What if everything you’ve done up until this point was actually preparing you for what comes next?
The career. Raising a family. The successes. The failures. The pivots. The years you may have dismissed as “just life.” The skills you picked up along the way. The relationships you’ve built. Even the things that didn’t work out the way you planned.
What if none of it was wasted?
That idea was at the heart of my conversation with Jannette Anderson, founder of Maturepreneur World, a global movement helping women over 55 turn decades of experience into income, purpose, visibility, and impact.
Jannette and I are incredibly aligned on something I wish more women understood: being over 50 doesn’t mean we’re supposed to start winding down.
For many of us, it may be the first time in decades that we have the freedom to ask a very different question:
What do I want?
Not what does my employer want? What do my children need? What does my family expect? What am I supposed to do?
What do I want this next chapter to look like?
And once you start asking that question, the possibilities get really interesting.
Your Experience Didn’t Suddenly Lose Its Value
One of the reasons Jannette created Maturepreneur World was her own experience with ageism.
She was at a networking event when someone asked what she did. As she began answering, the person essentially dismissed her and turned to someone else.
Jannette realized she was experiencing ageism, and she’d had enough. She’d encountered other forms of discrimination throughout her life, and this became “one ism too many.”
That experience helped inspire her current mission of helping mature entrepreneurs become visible, financially viable, and recognized for their value.
During our conversation, Jannette summed up the problem with one word:
Relevance.
There is a perception that what we did and learned decades ago somehow doesn’t apply anymore.
I completely disagree.
Think about what someone in her 50s, 60s, or beyond may bring into a room.
Decades of professional knowledge.
Relationships.
Perspective.
Problem-solving skills.
Leadership experience.
Resilience.
The ability to recognize patterns because we’ve seen them before.
And something AI or a textbook can’t manufacture: lived experience.
Yet too often, businesses look at age as a liability instead of recognizing the extraordinary value sitting right in front of them.
Jannette believes that ageism is one reason entrepreneurship can become such an important option for people later in life. If the traditional workplace doesn’t recognize your value, perhaps it’s time to create a place where you determine it yourself.
Retirement Doesn’t Have to Be the Goal
We also talked about the traditional idea of retirement and how outdated it can feel.
The old model was fairly straightforward: work for decades, reach a certain age, retire, and spend the remaining years relaxing.
But what if you don’t want to stop?
What if work gives you energy?
What if you still have ideas?
What if you need income?
What if you simply can’t imagine spending the next several decades golfing or playing pickleball?
Jannette made a point during our conversation that really puts this stage of life into perspective.
For someone retiring in her late 50s or 60s, there could potentially be decades of life ahead.
Instead of looking at that as a small amount of time remaining, Jannette encourages people to think of it as another entire chapter that deserves to be designed intentionally.
That’s a very different mindset.
The question becomes less about when you’re going to stop working and more about how you want to live.
Maybe you want to continue working full-time.
Maybe you want to consult.
Maybe you want to start a business.
Maybe you want to work six months and travel six months.
Maybe you want to create several income streams.
Maybe you want something completely different from anything you’ve done before.
The beauty is that there isn’t one right answer.
What Do You Actually Want?
This was one of my favorite parts of our conversation because I think it hits so many women right where we are.
Jannette asks people what they want their next chapter to look like, and often they don’t know how to answer.
Why would we?
For decades, so much of our lives has been based around expectations and obligations.
Build the career.
Raise the children.
Pay the bills.
Take care of parents.
Support a spouse.
Meet deadlines.
Keep the household running.
Do what needs to be done.
Then suddenly someone asks, “What do YOU want?”
And we freeze.
Jannette says this can be incredibly confronting because many people haven’t had a stage of life that was purely about answering that question.
So maybe that’s where reinvention begins.
Not with a business plan.
Not with a website.
Not with a new LinkedIn profile.
With a blank sheet of paper and one question:
What do I want my life to look like?
Build the Business Around Your Life
Jannette said something that I absolutely love:
For most of our lives, we’ve built our lifestyles around our careers.
Now we have the opportunity to flip it.
Build the business around the lifestyle you want.
That is such an important distinction.
Before deciding what kind of business to start or what job to pursue, Jannette recommends thinking about the life you actually want.
Do you want to travel?
Where do you want to live?
How much do you want to work?
What relationships matter most?
How do you want to spend your days?
Who do you want to become?
Only then do you start figuring out how your work and income fit into that picture.
For someone who spent 30 years structuring vacations, family time, and personal commitments around an employer’s calendar, that can feel almost revolutionary.
But why shouldn’t we do it?
If we’re creating something new at this stage, why automatically recreate the rules of our old life?
Your Purpose Is Bigger Than Your Job Title
Purpose came up repeatedly in our conversation.
And Jannette makes an important distinction between what you do and why you do it.
Your purpose isn’t necessarily your job.
That’s important because so many of us attach our identity to our roles.
I’m a CEO.
I’m a teacher.
I’m an attorney.
I’m a stay-at-home mom.
I’m an executive.
Then the role changes and suddenly we’re asking, Who am I now?
Jannette describes purpose as an intersection between what we’re healing from our past and what we long to create for ourselves and others in the future. When we understand that deeper why, we can begin aligning our choices, work, relationships, and lifestyle around it.
Your title can change.
Your business can change.
Your circumstances can change.
Your deeper why can continue guiding you through all of it.
Don’t Ask the People Who Still See the Old You
So how do you figure all this out?
One of Jannette’s first recommendations is to get support.
She says our generation has a tendency to be “lone wolves.” We’ve figured things out for ourselves for decades, so we assume we should be able to figure out this transition too.
But Jannette uses a great analogy: when you’re inside the jar, you can’t read the label.
Sometimes we need someone outside our lives who can see possibilities we can’t.
And that person may not be your best friend or even your family.
Why?
Because the people closest to you often see you with what Jannette calls “old eyes.”
They know who you’ve always been.
They may have a harder time imagining who you’re becoming.
That doesn’t mean they don’t love you. But they may be invested in the version of you they know and understand.
A coach, mentor, therapist, or sounding board can sometimes hold space for a future version of you before you’re even able to fully see her yourself.
Entrepreneurship Can Put Your Destiny Back in Your Hands
Jannette’s relationship with entrepreneurship actually began when she was about five years old.
Growing up with poverty, she desperately wanted a copy of Heidi. When her mother told her they couldn’t afford it, young Jannette came up with what seemed like an obvious solution.
She held a garage sale.
Unfortunately, much of what she sold belonged to her mother.
She made exactly $13.72, a number she still remembers.
Her mother was not impressed. Jannette had to return the money and buy back as much of their stuff as possible.
Not exactly a Silicon Valley success story.
But Jannette says that first entrepreneurial adventure taught her something that has stayed with her for more than 60 years:
We can take our destiny into our own hands through entrepreneurship.
That’s a powerful message for someone who has been pushed out of a job or is struggling to find another position because of ageism.
Entrepreneurship gives you another option.
Use AI, But Don’t Discount Your Wisdom
We also talked about one of my favorite tools for figuring out what’s next: AI.
If you’re staring at that blank sheet of paper thinking, I have no idea what I want to do, tools like ChatGPT can be an incredible brainstorming partner.
Tell it what you’ve done professionally.
Tell it what you’re good at.
Tell it what you never want to do again.
Tell it what you’re passionate about.
Describe the lifestyle you want.
Then ask for 20 possibilities for your next chapter.
You don’t have to choose one of them. Maybe one sparks another idea. Maybe you combine three. Maybe it simply helps you see something about yourself differently.
Jannette agrees that AI can be an incredible strategy partner and sounding board, but she also cautions against believing it replaces human support. A human coach may hear what you’re not saying, push you outside your comfort zone, or hold you accountable in ways technology doesn’t.
And she made another point I loved.
AI has knowledge.
What it doesn’t have is your lived experience and your heart.
Jannette describes wisdom as knowledge plus lived experience plus heart.
That’s exactly why I don’t buy the idea that women become less relevant as we get older.
We have something technology can’t replicate.
Wisdom.
You Are Not Too Old for Technology
Another stereotype Jannette wants to eliminate is the idea that older people simply aren’t good with technology.
She pointed out that the generations now being dismissed as technologically irrelevant actually helped create much of the technology the world relies on.
And she shared a fantastic example.
Jannette knows a woman in Calgary who started her first technology business at 69 despite knowing nothing about tech when she began. She built what Jannette described as the largest woman-run data center in North America and, at 89, was starting another technology business.
Eighty-nine.
If that doesn’t challenge our assumptions about what’s possible later in life, I don’t know what will.
You don’t need to know everything before you begin.
You need to be willing to learn.
Jannette Built Her Own Version of Freedom
Jannette isn’t simply teaching people to build a life around what they want.
She’s doing it herself.
At 66, she has been a digital nomad for about 11 years.
She sold her house and virtually everything she owned after realizing she no longer wanted to be tied down by possessions and property.
For the past 18 months, she has also been house- and pet-sitting, allowing her to enjoy animals without the permanent responsibility while eliminating rent and mortgage payments during that period.
She even coined a word for her lifestyle: “polyhomorous.”
But getting there required letting go.
At one point, Jannette looked around her home at plants she loved and became emotional about leaving them.
Then she caught herself.
Was she really going to give up her ideal life because of a ficus?
As funny as that sounds, how often do we do exactly that?
Maybe your “ficus” isn’t a plant.
Maybe it’s a house.
A title.
Someone else’s expectations.
Fear of judgment.
A routine you’ve outgrown.
Jannette’s point isn’t that everyone should sell everything and become a digital nomad.
It’s that we should examine what we’re allowing to own us.
She says changing your lifestyle requires being willing to risk disapproval because when you step outside your comfort zone, it can make other people uncomfortable too.
You Are Not Done
If there is one message I hope you take from my conversation with Jannette, it’s this:
You are not done.
You don’t have to know exactly what comes next today.
You don’t have to launch a business tomorrow.
You don’t need a perfect plan.
But you can start asking questions.
What do I want?
What gives me purpose?
What wisdom have I accumulated?
What could I monetize?
How do I want to spend my days?
What would I try if I weren’t worried about what everyone else thought?
And perhaps the most important:
What do I want the next chapter of my life to look like?
Jannette’s advice is to get support, get clear on your vision and your why, and then take one step.
Not twenty.
One.
At the end of our conversation, she left us with a question that feels like the perfect place to end:
If not now, when are you going to be the difference that only you can be?
We have too much experience, too much wisdom, and too much life ahead of us to play small now.
Listen to my full conversation with Jannette Anderson, founder of Maturepreneur World, on Living Ageless & Bold wherever you get your podcasts.
And then ask yourself:
What do I want now?
Watch her full episode here:
https://www.youtube.com/watch?v=EYDNY7hC-_4
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