The GPS was not making any sense and the over­sized map was now a crumpled ball of frustration on the back seat of the rental car. We were lost. My hus­band was grumpy and I was frazzled. Hans made another turn and we bumped our way down another white gravel Tuscan lane that glared back at us in the midday sun. We were trying to find our way to a small, rural bed and breakfast where we would spend a few rare days alone together.

Around the next corner, a stooped old man was ambling along minding his own business. We stopped, I jumped out, unravelled the map and showed him the place we were desperate to find. His face lit up and to our astonishment he climbed right into the back of the car. “Avanti,” he shouted, thrusting his walking stick between the seats, and we set off, following his emphatic instructions.

Ten minutes later, we found ourselves in a rustic farm kitchen surrounded by the old man and his family. The table was piled with steaming dishes of delicious food and jugs of red wine, and children were everywhere. Amongst the Italian chatter, of which we understood little, a young woman introduced herself in English. “I am Marissa and this is my family and our farm,” she said. “I am sorry but my grandfather loves to pick up strangers, especially at lunchtime. Please stay for pranzo. He would like that.”

And so we stayed for pranzo (Italian for lunch). Before the meal ended, a gaggle of neighbours dropped by. Some of them joined us for coffee, and some made a feast of the leftovers. I wondered aloud to my husband if we had fallen upon a celebration of some sort. Marissa overheard me and told me that no, this was normal, it was always like this—Italians were a sociable people. That I did not doubt. I also thought that their sociability must be really good for them: the crowd looked happy, healthy and madly alive—including the five animated octogenarians among us.

Three hours later we were back in the car with clear instructions on how to find our B & B. As we drove away, we could not stop grinning. What had just hap­pened? That gathering had all the noise and energy of the parties I used to go to in my twenties. No wonder the Italians needed an afternoon siesta.

Two weeks later, I was back at work. The board­room at the television network always smelled of stale coffee. As the discussions droned on, my mind wan­dered back to that farmhouse kitchen. Everything about the experience had excited me. The family’s kindness and generosity had been overwhelming. They had wel­comed us, fed us and sent us on our way with arms full of their homemade goodies. They hadn’t been rushing anywhere. They hadn’t said, No, I can’t, I’m too busy. On the plane back from Thailand, I’d realized that I really did need to change my life. No more driving myself into the ground. I needed time to reconnect with my hus­band, my family and friends in a serious and sustained way. Now this simple Italian experience lit up in my head like a beacon.

Was Italy where I’d find my next chapter?

The spooky thing was that as soon as I’d admitted to my daily turmoil of discontent, I saw similar signs of dis­tress and longing everywhere. It’s like after you buy a new car—suddenly you notice the same model all over the place. “Look, he’s got one just like me, only in red. Hmnn, I like it in red.”

I was like a moth to the flame of change, drawn to stories of how others had transformed their lives after hitting adversity or burn-out or just plain boredom. Each was like a spur, prodding me on.
 
At my retreats I have now met hundreds of people of a variety of ages and from all walks of life whose heads are in a similar place as mine used to be when they arrive for a week at my villa.

Some are about to become empty nesters; their sadness is palpable. I remember the way one single mother put it: “I have a year left before my last one leaves home and the loneliness is already too much. I know it’s dramatic, but it’s like I have a black hole growing in my heart. My daughters have been my entire life for eighteen years. I am intensely happy for their futures but I cry for myself.”

Many have reached the point where they are just bone-tired with the daily commute and the same old routine. They are fed up with a work culture where being overloaded is the norm and being way too busy is the measure of success. Committing to a week in which they are able to step out of those roles lets one little question come to the surface: “What about me?”

Then there are those who have climbed the employ­ment ladder successfully, but now that they are perched at the top, they have begun to sway. “I was happy during the climb but the summit has left me wanting some­thing different. What do I do now?” Or “I’m at the top of my profession but each day has begun to feel like a car­bon copy of the day before.” There is nothing more deadening to the spirit than feeling like you have noth­ing left to learn.

Men are not immune to these same regrets and questions about whether what they’re doing has any meaning, either. My brother is only forty-seven, hand­some, lively and always young to me. He was the CEO of a major ad agency in New York but, around his office, he was known as the “old man.” He found it disconcerting when his young colleagues assumed they needed to explain a business concept to him. “It’s as if experience today means nothing,” he told me. “It just got tiring.” (He quit: more about that later.)

Life can be a series of blind curves, but there can be even wilder turns as we get older. I have heard the stories of women, unexpectedly and prematurely widowed, whose melancholy wraps them in a blanket of fear for their future. I also can’t count the number of women at the retreats who are dealing with the end of their marriage. One of them told me, “After the anger and tears I feel dead inside, dull and old.” This past summer I heard the cruellest story from one of our guests. “I woke up one morning next to my husband of twenty-eight years and he was staring at me,” she said. “Then he announced that I was past my expiry date and walked out for good.” I will never forget the way all the women in the group gasped in horrified sympathy when she said this.

So many women are troubled by less dramatic issues: lives that are full of obligation but lack joy. As one announced, after several glasses of Prosecco, “I feel like the passion for life I once had has gradually dripped away, like water from a leaky faucet. I try to tell myself that I don’t care, but I do care.”
 
Sometimes what troubles them is as simple as this: “I’m bored—bored with my life.” With so many wonders in the world, I think we are almost obliged to live every day as if it’s our last. But many people feel so trapped they’ve forgotten how to be amazed by life.

Our guests come to the Tuscan retreat to have a glorious adventure. But many, under the influence of the time they spend together, have felt comfortable enough and bold enough to admit that their life feels like it has come to a screeching halt. Where did all the excitement go? They spent decades with one main purpose in their lives—raising their children. This role has defined them. Now that those children have moved on, they’re left alone to face oversized question marks. Who am I when I don’t have to be a mother every moment of every day? What do I do now? Often these questions spark fear and despair. Not to mention guilt, a mother’s default setting. Trying to shake off that reaction was the subject of my last book, Not Guilty, a memoir on the (often really funny) chaos of being a working mother.

When I was on a publicity tour for that book several years ago, I had begun a speech on a small platform in a bookstore in front of about two hundred people. In the front row, I noticed a mother with twins who were fast asleep in a double stroller next to her.

No more than five minutes into a talk about mater­nal guilt that I thought was quite light and humorous, I heard crying. I glanced at the twins, but it was neither one of them—it was their mom. I tried to carry on, but her wails only became louder and finally I had to stop and ask her what was wrong. She managed to pull herself together enough to say that she, the mother of ten-month-old twins, had a terrible secret.

Oh no, I thought, what is coming next?
“Sometimes,” and here she started to cry even harder, “sometimes I like one better than the other!”

Before I could react, a smartly dressed elderly lady stood up at the back of the crowd and announced with a wide grin that she had seven children and most of the time she didn’t like any of them. The audience roared with laughter, including the young mom, who must have felt her guilt dissipate in an instant. I carried on with my talk, but I thought about this mother afterwards—and I’ve thought of her often in the years since.

Sometimes all it takes to get over that next hurdle is to understand that it’s normal to have these feelings, that everyone has such moments. We are not alone. This is something all the women who come to my retreats realize as they sit around a fire, wrapped in wool blan­kets under a starlit Tuscan sky, while the strangers around them spill out their hearts. Soon they find themselves sharing their own hearts too.

Instead of a Tuscan night around a fire, I hope in this book to offer you something almost as good! Also, over the years I have devised a list of questions for my guests to help them find the answers they seek. They don’t do this in public, and there’s no obligation on them to share their answers. But many of them have told me that facing these questions later, alone in their room, is a crucial first step to waking themselves up and remembering that life only runs one way.

So here are my questions. Grab a coffee or a glass of wine and find a quiet place away from other peo­ple . . . and away from your phone. I know it’s hard, but try to be in the moment. Remember what happened to me in that Thai sauna and be prepared for anything. Intense, personal scrutiny can inspire a sense of rev­erence and possibility, but it can also spark fear and sadness. Being honest with yourself almost always produces startling results.