The accidental retail career: 9 leaders on how they fell into the industry and never left

Nine guests. Nine paths nobody planned. One reason they all stayed.

An accidental retail career is one that begins as a stopgap, side job, or unplanned pivot and becomes a long-term professional path. Across two seasons of the Frontline Fridays podcast, nine retail leaders, including senior executives at Pandora, Peloton, Akris, Pollo Tropical, and the Retail Industry Leaders Association, have described their own version of that story.

Key takeaways

→  Almost none of the nine retail leaders profiled set out to work in retail. They planned medicine, law, law enforcement, literature, or corporate buying.

→  Most credit a specific mentor, manager, or moment for the pivot from a stopgap job into a career.

→  When asked why they stayed, none of them named the product. They all named the people.

→  The pattern holds across hospitality, luxury, mass, big box, and convenience retail.

→  The book Retail Pride by Ron Thurston, host of Frontline Fridays, is the source material for the broader thesis.

Ron Thurston wrote a book called Retail Pride: The Guide to Celebrating Your Accidental Career. The subtitle is the part that lands hardest.

Almost nobody we have interviewed on Frontline Fridays planned a career in retail. They walked in for a part-time job, a stepping stone, a way to pay the bills, and stayed for reasons they could not have predicted at the time. Some had their plans interrupted. Some had their plans quietly replaced. A few woke up ten years in and realized the thing they were doing on the side had become the thing they were doing.

Across two seasons of the show, we have heard nine versions of that story that we keep coming back to. They sit alongside each other in a way that feels less like a coincidence and more like a pattern. So we pulled them together. Here is what each one tells us about why retail keeps catching people who never planned to stay.

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01

Sam Rubino traded a healthcare calling for a hospitality career

Sam had an innate calling toward healthcare. Service ran in the family. Her parents had a restaurant. Her grandmother had a restaurant. But the plan was medicine, and she was studying for it while bartending and serving at Outback to get herself through school.

She kept getting drawn back to hospitality. She built experience at the Ritz-Carlton. She played a pivotal role in the inception and growth of Bolay. Somewhere along the way she realized that the part she loved most was empowering other people to find their own potential. Healthcare had pulled her toward helping people. Hospitality, it turned out, was a different way of doing exactly that.

Today she runs training and communications at Pollo Tropical. If she had forced the medicine plan, she might still be wondering why the energy was not there. The career that pulls at you is usually the one worth investing in. The trick is letting yourself notice.

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02

Khris Hamlin chose asset protection over law enforcement

Khris was studying criminal justice at George Mason. The plan was law enforcement. Retail was the job that paid the bills while he worked through his next step.

He started in asset protection at Hecht’s, the department store chain that would later become part of Macy’s. What he thought was a stopgap turned into 25 years across asset protection, operations, and store management. He moved on to senior AP roles at Belk, Nordstrom, and Saks OFF 5TH. Today he is Vice President of Asset Protection at the Retail Industry Leaders Association and runs The Khris Hamlin Company on the side, coaching the next generation of AP leaders.

The thing he picked up to pay the bills became the thing he built a 30-year career on. Sometimes a stopgap is just a stopgap. Sometimes it is the door you walked through without noticing.

•   •   •

03

Payton McFaden built Peloton’s sales operations function from the inside

Payton spent her early career running stores. At Peloton, she became one of the top store managers in the company. In 2019 the brand recognized her with the “Think and Act Like an Owner” award, which sounds like a marketing line until you understand what it actually meant: she had been treating one store like it was her own business for years.

She wanted to move into corporate. She applied seven times before she got in. She talks about that number openly, because she thinks the store teams reporting to her right now should know it. When she finally crossed over, she built Peloton’s sales operations function from the inside, drawing on everything she had learned standing on the sales floor. Today she leads global sales operations.

Seven rejections is not a story most leaders tell. It is also exactly why hers is worth listening to. The path through retail is rarely linear, and the people who make it tend to be the ones who let the messiness happen without taking it personally.

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04

Kelly Anderson left a pre-law track for 20 years in luxury retail

Kelly was studying at York College in Queens, on track to become a corporate attorney. She had landed two prominent internships in her freshman year, ahead of graduating seniors. Then her mother got sick. Kelly became the family’s provider, working two jobs through college while she tried to keep the law school plan alive.

She shopped at an Aldo on 17th and 5th Avenue. The manager got friendly. A conversation led to an interview. She got the job. She was still conflicted about leaving law behind until a mentor teaching at Columbia gave her advice she still uses: people spend so much of their lives focusing on what they think they want. Focus on what makes you happy now, and let it grow from there.

Twenty years later she has led retail teams at Aldo, Kenneth Cole, Louis Vuitton, and Moncler. Today she is Director of Stores, Retail & Concessions at Akris, the Swiss luxury fashion house. The blueprint she had at 18 looked nothing like the career she ended up building. That is true for almost everyone. The energy is more reliable than the plan.

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05

Sherrica Hill built every next role from the one she was already in

Sherrica spent two decades in retail. She started as a seasonal sales associate at Gap and advanced into corporate leadership. Years later, after taking time off with her kids, she came back through fill recruiting, hiring forty sales associates at a time for stores that needed them.

She kept pausing the process. She did not want to send people into stores that were not set up to receive them. So she added training. Then she made the case to lead Gap Inc.’s This Way ONward program, which she eventually ran, tackling systemic barriers to employment for over 15,000 underrepresented early-career talent. That work led her to Jobs for the Future, where she now designs first-job programs for the kind of young workers she used to recruit. Across all of it, she earned her degree while working full-time.

Sherrica did not wait for permission. She used the job she had to test the work she wanted to do next, then built the case for the role. That instinct, more than any single decision, is what shaped her career.

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06

Brandon Lee turned an English Lit degree into a 20-year visual merchandising career

Brandon did not study design. He studied English Lit and Communications. His first internship was at Barneys, where he was the young one on the team, sometimes literally gluing mannequin hands to the ceiling. His boss walked by once, watched him work, and let him keep going.

From there he built a 20-year career across Ralph Lauren, Bonobos, Gap, Moose Knuckles, and Brooks Brothers. Each move was a yes to the next thing that interested him. Then he left full-time employment to launch Brandon Lee Designs, his own LLC. His current clients sit across industries you would not necessarily associate with traditional VM, including cannabis and furniture.

None of that was on a plan. The literature degree taught him to read stories. Visual merchandising, as he describes it, is just another way of telling them. The point is not that English majors should do retail. The point is that careers like this one get built one yes at a time. You do not need the five-year plan. You need the next thing worth trying.

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07

Brian Librach found the industry that fit his ADHD wiring

Brian grew up with undiagnosed ADHD in an era that had no language for it. He learned his coping mechanisms by trial and error, using the driven nature ADHD often brings to chase what energized him. School did not always work. Retail did.

He started in the stockroom. He became a district manager at 21. He climbed from the stockroom to the corner office at Urban Outfitters, PacSun, and internationally with Old Navy in Canada. He still talks about retail as the place that let him use the parts of himself other industries treated as a problem. The improvisation. The energy. The ability to read a room and adjust in real time.

Today he writes about that journey. The Retail Leader’s Roadmap is the book. The Wellwisher Company, which he co-owns with his wife, is the platform. Brian’s story is a useful reminder that retail rewards a particular kind of wiring, and that the people who get told they are wired wrong sometimes find themselves in exactly the right place.

•   •   •

08

Adimika Owens stepped back to step forward

Adimika started in retail as a buyer at Bloomingdale’s after studying at Clark Atlanta University. Then she relocated to Los Angeles. She walked into a Zara and applied as a sales associate. She calls it the best career decision she ever made.

Working alongside the team that had come over from Spain showed her that retail was not just a corporate function. It was a career, and the stores were where it actually happened. Twenty-five years later she has led visual merchandising at Bloomingdale’s, Forever 21, Victoria’s Secret, and Floor & Decor. At Forever 21 she pushed for mannequins in different shapes, sizes, and skin tones before DEI was a phrase anyone was using. She calls it a small thing that signals a big thing to a customer walking in: you are welcome here.

Going from corporate buyer to sales associate looks like a step back on paper. It taught her more than the next promotion would have. The view from the sales floor is the view every retail decision should account for, and the leaders who have stood on it tend to make better calls when they leave it.

•   •   •

09

Detria Courtalis said yes to every next question at Pandora

Detria joined Pandora in 2011 as a training manager because she wanted to get into the brand. Then she raised her hand to run franchise and real estate, which at the time meant the mall stores. Then corporate stores started opening. Then she ran wholesale. Today she is Vice President of Sales for the US and Caribbean, sitting on Pandora’s North American Executive Leadership Team.

None of that was a planned career path. It was a series of yeses to the next question. She tells leaders to be Gumby. She tells store managers to raise their hands, even when they are not sure. Worst case, you get knocked down. You get up. You learn.

Earlier in her career she left Gap for a DM role at Structure when she did not get promoted at Gap. Six months in, she realized she was not ready. She calls it a dose of humble pie and one of the most useful mistakes she has made. Stretch assignments do not need to be linear, and they do not need to work the first time. They just need to teach you something.

•   •   •

Why retail keeps catching people who never planned to stay

Read the stories back to back and the pattern is hard to miss. Almost none of them planned a retail career. They planned medicine, law, law enforcement, literature, buying offices, or something else entirely. Retail was the part-time job, the lateral move, the thing they did while they figured out the real thing.

Then the real thing turned out to be this.

When asked why they stayed, none of them talk about the product. They do not talk about the discounts, the pace, or the brand on the building. They talk about the people. The teams who pushed them to apply for the corporate role. The mentors who saw a skill set they had not spotted in themselves. The store managers who asked what they wanted to do next, and then helped them get there.

Ron calls it the accidental career. That is accurate. It is also the reason retail keeps producing leaders that other industries cannot quite replicate. People stay because someone invested in them. They grow into the kind of leaders who invest in others. The cycle is the product.

If you are in this industry, you are part of it. If you lead a team, you are responsible for the next nine stories that get told.

•   •   •

The nine guests featured in this article

Each guest below was interviewed on the Frontline Fridays podcast, hosted by Ron Thurston and presented by YOOBIC.

Sam Rubino is Director of Training and Communications at Pollo Tropical. Featured on Fostering Proud Frontline Career Paths in Retail & Hospitality.

Khris Hamlin is Vice President of Asset Protection at Retail Industry Leaders Association (RILA). Featured on Asset Protection’s Key Role in Modern Retail Leadership.

Payton McFaden is Director of Global Sales Operations at Peloton. Featured on Embracing Vulnerability in Modern Management.

Kelly Anderson is Director of Stores, Retail & Concessions at Akris. Featured on Inspiring the Next Wave of Retail Talent.

Sherrica Hill is Director of Solutions Design and Delivery at Jobs for the Future (JFF). Featured on Hiring For Potential, Not Credential.

Brandon Lee is Creative Director and Owner at Brandon Lee Designs. Featured on Balancing Creativity & Operations in Retail Design.

Brian Librach is Author and Co-Owner at The Wellwisher Company. Featured on Finding Career Growth When You Feel Stuck.

Adimika Jaia Owens is Brand Experience Executive at (formerly Floor & Decor, Forever 21, Victoria’s Secret, Bloomingdale’s). Featured on Visual Merchandisers as the New Keepers of Company Culture.

Detria Courtalis is Vice President of Sales US and Caribbean at Pandora Jewelry. Featured on How to Stay Flexible When Everything is Changing.

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Worth a read

Retail Pride: The Guide to Celebrating Your Accidental Career by Ron Thurston is the source material for a lot of how we think about frontline talent. If these stories landed, the book is worth picking up.

Every Frontline Fridays episode is on Spotify, Apple Podcasts, and YouTube.

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