By Mimi Santry
You could say I’m a late bloomer…
I didn’t marry until I was 32.
I had my fifth and final child at 44.
I launched a second career in eldercare advisory at 54—becoming a small business owner.
And at 60, I became an advisor to a tech startup.
When I speak to groups about my eldercare advisory business—especially when the audience is women between 40 and 60—the conversation often shifts to one thing: relaunching. Such a great word. It’s a powerful word. It conjures an image of someone who’s been stuck on land too long, finally pushing off into unknown waters. That’s what it feels like to start something new at this stage: exciting, a little terrifying, and full of questions. Do I still have what it takes? Am I ready?
Why is relaunching such a hot topic?
People are living longer—and healthier. According to the Society of Actuaries, a 45-year-old non-smoking woman has a 50% chance of living to 90, a 37% chance of reaching 95, and a 20% shot at hitting 100. For men, the odds aren’t far behind.
Many men and women in their 50s and 60s find themselves at a turning point. They’ve raised their children or stepped away from earlier careers, and now they’re wondering, what’s next? For some, the answer is financial: “Wow, if I’m going to live until I’m 100, I better earn some more money for retirement.” For others, it’s about passion and purpose.
So, what advice can I offer? Nothing earth-shattering, but it starts with honest self-assessment.
How much free time do you have?
How much flexibility are you willing to give up?
What kind of compensation would make it worth it?
Are you a self-starter?
Are you an extrovert of introvert?
Are you energized by being busy—or stressed by it?
Take inventory of your skills. Do you need to update them? Especially when it comes to new technology or regulations? And then do a gut check: what actually excites you?
I think a dose of realism is key. Don’t confuse a hobby with a career. Look at fields where there is vibrancy and demand for talent. Play the odds. Remember the saying, “Rising tides lift all boats.” Don’t dive into a shallow pool or one with rocks.
And if you value your freedom and spontaneity, lean into that. Maybe part-time, remote, or volunteer work is the better fit. There are real opportunities out there. One example is Sidekick Concierge, a Larchmont-based company that connects highly educated women with families who need flexible, part-time support. There are also volunteer options with organizations like AmeriCorps Seniors (americorps.gov) or VolunteerMatch.org. Even your local senior center might know of nonprofits looking for help.
There are many inspiring stories out there.
Take Debbie Huffard, an avid squash player with a huge heart. She combined her love for squash and children by volunteering with CitySquash (https://www.citysquash.org), a Harlem-based after school program, that supports kids academically and athletically. I would see her at many of the Greenwich-based junior squash tournaments, shepherding three to four boys with pride and care. Debbie says, “This all started back in 2002 and I’m still actively involved. I had just lost my husband Flip and we were attending a local tournament when a huge blizzard hit. My 7th grader Gray invited Tim Wyant (head of City Squash from 2002-2013) and a few others to crash at my nearby home. We had dinner and by the end of the evening we had agreed to be hosts to the City Squash kids. My son Gray is now head of the City Squash Junior Advisory Board. Some of the kids have become part of our family. I can’t relay how much joy this has brought me.”
For those ready to go all-in, starting or buying a business is another path. In 2017, I worked with a business broker who provided me with a number of options to consider and helped me to understand the risk/reward trade-off. He also had me take several tests to assess my strengths and weaknesses. Franchises can be a less risky way to own a business, because, if we are sticking with the sailing analogy, they give you a map, a compass, and the support of a fleet.
Lauren Driscoll is a great example of someone who returned to her roots in healthcare to make a big splash by founding Nourished RX, a “food as health” business that supports health plan members with diet related conditions. www.nourishedrx.com
Lauren Driscoll, a graduate of the University of Virginia with a Master’s degree in Public Health from Columbia University, began her career working on healthcare policy as part of the Clinton Administration’s Healthcare Reform Task Force. She later served as Corporate Director of Oxford Health Plan’s Medicare business before stepping away from her corporate career in 2000 to raise her sons, Mac and Hill Kelley.
In 2010, Lauren returned to the healthcare field, volunteering as a healthcare policy advisor for Governor Ned Lamont’s first gubernatorial campaign. “Working with Governor Lamont gave me the opportunity to refresh my knowledge of the U.S. healthcare landscape at a time when everything was changing,” she said. That experience led to an introduction to former Utah Governor and U.S. Secretary of Health and Human Services under President George W. Bush, Mike Leavitt. This connection opened the door for Lauren to join Leavitt Partners, where she worked both full-time and part-time on healthcare strategy and innovation
Lauren’s advice? “Be humble and recognize there’s a learning curve. The landscape may have changed since you last worked, and you’ll need to put in the effort to get back up to speed. Don’t be afraid to volunteer or take on smaller roles to build your knowledge and confidence. Just get in the mix—opportunities will follow.”
Then there’s Stapley Russell, who went in a completely different direction. A former writer, editor and communications expert with major publishing houses, she trained to become an EMT. She admits it took some trial and error—French lessons, woodworking, even a comedy writing class—before she found her new calling. Inspired by her son’s experience with GEMS (Greenwich Emergency Medical Services), she signed up. Now, not only is she certified, but she’s also on the GEMS board and co-chairing their main fundraiser. Her advice: “Get out of your comfort zone. Try things. Be brave. You might just surprise yourself.”
On a personal note, I’ll say this: relaunching is hard and scary. I have had many moments where I doubted my decision, but after nearly eight years, it has been an incredible journey. I love having a sense of purpose and helping others. I have wonderful clients and learn every day. I am happiest when I am busy — but I admit I may be overdoing it!
To anyone out there considering a relaunch: do the work, be brave, and trust that something wonderful could be waiting for you.
Mimi Santry is a local senior care and housing advisor with Assisted Living Locators.
