The interview was going great. Dorothy was sure they were going to offer her the job.
That was the problem.
It was the day her “Who Are You Now?” workshop with Jill Nykoliation started. Dorothy had arrived at MEA’s retreat center in Baja and had several hours before the welcome reception, so had agreed to an interview with a large non-profit that was looking for a new CEO.
After leaving her last position as chief of staff for a $1 billion healthcare system a year earlier, she had co-founded a consulting business. But it wasn’t paying the bills, and she had reluctantly decided she needed to find another job.
“I thought, well, if I’m going to do anything, it’s going to be a CEO role,” she says. “There’s no other choice. That’s the last frontier.”
But she didn’t know if it was really what she wanted. And as she listened to what the interviewers had to say about the role, she felt a growing sense of dread.
“My gut was in a knot because I was like, ‘Oh, I think I’m going to have to go back to what I was doing,’” she confesses. “I’m going to have to jump in and save this organization.”
It would take her another day to find the words for it. But she knew she didn’t want to play the hero anymore.
The workshop opened that evening with seven women in the room, all of them in the middle of a major transformation.
As Jill guided them through activities designed to help them understand the roles they were playing – and what they were ready to let go of – Dorothy realized that her entire career had never been her own vision for her life.
“I had been wearing the costume of a hero for a long time,” she says. “I am a mom of a challenged individual. I was a hero for all kinds of people, places, and things. Even the companies that I worked for. I wanted to go into leading nonprofits because I was going to save the world.”
During the workshop, she had an epiphany: her career had never really been her choice.
“I was just kind of pushed into it initially,” she says. “My dad managed my career and my launching after I graduated from college. So everything I did was a little bit by his design and in his image.”
As she built her career, the accolades came. “The salary comes, the titles come. And even then, I’m the hero, right?” she says. “Because I want to break through for other women. And I did, you know, in all respects.”
But in the workshop, as she thought about the job she had just applied for, she had to admit the truth: the work had never fulfilled her.
“My whole career was stressful. I rarely enjoyed it,” she confesses.
By the end of the second day, she had called back the company that had interviewed her, removing herself from the process. “I thought, I don’t have to go save this organization in this large nonprofit,” she says. “I’m going to say no and keep myself open to what else there is.”
She’d just closed the only door she thought was worth walking through. So what was left?
For the first time in 35 years, she explored that question not from the perspective of what would look good on a resume, but what would actually make her happy. Beyond the titles and accolades, she’s someone who cares deeply about others. She likes being the one who brings joy into a room and makes people laugh.
So what would a life built around the things that made her feel alive actually look like?
“I realized I want to perform and entertain and make people happy,” she says.
Before the workshop had even finished, she’d sent off an application and a demo reel for a job as a DJ. She didn’t get it, but just the act of applying was liberating.
“The feeling that I have now is comfort and happiness. I feel happy – and it shows.”
After she returned home from the workshop, Dorothy worried that she might have to return to corporate life. But then she told herself: “Nope, I don’t have to do that. That’s the hugest shift for me.”
But she still needed to get a job. So with eyes wide open, she applied to the last place people might expect: her local Trader Joe’s.
“The people at Trader Joe’s seem to really like what they’re doing. And I love shopping there,” she says. “I’ve been shopping at Trader Joe’s since the 90s.”
Plus there was something about it that appealed to her inner child. As a kid, she used to play store, taking every can and box out of her mother’s pantry, stacking them on shelves, and ringing them up on her mother’s calculator.
“I thought, well, what’s that about?” she says. “Maybe there’s something to this that I like.”
So she applied to be a crew member, and they offered her the job.
“I was really surprised that they did, because I have zero retail experience,” she says. “But they liked my personality and they liked that I care about people, and that’s kind of their philosophy.”
The first week nearly took her out.
Though she considers herself fit, it left her exhausted and covered in bruises. And as she spent her days stocking shelves, the questions showed up.
“I found myself thinking, what are you doing here? What is the purpose of this? Then I realized, oh, it’s how I made that 80-year-old woman’s day when I helped her find the sauce she was looking for. The guy I bumped elbows with, then danced with in the aisle for a minute. The younger woman I sang Rocket Man with in the aisle, or the woman I helped who had three kids in her cart. I was like, oh, that’s what this is.”
She loves that the job lets her connect with so many people, including her coworkers. “I’m the oldest one on the team. They’re all awesome, different, quirky, from different generations and backgrounds. I’m fascinated with each and every one of them.”
Nobody at the store knows about the C-level positions she’s held over the past thirty-five years. She hasn’t told them, and she isn’t going to. “It’s immaterial. It means nothing,” she says.
She’s also clear that being able to choose this path is a privilege. Working at Trader Joe’s isn’t most people’s idea of exciting. But it’s exciting to her.
“Oh my gosh. I’m happy,” she says. “And I don’t know that a lot of people can say that truly… This face that you’re seeing, that’s all bright and light. That’s who I am now.”
One thing she hadn’t figured out: what would she do if someone from her former life came through her line?
A former boss. A colleague. Someone who knew exactly what she used to be.
“What are they going to think of me?” she says. “That I’m working at Trader Joe’s.”
When she asked Jill about it, Jill said, “You just smile to yourself, knowing it all worked out.”
Then, her first week on the floor, it happened.
She looked up and saw a man she’d fired years ago when she was the CEO of a media company. He saw her and did a double take. She smiled at him the way she’d smile at any customer, asked him how he was doing, and kept walking.
Then the stories came up in her mind around everything he might be thinking about her. “It lasted for about five minutes, which was remarkable to me,” she said. “That’s how far I’ve come.”
Because she knew that’s all they were: stories. And the happiness she felt was real.
Now when people ask her what she’s doing, Dorothy tells them she has completed a 35-year corporate career. “I say that I have completed it. So that’s a big shift because I now know I’m never going back to that.”
Dorothy doesn’t call this a retirement gig, or a detour.
She calls it her first job.
“It’s like if I had graduated from college and actually chose what I wanted to do,” she says. “That’s how I feel right now. I get to set my boundaries. I get to not give a hoot about what anybody else thinks, and just be me.”
Outside of her job at Trader Joe’s, Dorothy is also planning to lean into her love of performing by producing a one-woman show that she’s been working on in the background.
“These are going to be the best 10 years of my life,” she says, beaming.
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If you’re looking for a career change or your current position no longer brings you joy or purpose, consider attending one of MEA’s Navigating Transitions or Cultivating Purpose workshops. You can also work with MEA senior faculty Jill Nykoliation at one of our Meaning Of Your Life workshops, based on Arthur Brooks’ latest book.