Unplanned Road Trips & Expectations


Jonathan Wong / March 22, 2018

4 min read––– views

DJI Mavic Photo of Rental Car

I’m the type of person who always plans in advance. I have notes and documents detailing goals and strategies for next week and into next year. It’s always been a critical part of my life. It’s not very often I do things sporadically without at least some thought, but I’m learning to embrace and invite these moments. That’s why when my new roommate, Kurt, asked me if I wanted to fly to Tasmania for the weekend and road trip the east coast, I said yes without hesitation.

Let’s backtrack a bit. Tasmania? Where in the world are you? I’m currently living in Melbourne, Australia for the month still traveling with WY_CO. So far, Melbourne has been remarkable. The proximity of Tasmania in relation to Melbourne makes it an attractive option at just an hour flight south. I’ll be honest, I didn’t know anything about the island at all before saying yes. They have Tasmanian devils, right? I actually thought it was its own country (it’s not - it’s a part of Australia). Nevertheless, I booked my flights and committed to the trip.

Side note: Traveling domestically in Australia was a breeze. There’s no getting to the airport 4 hours early. Hell, they never once checked my ID. Even the baggage check-in process was all automated. C’mon, USA.

The beauty of the unplanned trip is the lack of expectations. I hadn’t spent weeks or months finalizing details and crafting the perfect itinerary. There wasn’t some set schedule of requirements. I simply looked up a couple places to photograph, helped choose our accommodations, and got a rental car. We were going to embrace the unknown and see where the road took us.

Wineglass Bay in Freycinet National Park

As I cruised down the narrow east coast roads with 4 new friends, I felt an overwhelming sense of joy. This place felt like our own little getaway. We were engulfed in nature, finding solitude in the absence of others. Every twist and turn uncovered pristine beaches, crystal clear water, and spotless national parks.

Our trip came to an end 4 days later as we arrived back in Hobart, the largest city, to fly home. However, this wasn’t the end of my spur of the moment adventures. Since I had arrived in Australia, I knew I wanted to visit Sydney. I wasn’t sure logistically how it would happen just yet. Would I drive or fly? How long would I stay? Where would I go? My initial thought was to fly to Sydney, rent a car, drive up the coast to Brisbane, and fly home. Sitting at the airport in Tasmania, I booked my flights to depart just 2 days later and found a couple Airbnbs that looked promising. What could go wrong?

Well, one thing went wrong. Extremely wrong.

Weather Radar

I didn’t check the weather close enough to my departure. Sitting in the airport, I pulled up Sydney’s weather expecting to see bright, sunny skies. Unfortunately, I was greeted with bad news. For the entire duration of my trip north to Brisbane, it was supposed to rain due to heavy, unseasonal weather. It was advised not to travel North unless absolutely necessary.

I arrived in Sydney to 25mph winds and a torrential downpour as I tried to stay positive and salvage the trip. My first thought was to switch my course and drive South back down to Melbourne. I'd need to cancel my prior accommodations and I'd miss my flight out of Brisbane, but at least I would get to drive the coast. The weather, however, did not cooperate. All of the coastal locations I researched to stay at faced the same problem of cloudy skies, high chances of rain, and low morale for the foreseeable future. After a day of frustration and many customer support calls, I threw in the towel and booked a flight back to Melbourne the following night. There was no way to salvage this trip.

Admitting Defeat#

I’ll be honest, I was bummed out. Canceling flights and backing out of reservations isn’t my favorite thing to do and I did lose a little bit of money in the process. However, I believe it's possible to turn almost any experience into a positive.

I took a leap of faith and traveled somewhere new by myself. I saw the Sydney Opera House. I stepped out of my comfort zone and embraced the unknown. I rolled with the punches when everything was going wrong and kept on fighting. Most importantly, I learned and I grew as an individual. And hey, I can always come back, right?

Sydney, Australia

See you again soon, Sydney ✈️

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