On The Long Game: Retire? From What, Skin in the Game?

Have you noticed every strength we have as Entrepreneur Owner-Managers brings with it a related inherent weakness? Holy S#$% (scratching my head), does every virtue have an associated wickedness in us? It’s not like an accounting balance sheet where we keep track of assets and liabilities in separate accounts, noooooo… our assets are our liabilities. It’s impossible to have our strengths without their equivalent flaws, isn’t it? Yet the conforming culture seems to think it can only see strengths as the essential determining factors of us, while writing off our difficulties as something we’ll get over (hahaha). For high performers, our weaknesses are part and parcel of our strengths.

Which is why it may make sense, for EOMs with skin in the game, that our professional strengths (and maybe personal ones too) lie in our passion and persistence for really long term goals—some of which we have been tirelessly striving to achieve for twenty, thirty, forty years. Good. But, are we as successful at declaring victory—of getting on to the next chapter? As we consider transitioning our role in leadership and ownership of our enterprises, we are energized by the thought of a new transformational challenge, new learning, and growing. New freedom. And yet, in a small way, it feels like “giving up.” Quietly, our surplus of natural Grit kicks in; it feels more natural to redouble our efforts, head down, in the challenge we have been striving for all these years, than it does to evolve to a new chapter.

As a practitioner, I carefully listen to seasoned, successful Entrepreneur Owner-Managers tell me their narratives. They are most commonly at an inflection point where they are facing questions about their future; about what comes next. I normally ask penetrating questions or repeat back to them what I think I have just heard to try to ensure that I “get” them, and they feel deeply understood. That I understand just how hard it is to be them. And naturally, their stories contain almost all the answers.

Only a few EOMs ever officially write their own autobiographies, yet it is right there, in our minds, in the background all the time. Every day we are writing our own stories in our own minds, weaving new chapters about why events happened as they did, and especially… about where we are going.

About that where we are going. There are two ways to bring about change in life, right? One way is to walk away from something. The other way is to deliberately move toward a new destination. Can you reframe your future, your future narrative, not as an “answer,” but as a question? Prospectively. So…what are your unfulfilled plans? What are your unrealized dreams?

Do you really want to retire—to withdraw—from something? Or do you want to move towards the next energizing chapter? Could a desire for retirement/withdrawal really just extract us from the risk of making a mistake? Withdrawing from the risk of loss? Are we withdrawing from one kind of risk only to be exposed to another, different one? Is retirement/withdrawal ever a sensible, palatable alternative? Sure, if you are not free and your own master now. For what else would you possibly retire from? Energy creating activities? Energy creating relationships? Energy creating domains? Skin in the game? The hunt for magic?

And yet just like when one has started nagging the student—so that’s when the learning is over—thus it is with ourselves. All of us advance only when we have not been badgered or made to feel guilty; only when we have the sense that we are deeply understood for the many reasons why change is so hard for us. We know what we should do. As Derek Sivers drolly relates, “Hey, if more information was the solution we’d all be billionaires with six pack abs.” Success doesn’t come from knowing, it comes from doing. But every successful EOM I have ever met will absolutely refuse to act if a stern-faced figure wags their finger and delivers energy draining lectures.

I am not sure why there is such a movement towards extending life, are you? We don’t have short lives. It strikes me life is long enough to accomplish anything if we don’t squander it. It’s just that many people don’t really begin living until the end of their lives. Devoted to sedentary, passive, comfort zone activities, their impulse to action passes away before they were aware it was possibly a germ of passion. So forget age, let’s think “chapters.” You continue to evolve as a human with skin in the game, as an entrepreneur, and it doesn’t end until you end. Life, if you know how to do it, is long. How crazy is it if we spend all our lives getting ready to live in the future?

We owe a debt that we cannot pay back; and so we gotta pay it forward. Why? We won the lottery. We are basking in the warmth of our Founding Fathers, of the guys who stormed the beaches at Normandy, on the works of Kahneman, Tversky, E.O. Wilson, and Seligman. We can’t pay it back, so we have to pay it forward.
As organization leaders and changers and disruptors, we are all called to be calmers of fear. Civil conversation about the future has never been more important. And hey, as EOMs leading to the change we want to see in the world, we accept that we may be—hell, we will be—misunderstood for long periods of time. So we have to keep each other company. Courage is needed to candidly address issues which have been protected and sanctified by the minority who favor polite avoidance, political correctness, and dodging the hard topics. Social courage presents and defends views and experiences that might be unpopular with the mass popular culture now (which isn’t the majority in any case). We have a lot of work to do.

Retire? From what, skin in the game? My friend Chris Peterson said “Days are long but life is short.” I guess my question is: Or is it just right if you take action prospectively on your chapters?

References and Further Reading:
Becker, W. & Fagen, D. (1976). “Deacon Blues” [Steely Dan]. On Aja [Record, 1977]. Los Angeles, CA: Village Recorders.
Brand, Stewart. (1999). The Clock of the Long Now: Time and Responsibility. Perseus Publishing.
Diamandis, P. H., & Kotler, S. (2016). Bold: How to Go Big, Achieve Success, and Impact the World. New York: Simon & Schuster Paperbacks.
Eagleman, David. (2012). Incognito: The Secret Lives of the Brain. Vintage Books.
Edelman, Gerald. (1987). Neural Darwinism: The Theory of Neuronal Group Selection. New York: Basic Books.
Ericsson, K. A. (2016). Peak: Secrets From The New Science of Expertise. London: The Bodley Head.
Grant, Adam. (2016). Originals: How Non-Conformists Move the World. New York: Viking.
Hirschman, Albert O. (1970). Exit, Voice, and Loyalty: Responses to Decline in Firms, Organizations, and States. Cambridge, MA: Harvard University Press.
Johnston, Randolph. Nine Ages of Man [Sculpture]. From http://www.petespub.com/gallery/people/ [Image 25]. Abaco, Bahamas: Johnston Studios Bronze Foundry.
Kelly, K. (2016). The Inevitable: Understanding the 12 Technological Forces That Will Shape Our Future. New York: Viking.
Kotler, Steven and Wheal, Jamie. (2017). Stealing Fire: How Silicon Valley, the Navy SEALs, and Maverick Scientists Are Revolutionizing the Way We Live and Work. New York: Harper Collins.
Lewis, M. (2017). The Undoing Project: A Friendship That Changed Our Minds. New York: W.W. Norton & Company.
McCloskey, D. N. (2016). Bourgeois Equality: How Ideas, Not Capital or Institutions, Enriched the World. Chicago: The University of Chicago Press.
McDougall, Christopher. (2016). Natural Born Heroes. New York: Vintage Books.
Russell, Bertrand. (2013). The Conquest of Happiness. New York: Liveright Publishing Corporation.
Russell, Bertrand. (2009). The Scientific Outlook. London: Routledge.
Seligman, M. E., Railton, P., Baumeister, R. F., & Sripada, C. (2016). Homo Prospectus. Oxford: Oxford University Press.
Sullivan, D. (2016). The Self-Managing Company: How to Build a Company That Manages Itself to Growth. (A Strategic Coach EBook Series).
Taleb, N. N. (2014). Antifragile: Things That Gain From Disorder. New York: Random House Trade Paperbacks.