3 lessons in 3 minutes

A year ago, my partner and I left our jobs to embark on a 12-month career break. When we met in 2019, we discovered a mutual passion for travel, and now we were set to spend the upcoming year fulfilling that dream!

Planning a 10 day vacation? Easy. Finding a great restaurant in New York where we could actually get a reservation? I was your girl. Certainly I could handle planning a travel sabbatical, especially when I wasn't working full time.

After providing my employers with a 12-week notice, I was inevitably asked the question, "where are you going?" I awkwardly replied, "everywhere we can before the budget runs out," because, in reality, we had no real plans.

Social media overflowed with bucket-list destinations, friends and family had endless recommendations, and we were optimistic we could see it all. But lesson number one felt more like a reality check: the world becomes much larger once you try and see it all.  We didn’t want to bounce from place to place every three days, but staying a month in each spot would mean missing so much. Finding balance was harder than expected, and suddenly, a year didn’t feel like enough time.

Determined to make a plan, we covered a wall in our Manhattan apartment with a life-sized calendar and color-coded sticky notes listing every country/city/experience we could dream of. We tried to slot in every destination we could, and while exhilarating, it also became overwhelming. Getting that initial roadmap was tough, and after 12+ hour workdays, planning felt like, and very much was, more work. The post-it notes sat untouched for weeks until we finally decided on our first destination and booked a flight to Europe. That commitment made everything real: two months to move out, pack our lives into backpacks, and start the adventure!

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Lesson number two came quickly: high-demand travel seasons and activities mean higher prices and limited availability. Our “loose” budget didn’t hold up against the realities of summer in Europe. Sure, we could have stayed in hostels or taken more inconvenient travel routes to save a few bucks, but at 30, we weren’t ready to strip away our standard of living entirely. We left with a detailed two-month itinerary and a vague idea for the next six—but when the plane landed, we fell in love with the experience of travel and unintentionally stopped planning. Before we knew it, our carefully crafted runway disappeared. Flights were booked, but we had no formal budget and no next steps.

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Lesson number three was the hardest: balancing the joy of living in the moment with the need for logistical planning. I’d prided myself on my productivity and organization in corporate America, but suddenly, our lives were very much in freeform. We fell into a stressful cycle—losing ourselves in the current destination, panicking when we realized nothing was planned for our next destination, finding the most reliable WiFi we could to frantically organize the next few weeks, and repeating it all over again. It was unsustainable, took a toll on our relationship, and made us miss out on fully enjoying the incredible places we visited.

Although stressful at times, being able to fully immerse yourself in travel is an unforgettable, inspiring experience and is exactly what inspired me to create Well + Wander — a travel advisory service that helps long-term travelers avoid the stressful logistics that come with it. Let's cut out the midnight planning sessions and focus on the eye-opening, adventure, and beauty that traveling offers.