At 40-Something and a Veteran at Career Shifts: Facing 83 Job Denials Last Month Yet Staying Optimistic

In September, I faced a daunting challenge in my quest for a new role by sending out 83 job applications, all of which resulted in being ignored or rejected.

Since the turn of the millennium, I've been part of multiple industries, and now I'm venturing into my dream field of design. Although I have an internship, a full-time position is critical for my finances.

The job search at the age of 43 feels like a relentless pursuit, a stark reminder of the challenges inherent in starting anew, no matter how experienced you are in reinvention.

A Journey of Reinvention

For a decade and a half, I mixed drinks and served customers as a bartender before transitioning to the role of a doula in 2015. This involved engaging deeply with childbirth, postpartum care, and end-of-life support. While rewarding on a personal level, the job’s irregular hours and financial uncertainty became too burdensome over time.

The outbreak of COVID-19 in New York City in 2020 brought a temporary halt to doulas entering hospitals. This pause allowed me the space to contemplate my future goals. Although technology and computer science fascinated me, my lack of a bachelor’s degree once seemed like an insurmountable hurdle.

However, the pandemic catalyzed a change in perspective. I shifted from 'someday' to a mindset of 'now or never.'

Embracing New Fears and Challenges

I started embracing activities that pushed me out of my comfort zone: taking up pole dancing, learning to decline offers without guilt, and pursuing a career many thought I lacked qualifications for.

Fast forward to November 2022, when I enrolled in Springboard's UX/UI Design Career Track—a decision that felt right intuitively. Recognizing the need for financial stability, I moved from the unpredictability of freelancing to stable earnings in studio management, gradually planning my departure from the birthing sector.

From Doulas to Design: A New Path

By 2024, I had fully transitioned from my career as a doula. The switch to routine hourly jobs brought its own hurdles, but I learned self-advocacy, honed negotiation skills, and integrated both interpersonal and technical abilities into each job.

Throughout my career, my changes in employment were driven not by inconsistency, but by a pursuit of personal advancement, improved remuneration, and the opportunity to apply my design and managerial expertise.

Facing the Avalanche of Rejections

Determined in September 2025, I set a nightly goal of submitting applications to at least three potential employers. My CV was impressive, my design portfolio adequate for my tenure in the field, and my resolve was unyielding.

Yet, rejections amassed. Despite nearly a hundred applications, I didn't land a single interview—a scenario that seems unjustly challenging for anyone attempting a career transition.

The redundancy of being overlooked remains unsettling. Transitioning careers in 2025 should not be this strenuous.

Holding Onto Hope Through the Struggle

My network of friends, who are engineers and designers in tech, remind me that perseverance and grit are essential in breaking into new fields. This isn't my first encounter with hardship; I've started from ground zero before—as a bartender, then a doula, and now entering the realm of product design.

Currently, my role as an executive assistant utilizes numerous skills I've accumulated: empathy, organization, communication, and creative problem-solving. On the side, I continue to design at 5wins, staying connected to the community that inspires me.

Undeniably, rejection's sting lingers, but I've gathered that every 'no' is merely a stepping stone to finding the right 'yes.' Reinvention demands courage, perseverance, and the ability to repeatedly rebuild self-esteem. Even on my third career change, my journey is far from over.