After Google, Katy Mogal builds Designing Your Life Italy
You can’t think or analyze your way into a meaningful life. You have to design it.
That’s the preface of Designing Your Life, the framework built on specific mindsets and practical steps to help people avoid getting stuck in traditional, rigid planning. Created by Stanford professors Bill Burnett and Dave Evans, Designing Your Life applies innovation principles and design thinking — typically used to invent products and systems — to the challenge of building a fulfilling, meaningful life and career.
Katy Mogal, an American now living in Rome, became a certified Designing Your Life coach to create supportive environments where reflection leads to purposeful change. She’s a seasoned facilitator and coach with over two decades of experience guiding individuals and groups toward meaningful insights and actionable transformation.
Mogal moved from the Bay Area to Rome with her husband, son, and two dogs in 2022 and hasn’t looked back. “It’s been a crazy adventure of adapting to life in a very different environment, making new friends, learning a new language, and helping our son make the transition to high school,” she says in spring 2026. “But overall, it was an extremely positive move.”
When she lived in San Francisco, Mogal lived a typical tech grind lifestyle in a bustling city — busy jobs, tons of activities, always overscheduled. But in Italy she can’t help but slow down. “It’s a different pace of life, with more emphasis on community and connection, and less on productivity and accomplishment,” she says.
Mogal has reduced her cost of living in Italy and co-founded Her Bold Adventure with Barbara Balletta, an Italian travel designer and real estate expert. In partnership with Designing Your Life, Her Bold Adventure is a retreat that gives women a magical space, a proven methodology, and a community of remarkable women to collaborate with.
The Midst: Your vision is to build a movement that supports women in midlife with tools, community and coaching to live the lives they dream of. How did you get here?
Katy Mogal: I’ve lived a pretty adventurous life — and not because I’m a careful planner. I tend to leap before I look. Three times I’ve packed up and moved abroad. In my twenties I took a sabbatical and spent a year traveling across Europe and Asia, including a stint working at Club Med in Thailand. I’ve done the things I dreamed of doing.
What I started noticing in the retreats I run is that women would say things like, “I wish I could find a way to live in Italy” — or start my own business, or make a complete career pivot. And I kept asking myself: Why do some women actually do those things, while others stay stuck?
I’ve always been motivated by helping people uncover the insights that lead to meaningful action. In my tech career, I did that for product design teams at companies like Google. Now I do it for the women I work with — helping them get unstuck, figure out what a more intentional life could actually look like, and then take real steps toward it. That’s what Her Bold Adventure is built around.
You’ve worked with all kinds of groups – from teams at Google to students at California College of the Arts and Stanford Continuing Studies, to entrepreneurs working in social impact. What is your approach to coaching?
My approach starts with creating the “container” — a space where people feel safe enough to say the things they haven’t said out loud yet, even to themselves. I use active listening, powerful questions, and the specific life design tools from the Designing Your Life methodology. But a lot of the real work happens in the group. The other participants become a kind of mirror — they notice things you can’t see from inside your own head.
My background in consumer insights prepared me well for this. Researchers are trained in the art of inquiry, asking the right questions in order to unlock what people really need, underneath what they say they want, in order to develop insights.
The most powerful example of a transformative insight I can share is my own.
I left Google in 2023 not entirely sure what came next. I knew I didn’t want to work full time, and I knew I didn’t want to be back inside a big company — but that was about as far as I’d gotten. When I heard that a Designing Your Life workshop was coming to Italy, it felt like the universe was speaking to me. Off I went to join the workshop in Matera, a magical ancient stone village in the South.
One of the DYL exercises is called the Odysseys. You imagine three potential future lives:
- The path you’re already on
- An alternative if your current assumptions fell away
- A wildcard — a fantasy you’ve quietly held. Then you share them in a small group and get feedback, not on whether the ideas are good, but on where you seem alive and where you seem flat.
At that point, I was convinced my next chapter was becoming a student of Italian. I love languages, and I had this vision of pursuing a master’s in Italian literature. That was my first Odyssey. And the feedback I got was immediate and a little startling: I had no energy for it. When I described it, I sounded deflated. I hadn’t noticed — the idea lived entirely in my head, where no one could reflect it back to me.
What I realized through that exercise was what I actually need from work: tight collaboration, the electricity of a group in motion, facilitation, the moment when something clicks for someone. Language study, as much as I love it, would never give me any of that. That insight is what catalyzed my journey to become a DYL facilitator — and eventually to build Her Bold Adventure.
You’ve written about how “some women in midlife find themselves stuck, knowing they want something different but unable to make the move. Others make bold leaps: changing careers, moving countries, building something entirely new.” You believe that audacity isn’t just a personality trait. It’s also what happens when a woman gets clear on what she wants and finds the courage to go after it. What makes that audacity possible? Why do you think some women are able to make a big change while others struggle to do so?
I’ve been running The Midlife Audacity Project for the last several months to explore exactly this question. It was borne out of curiosity of something I was seeing in my retreats. Some women in midlife were making what I call “bold leaps” while others wanted to, but imagined all kinds of obstacles. I wanted to understand what differentiated these two groups of women.
So far my research partner and I have interviewed 12 women and we’ve seen a few patterns emerging:
1. Nobody leaps alone. All the women we spoke to had a support person — for many, a coach, others a life partner, or a dear friend — who helped them work through what needed to change and held them accountable to follow through.
2. Women who make these big pivots are willing to listen to the signal that something is misaligned and needs to change. They don’t ignore that feeling – they explore it, try to understand it.
3. Bold leapers are natural experimenters. They aren’t afraid of failure — they try things, and when things don’t work out they learn something and try again.
Tell us about your next Designing Your Life Italy retreat, November 1–5, 2026.
Her Bold Adventure grew out of a conversation that had been years in the making. My business partner Barbara is a Roman and we’d been circling the idea of doing something together for a long time. When I got my Designing Your Life certification, we finally had the structure to build around. The question became: what does a DYL retreat look like when it’s fully immersed in Italy?
We spent a lot of time thinking about where. Italy gives you almost too many options — Tuscany, Puglia, the Dolomites. But we kept coming back to Rome. Rome has reinvented itself for 3,000 years. It holds that tension between the ancient and the living in a way that feels almost designed to shake something loose in you. For women at a moment of transition — questioning what comes next, trying to hear themselves think — Rome turns out to be a surprisingly powerful place to do that work.
We hold the retreat on the Aventino, one of Rome’s quieter hills, in a converted monastery that still has that quality of stillness about it. The workshops happen there. Then we take people out into the city — not the tourist Rome, but the neighborhoods and sites that tell the story of human creativity and reinvention across centuries. And yes, the trattorias and the local wine are very much part of the experience.
November 2026 marks our third retreat. Every time, we get to watch women leave with something they didn’t have when they arrived — clarity, direction, and a version of Rome that most visitors never find.
For your Midlife Audacity Project, you are interviewing women who’ve made big pivots in life. Can you share a slice?
One of my favorite stories is my former Google colleague Alana, who for decades had a dream to ride her bike around the world. In her early 50s, she decided that it was time. She spent a couple years getting ready by working with a biking coach, learning how to camp and fix a bike and all the other things you need for a road trip. And then off she went!
Her goal was to make it into the Guinness Book as the oldest woman ever to ride a bike around the world, and she succeeded. One of the things I love about her story is that she insists that she doesn’t see herself as a cyclist — even though she’s probably put more miles on a bike than almost anybody in the world. She’s just really good at figuring things out and managing through the unexpected. Her interview makes me hopeful that any of us can realize our dreams.
What’s the most surprising or exciting thing you’ve learned about yourself lately?
How little I need the trappings of a corporate identity to feel like myself. I spent years at companies like Google where your title does a lot of work. It’s like a badge that signals to the world where you belong, and of course there’s all the great support and perks. I assumed losing that would be harder than it has been.
I really miss the IT support. But building Her Bold Adventure from the ground up has turned out to suit me in ways I didn’t anticipate. I don’t mind figuring out the website, learning how to manage social media, all of it. There’s something satisfying about getting your hands dirty with something that’s entirely yours.
What’s one of the most challenging things you’ve ever done?
The day after I graduated from college, I moved to rural Japan to teach English. I was 21, from California — a windsurfing, taco-eating kid who spoke precious little Japanese. The village I landed in was so remote that most people there had never seen a foreigner. There were no flush toilets. English speakers were essentially nonexistent.
I felt isolated in a way I hadn’t anticipated, and genuinely stupid much of the time — committing faux pas that horrified my neighbors, like wearing the bathroom slippers to take out the trash — and mangling Japanese in ways that probably still haunt my former teachers. But I got through it and it gave me the confidence that I can figure out almost anything if I stay with it long enough. It’s a belief I’ve drawn on ever since, including every time I’ve made another leap I wasn’t entirely prepared for.
More about Her Bold Adventure
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Katy Mogal is a member of The Midst Founder network of entrepreneurial women. Learn more about the community and how to join here. Thinking about starting a business or seeking a community of supportive women to grow? You might like The Midst Mastermind.
