In its fifth year the digital design business I'd started in my bedroom had completely outgrown my ability, experience and temperament. I had a "funky" office, great clients, eight dedicated employees and a healthy ego. But behind the façade of a small business with a bright future I struggled privately. A constant inferno of problems raged while I tried to maintain the quality of work, relationships and lifestyle I felt obligated to.

When things reached breaking point I scheduled the day of defeat. A day soon enough but not too soon. I needed time to plan things that were already done. When the day came, I ground my way to the office and one-by-one walked with my employees in the park to explain a hard truth softly: I was giving up and so they had to, too. With each conversation I shed the trust I'd built with each of them, and a large nugget of pride with it.

Over the next few months, I shrunk into a personal and professional husk, keeping to myself and cleverly diverting attention away from questions about what I did-a classification so critical in the City of Sydney's social framework of corporate morality. I did odd projects for old associates and re-hashed stories of the golden days, drawing down slowly on my professional reputation. I felt shrivelled and invisible—highly sensitive to the change in pace, respect and attention (especially from the girls at the fancy rug shop down the hall from the office who I could no longer invite to Friday-night drinks).

Through the fog of failure I felt a faint beat: The Trip. The Trip, The Trip. Slowly, its intensity grew. It drowned out doubts, inadequacies and a lack of direction. The Trip fed on my resentment, shame and self-pity. It dangled salvation. It whispered promises of success and status—even revenge. Built from anger, irreverence, excitement and potential The Trip would be my second chance (or probably my fifth for anyone keeping score, but life is short and memory is selective).

While the desire to go was welling up in me the window of opportunity to do it started closing. I wasn't getting any younger, and the woman in my life's biological clock was tick-tocking louder with every month that passed. She was sick of hearing about this theoretical threat to her own plans and wanted it over and out of her life. I had been saving, reading, riding, tinkering and talking for years but I'd never truly taken action. I was to shit or get off the pot.

It was that little shove that forced the decision to actually go. Until then I had just been procrastinating—but at an elite level. Years of procrastination had inadvertently taught me to save, to ride, to repair my bike, to camp, to be strong.

I'd started from below zero with no bike or license and tens of thousands in credit card debt. By the time I boarded the plane for London I'd saved enough money to fund my trip and buy an apartment. I'd learned to ride well enough to cross the Simpson desert on my dirt bike. My mechanical skills had developed from my being unable to change a tyre, to rebuilding my bike's engine myself. I could dead-lift 2.5 times my bodyweight. I'd ridden solo across the Outback from Sydney to Alice Springs. Arguably, that time would've been better spent meditating and learning French—I was both horribly over- and under-prepared for what was to come.

And so, The Trip became real—the mission of a man who had waited too long to make his mark on the world. It was my chance to earn the respect of others but also prove to myself that I was worthy and capable. I was going ride or die trying.

© David Baskind · 2022