At age 39, Francesca Montillo had a thriving healthcare career at a prestigious Boston hospital—but her heart was in Italy, dreaming of pasta, wine, and sun-soaked adventures. In this episode, she shares how she slowly and strategically built a food and travel business on the side, eventually trading her secure 9-to-5 for a life she once thought was too good to be true. From pandemic pivots to cultural expectations and midlife realizations, Francesca’s story is a masterclass in following your gut, even when it takes 20 years to listen. If you’ve ever wondered what might be waiting on the other side of “what if,” this conversation is for you.

Guest Bio 

Francesca Montillo grew up in Italy until the age of 11, upon which time she moved to Boston with her family. She spent every summer after the move back in Calabria, enjoying time at the beach, local markets and spending time with childhood friends. It was during her trips back that her love for Italy grew even more intensely. 

Her initial career ambitions were to work in law enforcement and she holds a Bachelor's degree in Criminology and Law. After a short stint in the field, she went on to earn a Masters in Healthcare Management instead. 

After a successful 22+ year career in healthcare management for both private and governmental sectors, Francesca reinvented herself again and took the leap and started her own business, combining her love of Italian travels and cooking. Via her business, Lazy Italian Culinary Adventures, Francesca is able to showcase her native land and its cuisine. Francesca has also written three Amazon bestselling cooking books focusing on Italian dishes.

Turning 40 and turning pasta into a paycheck

Francesca Montillo was living the dream—on paper. With a master’s degree in healthcare administration and a thriving job at a Harvard-affiliated hospital, she had what many would call a “great job.” But deep down, Francesca knew it wasn’t her dream. At 39, just shy of her milestone 40th birthday, she quietly began building a very different life—one steeped in Italian cuisine, rolling Tuscan hills, and the freedom of self-employment. Today, she leads delicious culinary adventures in Italy and has turned her side hustle into a full-blown business and lifestyle. In this episode, Francesca shares how she slowly and strategically transitioned from a traditional career to creating Lazy Italian Culinary Adventures, proving that it's never too late to design a life you love.

Episode Highlights:

• How Francesca’s childhood in Calabria and Boston shaped her love for Italian food and culture.
• The early whispers of entrepreneurship—and why it took nearly 20 years to act on them.
• The delicate balance of building a business while holding down a demanding 9-to-5.
• How COVID nearly derailed her dream—and how she pivoted to Zoom cooking classes and writing cookbooks.
• What finally pushed her to walk away from a safe, successful career in healthcare.
• The cultural tug-of-war between traditional expectations and personal fulfillment.
• Why midlife was the perfect time for Francesca to bet on herself—and what she’d tell others standing at the same crossroads.

This conversation is a reminder that the path to your dream life might not be a straight line—and that’s okay. Francesca’s story shows us the power of patience, planning, and trusting your gut—even if it takes two decades to do something about it. If you’ve ever thought “someday” could be “today,” this is the inspiration you’ve been waiting for.

If you enjoyed this episode, don’t forget to rate, follow, and review The Big Four Oh Podcast. It helps more people find us—and find the courage to make their own big midlife moves.

Guest Resources

Connect with Francesca on Facebook

Connect with Francesca on Instagram 

Get Francesca’s Guide, What to Pack for Italy, on her website! 

Do you have the Midlife Ick? 

Download Stephanie’s guide to the Ick to diagnose whether you or someone you love is suffering from this insidious midlife malaise. www.thebigfouroh.com/ick  

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The Big Four Oh Podcast is produced and presented by Savoir Faire Marketing/Communications