I Quit My Corporate Job and Moved to Italy 20 Years Ago—Here's How I Did It

Although Cortney McDermott has found a way to thrive through embracing her inner creative, the journey to sunny success wasn’t without its rainclouds.

Photo: Courtesy of Cortney McDermott.

When I moved to Italy 20 years ago, I did so for love. I had no savings, no lined-up job, and no connections. Skype did not exist, and calls home were really expensive. Plus, I ended up in a tiny medieval town “dimenticato da Dio” (“forgotten by God”) where people spoke in dialect or a bit of broken English. My Italian vocabulary consisted of Ciao! and a passionate Ti amo!, and I lived on a deserted country road under the Dolomites, also known as the Pale Mountains. So… I guess you could say the odds were stacked in favor of me hightailing it back home.

Surely the notions of corporate executive, best-selling author, TEDx speaker, and successful entrepreneur were not painted clearly anywhere on that horizon. But even if the outlook wasn’t always rosy and resources were scarce, all of those creative dreams did come true in that unlikely setting.

Side note: This is not a post about the technical things that you need to know if you want to move to Italy. It’s about how to follow your intuitive hits and create the life and business you want, no matter where you are or what you fear.

Here’s what I can tell you about living creatively (in Italy or wherever you want) …

It’s going to be scary.

Living creatively is akin to the ultimate rollercoaster ride. When you decide to go for it and begin taking those first tentative steps, it’s like buying your ticket and getting in line with a friend… Are we really gonna do this?? (The friend is your own creativity.) As you inch closer to the launch pad, anticipation rises. You might feel light-headed cold sweats or a kind of euphoric jitteriness — that’s your body’s way of preparing you for the wild, crazy, often frightful exhilaration of riding out your creative impulses. And when you’re strapped in and there’s no turning back, that rollercoaster will drop you down and rocket you up — it’ll take you on multiple rounds of free-falling to flying, your insides going every which way as you sort through tears of fright and delight.

When that ride slows down and comes to an end and you wobble your way back to solid ground, the only seemingly-illogical wonder buzzing around in your head and heart will be, “Which one should we ride next?!” 

Let’s dissect all that…

STEP 1: YOU HAVE TO DECIDE

Buying your ticket is the equivalent of making a concrete decision.

So many of us underestimate the simple potency of deciding. When we “decide” we “cut off” the other options, we commit to a single-minded outcome. And one of the ways we can reinforce that commitment is by creating a symbol (our “ticket”).

Before he was a world-famous actor, Jim Carrey wrote himself a check for $10 million in exchange for “acting services rendered.” He dated it and signed it and carried it everywhere until he was presented with that exact opportunity and the amount for the film Dumb & Dumber.

TIME FOR ACTION:

If you’re reading this, you’ve probably already made the decision to honor and pursue your creativity. Now it’s time to create a token of your commitment. You can get as inventive as you want with this; there’s no wrong way to symbolize your dreams. Like Jim Carrey’s check, it can be a visual reminder that stays in your pocket as a constant source of inspiration, or it can be an audio recording that talks and walks you through your dream as often as possible throughout your day, or anything else that is meaningful for you and that speaks to as many of your senses as possible.

STEP 2: GET IN LINE, SWEETHEART

Now that you have your ticket, it’s time to get in line. Lines can be boring, straight-up frustrating, or positively nerve-wracking. You can feel like you’re getting nowhere as you inch forward, or like you’re mazing back and forth in those awful customs queues at the airport. But each step is getting you closer, that’s a promise. And if you lean on your trusty inner creative source, you’ll move much faster through that line. 

Think of this as an active wait.

TIME FOR ACTION:

For our creative impulses to take root and bloom, we have to keep walking toward them. But the steps we take don’t have to be huge. In fact, small and steady is almost always the unsexy side of success. So: what simple action can you take right now to put your creativity to work? Can you carve out 5-10 minutes (first thing in the morning when you’re freshest) to start brainstorming ideas for that travel/beauty/wellness blog you’ve been meaning to start? What other ways can you carve out time every day to honor your creative decisions?

Ask your creativity directly: What steps forward can I take today? Listen for the answers and be ready to take action in small, consistent ways. Magic invariably follows. 

Remember: ONE step at a time, because slow and steady almost invariably wins the race. When I first decided to follow my creative passion for writing, I didn’t up and quit my corporate job. Instead, I used my evenings and any other free moments I could find to start writing. One crossed-out-and-rewritten word after another. Over time, those words added up to multiple posts in some of my favorite publications and an internationally best-selling book. When I finally decided to pursue my entrepreneur-creative side full time, I had enough small actions under my belt to have secured writing and speaking and other client work on the side. And that made me feel as secure as I’d ever been to more fully dedicate myself to my craft.

“If you decide to move to Italy or start a business or write a book or run any other creative experiment, know that it ain’t gonna be easy, that it’s going to be downright hard at times. Honor the not-easiness of it, instead of trying to ignore it (which only makes it bigger and hairier, by the way).”

—Cortney McDermott.

STEP 3: LEAN ON YOUR FRIENDS… & CURSE ALL YOU WANT

As you walk that line and slip into the ride, remember: You’re not in this alone. Even if you don’t have anyone super close who is supporting your creative expression, your loyal inner sidekick, “creativity,” is ever-present and ready for any and all outbursts of momentary despair, delirious laughter, and delicious excitement. Trust in this part of yourself. And know that people you don’t know are also there to encourage and empower you.

(And… feel free to curse all you want)

If you decide to move to Italy or start a business or write a book or run any other creative experiment, know that it ain’t gonna be easy, that it’s going to be downright hard at times. And that you have full permission to curse, cry, dance wildly, or throw any other creativity tantrum you like. Honor the not-easiness of it, instead of trying to ignore it (which only makes it bigger and hairier, by the way).

TIME FOR ACTION:

Whether it’s a close, supportive friend or a mentor or coach, find one to two people you can share this experience with and lean on when the going gets tough. Because it will get tough. If you don’t have the resources to hire a coach or trainer, start with reliable books and online resources to learn and action your insights. Case in point: This past year I reignited my passion for guitar and singer-songwriting using great (and mostly free) online resources. My next (bigger) step is to take a course in Tuscany with “Justin Guitar” (the super cool online teacher I’ve been learning from) — but I tested the waters first to be sure I was committed enough before investing more.

STEP 4: WHEN YOUR DREAM STARTS TO CARRY YOU

Can you really make money doing what you love? Yes. Can you create a thriving business anywhere? Yes. Can you afford to follow your creativity—financially, physically, emotionally? Yes, Yes, Yes.

How do I know? Because I’ve done it.

Will it be easy? No. Will it be scary? As hell. Will you survive? Yes, and you’ll be a stronger and more evolved human as a result.

Only… You have to decide. You’ve gotta get in line. And you have to trust that creative push-pull.

As you continue to invest your energy and effort, your ‘interest’ earns interest; in other words, you gain momentum. And momentum is a powerful force. It’s when your growth starts to become exponential, unstoppable. 

And that’s when your dream starts to carry you—when the “whoosh” gets so loud and so clear and so strong that it upscales you and drops you in front of an even bigger dream, an even greater potentiality of YOU.

TIME FOR ACTION:

Life with creativity is not an all-or-nothing, zero-sum game, so decide what you need to feel safe before doubling down on your commitment to living creatively. You might need to learn more about managing your finances, cracking down on spending and saving (that was one of the things I had to—sometimes painfully). Or you might need another kind of cushion, like a supportive mentor. But don’t let that cushion be an excuse to not start at all. Keep experimenting. Ask for guidance from the Universe, Spirit, the Creative Force in you an all-around you. And then start “testing” your creative impulses in small, consistent ways. Keep it playful. Because living creatively is ultimately about the thrill of becoming who you are.

About the Author

Cortney McDermott is a best-selling author, TEDx speaker, and strategic trainer to corporate executives, business students, and entrepreneurial leaders around the world. Her work has been featured in multiple major media including Success Magazine, Women's Health, Fox News Chicago, MindBodyGreen, Startup Canada, and The Huffington Post. Cortney's debut book, Change Starts Within You: Unlock the Confidence to Lead with Intuition was selected for Inc. Magazine's "26 Favorite Books of High Achievers" and has been described as "'Eat, Pray, Love' meets 'The 4-hour Workweek.'"

Before turning entrepreneur, Cortney served as an executive at Vanity Fair Corporation, vice president at Sustainability Partners, professor of graduate studies for Big Ten US universities, and global associate for the renowned Consortium. (She also moonlighted as a deli waitress, secretary, and everything in-between, as a way to put herself through school and life.) Cortney is a graduate of the London School of Economics and a certified cultural-linguistic mediator. She lives with her family between the United States and Italy.