Natalie Caine has lived through — and grown from — difficult life transitions. While raising her young daughter, for example, she was diagnosed with a life-threatening illness.
But nothing could have prepared the 76-year-old for the loss of her home, and the life she had built over decades, in last year’s California wildfires.
Things had been going well. Years ago, when her daughter went to college, Caine created Empty Nest Support Services. She was a sought-after speaker for corporations and high-end resorts.
Natalie Caine
That led to Life in Transition. At disorienting, lonely times when everything changes — a relationship ends, a diagnosis arrives, a loved one dies, whatever — Caine helps people pause, rediscover who they are, and imagine the possibilities ahead.
When her daughter, living in Stamford, had twins during COVID, new grandmother Caine branched out to help grandparents understand their roles, and deal with “unrealistic expectations.”
Then, in January 2025, came the Pacific Palisades fire.
Caine fled in her car. Passing burnt homes, with ashes falling from the sky, she sang childhood songs to distract herself.
On the Pacific Coast Highway, she realized she could not turn back. But an enormous plume of smoke prevented her from seeing what was ahead. It was a compelling metaphor. “I had nowhere to go,” Caine says.
Eventually, through 90-mile-an-hour winds, she reached Santa Monica. All the hotels were filled.
California wildfires
Her daughter said, “Get on a plane here.” The next morning, Caine flew to Connecticut.
She ended up at the Delamar Southport. “They were so kind,” Caine recalls. “All I had was a bag with essentials. I was so shaken.”
Though it was winter, and she was shaken, she felt the need to be outside. “I asked if they could watch me, to see if I was okay. They watched all over me.”
Caine spent 5 months in hotel rooms. With the help of a great broker, Emily Gordon of Coldwell Banker, she found a rental: an old home in the Coleytown neighborhood.
She had already fallen in love with Westport.
The town is very similar to Palisades, she says. “It’s friendly, artistic, creative and beautiful. The people are so kind. There is open space. It’s easy to get around.”
Caine has no plans to leave Westport. Her house sustained heavy smoke damage. Full remediation is needed.
She transitioned to a new life, 2,500 miles from her old one.
The Newman Poses Preserve is not far from Natalie Caine’s new home. (Photo/Michael Tomashefsky)
The only people Caine knew in the area were her daughter and her wife, in Stamford. They’re busy with their work and kids.
“I’ll find my way,” Caine promised herself. “I’ll build my community.”
She has.
Caine found the Westport Library (“oh my gosh!”), the YMCA (“amazing, and everyone is so nice”), the Senior Center, and Neighbors & Newcomers. She looks forward to her first Levitt Pavilion concert (“an outdoor show 10 minutes from home — this is definitely not L.A.!”). She hopes to give back to her new community, in any way she can.
This past winter was an eye-opener for the former Californian. She was unprepared for everything. But she figured it all out — what road salt is, and where to get it, for instance — and got through it, herself.
She is exploring the area, as far as Mystic and Rhinebeck. As a photographer, she is delighted at the variety of the area. She has learned to appreciate the train to New York City.
Now, Caine has redoubled her efforts to help people going through transitions.
Natalie Caine
She offers “Grandmother Moon” workshops through the Omega Institute. Through LifeinTransition, she mentors, writes, and delivers keynotes for organizations, retreats, wellness centers, conferences and community groups.
She coaches and consults individually with women navigating life transitions like parenting, empty nest, retirement, relocation, divorce, widowhood, caregiving, illness and more.
“Transitions teach you a lot about yourself,” Caine notes. “They can break you open with grief.
“And yet within then, there can also be growth. You find joy. resilience and unexpected strength. Your life expands in ways you’d never imagine.”
The Palisades fire was a curse. It forced her to move all the way across the country, away from her home, friends, community, work and joy.
But it was also a gift. Without it, she never would have lived near her daughter and grandchildren.
Nor would she ever have discovered Westport.
When people go through unexpected changes — and who doesn’t? — Natalie Caine says, “I’m there for them.”
Because others — including in Westport — were there for her, during her biggest transition of all.
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Where Westport meets the world
In our group, quiet voices shared their disappointment that other women were not applauding them for all the personal work they did to be MORE MYSELF. We wrote, we shared, we passed the Kleenex box.
They became aware of over-giving. Giving for approval. The surprise that I asked them to write about, “How is giving a way to control a situation?”
Have you thought about that in your friendships and family? NO judgement.
Take good care,
Natalie
There’s a moment that doesn’t get talked about enough.
The house gets quieter. The rhythm changes. The role you’ve lived inside for years begins to shift. And somewhere in the middle of loving your children and letting them go, a question quietly rises:
Who am I now?
My work is devoted to supporting women through this exact transition, the empty nest not as an ending, but as a powerful doorway into reinvention.
In my groups, we explore what it means to move into this stage with intention and not isolation. We talk honestly about the emotional landscape, grief, relief, disorientation, possibility, and begin to reconnect with parts of ourselves that may have been set aside for years.
This is not about moving on or filling time. It is about coming home to yourself.
Together, we look at:
What I see again and again is when women are given space, language, and community around this life transition, something opens, there is clarity. There is energy. There is a return to self that feels grounding and expansive.
If this speaks to you or someone around you, I would love for you to join us and share this with a friend, a sister, a colleague, or a community that could benefit from this support.
No one needs to travel this passage alone.
New groups will be forming. One of my favorite gatherings over the decade has been friends who offer their home for a light lunch and conversation with their friends who are sitting in the empty nest or on their way to this major life transition. I held it together at her dorm and then wept, leaning into the airplane window, flying 3,000 miles back home. If you would like me to tailor a presentation and Q and A, conversation, just email. One group presentation that I am thinking of now, was lawyers during their lunch time in their office staff room, who said, “I can’t believe I can’t handle this. I cry. I feel unmotivated. What is happening?”
This is a cycle of OPEN DOORS. I have never liked the term. EMPTY NEST.
Take care,
Natalie
I was in one of the happiest moments of my life, being a mother to my 18-month-old daughter. Everything CHANGED.
Illness doesn’t wait for the right time.
It interrupts. It rearranges. It asks more of you than you feel ready to give.
What I didn’t expect was how much it would affect not just my body, but my sense of self.
What No One Tells You
Illness is not only physical.
It brings fear, uncertainty, and a quiet grief for the life you were just living. It can feel disorienting—like you’ve been taken out of your own story.
And healing is not linear.
There are moments of strength, and moments that feel raw and overwhelming. Progress and setbacks. Hope and exhaustion—all existing at once.
What Helped
Not everything helped.
What mattered most was:
I began to understand that wellness isn’t about going back.
It’s about creating a new relationship with yourself.
What Changed
I didn’t come through this the same.
I became more aware, more attuned, and more honest about what matters. Illness has a way of stripping things down to what is essential.
I wouldn’t have chosen that path—but it shaped how I live and how I support others.
Why I Share This
Because so many people are moving through illness quietly, without the support they truly need.
If that’s you:
A Quiet Offering
This experience informs the work I do now—supporting individuals through illness, recovery, and meaningful life transitions.
If you’re navigating your own path back to wellness, or supporting others who are, I’d be glad to connect.
You can reach me directly at natalie@lifeintranstion.org to start a conversation.
Be Gentle With Yourself,
Natalie
You have asked me to speak a little about Life in Transition. I have lived a long list of unexpected changes. Just ask me and I am happy to share. natalie@lifeintransition.org
The space between the shock and the moving forward is where I have learned even more about myself. Last year, evacuating from The Palisades Fires of Los Angeles was terrifying and yes , traumatic.
I didn’t “NEED” it to grow, and yet I did. i have had enough unexpected changes, but you know how life goes… not always a choice.
I am here if you need help on your journey of change.
In my work with individuals, groups, and organizations, I focus on creating environments where people can move through change with greater clarity, connection, and coherence.
This includes:
These are not quick fixes.
They are spaces where people can pause, reflect, and re-orient—so that change becomes something they can engage with, rather than something they simply endure.
Let me know how I can be there for you. Add a comment or email me natalie@lifeintransition.org
Be gentle with yourself,
Natalie
Artemis returning from the Moon feels familiar and hopeful.
A leaving.
A becoming.
A returning.
I keep thinking about grandmothers—the wisdom that travels through us . How we go far out into experience, into discovery, into the unknown… and still, something in us is always called back home.
Maybe that’s what becoming a grandmother is too. Not just a role, but a remembering.. A return to what has always been there beneath everything.
Artemis comes home to Earth, and I think about all of us—women, grandmothers, daughters—moving in these cycles of departure and return. Of carrying light outward and bringing it back transformed.
I would love to have you join me at the Omega Institute, October 2–4, where we’ll be exploring the quiet power of grandmothers, our current stories of joy and challenges and the deeper cycles that shape our lives.
More info + registration: https://www.eomega.org
Natalie
Grandmothers hold a quiet, transformative power — one rooted not in achievement, but in presence. In the sacred sharing of Grandmother Moon circles, stories unfold, wisdom deepens, and women remember the profound influence they carry across generations.
This forthcoming article explores the emotional strength of grandmotherhood, the healing that happens when we gather in circle, and why the moments we share with our grandchildren become our truest legacy.
The full piece will be published this Spring in GRAND Magazine.
Your grandchildren begin to show you who they are becoming — full of ideas, stories, and independence. Your role moves from doing for them to listening to them. From leading the play to following their imagination.
The love doesn’t change — it deepens. You are no longer just holding them; you are witnessing them.
Natalie
I am so excited to invite you to join me at Omega Institute.
You have heard of a BABY MOON. Well, I thought, why not create one for grandmothers? I am a grandmother and have been working with grandparents across the country for years. We have gathered to explore both the joys and challenges of embracing this major life role in the family.
Do you want to know what I hear more than anything from grandparents? “Finally, I don’t feel alone with my story of grandparenting because I have heard yours.”
Whether you are a first-time grandmother or about to add another life to your family, I hope you join us. Go to Omega Institute Website to learn about the weekend of being with other grandmothers, what you will discover, and the takeaways from the weekend.
The workshop is called GRANDMOTHER MOON. https://www.eomega.org/workshops/grandmother-moon .
I am here if you have any questions or thoughts to share with me, natalie@lifeintransition.org
Grandparenting may be one of life’s most unexpected adventures.
I am honored to be at Omega Institute with you.
Reflect, connect, and discover this meaningful chapter in your life.
Natalie Caine, M.A. Life in Transition
It is hard to believe a year ago my neighborhood friends stood outside with me, chatting, “Is it time to pack up and leave? Did anyone get a notice to evacuate? Well, we didn’t wait. We hoped to caravan down the canyon. That didn’t happen. We thought we would be back in two days. We took little.
I drove down the canyon that many of you probably saw on the news. Palm branches falling from fire, burnt cars, and flames from homes. On Pacific Coast Highway, I saw the gigantic plume ahead of me. No cars in front of me. I couldn’t turn back. I had no idea what would be on the other side of the dark grey flames. I sang out loud, “Just a spoonful of sugar helps the medicine go down in a most delightful way.” I am a bit tearful now, remembering what I didn’t choose.
Then it got dark, and I was driving in 80-mile per hour winds. Hotels were booked. I checked into one and sat. The front desk’s lovely woman came over and checked me in.
The next day, I flew to Connecticut. Four different hotels and then four months in what I called my YELLOW ROOM in a friendly hotel. The staff became my new connections.
I found a rental and now live in Westport, CT.
The shock is over. Every day was a to do list to build a foundation in Westport and manage my Palisades home. It stands.
Today I watch a video of the rally in the Palisades, and I think of the song, “I RISE UP” Andra Day.
I didn’t choose the unexpected. It grew me. It changed me. I am grateful for those who showed up for me and gave me shoes and clothes in the winter at Westport and sat with me.
Here I am moving forward. I am more than OK. I have a new adventure and wellness that surprisingly walks with me. Grief, unpredictable. Love, always a choice. Beauty, where I am only asked to pause.
I am more than OK. I live.
I am wondering, what have you unexpectedly lived?
Take good care,
Natalie
PS: My background music as I write this note to you is, “WHAT THE WORLD NEEDS NOW IS LOVE SWEET LOVE.” I choose that song forever.
Slip the memories inside like a card into an envelope.
Thank you, 2025, for my personal growth through the Palisades fires, for the love shared and received, and for the new adventures ahead.
As I step into 2026, living in this East Coast world of stunning beauty with endless roads to explore, may I know when to rise, when to rest, and when to trust life’s journey.
My daily companions remain the same. Adaptation and curiosity.
What about you? Can you believe the year you lived and who you’ve become?
Sometimes I feel tearful from the losses and the world’s heartbreaks.
Life remains a mystery to me. Here we go…. New Beginnings, don’t you love that?
We are here, together
Natalie
The past year has reshaped how I understand transitions, belonging, and resilience.
In 2026, I’m offering new experiences designed to support moments of change, happy and challenging, deepen connections across generations, and creating space for reflection, ritual, and meaning.
New offerings will be announced in 2026. If you would like early invitations and thoughtful updates, you are welcome to join my email list, natalie@lifeintransition.org.
Here we go into new possibilities and building your inner world that never leaves you.
Natalie
Natalie Caine, M.A. natalie@lifeintransition.org
