What Ted Lasso Taught Me About Planning Your Next Trip

Richmond Green and the Prince's Head in Richmond, better known to some of us as the Crown and Anchor. We tracked this down on a family trip to London!

My favorite scene from Ted Lasso lives rent free in my head.  It’s the dart scene.  And if you’ve watched Ted Lasso you undoubtedly know that moment of satisfaction when Ted wipes the floor with Rupert’s smugness.  In a quintessentially Ted way, he manages to teach a lesson, stand up for what is right and good, and lift up Rebecca in the process.  And while it’s easy to cheer for his take down of such a callous and unlikeable character as Rupert, it’s equally as easy to take Ted’s lesson to heart: Be curious.

📚 Two Former Teachers, Forever Students

I’ve spent my life being curious about the world around me.  I loved doing research papers in high school, even though I lived in the pre-Google era.  Research papers gave me an opportunity to get lost in a library or a book store.  And even in the microfiche…kids, look that one up!  I’m not THAT old, but I’m learning that I am, in fact, that old.  This curiosity likely led me to my first career…a teacher.  A middle and high school English teacher, actually.  So I could continue that love for research papers even as an adult!

Aside from our incredible sense of humor, I think the fact that Cindy and I were both teachers in our former lives is one of the things that drew us together as friends.  Cindy was an elementary math specialist before we met.  So between the two of us we have the words and numbers covered, which turns out to be a handy way to run a business.  But what we really share goes beyond that: neither one of us ever stopped being a student.  We just traded a classroom for the whole wide world!

Here’s why that matters…curiosity is basically our entire job.  When you travel with us, you know that you are going to get the perfect trip for you.  We will always take the time to learn the options…the ships, the destinations, the tiny details that make one experience perfect for you and completely wrong for the next person.  When Cindy and I launched Destination Exploration we made ourselves a commitment.  Learn something new every week.  No exceptions.

Celebrity Beyond ship touring in PortMiami. Somebody has to do it…may as well be me!

🚢 Just One More Ship Tour!

Now, listen.  Sometimes that homework is a genuinely good time. In seven months I've toured three ships...Star of the Seas, Utopia of the Seas, and Celebrity Beyond, which I walked just last weekend.  And by the end of the summer I'll be revisiting Disney Cruise Line and adding MSC to my list of cruise lines I’ve sailed.   And no, I'm not just collecting door magnets (okay, maybe a little). I go because you can read every brochure ever printed and still not know how a ship actually feels until you're standing on the deck. For each of these cruise lines and ships I can name a specific client or family who would be perfect for it.  And a client I’d never recommend it to.  Because a ship that's pure magic for a young family might be all wrong for a couple celebrating 40 years together. The only way I know the difference is to go see for myself. Be curious.

📋 Nobody Writes a Blog About Insurance

But curiosity isn’t all thermal spa tours and cruise ship lunches.  Some weeks “learn something new” means endless webinars or finally getting the hang of a travel consortium so we can pass along better perks to you!  One week, before we officially launched, it meant truly understanding Errors and Omissions insurance…about as thrilling as it sounds, but one of the most important things to understand when someone trusts you with their trip of a lifetime. 

We also did extensive research before choosing a CRM, and landed on Tern, a platform that actually listens to advisor feedback and makes updates every week.  Which means I’m never quite finished learning it.  It also means that your trip lands in your hands as a beautiful, easy to follow itinerary that you can access on your phone, in the middle of a foreign country with zero signal.  Learning the “boring” stuff is how the good stuff quietly gets better for you. 

✨ The Rabbit Hole

Explora Journeys' first-ever Alaska season kicks off in 2027. We'll be on it.
Photo Credit: Explora Journeys

Every now and then, a little curiosity turns into something you never saw coming. A few months back, I barely knew a thing about Explora Journeys, the luxury brand of MSC. I got curious, started asking questions, learned everything I could...and that rabbit hole became a group of 50-plus travelers setting off on a Mediterranean yoga retreat aboard one of their ships next year. A brand I'd hardly heard of turned into one of the trips I'm most excited to be planning…and one I’m most excited to sail! My family heads to Alaska aboard Explora III in May 2027, for Explora’s very first season sailing there.  That's the sneaky thing about curiosity. It grows!

Curiosity doesn’t make our weeks shorter.  But it is the reason we can hand you a trip that feels elevated…not just booked…but genuinely yours, crafted for and matched to you because we took the time to learn.  We don’t have all the answers.  We’re just stubborn about finding them.

So here’s to Ted.  To three perfectly thrown darts.  And to learning something new every week.

Be curious.  We always are!

And if you’re wondering where a little curiosity might take you next, send me an email.  You bring the “what if” and I’ll do the homework!