Identity Part 2: The Paradox of Prosperity

As I had teased in my first post on this topic (From the Coaches Corner: Self-Actualization and the Path to Fulfillment in Entrepreneurial Success), the pursuit of entrepreneurial success often culminates in an existential quandary: is the journey only about the accumulation of wealth? My familial background—a mother with an immigrant's cautious financial mindset and a father who equated spending with therapy—set the stage for my complex relationship with money. As I age, I find the crude mechanics of wealth less enthralling, my focus drifting towards the enigmatic forces driving my life's work.

Judith Viorst's seminal work, "Necessary Losses," which I stumbled upon via my therapist's recommended readings, provides a lens through which to scrutinize these forces. Though only halfway through the book, Viorst has already challenged me to dissect the narrative I've authored about my entrepreneurial drive. What do I truly value? What fears govern me?

Our culture champions money as the ultimate barometer of success. Yet, I'm realizing that it is merely one facet of a multifaceted self-actualization. Pausing in the shadow of the proverbial windmill, I ponder the reality that my efforts often prioritize monetary gain—revealing my true, albeit subconscious, belief system.

This epiphany is intrinsically linked to my identity as an entrepreneur. To be sure, I have experienced a modicum of success in manifesting vision into reality, and imagination and curiosity are my superpowers. All of these have led to an enterprise that sustains me and my family. Yet, it is my hesitations, the investments not made, and the opportunities missed that haunt me. Viorst's insights provoke a reexamination of these preoccupations.

The notion of loss is introduced to us from our very first breath—departing the womb's sanctuary. This primal loss is echoed throughout life's stages, shaping our relationships and self-perception. Yet, in a ray of light, Viorst offers a quote from Margaret Mead, highlighting that understanding our materials' limitations doesn't restrict the art we can create but rather defines it. 

"The potter who works clay recognizes the limitations of his material… But by recognizing the limitations of his material, he does not limit the beauty of the shape that his artist's hand, grown wise in a tradition, informed by his own special vision of the world, can impose upon that clay."

Translating this to the entrepreneur's experience, a loss all will suffer eventually is the separation from the business, either by their hand or another's. However one may have arrived, the ubiquitous experience is a void post-exit, regardless of the exit's financial success or lack thereof. Further, the sense of purpose they once experienced diminishes when the stakes are lowered. In this complex tapestry of gain and self-worth, the true challenge lies not in staking one's identity on net worth but in reconciling with a sense of self-independent of the ledger.

As I wrestle with these questions and slowly prepare myself for an eventual departure from my entrepreneurial role, it is through introspection and guidance from texts like Viorst's that I seek to recognize the deep-seated motivations and narratives that have propelled me through life to date and ultimately to understand the context in which they teach me now. This understanding is critical to mitigating the emptiness that could follow the exit, enabling me to embrace a narrative that isn't new but has long-awaited discovery. As a good friend and mentor once advised, "Once you can understand what it is that you are moving toward, rather than what you are leaving, is when you know you are ready."

As entrepreneurs, we must recognize our motivations, the inherent losses we will encounter, and the stories we have told ourselves. In doing so, we can distance ourselves from the potential abyss and pivot towards a narrative enriched with meaning, tradition, and personal vision—much like the potter who shapes clay with both wisdom and limitations in mind.

The journey of detaching from a business is not merely a financial transaction; it is a rite of passage that demands psychological preparation and narrative reframing. By acknowledging the spectrum of motivations beyond monetary gain and understanding the complex interplay of loss and identity, we can equip ourselves for the transition—transforming from entrepreneurs into architects of our next grand endeavor.