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| Dianne Michels, 81, works at Trader Joe's while starting a consulting business. Dianne Michels |
At 81, Dianne Michels is proving that purpose doesn’t retire. While many her age are winding down, she’s charging ahead with a cash register in one hand and a business plan in the other. By day, she works shifts at a Trader Joe’s in suburban Chicago. On her days off, she’s building a consulting and coaching business she believes will outlive her. And she’s doing it while actively paying off nearly $70,000 in debt.
“I never want people to treat me like I’m old,” she said. “The way society often talks about retirement it’s like you're irrelevant. But I’ve never felt more focused or driven than I do right now.”
A Lifetime of Reinvention
Dianne’s story begins in Fargo, North Dakota, where she took her first job at a telephone company at 19 after dropping out of college. At the time, the only real career paths for women seemed to be nursing or teaching neither of which appealed to her. Instead, she began as a service representative, married young, and had two children before divorcing at 25.
The next phase of her life was marked by experimentation both personally and professionally. She worked for the State Attorney’s office, volunteered on political campaigns, and eventually became the first female vice president at a medical office supply company. But when the company was acquired and her department relocated, she discovered just how suffocating corporate life could be for women in the late 1980s.
“I wasn’t cut out for corporate politics in a male-dominated environment,” she said. “I wanted to make a real impact not just survive the hierarchy.”
From HR to Her Own Brand
In 1990, Dianne launched her first career consulting firm, but without the financial structure to sustain it, the business closed after two years. She moved to Chicago in 1993, pursued her college degree on evenings and weekends, and worked in public relations and human resources until eventually launching Serendipity HR in 1998 a venture she ran successfully for over 15 years.
In 2014, she took on the title of “Chief Possibility Officer” at YWCA Metropolitan Chicago, a role focused on impact and innovation. She left in 2018 to write a book and focus on what she hoped would become her legacy: a company built around creating real possibility for people inside organizations.
That vision evolved into her current company, Possibility Partners, where she now offers strategic coaching and consulting with a focus on productivity, retention, and sustainable growth.
“I Made Financial Mistakes, But I Refuse to Be Defined by Them”
Despite a long and varied career, Dianne is still $70,000 in debt a mix of credit card debt, business startup costs, publishing expenses for her book, and personal obligations.
“I didn’t grow up in a family that understood investing or financial planning,” she said. “We were taught to get a job and keep it. I’ve been irresponsible with money at times but I’ve also invested in myself.”
She now receives $2,500 a month from Social Security, which she began collecting at age 62. Looking back, she says she wishes she’d waited. “It would’ve given me a third more, but I didn’t have the long-term financial outlook I needed at the time. I was thinking about cash flow, not future security.”
Still, she doesn’t dwell on regrets. “I’ve always refused to let money or the lack of it dictate what’s possible.”
Trader Joe’s: A Bridge, Not a Destination
To fund her business and pay down her debt, Dianne picked up part-time work at Trader Joe’s a job she chose deliberately.
“I dropped off résumés at six locations. Two days after an interview, I was hired. The whole process was incredibly respectful,” she said. “And let’s be honest I have a little snob in me. I wouldn’t work just anywhere. But I knew from past experience that Trader Joe’s was the right fit.”
Dianne works Friday through Monday, handling everything from cashiering to shelf stocking to food demos. She spends Tuesday through Thursday growing Possibility Partners networking, sending sales emails, and refining her messaging to better align with what clients care about: results, retention, and revenue.
“There’s very little hierarchy at Trader Joe’s,” she said. “That means less competition, more collaboration, and a team that genuinely respects each other.”
Family, Freedom, and the Future
Dianne’s business isn’t just about making money it’s about building something that lasts. And something that gives her the flexibility to show up for the people who matter most. She plans to move closer to her daughter in Michigan next year.
“I want to be able to babysit when she needs me to, or just be nearby,” she said. “Working for myself gives me that freedom.”
She makes no secret of her ambition to one day leave her Trader Joe’s apron behind. “It’s temporary,” she said firmly. “Once my business is thriving with active clients and partners, I’ll leave Trader Joe’s and go all in.”
More Than a Paycheck: A Purpose
For Dianne, the journey isn’t just about financial survival it’s about redefining what it means to age in a society that too often sidelines older adults.
“If I see one more ad with a retiree saying they just want enough money to go to dinner and see their grandkids, I’ll scream,” she said with a laugh. “We are capable of so much more. We are still valuable. We still have work to do.”
