New Direction, New Clothes, New Job


Diana Leon has come a long way – both geographically and spiritually.

After moving from San Diego to Hau‘ula, Diana turned her life around with the help of YWCA Oahu’s economic advancement programs, including Dress for Success. Nearly a year ago, Diana described herself as a depressed, shut-out woman struggling with a mid-life crisis. Today, she is ready to take every opportunity that comes her way with a positive outlook on life.

Diana felt confident going into her interview, thanks to her new outfit from Dress for Success, and recently got hired on the spot as an A+ Group Leader at Laie Elementary School. She dressed so well, employees thought she was an auditor from the state! 

Born in Los Angeles and raised in Tijuana, Mexico, Diana entered the workforce straight out of high school. After a brief stint as a telemarketer in Tijuana, she moved to San Diego for better opportunities and found a retail position at The Gap, where coworkers praised her meticulous and creative merchandising displays.

Despite her success, Diana felt unfulfilled in life and wanted something more. After eight years in retail she quit her job, left her apartment and moved back with her parents. During this transitional period, a friend invited her to live with him on Oahu’s North Shore.

“I was just looking for a whole new perspective on life and an opportunity to start over,” Diana said. “I was kind of feeling stuck, like I didn’t really know where to go or what to do.”

Diana took a leap of faith and made the journey to Hau‘ula, where she lived rent-free by taking care of the owner’s property. Although she had a place to live, Diana lacked income so she relied on food stamps while looking for a job. She applied to nearly 20 openings, from Haleiwa to Kailua, but only heard from a few employers. One of the barriers that Diana worried about during the hiring process is that she didn’t have appropriate attire for interviews.

“That was my main concern, because I can work on my resume, I can work on my cover letter, but when they see me…I have no work clothes at all, I have flip flops and shorts,” Diana said. That’s when her case manager suggested she apply to Dress for Success.

After speaking with one of the coordinators, Diana also enrolled in the Going Places Network (GPN) by Walmart, an eight-week program that helps unemployed and under-employed women build and develop professional skills as they search for jobs.

During her first GPN class, Diana and the rest of the participants received cell phones through the “Success is Calling” partnership with TracFone. She didn’t have a phone at the time and knew that this was a major asset as a job seeker. Diana also worked one-on-one with a mentor to help her prepare for an interview the following day.

After the class, Program Coordinator Bettelyn Smith helped Diana select an outfit in the Dress for Success boutique, which is supplied with clothing donations from the community. Once Bettelyn put together several professional options, she gave Diana the freedom to insert her own style into the mix. Diana decided on a mustard top with a blue cardigan, paired with grey dress pants and a thin tan belt, plus a red pendant necklace for a pop of color.

“I was going for bright colors, because I didn’t want to be so serious in my outfit, and it worked great because the people I went to interview with thought I was a completely different person,” she said. “They saw me walking in with my nice shoes and my dress pants and my cardigan and my purse. They thought that I was the auditor and they were scared!”

With the confidence she received from her new outfit paired with her mentor’s advice, Diana was instantly offered the job. As a group leader, she’ll be supervising children after school by helping them with homework and keeping them active through games and crafts.

Diana can’t express how grateful she is for YWCA Oahu’s programs and says her experience with Dress for Success played a big role in landing her new job.

“Having a coach work with me, having the new phone and the new outfit, that whole thing just made it all come together and helped me feel empowered to go out there and knock them out. Even if that didn’t work, then I was ready for the next one,” she said.

Diana believes that taking action and stepping out of her bubble was the hardest step in getting over her depression, and now she wants to pay it forward by spreading awareness of these free resources to her friends and others in the community.

“If you just say ‘yes’ or go in and ask, all of a sudden it’s like these people are taking your hand and helping you out to land the job that you want. You can’t lose anything if you don’t have anything to lose,” Diana added. “As soon as I started saying ‘yes’ to the opportunities, that’s when they started appearing. Now I get to start this new job in this new field, and I’m really excited about that.”