Special For Oswego County Business
By Elizabeth Zelinka Parsons
Retirement.
The word itself conjures images of leisurely pursuits, freedom from deadlines and the long-awaited opportunity to finally enjoy the fruits of one’s labor. For many, it represents the ultimate reward for decades of hard work and dedication.
Yet, for high-achieving professionals, the transition into this supposedly idyllic phase of life can often be fraught with unexpected challenges, anxieties and a surprising sense of unease. The very traits that propelled them to the pinnacle of their careers can paradoxically make the absence of work a difficult and disorienting experience.
This article, drawing from insights in my book “Encore: A High Achiever’s Guide to Thriving in Retirement,” delves into the multifaceted reasons why life after work can be harder than anticipated for those who have spent their lives striving and achieving.
One of the primary reasons for this difficulty lies in the profound loss of identity that retirement can trigger. For high achievers, their professional roles often become inextricably linked to their sense of self-worth. They identify strongly with their titles, their accomplishments and the communities they inhabit through their work, tending to conflate who they are with what they do and what they have achieved.
Howard Marks, a successful lawyer, exemplifies this. His impending retirement felt like “the end of Howard” because he had become so identified with his career and related achievements. The prestige of their firm, the ability to deliver superior results under pressure and the validation from positive feedback all contribute to a robust self-concept built upon professional success. The sudden absence of this framework can leave a void, making them question, “Who will I be if I’m not what I do?” The “illustrious law firm” or the “billion-dollar deals” they once closed become irrelevant in their new context, as the author herself experienced after leaving her demanding legal career.
This loss of identity is often compounded by the anxiety surrounding the very concept of retirement. Despite years of diligently saving and planning, many high achievers find themselves feeling a “gnawing dread” as retirement approaches. This anxiety is often fueled by the negative connotations associated with the word “retire,” which in Middle French meant “to withdraw or pull back.”
Modern definitions continue this theme of retreat, offering no sense of forward motion or expansion. This paints a picture of decline rather than opportunity, leading to what I refer to as “retirement anxiety.” Research even suggests that retiring from a career is only slightly less stressful than being diagnosed with a serious illness or being incarcerated. This level of stress stems from the threatened losses of identity, community, structure and purpose — losses that money alone cannot solve. Like Jim, one of my early clients, many feel like they are “running toward the edge of a cliff” with no clear vision of what awaits them.
Furthermore, the highly structured and demanding nature of their previous careers often leaves high achievers ill-equipped to navigate the unchartered territory of abundant free time. They are accustomed to time scarcity, where every moment is accounted for and productivity is paramount. As one client put it, “We sell our availability for a living.”
Decades of hypervigilance and constant responsiveness have become an ingrained way of life. The sudden release from these pressures can be disorienting, leading to a swing between frantic busyness and profound boredom. The “appalling thought of free time” arises because they lack the internal organizing principles that their work once provided.
Andrew, a retired investment banker, found himself aimlessly wandering into his home office, “frittering the time away because I don’t know where else to be or what else to do.” Without the familiar rhythm of deadlines and demands, their well-honed time management skills feel obsolete and creating a new structure can be a daunting task.
The fulfillment of their primary career purpose also presents a unique challenge. For many high achievers, their professional lives have been driven by the purpose of providing for their families and building financial security. Retirement signifies the achievement of these long-term goals, yet this very fulfillment can lead to an existential questioning: “If I no longer need to work, what will get me out of bed in the morning?” is a common refrain.
The drive for success that once energized them now seems to have been fulfilled, leaving a void in their sense of purpose. As Ann Lamott’s father, Kenneth, astutely observed, “A life oriented to pure leisure is, in the end, a life oriented to death — the greatest leisure of all.” High achievers, by their very nature, are driven individuals who seek meaning and contribution and pure idleness rarely satisfies this deep-seated need.
Adding to this complexity is the paradox of choice. Faced with an abundance of time and resources, retirees might expect to feel liberated. However, the sheer number of possibilities can be overwhelming, leading to intellectual paralysis and indecision. Without a clear path or a defined set of objectives, they can struggle to choose a direction, much like being overwhelmed by too many flavors at a gelato shop. Furthermore, many high achievers find themselves lacking positive role models for this new phase of life. They may have witnessed colleagues or mentors who retired poorly, entering a rapid decline or experiencing a loss of purpose. These negative examples can fuel their anxieties and make it difficult to envision a fulfilling post-work life.
John, a tech executive, lamented “I don’t have any role models for retiring well” after witnessing his mentor’s isolation in retirement.
The ingrained mindsets that fueled their professional success can also become obstacles in retirement. They are accustomed to a “success” mindset, constantly measuring themselves against external benchmarks like income, accolades and power. The competitive environments they thrived in often fostered a need for constant achievement and the fear of being overtaken. Retirement removes these external scorecards, requiring a shift towards internal measures of fulfillment and contribution.
Similarly, their “expert” mindset, characterized by mastery and competence, can make the idea of trying new things and being a novice feel uncomfortable. The “reactor” mindset, honed by years of responding to immediate demands and crises, needs to evolve into a “creator” mindset, where they proactively choose their engagements based on personal interest and purpose.
Overcoming these challenges requires intentional planning and a shift in perspective. Retirement should be reframed not as an ending but as a “graduation” into new opportunities. High achievers need to actively explore and reconnect with the enduring aspects of their identity beyond their careers. They must identify new sources of meaning and engagement that align with their values and skills, moving beyond default ideas that are merely adjacent to their former professions. Engaging in activities they find intrinsically motivating, rather than seeking external validation, becomes crucial.
Building a new structure for their time is also essential. This involves experimenting with proactive annual planning, establishing positive routines and habits, and utilizing tools like batching and delegation for less fulfilling tasks. The focus should shift from managing time as a scarce resource to understanding “time sovereignty,” where time is an abundant resource to be used intentionally.
Furthermore, maintaining and cultivating social connections is vital for emotional well-being and can help replace the community lost through work.
Finally, adopting a mindset of realistic optimism and relaxed determination can aid in navigating the uncertainties of retirement. Embracing the journey with curiosity and a willingness to experiment, while also allowing for patience and perseverance, is key. As I always emphasize, it is about “enjoying the ride” and finding meaning and satisfaction in the present moment.
In conclusion, while retirement is often portrayed as a period of effortless bliss, the reality for high-achieving professionals can be more complex. The loss of identity, the anxiety surrounding the transition, the challenge of unstructured time, the fulfillment of their primary purpose, the paradox of choice, the lack of role models and the need to shed ingrained mindsets all contribute to making life after work a potentially difficult adjustment.
However, by acknowledging these challenges, engaging in thoughtful planning, redefining their identities and purpose, creating new structures, nurturing relationships and embracing a positive and determined outlook, high achievers can navigate this transition and design a new chapter of life that is not just restful, but also meaningful, engaging and ultimately, deeply fulfilling.
Author Elizabeth Zelinka Parsons, J.D., is a retirement transition expert, lawyer and co-founder of two consulting firms, Zelinka Parsons and Encoraco. A magna cum laude graduate of Georgetown University Law Center and summa cum laude graduate of James Madison University, she has spent more than two decades shaping professional development and transition strategies for legal professionals. A former attorney at Milbank, she built a national consulting firm assisting AmLaw 100 firms with talent solutions. Author of “Encore: A High Achiever’s Guide to Thriving in Retirement “ (Feb. 5, 2025), she combines analytical rigor with creative vision to help professionals redefine retirement as a dynamic opportunity for growth and fulfillment. Learn more at encoraco.com.
