#123 Holly Oh Diamond is Bringing Dignity to Job Hunting
Hi! New here? Welcome to the Uplifters! I'm Aransas Savas. I've spent the last 20 years at the intersection of behavior change research and coaching. On The Uplifters Podcast, we share diverse stories of trailblazing, change-making women who have done big, brave things and show us how we can too!
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You've ever felt overwhelmed by a problem and wondered if you're the right person to solve it
You're navigating career transitions or job searching challenges
You want to understand how to turn personal struggles into meaningful impact
You're curious about social entrepreneurship and creating businesses with purpose
You need inspiration for taking action before you feel "ready"
This Week’s Featured Uplifter: Holly Oh Diamond
The most relevant and impactful solutions to our biggest problems always seem to come from people who've lived them firsthand. When Holly Oh Diamond arrived in New York in 2009 with just $400 in her bank account, she couldn't have imagined that her own struggle to find work would eventually become the foundation for a platform helping thousands of others navigate their career journeys.
Holly is the CEO of Work Onward, a map-based hiring platform that connects small businesses with local hourly workers, specializing in immigrant-owned businesses and blue-collar industries. But her story isn't just about building a tech company—it's about what happens when we refuse to accept that "this is just how things are" and instead ask, "What if it could be different?"
In December 2020, at the height of the pandemic, while restaurants were shutting down left and right, Holly made what felt like a crazy decision. Her Korean-immigrant parents, who had worked in restaurants for over 20 years, had just lost their jobs. As a recruiter and daughter, she tried everything to help them find work, but nothing was working. So she did something that most of us would never even consider: she opened a restaurant. In Manhattan. In a pandemic.
When her mom took pen and paper and wrote a handwritten "Help Wanted" sign in Korean for their storefront window, Holly had her lightbulb moment. We need a map, she thought. Not just for getting around geographically, but for navigating the often invisible world of job opportunities.
For Holly, it's about recognizing that when you're in survival mode, when people you love are counting on you, you don't have the luxury of perfect planning or endless contemplation.
"You just have to do it. You can't be contemplating or building up strategies—you don't have the time for that, you just have to do it."
5 Ways Holly Shows Us How to Build Our Courage Capital:
See problems as invitations, not obstacles. When Holly's parents lost their jobs, she didn't just see a personal crisis—she saw a systemic problem that needed solving. Instead of wringing her hands about the unfairness of it all, she immediately started asking, "How can I fix this?"
Act from your authentic experience, not your credentials. Holly didn't wait to become a restaurant expert or a tech CEO before taking action. She moved forward with the expertise she had: understanding what it felt like to be job-seekers who are overlooked, and knowing firsthand the challenges facing small businesses and immigrant families.
Create the change you wish you'd had. Work Onward exists because Holly remembers what it felt like to submit thousands of job applications and get no responses. She's building the platform she wishes had existed when she was struggling—a map that shows not just where the jobs are, but which employers actually value the workers who apply.
Turn your survival skills into superpowers. Holly's ability to pivot quickly, work without a roadmap, and keep going when things get tough weren't developed in business school, but through necessity. She's transformed what could have been limits into her greatest professional strengths.
Remember that dignity isn't negotiable. Throughout everything, Holly centers the concept of dignity. "I deserve to be treated better," isn't just personal motivation; it's the foundation of everything she builds. When you make dignity non-negotiable for yourself, you naturally create it for others.
Lift Her Up:
Support Holly's mission by:
Downloading the Work Onward app if you're a job seeker or small business owner
Visiting her family's restaurant to try their from-scratch kimchi (and tell her parents you heard their daughter's story!)
Sharing this episode with anyone who might benefit from Work Onward's services
Following Work Onward on Instagram and LinkedIn for updates on their expansion
If You Liked This Story, Check Out These Episodes:
Emily Levin (Episode 116) - Holly’s nominator, a social worker and therapist, who is solving systemic issues through founding Axcces, the first AI-powered platform that streamlines the affordable housing process.
Jenny Jing Zhu (Episode 84) - Lush Home Decor founder, who built a $100 million company after immigrating from a small village in China
Tai Abrams (Episode 40) - Another entrepreneur who transformed personal challenges into business solutions
Kymme Williams-Davis (Episode 25) - Fellow business owner creating community impact through her café
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This was beautiful!