Editor's Note: This story is part of the series "Entrepreneurship: Square One and Beyond," a Next Avenue initiative made possible by the Richard M. Schulze Family Foundation and EIX, the Entrepreneur Innovation Exchange
One day, Janice Costa was running around in suits and heels, attending luxury home design shows from Milan to London to Las Vegas. Today, she runs a dog vacation camp in upstate New York, spending most of her time in t-shirts “accented with dog hair.”
“My second act is as far removed from my career in the design industry as one could possibly imagine,” says Costa, owner and founder of Canine Camp Getaway. “Yet I love working with dogs and dog lovers, planning vacations for them and putting together creative programming.”
Costa spent more than 30 years as a design editor before the pandemic decimated the publishing industry in 2020. Facing the prospect of returning to 70-hour corporate weeks — and already sitting on a dog camp she’d quietly run as a side project since 2009 — she took a second look at what it could become. She added a second location, converted the business to an S-Corp, began paying herself a salary and started exhibiting at pet expos across the Northeast. Today, her events draw more than 125 people and 150 dogs.
“I find that I enjoy both the differences and the synergies of skills learned in my previous jobs,” she says. The creativity she poured into planning magazine content and conferences? It translates beautifully to designing doggie sweet-sixteen parties and beach events.
Costa’s transformation is far from unique. Across the country, professionals in their 50s, 60s and beyond are trading in their former identities not just for retirement, but for something brand new — second acts that may look nothing like what came before, yet draw deeply on decades of hard-won experience.
“I find that I enjoy both the differences and the synergies of skills learned in my previous jobs,”
The Skills You Don’t Know You Have
For anyone worried that a late-career leap into unfamiliar territory is too risky, Dr. Kelly Heuer, Vice President of Learning at the Project Management Institute (PMI), the leading authority on project management, has an encouraging perspective.
“When I think about mature career professionals, it’s like you’re ideally set up for a dramatic pivot in a way that I think it’d be hard to appreciate if you’re not taking that lens to it,” Heuer says.
At PMI, Heuer and her colleagues study workforce skills development and how professionals succeed across career transitions. They divide professional skills into two broad categories. The first are “perishable skills” — highly technical, industry-specific capabilities that are enormously valuable in the moment but have a shrinking half-life. “The half-life of skills is shrinking with the pace of technology,” she notes.
The second category is where experienced professionals hold a distinct advantage: durable, enduring skills. “Things like communication, leadership, conflict resolution, systems thinking, critical thinking, analytical skills,” Heuer explains. “These are valuable even after a dramatic career pivot,” she says. These harder-to-measure capabilities take years to build, but they are the true differentiators that make experienced professionals more hirable and more effective than their less-seasoned counterparts, Heuer says.
“If you’re experienced in one field — or several — or as a parent who’s taken care of aging parents, you are seasoned in a way that generally means you have built the capability types that matter most and translate best to a new work context,” Heuer says. Consequently, someone striking out for the first time in a new field at 55 or 65 may be better equipped than a 25-year-old attempting the same leap.
Heuer also pushes back against the fear of learning new technical skills. “There have never been so many opportunities to keep learning new skills throughout the entirety of your career,” she says, pointing to professional certifications — some requiring zero years of prior experience in a field — that can provide both a foundation and external validation for potential employers. A basket of durable human skills combined with a formal certification, she argues, is a compelling combination for any hiring manager.
“The half-life of skills is shrinking with the pace of technology,”
“Everybody’s got hills and valleys throughout their career,” she says. “You can spot a pattern in moments with high points, whether that was camaraderie, working with a tight-knit group, working at the edge of your capability, or being in a teaching role as opposed to an analytical role.” Those recurring patterns of fulfillment, she says, are a map.
The negative experiences are equally instructive — particularly when patterns emerge. The work that consistently drained you is as informative as the work that lit you up. Together, they can help rule out directions that seem appealing on paper but would ultimately leave you depleted, and point you toward environments and types of work where you’re most likely to thrive.
Purpose Over Profit
When Sue Ryan, co-founder of The Caregiver’s Journey in Naples, Florida, stepped away from a more than 30-year corporate leadership career focused on strategic growth and major client partnerships, she had no intention of launching a nonprofit podcast organization.
But after caring for both her father — who was diagnosed with dementia in 2006—and her husband, who was later diagnosed with Alzheimer’s disease, Ryan found herself with a body of hard-won knowledge that other caregivers desperately needed. “The lessons I had learned the hard way were exactly what others needed most,” she says.
When her husband passed away in 2023, Ryan chose not to return to corporate life. Instead, she co-founded The Caregiver’s Journey, a nonprofit that provides practical guidance for dementia caregivers worldwide. The podcast she co-hosts earned the 2025 Gold Stevie Award for Advice and How-To Podcast and now reaches more than 35,000 subscribers.
Ryan’s pivot reflects what retirement transition expert Elizabeth Zelinka Parsons, a Tucson, Arizona-based lawyer, co-founder of Zelinka Parsons consulting, and author of “Encore: A High Achiever’s Guide to Thriving in Retirement,” has observed across her practice: for most people, the impulse to pivot has nothing to do with money.
“It will not be financial need that drives most people to ‘unretire,’” Parsons says, “but rather a need to be engaged and contributive.” Many of the entrepreneurs she works with also shift their goals from profit to purpose — finding it far more motivating to build something that matters, whether to a targeted community or to the world at large.
“For most people, the impulse to pivot has nothing to do with money.”
Translating Experience Into a New Language
Yaa-Hemaa Obiri-Yeboah, founder of The Y Variable, a consulting and advisory practice specializing in intergenerational workplace dynamics, spent nearly 20 years in the Canadian federal public service with Global Affairs Canada before pivoting into entrepreneurship. A Rhodes Scholar with two master’s degrees from Oxford, she thinks about career pivots as an exercise in translation.
The key to a post-retirement pivot is an ability to translate one’s expertise and experience, she says. The problem she most often encounters is not that people lack valuable skills — it’s that they try to lead with credentials rather than capabilities.
“Your title — ‘Senior Director’ — doesn’t really tell the story,” she says. “What you’re capable of doing: ‘I help organizations navigate the friction between their experienced leaders and their next generation of talent’ — is a business.” The former closes doors, she argues; the latter opens them.
Her advice: ask yourself what people consistently came to you for, not because of your title, but because of who you were. Those recurring patterns are the seeds of a viable pivot. “Often, post-retirement, it’s the first time your full identity can show up in the work you do,” she says. “Rather than showing the edited version you think an organization needs, you can now show up more fully.”
The Emotional Dimension
Veronica Scarpellino, an executive career transition coach, founder of Goldfinch Leadership, and author of “Second Draft: Rewrite Your Midlife Career with Creative Intelligence,” cautions that the emotional weight of a career pivot is easy to underestimate.
“When a role ends, it’s not just the work that disappears,” she says. “A sense of identity, relevance, relationships, and daily structure can disappear with it. That grief is real, and it’s often the hidden obstacle that makes people feel stuck.”
Scarpellino advocates for small experiments over dramatic single leaps — advisory work, mentoring, teaching, nonprofit leadership, or launching a small venture that can organically grow from strengths developed in a traditional career. “Later-career pivots tend to work best when people allow themselves time to process the identity shift and then approach the next chapter with curiosity and experimentation,” she says.
She also reframes what creativity means at this stage of life. “Creativity isn’t limited to artistic expression. It’s the ability to look at decades of experience and recombine skills, interests, and relationships in new ways.”
Later-career pivots tend to work best when people allow themselves time to process the identity shift and then approach the next chapter with curiosity and experimentation
The Serial Pivoter
Then there’s Jack Schacht of Chicago — proof that the impulse to pivot doesn’t necessarily stop at one and that there’s no expiration date on reinvention.
At 86, Schacht has launched five businesses in his nearly seven-decade career: a career recruitment firm, a national backgammon league, a commercial barter exchange that grew into the largest in the country, a college financial planning service, and now, in 2026, the Chicago Backgammon League, a return to one of his earliest and most beloved ventures.
At 72, Schacht launched My College Planning Team to address the financial struggles of middle-income families facing daunting college costs. He sold the business in 2025. Now, as backgammon trends again in major cities as people seek authentic face-to-face social experiences, he’s back at the table — recruiting talent, building clubs across Chicagoland, and partnering with the U.S. Backgammon Federation to help high school students develop critical thinking skills.
Ready to Pivot? Start Here
Taken together, the advice from experts and real-world pivoters points to a handful of principles for anyone considering a major career shift.
Map your high points. Reflect on the moments in your career and personal life when you felt most fulfilled and look for patterns — in the type of work, the setting, the people. The low points are equally instructive.
Separate perishable from durable. Your industry-specific technical skills may be less transferable than you think, but your communication, leadership, problem-solving, and relationship skills are gold. Lead with those — and don’t underestimate how quickly you can add new technical knowledge through certifications and targeted learning.
Experiment before you leap. Try consulting, volunteering, freelancing, or taking a course in your target field before making a full commitment. Testing a direction, can help you determine whether the pivot will actually be a good fit for you.
Find your community. Seek out professional associations, job boards tied to specific fields, and in-person or online communities where people doing the work you want to do congregate. That’s where opportunities often surface organically.
Reframe your value. Stop marketing yourself by title. Articulate what you can actually do — and why it matters to the people you want to serve.
And perhaps most importantly: give yourself permission to grieve the old identity before rushing to build the new one. The best second acts aren’t escapes from what came before — they’re fuller expressions of everything you’ve become.