In February 2024, our lives took an unexpected turn. The Montessori school our boys attended shut down with only a two-week notice. Our 6-year-old transitioned to public school where my wife teaches, but we suddenly had nowhere for our 3-year-old to go. For those unfamiliar with the childcare world, a two-week notice is the equivalent of quitting your job over the phone. It’s nearly impossible to find daycare availability within such a short timeframe. Some waiting lists, it seems, require you to sign up before you’ve even decided to have children!

So, here I am, now a “stay-at-home dad.” This wasn’t the plan when I quit my full-time job last summer to jump-start my travel business as a full-time travel planner. Many of my plans to invest in growing my business have been put on hold. My priority now is my children, but when I do find time to work, I focus on assisting my clients with their booked or upcoming vacations.

Sometimes, life throws us curveballs. We often think of the unexpected as inherently negative—and sometimes it is. But the unexpected can also bring blessings, like the free upgrade to first class I received on a recent flight to Jamaica. And sometimes, it’s a mix of both: staying home with my 3-year-old has been a challenge in terms of business growth, but it’s also a precious opportunity to spend quality time with him.

So, how does this relate to travel? Travel, like life, is full of surprises. Whether good or bad, the unexpected can shape our experiences and create lasting memories. Here are some tips to help you embrace the unexpected during your next vacation:

1. Protect Your Investment with Travel Insurance

Travel insurance might seem like an optional add-on, but it’s a small price to pay for peace of mind. Typically costing around 4-8% of your total vacation expense, it can safeguard you against unforeseen events like cancellations, delays, or medical emergencies. Knowing you’re covered will help you relax both before and during your trip.

2. Anticipate the Unexpected

It’s one thing to know the unexpected might happen. It’s another to try to anticipate what it could be and plan for it. While you can’t predict everything, asking questions like “What if it rains all day?” might prompt you to pack a quality rain jacket instead of a flimsy poncho. Thinking ahead can make surprises more manageable.

3. Embrace Flexibility in Your Plans

Planning is essential for a great vacation, but over-planning can lead to stress. Allow for some wiggle room in your itinerary. I often compare planning a Walt Disney World trip to planning a wedding: no matter how detailed your plans are, something will go off-script. And that’s okay! You’ll still have an amazing time and create wonderful memories.

4. Leave Room for Spontaneity

Not every moment of your vacation needs to be scheduled. Sometimes, the best experiences happen when you leave space for the unexpected. As a planner by nature and profession, I know the value of having a structured itinerary. But I’ve also learned the magic of leaving room to explore. Some of the most beautiful moments can only be discovered when you stray from the beaten path. As J.R.R. Tolkien wisely said, “Not all those who wander are lost.”

Life and travel have a lot in common: they both remind us that flexibility, preparation, and an open mind can turn unexpected challenges into opportunities for growth and joy. Whether you’re planning your next trip or navigating a sudden life change, remember to embrace the journey—unexpected twists and all.