Desk to Glory: From 9–5 to South America
On the road from corporate jobs to remote summits, this Canadian couple redefined freedom behind the wheel of a Toyota 4Runner.
What began as an escape from routine became a lifestyle built on slow travel, vehicle restoration, and wide-angle horizons. Desk to Glory is the digital trail of Richard and Ashley, a Canadian couple who left office life behind to drive from Vancouver to Patagonia, documenting both the mechanical grit and quiet joy of overland life.
At-a-Glance:
Web Name: Desk to Glory
Name: Richard Giordano & Ashley Giordano
Generation: Millennials
FI status: Partial FI: earning through freelance & overlanding media
Travel type: Vehicle-based overlanding in 4WD vehicles
Travel Regions: North, Central & South America
Media Platforms: Website, Instagram, YouTube, Overland Journal contributions
Backstory:
Before the road, Richard and Ashley lived in Vancouver, Canada, holding standard 9–5 roles in design and administration. Both were drawn to the outdoors, but their time was rationed between deadlines and weekend getaways. A 2013 road trip in a 1990 Toyota pickup hinted at something bigger. That short drive south of the border marked the beginning of their shift toward a more flexible, mobile lifestyle. The push for change came less from drama than from a slow, mounting restlessness. The pair weren’t looking to leave it all behind so much as to find something that matched their pace.
The Shift:
The decision to drive from Canada to South America unfolded gradually. The idea formed quietly and practically, grounded in curiosity and mechanics. They rebuilt their pickup from the ground up, learning as they went. Ashley began writing and sharing their travels online. Richard tackled the practical side of vehicle maintenance and planning. By late 2013, they had both quit their jobs, moved out of their apartment, and committed to the long road south. It was not a leap of faith so much as a carefully studied pivot. The journey became their new architecture: a life lived outdoors, on their own time.
How They Made It Work:
Neither of them had a travel background or mechanical training. But they taught themselves. Vehicle maintenance, website creation, storytelling—all were self-acquired skills. Ashley’s background in writing and interest in research led her to contribute regularly to Overland Journal. Richard handled photography, logistics, and vehicle projects. They kept expenses low by wild camping, cooking meals on the road, and planning border crossings carefully. Their income came gradually: through freelance writing, editorial work, and occasional sponsorships. They adapted rather than scaled, keeping their travel style lean and close to the ground.
Where They Travel & Why:
Their route from Canada to Patagonia was shaped more by road conditions than tourist maps. They favoured dirt tracks, quiet coastlines, and conversations over checkpoints. Mexico taught them the art of slowness. Guatemala offered mountain roads and mechanical challenges. Colombia felt like a new beginning after shipping their vehicle across the Darién Gap. Chile and Argentina delivered the remote vastness they craved. After returning to Canada, their passion for overland life remained. They later modified a Toyota 4Runner for new trips through British Columbia and the western US, showing that the journey didn’t end when the blog updates slowed.
Challenges & Real Talk:
Vehicle troubles were constant companions. From altitude sickness in the Andes to cracked windshields in Alaska, each leg of the trip brought fresh obstacles. But the couple remained calm and methodical. They rarely glamorised the hard parts. Instead, they posted honest updates: about engine failures, bureaucratic snags, and homesickness. They also spoke candidly about returning home. After nearly two years on the road, they moved back into a small apartment in Canada, unsure of what came next. The shift back to routine was hard, but not unwelcome. It gave them space to reflect and reconfigure.
What Keeps Them Going:
Curiosity remains their compass. The joy comes less from reaching a destination and more from understanding it, through food, history, and hard-earned miles. Ashley has since earned a degree in archaeology and writes for various overlanding and adventure publications. Richard continues to work on vehicles and photography. Travel is no longer their full-time occupation, but it remains central to their identity. The slow return to settled life hasn’t erased their instinct to move: it has simply made their choices more deliberate.
Advice to Readers:
They encourage aspiring overlanders to “just start small.” Buy a reliable vehicle, take short weekend trips, and build skills slowly. Don’t wait for perfect gear or full-time freedom. Also, learn basic vehicle maintenance: it builds confidence and reduces reliance. Their approach stresses preparation and patience over spectacle. Real travel, they say, is made in the quiet hours, the waiting, and the breakdowns.
Links to More:
Website: https://www.desktoglory.com
Instagram: @desktoglory
YouTube: Desk to Glory
Facebook: Desk to Glory
*Disclaimer: Income, income streams and financial independence details & status are drawn exclusively from publicly available sources. No inference, harm, or misrepresentation is intended toward any individual or entity.
