Entrepreneur Owner-Managers: Is It Better to Choose the Next Thing, or to Rust in Place?

Okay, try to be as coldly objective as possible: after ten or twenty or fifty years of vision and hunger, do you lead the enterprise now with the same purpose, energy, and passion that you did when you first began?

Beginnings or Endings? Is it the beginning of 2024 or the ending of 2023? As the grown kids move out of the house, is it the beginning of their adulthood or the ending of our being needed? Is the breakup of the Beatles the ending of that music or the beginning of spectacular solo creations and careers? Is the collapse of a relationship a regretful ending or is it the unlocking of a new beginning? As we lead our enterprises over the course of our lives, there are moments when we are reminded that we are unfinished, that the enterprise is unfinished, that the story we have been telling ourselves about who we are and where our life leads is yet unwritten. Frequently, such aha moments come most readily when we begin something new.

I have been engaged in a more or less continuous conversation for four decades with high-performing Entrepreneur Owner-Managers (“EOMs”) about the ways to unlock their potential and experience their freedom.  That may be why I understand so vividly that EOMs with skin in the game are challenged by the fact 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. Yet, are we as successful at declaring victory—of ending this chapter—so that we can get on to the beginning of the next?

Our challenge is allocating our energy and our attention to enterprises or activities that in their youth were vital and energy creating and value contributing, but may now be a bit… compromised, corroded, tired, dare I say even boring? Devolving, blocking progress by holding onto the past in desperate bids for relevance, frantically trying to justify your ongoing time/energy investment, despite dysfunction and escalating bureaucracy. As we consider transitioning our role in leading and owning 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.

Beginning something is usually only possible by ending something else. And when something is ending, look carefully, and we will see within it the seed of a new beginning, and a whole new spectrum of potential. In a sense this is exactly what a beginning does—it is an opening for surprises, for new discoveries. Surrounding our deliberate intention and the very act of beginning, there are energizing possibilities we hadn’t planned for. Paying attention to these inflection points of possibility is an act of self-respect.

And yet as homo sapiens, we are homeostasis seeking machines, aren’t we? Our very species is oriented toward maintaining the status quo of comfort and predictability and security which every beginning inevitably disrupts—with its pivot to change and its temporary feeling of insecurity. What does it take to overcome the mass popular culture’s cult of comfort, security, and stasis?

Frequently the greatest challenge is simply to just begin. There is something deep in us that conspires with what wants to remain within safe boundaries and stay the same. So, it makes sense that almost always a period of preparation is necessary, where the idea of the beginning can hatch, and where we should simply take the risk of moving from ambivalence to boldly spring into a new beginning.

A profound misstep some highly-successful EOMs make is attempting to sustain their peak accomplishment indefinitely, trying to repeat the excitement, wonder, adventure that they experienced relatively early in the organization’s life. It’s not possible. Every thing and every person are transitory. The year comes to an end. Kids move out. The Beatles broke up. The relationship is concluded. Rust never sleeps. Fighting that evolution is merely empty raging against the dying of the light.

Beginnings might frighten some of us because they seem like lonely voyages into the unknown. They can be, yet… no beginning is empty or isolated. Some people seem to think that beginning is setting out from an already lonely point to the murky unknown. This is not the case. A beginning is ultimately an invitation to unlock our potential, experience our freedom, and access the learning and growing that are stored up in us. To refuse to begin afresh can actually be an act of great self-neglect and self-disrespect.

After ten, or twenty, or fifty-years of vision and hunger, do you lead the enterprise now with the same purpose, energy, and passion that you did when you first began? Hey, we’ve been striving for achievement at a high level for a really long time, so it’s sure understandable we might not. But if not, doesn’t the business deserve a new majority owner brimming with new vision, new hunger, and new energy… like you had in the beginning? And if we apply ourselves to literally choose who will be the next new majority owner, isn’t that just being responsible to all the stakeholders we care so much about?