There’s something about the end of the year that invites reflection. We look back at what worked, what didn’t, what surprised us, and what we’re quietly proud of surviving. But as the calendar flips and we head into a brand-new year, I want to offer a different invitation:
Let’s laugh ourselves into the New Year.
Not the polite, social-media-approved chuckle. I mean the deep, unexpected, maybe-snorted laugh that reminds you that you’re alive, resilient, and still very much in the game.
That’s exactly the energy of my recent conversation on Living Ageless and Bold with Carole Montgomery — a woman who didn’t just make people laugh for more than four decades, but proved that humor, confidence, and creative power don’t diminish with age. They sharpen.
Why Laughter Matters More Than Ever Right Now
We are living in heavy times. The news cycle is relentless. Expectations are high. And somewhere along the way, many women were taught that maturity meant being quieter, more serious, and less visible.
But laughter has always been a form of rebellion.
It disrupts tension. It releases pressure. It reminds us that even in hard seasons, joy is still accessible. And for women — especially women in midlife and beyond — laughter becomes a declaration: I’m still here, and I’m not done.
Carole understands this deeply. Not just as a comedian, but as a woman who has lived enough life to know that humor isn’t a distraction from reality — it’s how many of us survive it.
Meet Carole Montgomery: Funny, Fearless, and Unapologetically Herself
Carole Montgomery has been doing stand-up comedy for more than 40 years. She started at a time when women were rarely welcomed on comedy stages, often being the only woman in the room and routinely underestimated.
Early in her career, she got paid five dollars a night, took long subway rides home at two in the morning, and performed for audiences who didn’t always want to see a woman holding the microphone.
And yet, she stayed.
She kept showing up. She kept honing her craft. She kept telling the truth — even when it was uncomfortable, even when it challenged norms, and even when the industry quietly suggested she should step aside.
Instead, she stepped forward.
The Birth of Funny Women of a Certain Age
As Carole moved through her forties and fifties, she began noticing something unsettling. Women over a certain age — women who were talented, experienced, and successful — were becoming invisible in comedy and entertainment.
Hollywood had an unspoken rule: once women hit 40, opportunities dried up.
Carole didn’t buy into that narrative.
What she did see was an entire generation of women with incredible stories, impeccable timing, and sharp perspectives forged by decades of real-life experience. These women weren’t past their prime. They were just getting started.
That realization sparked an idea.
Funny Women of a Certain Age began as a live comedy show, rotating veteran female comics through performances that showcased wit, honesty, and fearlessness. It quickly gained traction, building a loyal following and proving something powerful: audiences were hungry for these voices.
Eventually, the show made its way to Showtime.
And not quietly.
Shattering Records — Not Expectations
When Funny Women of a Certain Age aired on Showtime, it didn’t just perform well. It shattered records.
It became the highest-rated stand-up comedy special in Showtime’s history.
Let that land for a moment.
A show built around women over 50 — a demographic often dismissed by mainstream media — became the network’s biggest comedy success.
Carole was nearly 60 when it happened.
This wasn’t a comeback story. It was a redefinition story.
Why Women Get Funnier With Age
One of the most refreshing parts of my conversation with Carole was her perspective on why women get better — not worse — with time.
As younger women, many of us are taught to be perfect. To be agreeable. To be palatable. To worry about how we look, how we’re perceived, and whether we’re doing things “right.”
Midlife changes that.
With age comes freedom. Freedom from people-pleasing. Freedom from unrealistic expectations. Freedom from needing approval.
That freedom fuels comedy.
Women over 50 aren’t trying to impress. They’re telling the truth. And truth, delivered with confidence, is funny.
The Confidence That Comes From Not Caring Anymore
Carole talks openly about the shift that happens when women stop caring what everyone thinks.
It’s not that we stop caring altogether. It’s that we start caring about the right things.
We care about authenticity. We care about connection. We care about saying what needs to be said — even if it’s messy, even if it’s imperfect.
That confidence doesn’t come from youth. It comes from experience.
And once you have it, it’s incredibly powerful.
Comedy as Legacy
What’s fascinating about Carole’s journey is that she had already built a successful career long before Funny Women of a Certain Age.
She had headlined shows. Worked in Las Vegas. Toured internationally, including military tours overseas. Built a life in comedy.
And yet, this project — the one she created later in life — became her legacy.
It’s a reminder that our most meaningful work doesn’t always come early.
Sometimes it comes after we’ve lived enough to know exactly what we want to say.
Laughing as an Act of Courage
There is courage in humor.
Comedy requires vulnerability. It requires honesty. It requires the willingness to be seen.
For women who have spent decades being told to shrink, soften, or step aside, laughter becomes a bold act.
It says: I’m not invisible. I’m not done. And I still have something to say.
What This Means for the New Year Ahead
As we step into a new year, many people are making resolutions about productivity, discipline, and self-improvement.
Those things have their place.
But what if we also committed to laughter?
What if we allowed ourselves to take life a little less seriously — not because it doesn’t matter, but because we do?
What if we embraced humor as a tool for resilience, connection, and reinvention?
Reinvention Doesn’t Have an Expiration Date
Carole Montgomery’s story is a powerful reminder that reinvention isn’t reserved for the young.
You don’t age out of creativity.
You don’t age out of relevance.
And you certainly don’t age out of joy.
In fact, many women don’t come into their full power until later — when experience meets confidence and freedom replaces fear.
Laughter as a Bridge Between Generations
One of the most surprising things Carole shared is how younger audiences respond to her comedy.
They don’t see an “older woman.”
They see someone who’s funny, real, and confident.
Laughter bridges generational gaps. It creates connection where assumptions once lived.
And it reminds us that humor is universal.
Permission to Be Imperfect
If there’s one takeaway from this conversation, it’s this:
Imperfection is not a flaw. It’s the point.
The stories that resonate most aren’t polished or rehearsed. They’re honest.
They’re the moments we once thought were embarrassing but now realize are hilarious.
They’re the experiences that shaped us.
Laughing Our Way Forward
As we move into the New Year, I hope you give yourself permission to laugh more.
Laugh at the unexpected.
Laugh at the things that didn’t go according to plan.
Laugh at yourself — kindly.
Because laughter doesn’t mean you’re not serious about your life.
It means you’re wise enough to enjoy it.
Women of a Certain Age…
Carole Montgomery didn’t just build a comedy special. She built a statement.
A statement that women don’t fade with age.
They get bolder.
They get sharper.
And yes — they get funnier.
So here’s my invitation as we step into a new year:
Let’s laugh ourselves forward.
Not because everything is perfect.
But because we’ve earned the right to find joy anyway.
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