic prosperity where options seem limitless, or to get married and start a family in a time of peace, or retire with secure investments and savings that have grown far beyond what was originally contributed in an economy of price stability.
The ones who do are the lucky ones — but luck is the riskiest of strategies.
Fortunately, individual lives of peace, abundance, and stability can be carved out of even the worst chaos. But it is neither straightforward, nor easy, and if you really want to do it, you must prepare yourself mentally, physically, and spiritually to become the rock that the crashing wave breaks against, unmoved.
This is barely even a theoretical possibility if you follow the main of society, absorbing the anxieties of the harried masses, reacting to every news of change with fear, which is the way most people live their lives. In our time of ubiquitous media, it is perhaps harder now than it has ever been.
That is the bad news. The good news is this challenge is balanced by a wealth of technological tools and information that any of our ancestors would have envied, if they even could comprehend them at all!
For the cost of fewer than a dozen restaurant meals, you can buy a plane ticket and be on another continent in a matter of hours. The phone in your pocket is more powerful than the most expensive desktop computer 20 years ago. You can take high fidelity photos with your phone.
Because of normalcy bias, this statement seems a bit silly. Normalcy bias is our tendency to treat the present as if it had always been this way. Questioning reality is a healthy intellectual exercise, but a particularly unhelpful practical one. So our mindbodies have become optimized for adaptation to reality at-hand.
We take almost everything we have for granted as a result. This lack of appreciation for the magic at our fingertips is a fractal of the magic we overlook within ourselves. Whatever our technology is capable of doing, we must remember that it is we humans who created the technology to begin with — and thus we are capable of even more.
The mind, the spirit, the will that sailed across oceans, built pyramids, discovered medicine, and split the atom — all of that human potential lies latent within each of us.
That means you, too.
Our study together starts here: your extraordinary potential.
As Fletcher wrote in the epilogue to An Honest Man’s Fortune in 1647:
Man is his own Star!
And the soul that can render an honest and a perfect man
Commands all light, all influence, all fate:
Nothing to him falls early, or too late.
Our acts our angels are, or good or ill,
Our fatal shadows that walk by us still.
Wherever you are in life, whatever your circumstances, you must first discover your own internal riches, the ones that money cannot and did not buy, that wealth which no thief or government of thieves can steal, that time and chance do not cause to decay.
In our society of balance sheets and Likes, of follower counts and photo brags, where everything is measured in money, it is all too easy to discount the value of what lies within. Yet, to live confidently among all circumstances, it is your appraisal of yourself that must count the most. You get no credit for false humility. You will gain nothing by pretending to be poor when you are actually rich.
Course Structure & Timeline
Our lives unfold in waves. Every second is a wave, building into minutes and hours, which are longer waves that push themselves up into days and weeks, months and years, decades, and lifetimes.
A second is neither distinct from the decade, nor less important — they are perspectives (that is, points of view) of the same continuity. We mistakenly think of units of time as discontinuous because we see death as an eventual rupture of continuity.
But it isn’t.
Time is duration, and time endures beyond us. This fact haunts and terrifies us from our earliest awareness of it, and leads us to all manner of hopeless evasion and bargaining. Most of the suffering we experience in life derives from our fear of death and attempts to ignore and avoid it.
Embracing the fact of death is not the same as embracing death itself, any more than accepting the reality of war in our world makes an endorsement of it. As Kierkegaard observes, it is only in the acceptance of ourselves and reality as they are that we have any hope of changing either who we are, or the reality in which we live.
Thus the fact of death must be accepted so that we might be free to live fully in the time available to us, however much or little that may be.
The good news about Time is that it is a quality, and not a quantity. When we subdivide our experience of life into units and measure them, we are only using a metaphor that allows us to make certain kinds of material calculations about motion through space: a useful metaphor, but still just a metaphor. To learn how to own the day is to learn how to use this metaphor without becoming ensnared by it.
The pearl at the center of our experience together is learning—and then remembering to remember— how to own the day.
Our course will unfold in the same scaling waves, to practice what we eventually want to perform: day after day of fulfillment, freedom from anxiety, a resolute willingness to meet the challenges of life head-on, embracing change as our ally, and making joy both our means and our ends.
Every morning for the duration of the course, you will receive a video and written meditation to guide you in the beginning of your day to help you set the tone of your experience, gain more agency and control over your direction, and root your life in the fullness of the present, balanced by the hopeful expectation that it will be followed by many more presents.
Each week, you will receive a longer lesson, sometimes more practical, sometimes more philosophical, as we proceed to examine the nature and inevitability of change from every angle.
We will talk about everything that is considered impolite to talk about at dinner parties: politics, religion, and sex. We will examine the role of exercise, nutrition, environmental contamination, technology & media use, sleep, and so on, in an attempt to cover every base. Undoubtedly, there will be omissions, but the goal is to be as comprehensive as possible, to reverse the fragmentation of understanding and experience that plagues our culture today.
To ascend the peaks of life, no route can be arbitrarily discarded. Many of them have only one path to the summit, and the limitations we apply to ourselves, whether fear, a desire for comfort, or the avoidance of repeating past suffering, are the only true barriers to climbing.
The infinitude of the human spirit cannot permit arbitrariness to block us from any avenue of progress.
Our weekly lessons will be coupled with small group discussions. You will meet (virtually or physically) with four other participants in the course to exchange reflections, share ideas, and build deeper relationships. One of our objectives is for you to walk away at the end with new relationships and sources of support and encouragement for your journey through this life of constant change.
Each month during the course we will conduct an all-group Q&A call where you can raise your hand and explore the questions that arise through your study and reflection. This will also be the opportunity to get to know and connect with the rest of the cohort, further building your network of relationships around the world.
Finally, at the halfway mark of the course, you will begin your capstone project, a dynamic portfolio of your life, comprehensive self-assessment, and personal development plan. Whatever the changes you face now, you can be sure that you will face even more in the future, and the purpose of the capstone project is to concretely establish your individual commitment to the ancient Greek maxim Γνῶθι σαυτόν, Know Thyself!
For only through self-knowledge can you ever hope to be true to yourself, to act in harmony with yourself — and in that harmony approach the transcendent.
As Ralph Waldo Emerson strikingly declares in Self Reliance, one of the core texts we will cover in the course —
“There is at last nothing sacred but the integrity of your own mind.”
- 180 Daily Reflections with Journal Prompts
- 25 Weekly Long-Form Essays/Videos & Self-Directed Small Group Discussions
- 6 Monthly All-Group Q&A Calls
- End of Course Capstone Project
Your Guide and the Content of Our Course
I’m Skinner, and I’ll be guiding you through this period of self-understanding and development. My own journey of personal growth began in earnest nearly 20 years ago when I finished university, came out of the closet to my friends and family, and abandoned my lifelong plans of going to law school and entering politics in favor of an independent, entrepreneurial path.
Little did I know at the time, this path would take me first to Dallas, then to South America, where I lived for 11 years in Chile and Brazil, and ultimately to Spain, where I have resided since 2019. As I tell people when I meet them, I’m a long way from my childhood home on a blueberry farm in rural northwest Arkansas. I was blessed with an upbringing at the edge of the dying light of the old ways, of a society that had already disappeared throughout the vast majority of the Western world decades before my birth, the vestiges of which lived on in isolated corners here and there.
I consider it a privilege to have witnessed the last gasp of our culture. Whatever ills and shortcomings it had, there is yet much we can learn from it, and a few embers which we can use to keep the lower lights burning during the darkness and uncertainty we now face.
In academic terms, I always thought of myself as a generalist. I triple majored in economics, political science, and philosophy in college, and I have read at least as much if not more in history, theology, sociology, and psychology since then. I have founded and managed a software startup, a private equity consultancy, an emerging technology & entrepreneurship academy, — and during the pandemic, a mushroom farm.
Yet I have come to understand that in reality, I really am a specialist.
I am a specialist in change.
I unwittingly dedicated my life to acquiring and honing both the knowledge and skills required to embrace change with resilience and adaptability. I have spent nearly the entirety of my adult life in foreign lands, dealing in foreign languages and cultures, and bridging the gaps between the known and the unknown with fruitful action.
Such a life has rarely been easy, and I have experienced more failure than my promising childhood could have anticipated. Yet the distance I have maintained with my home culture has enabled me to see beyond its value system.
Financial success is a great reward but it is not life-defining.
Relationships are essential, yet sometimes you have to go it alone.
Reputation is a scam that keeps us in chains to the fickle and malformed opinions of people we do not even respect.
Time flows in only one direction, yet our mistakes are more reversible and recoverable than we imagine.
Throughout my journey, I have leaned more often on my relationships to dead men I never met than on living friends and extant institutions.
In Self Reliance, Ralph Waldo Emerson inspires me daily to keep going in life’s darkest moments:
He has not one chance, but a hundred chances. Let a Stoic open the resources of man, and tell men they are not leaning willows, but can and must detach themselves; that with the exercise of self-trust, new powers shall appear; that a man is the word made flesh, born to shed healing to the nations, that he should be ashamed of our compassion, and that the moment he acts from himself, tossing the laws, the books, idolatries, and customs out of the window, we pity him no more, but thank and revere him,--and that teacher shall restore the life of man to splendor, and make his name dear to all history.
How difficult it is to live up to this aspiration of total adaptability, of the free-flowing submission to the tide of life!
I have given up in my head more times than I can count. I have cried in despair and wanted an easy way out, I have wanted my problems to magically disappear. Yet, the voice inside always tells me to keep going no matter what. No matter the change.
Most of my lessons, I have learned the hard way: through my own error, miscalculation, overestimation of myself, and underestimation of problems. Perhaps in theory I could have learned some of these an easier way. But I am stubborn, if anything.
So I want to offer the benefits of that stubbornness to you, minus a lot of the costs. This will not save you from your own error — far from it. But it means that you can save that energy for recovering from your own mistakes, the ones I haven’t yet had the opportunity to make.
By the age of 41, I have managed to live several lifetimes worth of experience packed into a mere two decades of experimentation. There is some advantage to always taking things to their extremes. I have been forced to accustom myself to the attendant nausea, and perhaps at last, in recent years, I have become more graceful in the art of nonconformity, which Emerson says is to learn how “to estimate a sour face.”
No matter your stage of life, you are either in the midst of some significant change, or one is looming on the horizon, maybe one that you cannot yet see.
When I look back on the past 20 years, I cannot find any 2-year period without some major change or disruption, whether moving, needing to find new sources of income, the beginning or end of business or personal relationships, the need to pivot a startup project, and so on.
The practical lessons I have learned, combined with my reflective approach to living, have yielded a robust perspective and worldview that have become rare in our time.
Much of the course has been pieced together from my lectures and workshops at Exosphere, the technology-entrepreneurship academy I founded in South America. We conducted 10 long-term residential educational programs in Chile, Brazil, and Hungary. With Exosphere I also delivered more than 35 workshops in 25 cities across Latin America and Europe on entrepreneurial psychology, and have spoken at startup conferences across these regions during the same period.
We achieved a lot in a short period of time on mostly bootstrapped finances, attracting >300 students to our programs, from 50+ countries and every continent except Antarctica, with our participants’ ages ranging from 16 to 65.
Throughout Exosphere’s existence, I resisted a lot of pressure to create a digital version of our program. So much of the experience centered around community-building and the daily disciplines of founding an entrepreneurial venture. As I have begun to restart my teaching and guidance work with WILD, I have had the time and space to distill much of the Exosphere experience into a digitally deliverable format. Moreover, the intermission has permitted many ideas to mature and expand, and I have added much to my own understanding.
The Life Transition course is the culmination of this thinking, as well as a great deal of additional critical self-reflection that was not possible when I was managing a complex, resource-constrained operation.
I will irk many by being too religious, and others by not being religious enough. I may bounce from quoting Jesus to citing some lesson from Napoleon’s military campaigns. You will hear me share the deep thoughts of Buddha and in the next breath irreverently quote South Park.
Together, we will read from Emerson, Kierkegaard, Jung, Huxley, Dostoevksy, T.S. Eliot, Scott Peck, Daniel Kahneman, James Carse, Nassim Taleb, Ursula LeGuin, Teresa Avila — and some days we may watch clips from Game of Thrones and Breaking Bad.
If there is one thing I am not, it’s an ideologue.
We will run the gamut of nutrition, exercise, and physical health.
We will practice journaling and thoroughly examine a whole range of cognitive biases, as well as practices for increasing control over our reactions, without muting our emotions.
I will share with you the current state of my (still ongoing) decade+ research into psychological types — and with the model I have developed, you will have new tools to navigate your interior world, as well as your multivariate relationships.
We will examine the exterior world of finance, economics, and politics, so you can make better decisions as you move through the implications of the changes you face in your life, and can prepare yourself and those around you for an uncertain future.
If my philosophy can be summed to a single statement, it would be this:
“Everything in service to life, love, health, joy, and beauty — in that order.”
All else is, to quote the Psalmist, “chaff that the wind scatters to the corners of the earth.”
The Course is NOT for you if you meet one or more of the following criteria:
- Looking for quick fixes to your problems
- Want guarantees of financial or material success
- Jerks, assholes, cynics, haters
- Unwilling to examine yourself critically and honestly
- Blame others for your problems
The Course is definitely for you if you are…
- Willing to go all the way in questioning your assumptions about life
- Committed to continuous learning & growth, even when painful
- Ready to take full responsibility for your life and meeting its challenges
- Able to let go of your ego/pride and ask for help when you need it
- Excited by the prospect of transforming yourself from the inside->out