04/05/2013 11:57 am ET Updated Dec 06, 2017

My Biggest Baddest Bucket List Entrance Video

While touring around Newtown, Sydney -- an alternative neighborhood of resident hipsters, punks, and misfits -- I became the local oddball ... an oddball with a crazy dream.

Along the main drag, King Street, I stood in front of a graffiti-covered wall, cleared my throat, then made a proclamation:

"I'm starving, so let's get something to eat!"

Heads turned, but I wasn't actually soliciting anyone to dine with me, just having a conversation with the camera in my hand. Film rolling, I shouted the phrase over and over, looking to record the right tone of emphasis. Meanwhile, a group of tattooed bystanders (some with purple hair) gathered to watch the scene, tilting their heads and bantering amongst themselves.

"What on earth are you doing?" a woman in rock-chic leather pants and Elton John-esc sunglasses demanded.

"I'm creating a video tour of Newtown for the Biggest Baddest Bucket List Competition," I exclaimed, then waved her over to join me. She raised her eyebrows and just continued to watch.

The stakes of this particular competition are high, so high that the silly antics of winning footage merit gutsy moves.


Sponsored by travel company My Destination, the Biggest Baddest Bucket List Competition seeks one person to travel around six continents and twenty-five countries in six months not only for free but also for a $50,000 cash prize. The winner will get to custom tailor their tour and craft a trip that knocks dreams off their bucket list. Earlier this year, My Destination asked entrants to craft a 3-minute video destination tour, write a travel tale, and submit three photographs. At the close of the competition on March 31, the company received over 1,200 entries from 64 different countries.

With such competition, slipping into a pink, full-body pig suit at a gas station to demonstrate Newtown's quirky attire did not daunt me, neither did barging into a tattoo shop, or chasing down a group of stylish punks for an interview.

Of course, no shoot is perfect, it simply becomes a matter of working around what elements exist and overcoming the hesitance of approaching strangers. In Newtown it rained, the neighborhood cleared out on Good Friday, and I got turned down to film at several shops. But finally, the sun came out, people came back to town, and I made local friends who introduced me to the right sources.

No matter the stakes, it's most important to have fun, keep the cameras rolling, and be proud of your mission.

The voting process has closed, but click here to watch my tour of Newtown, Sydney. The top ten finalists will be announced on April 15.