After 83 Job Rejections, I’m Still Chasing My Dream Design Job

In September, I applied to 83 jobs — and got ghosted or rejected by every single one.

While I’ve been working since 2000 in different industries, I’m starting a new career following my passion in design. I have an internship, but need a full time job to cover the bills.

Job hunting at 43 has become a full-time hustle — and a brutal reminder that starting over never gets easier, no matter how many times you do it.

Reinvention is nothing new to me

I was a bartender for 15 years before becoming a doula around 2015, diving into birth, postpartum, and end-of-life work and education. That work was deeply fulfilling. I supported people through life’s most vulnerable moments, but the financial instability and long overnight shifts took their toll after nearly a decade.

When the pandemic hit New York City in 2020, doulas were temporarily banned from hospitals. Suddenly, I had time to reimagine what I wanted next. I’d always loved technology and computer science but figured that without a bachelor’s degree, that dream wasn’t for me.

But something shifted during the pandemic. My mindset changed from “Maybe someday” to “it’s now or never.”

I started doing things that scared me: trying pole dancing, saying no without guilt, and pursuing a career that many would say I wasn’t “qualified” for.

I went back to school

Fast forward to November 2022, I enrolled in Springboard’s UX/UI Design Career Track. I felt it in my gut, this was the right move. But I also knew I needed to make a financial shift from being an independent contractor (as a doula) to earning steady hourly pay. I transitioned into studio management and slowly began planning my exit from birth work.

By 2024, I had fully retired from my doula career. Working hourly jobs brought new challenges, but I learned how to advocate for myself, negotiate raises, and apply both soft and technical skills to every new role. I’ve now changed paid positions three times not because I’m inconsistent, but because I’ve fought for growth, for better pay, and for opportunities to use my design and management skills.

Rejections piled up

In September 2025, I made it my mission to apply to at least three companies every night. My résumé looked strong, my portfolio was solid for my level of experience, and my determination was unshakable.

Still, the rejections piled up. Eighty-three applications later, I hadn’t received a single interview. Not one.

What I find most disturbing about this product design job-hunting saga is that I’ve applied to nearly a hundred positions and have nothing to show for it.

Making a career change in 2025 shouldn’t feel this impossible.

I’m not giving up

I have close friends in tech, engineers and product designers, who remind me that breaking in takes time, persistence, and resilience. I’ve experienced this wave of disappointment before: when I became a bartender, when I transitioned to being a doula, and now as a product designer. Each time, I started from scratch, built new skills, and found my footing.

Right now, I’m working as an executive assistant, a role that combines many of the skills I’ve developed over the years: empathy, organization, communication, and creative problem-solving. And I’m still designing part-time at 5wins, staying connected to the craft and community that remind me why I chose this path in the first place.

The truth is, rejection still stings. But I’ve learned that every “no” brings me closer to the right “yes.” Reinvention isn’t easy, it takes courage, grit, and the ability to rebuild your sense of worth again and again. I may be on my third career change, but I’m far from done.