From The Office to Italy: How Francesca Montillo Created Her Dream Career | Ep #185

Have you ever dreamed of leaving your corporate job to follow your creative passion? In this episode of Second Act Success, Shannon Russell sits down with Francesca Montillo, founder of Lazy Italian Culinary Adventures. Francesca shares her incredible journey from a stable career in healthcare management to building a thriving business centered around Italian food, wine, and travel.

Born in Italy and raised in Boston, Francesca always had a love for Italian culture and cuisine. But it wasn’t until she was on the verge of turning 40 that she decided to take the leap and reinvent her career. She started small, running food and wine tours to Italy while working her full-time job, and eventually transitioned to running her business full-time. Along the way, she also became a published cookbook author and embraced the challenges of entrepreneurship.

Join us as Francesca shares her insights on making a career pivot, testing a business idea before going all in, and how she turned her lifelong passion into a fulfilling second act. If you’ve ever considered following your dreams and starting something new, this episode is for you!

Key Takeaways:

✅ Test Before You Leap – Francesca started her business as a side hustle while working full-time to ensure it was viable before making the transition.
✅ Follow Your Passion, But Be Smart About It – Taking calculated risks and planning ahead helped Francesca successfully pivot careers.
✅ Organic Growth is Powerful – She built her business through word-of-mouth, blogging, and social media rather than paid ads.
✅ Never Burn Bridges – Maintaining good relationships in her corporate career allowed her to extend her job when COVID disrupted her plans.
✅ Adapt and Innovate – When travel shut down, Francesca pivoted to Zoom cooking classes and writing cookbooks, keeping her business relevant.
✅ The Best Time to Start is Now – Don’t wait! If you have a dream, take small steps toward making it a reality.

🔗 Connect with Francesca Montillo:
📍 Website: https://www.thelazyitalian.com/
📍 Facebook: https://www.facebook.com/lazyitalian
📍 Instagram: https://www.instagram.com/lazyitalianculinaryadventures

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Transcript

Second Act Success Career Podcast
Season 1 - From The Office to Italy:  How Francesca Montillo Created  Her Dream Career | Ep #185
Episode - #185
Host: Shannon Russell
Guest: Francesca Montillo
Transcription (*created by Descript and may not be perfectly accurate)

Shannon Russell: [00:00:00] Hey my friend. Welcome to another episode of the Second Act Success Career podcast.

On today's show, we are talking all things Italian. Yep.

My guest is Francesca , and she's the founder and owner of the Lazy Italian Culinary Adventure. 

Francesca was born in Italy and moved to Boston when she was 11. She later had a successful career in healthcare management, but on the verge of turning 40, she decided to completely reinvent herself.



Shannon Russell: Now she specializes in all things Italian travels, especially Italy's food and wine. She is also a published cookbook, author and hosts occasional cooking classes, but most importantly, she takes people on trips to Italy to show them Italian life up close. 

I can't wait to bring this conversation to you let's get started.

Shannon Russell: Are you ready to quit your nine to five job and start a business of your own? Well, you're in the right place, my friend. Welcome to the second act success career podcast. I am your [00:01:00] host, Shannon Russell. I am a former television producer turned business owner, career transition coach, and boy mom. My mission is to help you produce your best life.

This podcast will teach you how to get from where you are now to where you want to be and how to build a business that fits your life and lights you up. Let's get started. 






Francesca Montillo, welcome to Second Act Success. 

Francesca Montillo: Thank you so much for having me. I'm excited to be here. 

Speaker: Love your story. I love everything about your background and what you've created.

You were born in Italy and your family moved to Boston where you are now, but let's take it back to the beginning. Where did your career begin? 

Francesca Montillo: as you said, I was born in Italy. We moved to Boston when I was 11. So I did all of my schooling pretty much here in Boston. And my career began in pretty much in health care.

I went to Suffolk University and to and then went on to get a [00:02:00] master's in health care administration. , I fell into that field. It was never really a field I had a strong passion for. I actually majored in criminology. I was going to go to law school and, , that didn't last too long.

And then, , when I was about 20, I was going to school at night , I was like, what am I going to do? I'm not, I don't think I want to go into more debt and go into law school. And being in Boston and having all of the hospitals and the healthcare seemed like a pretty safe.

, venue to go, , it was safe, I wasn't going to be out of work. , so that's really what kind of started my career, was the healthcare field. And you did healthcare management, is that right? So the admin side? I did healthcare management for a number of years. I worked for the government here in Mass.

It's for the state government. After that, I worked for a private company again in healthcare, , helping the disabled and the uninsured obtain disability benefits. So I did that for another good five, six years. And then after that, I went on to work for a Harvard hospital for almost 11 years. That was my [00:03:00] longest tenure was at, a Harvard medical school hospital.

Speaker: Did you enjoy your work? , was it something that you enjoyed throughout all those years? 

Speaker 2: it was safe and secure and it certainly wasn't bad for lack of a better term. My bosses were great. , I had stability. I had good time off, good salary.

You know, it wasn't the job for me. , it wasn't what. I was called to do and somebody else would have loved to be in that role, but it wasn't it. It wasn't me. 

Speaker: So around 40, when you were turning 40, you kind of decided it was time to reinvent yourself.

How did that come about? 

Speaker 2: , so I had always had this idea that I wanted to do food and wine travel to Italy, , because I loved going back to Italy all the time, I loved traveling, I loved returning to my home country, , and people would always ask me all the time, where should I go, what should I eat, what should I eat, you know, and so it was always kind of planning people's itineraries.

, from the time, honestly, I was 20 from my first healthcare job. I was like, I don't want to do healthcare the [00:04:00] rest of my life. And I had had this idea for this business, but we're going back some 25, almost 30 years ago. It's not like it is now where there's a lot more, people doing what I'm doing back then.

It's, you know, it seemed almost far fetched. You want to have a business, basically bringing people to Italy to eat and drink, , So I had had this, this thought since I was 20. And then when I, on the verge of turning 40, things had changed, the internet had gotten much better.

I was, by that point, I was like older and more, a little bit more gutsy to take risk. At 39 on the verge of turning 40 is when I just finally decided to, to start this business , on the side from my day job. 

Speaker: First I want to know, do you still have family back in Italy?


You still have roots there? I 

Speaker 2: do. Yep. Yep. So my, all of my, mom's side and my dad's side, they're all still in Southern Italy in Calabria. 

Speaker: So I'm sure when you're cooking, even here in the States, you're cooking your Italian recipes and you're, you're bringing a lot of Italy here to [00:05:00] Massachusetts.

Speaker 2: Definitely. You know, my father, , never learned English. He was stubborn Italian. , so we always kept our Italian traditions. My mom had actually been raised in, in the U. S. , she went back to Italy and got married. , so she was always, even though she was born in Italy, she was always the more American one, whereas my dad Right.

Never assimilated as much as my mom had. So we always, you know, we talked the Italian at home. We cooked all, most of our meal meals at home. I traveled back with my dad a lot when I was younger. My dad and I always had one foot firmly planted into each country, 

Speaker: right. So it really was always in your, literally in your blood and you were, you know, at this reinvention stage and you decide to start a second act and it's that business that you've always kind of had in the back of your head. Were you kind of at this crossroads of how do I actually start it?

What is my first step? Right. 

Speaker 2: Yeah, so that's exactly where I was. I wanted to be smart about it and not burn any bridges through [00:06:00] health care. I had built a successful 20 plus year career in health care. And I didn't want to burn those bridges. So I said, let me just start on the side. You know, I have time off from my day job.

I can do a few tours a year using my time off. And so that's what I did for 19. , I would just do my tours on the side because a lot of times we like things in theory, but when we actually practice them too, you know, I wanted to make sure that it was something that I was going to like,

I wanted to test the waters to make sure it was something that I was going to actually enjoy because it's one thing to go to Italy with your family and go on quote unquote vacation.

It's another to take other people on their vacation. So, before I made any, career decisions about quitting my full time job. I wanted to test the waters and make sure that business was going to be viable and that I was actually going to enjoy it. , 

Speaker: and that's so brilliant, Francesca, too, because I, I find that a lot of people get excited and they take that leap and then they realize it's not exactly what they [00:07:00] had envisioned. It's always, there's always parts of the business that are, that you weren't anticipating or the non fun parts, 




I find that it's really smart to dabble into it and see. And I think for you, that was a really excellent point that you brought up about it's not going on vacation. Now you're planning someone else's vacation, and there had to have been a lot of pressure in doing that, I bet.

Speaker 2: There is, you know, and still to this day there is. It's not something I take for granted because people are investing their time and their money. I always say you can, we could always make more money, but still, this isn't something cheap, so you don't want to be wasteful with them. And it's also a week of somebody's life.

They're taking out of their job to spend with me. I need to make sure it's worth their while and worth their time. , so it's definitely, you know, it's not the same as going on vacation. That's for sure. Right. Yeah. There's a lot of planning involved. But thankfully, , it is all work that I love now.

Now that I've been doing it for years and I've gotten better at it I've been able to manage my time more [00:08:00] wisely, , still what I thought it would be and I love it. 

Speaker: So what was it like then on your first trip? What were some of the kinks that maybe you had to work out after that?


Tell us how that went. 

Speaker 2: So my first trip, my first few trips actually, I almost felt like a fraud during the entire time because I still had my day job it wasn't something that I like publicly promoted to my clients it wasn't something I hid. If they asked, I was honest about it, but at the same time, I didn't want them to think that this was just my little, you know, paid vacation.

Mm-hmm . I took your money and now I'm gonna go back to my day job. I felt it was very strange and very weird. The very first tour I ran, I think my legs were shaken for the whole week. , just from anxiety and making sure things went well. , one of the things that definitely I had to get better at was pricing For the first tour, I think I paid, I ended up paying for everybody's vacation. 

Speaker: Right. 

Speaker 2: You don't want to price it so high that it turns people away, but at the same time, you don't want to do it [00:09:00] for free and end up, , running trips on a loss. So the, definitely the pricing. Also too, I overpacked too many things during the week because I always said, you know, I want to get their money's worth.

So I want to make sure they do a lot, but at the same time, by the end of the day, folks were just like exhausted. Like, we're done, we're drunk, we're full, we're tired. So I've learned to actually pack a little bit less into the week and built in a little bit more time on their own.

I always say with every trip, I learn something with every trip. 

Speaker: And it's interesting because your business is lazy Italian culinary adventure. Yes. And so you're not just taking them to see the sights of different areas of Italy, , tell me more about the food and wine aspect .

Speaker 2: People always ask me like, where's the lazy come from? Because by the end of the day, they're tired. we do a lot. It's a food and wine focused, of course. It's Italy, so there's going to be art, there's going to be history, , but it's mostly food and wine. So we do cooking classes, wine tastings, olive oil tasting [00:10:00] lessons, hands on experiences.

Depending on where we are, we might go see where the cheese is produced, we might go see where the honey, is produced, balsamic vinegar, wine, you know, all of the food that they meet, all of the producers and the, you know, in Tuscany we go truffle hunting in the woods, with the dog. That's always, a favorite experience for the folks , that join, I think it gives people a whole new level of appreciation for the imported products that we buy here in the U.

S. 


Things are expensive, but once they meet the makers and the producers and they see the work that goes into it, they come back to the U. S. with a greater appreciation for the products 

Speaker: cost. The cost. Yeah. And just the food and the taste and how it's so authentic there compared to our Italian that we might have here in the States.

Speaker 2: Yes. We shall not mention any chain restaurants, but yes, definitely. Not the same thing. 

Speaker: How dare they call themselves Italian. 

Speaker 2: Italian. 

Speaker: So are you actually the [00:11:00] one cooking on the trip itself? Because I know you're also a cook, 

Speaker 2: no, uh, more often than not, no, I work with a local instructor or local chef or a local cook.

Sometimes it's a nonna, you know, a grandmother. Sometimes it's a professional chef. It depends on where we go. But most often not because it's not my kitchens. It's not my equipment. So it would be a bit, uh, too complex to do it that way. 

Speaker: Oh, yeah, absolutely. And so that's an incredible part of your business, but you're also an author.

So tell us about your cookbooks. 

Speaker 2: I have three cookbooks out. So during the time of COVID where we couldn't travel, I try to use that time as wisely as possible. I had already published one cookbook in 2019. And then during COVID, I ended up publishing two more because I had to keep myself busy and relevant During that time is when the cookbooks came out. I did a lot of Zoom cooking classes during that period where we couldn't travel. So, , try to be productive as [00:12:00] possible despite, the inability to apply. 

Speaker: Were you still working at that time? Let's talk about when you actually gave your notice from the healthcare job.

Speaker 2: So at the end of 2019, I had been in business by that point about three years, things were picking up, I was seeing a lot of momentum, so at the end of 2019, , right before the Christmas holidays, I actually gave my notice, I said I'm gonna give it like a three month notice, , just so I could find a replacement, train somebody, and that was in about December 2019 with a plan of leaving that job around March, because I had trips in May.

so that timing did not work out quite well. , in February, my boss, who I had, I had always had a great relationship with and he was very supportive of my business and in February, he came to me and said, , are you still planning on leaving and are you still planning on running your tours in May?

And I'm like, of course I am. That was the plan. They're all sold out. It's exciting. He's like, I don't think you're going to be traveling. He is an emergency medicine doctor and he said there's something coming down [00:13:00] the pipeline, it's going to be bad, you're not traveling and I don't think anybody's going to be traveling.

You may want to rethink that So that's exactly what happened. I didn't end up quitting. I had to cancel all my trips. 

Speaker: Oh, so you extended , Oh, that's really interesting. 

Speaker 2: Yeah. He was, , thankfully, I mean, it was healthcare during a very critical period. So healthcare is what was needed.

We hadn't hired somebody new to replace my position. So that worked out good. So I ended up, Staying. I lucked out for, lack of a better term, I lucked out. So We started working from home right away all of 2020 I worked from home for the hospital.

2021, the same thing. I was, doing my day job and still plugging away on Zoom classes and other cookbooks. And then by, I would say by the middle of 21, I had already sold all of my 22 trips. Even before we were able to. We had the okay to travel. I was worried. Of course I was worried. I was still a small business.

I said, people are not going to want to travel. It was the absolute [00:14:00] opposite. People were dying to travel. They were dying to get out. And, , I said, okay, well, now maybe I can actually quit. So I stopped working at the end of 21 for the hospital completely.

Cut the strings, and 22 was when I took my business full time. 

Speaker: , what a blessing, honestly, that you just happened to be in the healthcare field and have this supportive boss. And it goes back to not burning bridges, right? And how important that is because you wanted to give them time to find someone new and replace you.

And it really, all of that effort worked in your favor. 

Speaker 2: Definitely, and I think that's one of the things I always, I always believe in is never burn any bridges because you never know when you're going to have to cross back on them. Especially when it comes to your career, to family, to whatever.

, I lucked out on a number of instances, and in a way, you know, I hate to say it. I hope that doesn't come off the wrong way, but in a way COVID helped my business because I was able to use that, that time wisely.

, [00:15:00] the cookbooks and out of the cookbooks, I got a lot of travel clients. I got to build my name a little bit more. I kind of needed those two years to, to get to the point where I ended up 

Speaker: being in 22. And there's a lot of people, it's not, I don't think there's any harm in saying that. A lot of people really had their businesses boom, whereas others not so much.

I think it's also fantastic that remote work was a thing during the pandemic.

During the pandemic, and you were able to not only work from home that you were working in health care, but had a job in health care where you could work from home because a lot of people in health care could not, but you were able to do that. And that you also were able to be so productive in building the business and writing these cookbooks.

You really made the most of a really bad situation, 

Speaker 2: right? Well, there was nothing else we could do. Like we couldn't get out of the house. We couldn't travel. We couldn't even meet up with friends. And I think that's why like the zoom cooking classes. I was having zoom cooking classes all the time because [00:16:00] family wanted to meet, but they couldn't meet.

The one way to do that is to cook together we would always have these cooking classes, these cooking parties, and then, like, if it was a private cooking class, what I would do is, I would literally, like, step out, close my screen, and let the family eat together what they had cooked, and let them have, a meal together, I mean, we're talking, like, three years ago, I remember how bad it was during that time.

Sometimes we forget, but. 

Speaker: Well, I'm interested to know how you promoted your business because, you're forming this small business on the side. How were you able to get your name out there and, and book out so quickly as you did? 

Speaker 2: Honestly, I never have paid for any kind of advertising or marketing.

I built the website myself. I didn't want to invest a lot of money into my business because I wasn't sure it was going to be worth it. You were testing it, yeah. I was testing it, yeah. So, you know, I, formed the LLC. Through the state, which was like 500. I built my website for literal 300.

I think my cost when I started was like, a thousand dollars. Um, [00:17:00] so after that, I built a Facebook page, which had a lot of followers. So that helped. I did a lot of blog writing and I still do a lot of weekly blog writing. And I think people find me through the blog. They'll Google for a recipe or some traveling tips and whatnot.

So they'll find me there. , I, , write for a couple of national publications. And they promote my writing, which brings people to my website. luckily they find me somehow, and the cookbooks again, the, the students from the zoom classes, a lot of them turned into travel clients.

So they're, They're finding me somehow. I'm just thankful they are. 

Speaker: Yeah, it sounds like you grew really organically. And now you have all the pieces in place to just keep on scaling. , especially with the three cookbooks. Now I'm sure you can go out and promote those more, whereas during the pandemic.

the pandemic, you weren't even able to go in person and promote your books. 

Speaker 2: No, I did a few cookbook signings. Very few just for like the chamber of commerce, the local library and now I'm where I'm trying [00:18:00] to work on a fourth cookbook, hopefully maybe this year or next.


Speaker: Well, give us the names of the cookbooks.

I'm so curious. 

Speaker 2: Sure, so they're all on Amazon and some local cookbook, , shops will have them. They're the fi the first one's the 5 ingredient Italian cookbook. The second one is Pasta in a Pinch, so it's all a pasta, cookbook. And , 30 minute Italian, so they're all recipes , that take just 30 minutes from start to finish.

I always wanted to publish, , recipes that folks could replicate at home. They weren't going to be too intimidated to follow like a four hour recipe or a recipe with extensive ingredient list. , it's one thing to teach something, but if you don't actually put that to practice ever, then what's the point, you 

Speaker: know?

Very true. And I love that there, that you can have a somewhat authentic Italian meal in 30 minutes and, and have these wonderful pasta recipes. That sounds delicious. 

Speaker 2: You can. You definitely can. And also, too, like, you know, The word authentic when it comes to Italian cooking, too, can be so, , people get [00:19:00] very, , what's the word I'm looking for?

They get very selective about it because, like, this isn't authentic. This is not authentic. You know, I always tell people, there are very few Italian recipes that are strictly 100 percent authentic that you can't mess around with, you know? Bolognese sauce, the pasta dishes from Rome, the carbonara and all that.

, but I always say no, it's Italian ish, you know. Yes! You know, you work with what you have here in the U. S., you're not going to find guanciale, which is pork cheek, which is the authentic ingredient in carbonara. Okay, well. I'm not going to go to Wagmans and ask for pork cheek, you know, we have to work with what we have here.

And your next option is to book a trip and have the actually come and have the actual authentic dish with me in Italy. 

Speaker: Sounds so delicious. I'm super hungry now. But I'd love to ask you my five fast questions that I ask all of my guests. Yes. 

All right, it's time for our five fast Q's of the week. Here we [00:20:00] go.

Speaker: So the first one is name one thing that these different chapters in your life have taught you 

Speaker 2: resilience.

Especially through the COVID and, all that just resilience and get knocked out, you just have to pick yourself back up. 

Speaker: And I think that with you, the idea that you had this brewing since you were 20 years old and you found it again, 20 years later and built this business, there's a lot of resilience in there too.

And just kind of sticking with that, that dream that you have when you're younger and how it really can come to fruition. 

Speaker 2: And definitely, you know, it was always in the back burner and you try to do the, what society tells you, you should do, you know, you go to college, you get the corporate job, you work your way up.

, but if you have this little inclination in the back of your mind, it's kind of hard to shut it up, you know, to turn it off. 

Speaker: And you don't want to, I always urge people, listen to that little voice, right? At least try it like you did and [00:21:00] you tested it in a safe way and you knew it was working.

So it's a little 

Speaker 2: voice until it screams and then you feel like you have no choice but listening to it. And that's what I was like around my 40th birthday, it was no longer like a little voice, it was like screaming at me saying, you got to try this. And if you fail, big deal, you'll go back to health care.

Mm hmm. Wow. 

Speaker: Very resilient. So would you recommend taking a leap into a big life change to your best friend? 

Speaker 2: I would definitely recommend it, but I would recommend it to do it wisely. Mm. You know, don't, just go off and, , quit your day job, give a two week notice and say, I'm gonna start, being a tattoo artist or a tour leader.

Do it wisely. 

Speaker: What is one piece of advice that you would give to someone who's about to start their second act? 

Speaker 2: Do it right away. Because you don't want it to be your third act. You're never going to be as young as you are today. , so, do it right away. 


Speaker: You've done so many things in your career up until this [00:22:00] point. You're building your business. You're writing cookbooks. What does your next act look like if there is one? I 

Speaker 2: don't know, you know, honestly, I'd be happy if it's more of the same. Yeah, I'm okay with that 

Speaker: way myself, yeah.

Speaker 2: More of the same is more than fine with me, maybe add a tour or two right now I do between six and eight, maybe go up to like ten. Add a new region or whatnot, but more of the same and I'm more than okay with that. It's a beautiful life. Where can our audience connect with you? I am, , thelazyitalian.

com is my website. I'm also on Facebook. , I tend to hang out on Facebook more than Instagram. I'm trying to be more present on Instagram. But I'm also on Instagram and Facebook, but, honestly, the website. Send me an email and connect 

Speaker: yeah. And your, your blogs with recipe ideas and about your travel sound amazing.

Speaker 2: yeah, I like to send out the weekly blogs, , I started doing it about a year and a half ago because I hated to just send email saying, Hey, I have a new tour coming up. , buy a tour. This is what I'm selling. I [00:23:00] felt it was very inauthentic. It's time consuming because you're writing new material every week.

, but every week there's something that goes out, either some travel tips, recipes, information about a particular city in Italy. And I get so much great feedback from people saying, Hey, , don't stop this. We really love the weekly newsletter. If anybody's just looking for free advice or free tips, definitely sign up for that on the website.

Speaker: Sounds great. I have to ask you before we wrap up, what is your favorite city in Italy to visit? 

Speaker 2: I never like to say, 

Speaker: honestly. 

Speaker 2: because I don't want to sway people to say I have to go there because she said it's her favorite.

The beauty of Italy, it's that it's so different, each region is different. It's completely different. You could come on all of my trips, and you would never see the same thing twice, because wherever we go and you go, it's different from the next. 

Speaker: Then let me ask you, where were you born?

What city? 

Speaker 2: I was born in Catanzaro in Calabria. Okay. Calabria. Calabria is probably one of Italy's most [00:24:00] least discovered regions. There's not an awful lot of tourism there. , so I try to do a, a tour there every year just to have something for people, especially frequent travelers who've already been everywhere else before.

Now they're looking for something different. 

Speaker: is my favorite. I feel like it looks like a movie set, right? It's just so beautiful that it doesn't look real. 

Speaker 2: Yeah. I remember the first time I went to Venice many years ago, you get out of the train and you're like, it really is a city on water.

Like, how can, how can this be? It sees so much tourism that hopefully it'll still be there years from now. I know, seriously. It is a beautiful city. 

Speaker: Well, Francesca, thank you for taking the time to tell us your second act success story and all of the wonderful things you're building with your business.

It's very, very inspiring and I just love hearing all about it. 

Speaker 2: Thank 

Speaker: you 

Speaker 2: so 

Speaker: much 

Speaker 2: for having me, Shannon. It's been great. Thank you. 

Thank you for joining us. I hope you found some gems of inspiration [00:25:00] and some takeaways to help you on your path to Second Act success. To view show notes from this episode, visit secondactsuccess. co. Before you go, don't forget to subscribe to the podcast so you don't miss a single episode. Reviews only take a few moments and they really do mean so much.

Thank you again for listening. I'm Shannon Russell and this is Second Act Success.