In September, I submitted no fewer than eighty-three job applications, casting my hopes broadly across countless companies and industries. Yet, despite this persistent effort, every attempt met the same quiet end: rejection emails or worse, complete silence. It was a humbling and exhausting experience, one that brought into sharp relief the challenges of beginning anew at a stage in life when many of my peers are comfortably settled in long-established careers.
My professional journey began over two decades ago, in the year 2000, and has woven through a variety of fields and roles. Yet now, as I embark on a transition toward a career in design—a long-held passion of mine—I find myself once again at the starting line. Though I currently hold an internship that nourishes my creativity and drives my learning, I need the stability of a full-time position to meet the demands of everyday life. At forty-three, job hunting has transformed into a full-fledged vocation in itself, a relentless pursuit marked by uncertainty and emotional endurance. More than anything, this process has illuminated a truth I already knew but am now forced to face daily: beginning again never truly becomes easier, no matter how familiar one grows with the art of self-reinvention.
Change, however, has been a constant companion throughout my adult life. Reinvention, for me, is neither foreign nor intimidating—it is a well-worn path, though a difficult one. For fifteen years, I worked behind the bar, mastering both the physical rhythm and emotional labor of hospitality. Then, around 2015, I took a bold leap into an entirely different world, becoming a doula. My work spanned birth, postpartum care, and end-of-life support—seasons of human vulnerability that taught me more about empathy, patience, and resilience than any classroom ever could. That decade of intimate, human-centered work was profoundly fulfilling, but the toll of financial instability and sleepless nights began to erode the sustainability of my lifestyle.
When the pandemic struck New York City in 2020, everything changed in an instant. New regulations temporarily banned doulas from entering hospitals, effectively halting my career overnight. For the first time in years, I found myself with time and space to reflect on the question I had long avoided: what comes next? I had always been fascinated by the intersection of technology, design, and human connection—intrigued by how thoughtful systems and interfaces shape how we live and communicate. Still, without a traditional college degree, I’d convinced myself that such a path was out of reach. Yet during those quiet, uncertain months, something fundamental shifted within me. What had once been a wistful “maybe someday” evolved into an urgent declaration: “It’s now or never.”
Embracing that new mindset, I began pushing myself far beyond my comfort zone. I tried activities that intimidated me, such as pole dancing, which demanded both physical courage and vulnerability. I practiced saying no without guilt, establishing boundaries that honored my time and values. Most importantly, I chose to pursue a design career—a field where, on paper, I had little formal qualification but an abundance of drive, curiosity, and empathy.
By November 2022, that commitment materialized into action. I enrolled in Springboard’s UX/UI Design Career Track, a step that felt both terrifying and exhilarating. Deep down, I knew this was the right move for me. Nevertheless, I also recognized that my previous model of working as an independent contractor no longer aligned with my financial goals. I needed structure and predictable income, so I transitioned into a studio management role as a bridge toward my next chapter. Gradually, I began to wind down my doula work, both emotionally and logistically, preparing to close a deeply meaningful but demanding era of my life.
By 2024, I had fully stepped away from the doula profession. The move into hourly employment came with its own set of challenges—learning to advocate for raises, developing new communication frameworks, and mastering the subtle art of balancing creative ambition with practical responsibility. Yet each new position deepened my understanding of how transferable my skills were. Over time, I changed roles three times, not from inconsistency or restlessness, but from a deliberate pursuit of growth, better pay, and opportunities that allowed me to merge design thinking with leadership and management.
Then came September 2025, the month the rejections reached their peak. I set myself a rigorous goal: apply to at least three companies every night. My résumé was polished, my portfolio showcased thoughtful projects reflecting real user empathy, and my determination remained unwavering. Still, with every click of the “submit application” button, I edged closer to an unwelcome familiarity—a growing collection of rejection emails and unanswered submissions. By the end of the month, I had sent out eighty-three applications and received not a single invitation to interview. Zero opportunities for conversation, for potential, for proving myself.
This reality is, frankly, disheartening. It seems illogical that in an age defined by innovation and inclusivity, transitioning careers—especially into a field as dynamic as product design—should feel nearly impossible. Yet here I am, an experienced professional with decades of interpersonal skills and an insatiable drive to learn, finding the doors stubbornly closed.
And still, I refuse to give up. Over the years, I have cultivated friendships with engineers, designers, and other professionals in tech who remind me that breaking into this field is rarely linear. They assure me that persistence, tenacity, and a willingness to evolve are the true currencies of progress. This isn’t my first experience with disappointment or reinvention. I faced similar uncertainty when I traded my bartender’s apron for a doula’s training kit, and again when I decided to step away from birth work to study design. Each transformation demanded humility, patience, and the courage to rebuild from the ground up. Each time, I emerged renewed.
At present, I work as an executive assistant—a position that synthesizes much of what I’ve learned across all my past professions. It requires emotional intelligence, organization, communication, multitasking, and creative problem-solving—all skills I’ve honed through years of navigating high-stakes, people-centered roles. Simultaneously, I continue to design part-time with 5wins, a studio where I can channel my passion for visual storytelling, user empathy, and digital craftsmanship. This balance, while imperfect, allows me to stay grounded in the community and discipline that first inspired my career shift.
Rejection, I’ve come to realize, will always sting. Yet, over time, I have learned to reinterpret each “no” as an incremental step toward the eventual “yes” that will make sense of this journey. Reinvention, after all, is not a task for the timid. It requires a rare blend of grit, courageous self-assessment, and the quiet confidence to rebuild one’s identity again and again. I may be navigating my third major career transformation, but my story is still unfolding. I am not finished—not even close.
Sourse: https://www.businessinsider.com/after-eighty-job-rejections-im-still-chasing-dream-design-job-2025-11
