I met Janine Vanderburg a few months ago, and within minutes we were finishing each other's sentences, like we’d known each other all our lives. This conversation continues in her interview with me for her new podcast, Build Your Own Boat.
Watch the Replay above. Here is a small clip
Overview
Janine is an award‑winning, 3x entrepreneur and nationally recognized expert on ageism and age inclusion who has spent decades helping organizations rethink how they see older workers and intergenerational teams. In this Real 50 over 50 conversation, she shares why her new project, Build Your Own Boat, is all about telling the stories of women who start entrepreneurial ventures in midlife and beyond.
The origin story is both simple and revealing: Janine asked five AI image tools for “an entrepreneur in a coffee shop,” and every result was a young guy in a hoodie with a laptop. When she told that story at a women’s conference and said out loud that she was going to tell the stories of women building their own ventures later in life, she spent the next two days hearing stories shared by women saying, “that’s me.” From there, she asked who wanted to share their story in a LinkedIn post and quickly had a list of 40 women to interview whose careers range from nonprofits to tech and AI, and they put aside the fear and the naysayers and build their own boat anyway.
Janine is candid about money and value: why so many women underprice, say yes to “exposure,” and believe they need one more credential before they begin. She shares the story of a small business she started years ago around recycled cashmere wall hangings and blankets—she loved the craft of creating, and they sold out, but it was clear that it was ’t paying the mortgage and couldn’t realistically support her financially. That experience became a barometer of sorts about how to think about the intersection of what you love, what you’re good at, and what the market will actually pay for.
We also talk about time and boundaries. Janine references Oliver Burkeman’s book Four Thousand Weeks: Time Management for Mortals and the idea that if you live to about 80, you only get roughly 4,000 weeks in your lifetime. She describes sitting down, calculating how many weeks she might have left, and using that number to get much clearer about what she will and won’t do. That clarity also shows up in the stories shared by guests in Build Your Own Boat. It’s a big part of the message she wants women to hear: you have less time than you think, and more agency than you’ve been told.
At the end, we touch on how closely our work mirrors each other—her “build your own boat” and my “don’t burn down the ships, call in the fleet,” as well as the StrengthsFinder themes we share, including futuristic and activator. It’s a conversation about the importance of sharing our stories. There is someone out there waiting and wondering if they can build their own boat. I say YES!
Her Wisdom Bomb at the close said it all:
“To be truly radical is to make hope possible instead of despair convincing.” — Raymond Williams, a line Janine tries to live by every day.
Highlights
How we stop “starting over” at 50+
Janine names the quiet panic so many women feel after a layoff, merger, or career pivot—and how often they don’t see the wide range of skills and relationships they already have. She talks about what changes when you stop treating midlife as starting from zero and instead build from everything you’ve done.
The anti‑bucket list and saying “no” on purpose
We get into the practical side of boundaries: making a list of what you never want to do again and refusing to design a business that requires those things. Janine shares how that practice, combined with her “weeks left” math, changed how she chooses projects and clients.
Stories from the fleet
Beyond the “AI entrepreneur in a hoodie” moment, Janine shares stories of women across industries—nonprofit leaders, tech and AI founders, consultants—who decided to build their own boats. Listen for how they pull past experience forward, find their pricing courage, and model what’s possible for the woman sitting at her kitchen table wondering “could I do this?”
Janine Says…
“Experience is our edge. The things we’ve done become, in a way, our unfair advantage.”
— Janine Vanderburg
About Janine
A 3x entrepreneur, Janine Vanderburg is a nationally recognized expert on ageism and age inclusion. She is the CEO of Encore Roadmap, which helps professionals turn their experience, insights, and connections into consulting practices and helps companies leverage the benefits of older workers and intergenerational teams. She is the host of Build Your Own Boat, a podcast series featuring the stories and advice of women who have started new entrepreneurial ventures in midlife and beyond.
Janine’s work has earned numerous awards, including the Colorado Women’s Chamber of Commerce’s Top 25 Powerful Women in Business and the American Society on Aging’s 2024 Award for Success in Diminishing Ageism.
Connect with Janine
Janine’s Website: Encore Roadmap
Have a question for Janine? Drop it in the comments — I’ll make sure she sees it. And come back next Wednesday at noon ET, we have interviews booked months in advance. Or catch the replays.
