Chapter Six: What Six Years of Entrepreneurship Taught Me

Six years ago, I built a boutique travel agency around one belief:

The best trips aren’t simply places you visit.
They’re experiences you feel and carry with you long after your return home.

As I reflect on the bespoke vacations we’ve curated at Conversational Traveler, such as milestone birthdays, “we finally did it” bucket-list (wish list) journeys, and the kind of luxury that actually restores you, I’m reminded of three lessons that still shape how I lead.

Lesson 1: Loving what you do doesn’t make it easy; it makes it worth it.

I didn’t wake up one day and randomly launch a luxury boutique travel agency. I was the unofficial vacation planner for friends and colleagues for nearly a decade. Some of you may recall that I loved pairing beautiful hotels with local experiences and the thoughtful details that make travel feel effortless.  I’m happiest when travel feels personal:

• the right accommodations that match your travel style (because comfort matters)
• the right pacing (because relaxation is the point)
• the “How did you even find this?” moments that turn a trip into an indelible story

And somewhere along the way, I learned something that changed me: more than one passion can coexist.

Lesson 2: Resilience is a choice.

A few months after I launched Conversational Traveler, the world changed. Momentum turned into cancellations, uncertainty, and an industry-wide pause that tested everything.  Family and friends told me that it might be time to walk away.  A pandemic was not one of the difficulties I anticipated.

Instead, I leaned into the unknown (and it felt like a vast ocean). I invested in training, deepened my network of top luxury partners, and kept showing up for clients planning future travel, even when nobody knew what travel would look like next. 

That season taught me this: resilience is a decision I practice quietly, daily.

Lesson 3: Don’t get attached to the outcome — stay committed to the work.

This one is hard when your business feels like your baby.

I’ve had to release timelines, adjust expectations, and stop measuring success only by the milestones I once pictured. Entrepreneurship requires wearing many hats, but growth also requires trusting your team, empowering their expertise, and letting go of control.

Letting go is uncomfortable. It’s also how I grew professionally and personally.

Six years in, I’m still learning weekly, and I’m deeply grateful.  Conversational Traveler is entering Chapter Six because of:

• clients who trust us with their celebrations and wish-list journeys
• partners who partner with us to deliver elevated services with consistency
• a team that believes luxury isn’t just “nice things,” but a thoughtfully designed experience where the little details become the lasting memories

If you’ve been thinking “Should I go for it?”, consider this your sign.

And if you want a trip that’s fully designed and handled for you, so you can actually relax, we’re here for you.  Here’s to more adventures, more meaningful connections, and more Experiences To Talk About®.

Michelle Green, ASTA Verified® Travel Advisor, is the founder of Conversational Traveler and a Board Member of the NYC Chapter of the American Society of Travel Advisors (NYC ASTA). She passionately believes that meaningful connections are the authentic souvenirs of every journey, inspiring her to curate milestone-worthy experiences that last a lifetime. Michelle’s blend of luxury travel expertise and heartfelt belief ensures every itinerary is intentional, elevated, and as uniquely personal as the travelers themselves.