10 Apr 2023
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The Adventures of a Sexagenarian Job Seeker

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By Tyrone Showers
Co-Founder Taliferro


In the autumnal season of one's life, when the hard-earned wisdom of experience has long supplanted the spirited optimism of youth, the prospect of embarking upon a new professional endeavor can prove an arduous and, at times, comical undertaking. Such is the plight of the intrepid sexagenarian job seeker, who, armed with an illustrious résumé and a steadfast determination to defy the inexorable march of time, sets forth into the uncharted territory of the modern job market. In this whimsical and piquant chronicle, we shall recount the adventures of our undaunted protagonist as they navigate the labyrinthine landscape of LinkedIn, confront the capricious whims of millennial hiring managers, and valiantly attempt to elucidate the enigma of the cover letter.

A Tale

Our tale commences with the valiant sexagenarian embarking upon their quest for gainful employment, equipped with an arsenal of transferable skills and a lifetime of professional achievements. In preparation for the journey ahead, our protagonist must first engage in the Sisyphean task of updating their résumé, condensing decades of experience into a succinct and palatable document designed to appease the attention spans of their younger counterparts. As the words "proficient in WordPerfect and Lotus 1-2-3" are reluctantly replaced with "adept at Microsoft Office and Google Suite," our hero is forced to confront the temporal chasm that separates them from the contemporary job market.

Next, the intrepid job seeker must traverse the digital domain of LinkedIn, where they are confronted by a veritable smorgasbord of endorsements, connections, and unsolicited sales pitches. Undeterred, our protagonist dutifully updates their profile, replacing their erstwhile glamour shot with a more recent photograph that discreetly obscures the crow's feet and burgeoning gray hairs. Armed with a curated list of accomplishments, meticulously selected recommendations, and a newfound penchant for gratuitous self-promotion, our hero sets forth in search of the elusive job listing.

The modern job market, as our protagonist soon discovers, is a veritable minefield of convoluted jargon and indecipherable acronyms. With a furrowed brow and a growing sense of trepidation, the sexagenarian job seeker endeavors to decipher the myriad job postings that demand proficiency in an ever-expanding array of esoteric skills. As our hero ponders the merits of obtaining certification in Scrum methodology or mastering the intricacies of TensorFlow, they are forced to confront the sobering reality that the job market, like the sands of time, has shifted beneath their feet.

Undaunted by the seemingly insurmountable obstacles, our protagonist perseveres, diligently submitting their résumé to a plethora of positions that bear only a passing resemblance to their hard-earned expertise. The perils of the modern job market are many, and the valiant sexagenarian soon finds themselves confronted by the dreaded "Applicant Tracking System," a sinister and capricious beast that devours résumés with reckless abandon, leaving only a trail of automated rejection emails in its wake.

Yet the indomitable spirit of our hero remains unbroken, and as they forge onward, they encounter the enigmatic and confounding task of crafting the perfect cover letter. With a steely resolve and a burgeoning sense of desperation, the sexagenarian job seeker deftly endeavors to extol their virtues while conveying an air of humility and self-effacement. As the words "enthusiastic self-starter" and "team player" grace the page, our protagonist is forced to confront the disquieting truth that their years of experience have left them woefully unprepared for the linguistic gymnastics required by this particular exercise in self-aggrandizement.

Yet, amidst the maelstrom of deciphering job listings and battling applicant tracking systems, our indefatigable protagonist stumbles upon a glimmer of hope: the serendipitous discovery of a networking event. Clad in their finest attire, the sexagenarian job seeker ventures into the fray, armed with an arsenal of business cards and a rehearsed elevator pitch. As they navigate the cacophony of small talk and forced laughter, our hero is confronted by the disconcerting realization that their encyclopedic knowledge of rotary phones and carbon paper is of little consequence in a room filled with aspiring social media influencers and cryptocurrency enthusiasts.

But, amidst the trials and tribulations of the modern job market, our intrepid protagonist perseveres, buoyed by the knowledge that their wealth of experience and hard-earned wisdom cannot be reduced to a series of bullet points on a résumé or the number of connections on a LinkedIn profile. For the sexagenarian job seeker is a veritable paragon of resilience and determination, steadfastly refusing to acquiesce to the tyranny of ageism that pervades the contemporary professional landscape.

As the sun sets on this whimsical tale of job seeking in the twilight years, our hero remains undeterred, buoyed by the knowledge that their indomitable spirit and wealth of experience are formidable assets in a world increasingly dominated by ephemeral trends and fleeting expertise. Though the path may be fraught with challenges, the sexagenarian job seeker remains an exemplar of tenacity and resolve, a shining beacon of hope for all who dare to defy the inexorable march of time and embrace the boundless potential of their autumnal years.


The arduous journey of seeking employment in one's 60s, replete with the challenges of navigating the digital realm and contending with the shifting sands of the modern job market, is a testament to the resilience and adaptability of the human spirit. The rewards may be uncertain for those who dare to embark upon this quixotic quest. Still, the journey is a poignant reminder that life, in all its capricious and unpredictable glory, is a continuous adventure filled with opportunities for growth, self-discovery, and occasional humor.

Tyrone Showers