I sipped tentatively from the miniature steaming cup of espresso, while the sleek office surroundings and an expansive, bird’s-eye view of downtown Chicago made me feel smaller than the delicate saucer I gripped tightly in my other hand. But then Karen smiled, and the intimidation I’d initially felt upon entering one of the towering black skyscrapers, collecting a badge from security, and zipping up an express elevator to the modest headquarters offices of The International Kitchen dissipated with the jolt of caffeine.

That foggy day in downtown Chicago

“You know, espresso actually has less caffeine than a regular cup of coffee,” Karen informed me. Her office was comfortable, and I could tell her small team was a tightly knit group — exceedingly friendly and down-to-earth. “You’ll probably be drinking a lot of those when you head to Italy!” she said. I laughed, still a bit enthralled with the fact that I was sitting face-to-face with Karen Herbst, Founder and President of The International Kitchen, the very tour company that kicked off this fast-approaching trip to Italy by inviting me to write about their Women Only Week on the Amalfi Coast.

In fact, the company was recently featured on NBC Extra’s Mansions and Millionaires! Though you definitely don’t have to be a millionaire to enjoy one of their culinary vacations.

Feeling very much the chic, sophisticated city dweller I must have been in another life, I’d ditched Justin, my dad, his wife, and my sister Kelly far uptown after our several hour Gold Coast food tour and used my sister’s Uber account to hitch a ride downtown to Karen’s office. Knowing they were headquartered in Chicago, I’d emailed Karen to see if she might want to meet while I was there, and she graciously accepted. And from that point on, I felt like I might throw up. I mean, what if we met and she decided she didn’t like me, after all? Not to mention the intimidation factor. Her first two careers were as a research editor for Playboy magazine and a director/producer for five talk shows at CBS Radio. With all of the mental build-up, I’d expected an ultra-sophisticated, commandeering, sharp-witted, deft, deliberate and maybe a little scary business woman a la Meryl Streep in The Devil Wears Prada.

Which she pretty much was.

What I didn’t expect, however, was to be completely blown away by her vibrancy, generosity, and thrillingly uninhibited passion for travel. And while her keen mind for business and no-nonsense ambition is certainly prevalent (and necessary to do what she does), she wasn’t scary at all.

We talked for over an hour about the business she’s built from the ground-up, trips she’s taken with her sons and their wives, and her love of authentic food and immersion travel. It turns out cooking wasn’t a skill that came naturally to her (umm… I can relate to that), but the interest developed out of necessity when she left her fast-paced career to raise her three sons, each born only one year apart. (Okay. I cannot relate to that.)

When I left our meeting, I was enamored. Karen has somehow managed to pull off three lives, while most of us struggle to get it together for just one. As I headed down the elevator with a boost of inspiration I haven’t felt in years, the thing that stuck with me the most was that she referred to her company as her “Act III.” Her first act, she’d explained, was her early career as an editor and producer. Her second act was being a stay-at-home mother. And her third, of course, was building one of the world’s first tour companies specializing in international culinary vacations.

The longer I live, the more I struggle to strike a balance between home life and pursuing my passion. But what Karen has proven is that you can be domestic without becoming domesticated. Complacency is an excuse used by those afraid to fail. Curious about what advice she might have for those of us looking for ways to achieve things others might deem “silly” or “frivolous,” and especially her advice for those who might feel it’s too late to make change, I called her up and asked her a few questions. Her responses are insightful, inspiring, and maybe exactly the right kind of motivational kick to the derrière. After all, if Shakespeare was right and “all the world’s a stage,” why are we so afraid to start another act?

Q: You initially left the workforce to raise your 3 sons. What inspired you to join the travel industry once they were all in school?

A: When you’ve been out of the workforce for a while and decide to enter back, there aren’t many choices available. At the time, most suburban moms went into real estate or travel because you could work your own hours and remain accessible to your kids. I’ve always had a tremendous wanderlust. I’d planned to move to Europe but never had enough money to do it, so choosing travel over real estate was an easy decision. It’s always interesting because there’s so much to learn. The problem with being a travel agent, though, is that you’re expected to know everything about every place, which is why I eventually focused on developing a regional expertise in Italy and France. I started incorporating cooking classes into client itineraries around 24 years ago, and even back then I knew it could serve as a stand-alone trip. And when clients returned home raving about the cooking aspect of their trips, I knew I was on to something big.

Truffle hunting in Italy.

Q: Many people — stay-at-home mothers in particular — find the idea of launching a new career daunting after being out of the workforce for several years. What kind of challenges did you face when starting from scratch, and what advice would you give to those considering doing the same?

A: It was challenging because I was entering an area I knew nothing about but had an interest in. But what I didn’t realize is that when I was a stay-at-home mom, I was doing things that honed business skills — managing hockey and baseball teams required setting up schedules, dealing with unexpected setbacks like cancelled rinks, and juggling various people. So my best advice is to keep those skills sharp, stay active, and don’t be intimidated or minimize what it takes to manage a family, time, and budget.

It’s a tremendous challenge and an important job. What more important job in the world is there?

“I was a very career-oriented person until I had a child and realized that I wanted to be the one to screw them up — I didn’t want anyone else to do it.”

When you financially have a choice, the hard choice is to stay at home. If you’re bored, then you’re not paying attention to your children because they’re very interesting little beings. I mean, no one ever said “I regret spending too much time with family.”

Q: You refer to The International Kitchen as your Act III. Starting a business is intimidating in itself, let alone later in life, after an Act 1 and Act II. What inspired you to do it?

A: Society idolizes youth, but that doesn’t mean you have to give into that. If there are things you want to accomplish, there’s plenty you can do — and it doesn’t even have to mean starting a business. There’s volunteering — surrogate grandparenting for children who don’t have any, for example — plenty of options at any age. The most important lesson I learned was to follow my instincts about people and business. I’ve done unconventional things. My first employee brought her baby to work because she couldn’t afford childcare. Just because something is usually done one way doesn’t mean it always has to be that way.

“I don’t believe in precedents.”

Don’t let yourself get boxed in by conventional thought and the way things have “always” been done. You can try something new and if it doesn’t work, so what? You tried it. We don’t have enough of a culture of failure in this country. We have a negative attitude towards failure, which is a shame, because it deters people from trying again.

Finding a fresh catch at the Catania fish market in Sicily.

Q: If you could change anything about your un-domesticated lifestyle, what would it be?

A: I would’ve liked to have had a partner in my business, but there was no one appropriate at the time. I did a lot of solo travel, and it would have been nice to have a trusted travel partner, which would have made the work even more enjoyable.

Q: I bet a lot of people call you “lucky” that you get to do what you do for a living. What’s your response?

A: My late husband’s answer always was, “The harder you work, the ‘luckier’ you get.” And that’s absolutely true. Through hard work, you create your own luck.

*This interview is not coverage I agreed to provide of my trip. I think Karen is a fascinating woman with incredible insight and advice, and I’d be selfish not to share. What do you think about her outlook on life and business?