After losing his job in the wine industry, one man rebuilt his life — and found both freedom and fulfillment as a house painter earning $150,000 a year.
Challenge
At 25, Simon thought he had found his dream career. He worked in Alberta’s high-end wine industry, surrounded by fine vintages and exclusive events. He had earned his prestigious Wine & Spirit Education Trust diploma — a credential recognized by professionals worldwide. His future seemed uncorked and full of promise.
But a few years in, something didn’t feel right.
One Monday morning, Simon’s boss called to discuss a client dinner that had cost $18,000 for just six people. For Simon, it was a turning point. The excess and extravagance of the industry suddenly clashed with his values. He wanted something simpler, something real.
So, despite the prestige and comfort of his job, he walked away.
Action
Simon and his wife, Debra, moved to British Columbia in search of a slower, more grounded life. He found a modest position at a local winery — a big pay cut, but a lifestyle upgrade. For a while, it felt right… until six months later, he was unexpectedly fired.
It was a hard blow. But as it turned out, it was also the best thing that could have happened to him.
Through a government program, Simon qualified for an intensive business workshop. For three weeks, he learned everything from marketing to financial planning, developing the framework for his next venture. During one brainstorming session, he remembered helping a friend with a window cleaning business years earlier. The work had been straightforward, the profit margins high, and the demand steady.
He decided to give it a shot — but with a personal twist.
Simon started by calling local homeowners and businesses to gauge interest. Before long, he had a few small contracts lined up — enough to get started. With minimal tools, some leftover supplies, and a borrowed ladder, he launched his own painting and window washing business.
He didn’t rely on ads or gimmicks. Instead, he went door-to-door, introducing himself to potential customers and handing out mugs filled with coffee and tea instead of business cards. “People throw away cards,” he said, “but they keep mugs.” His thoughtful approach worked — people remembered him, and referrals began to roll in.
Result
In his first year, Simon earned $36,000 — modest but promising. Soon, he dropped window washing to focus entirely on painting, which offered better margins and a more flexible schedule. Word of mouth became his strongest marketing tool, with over 75% of his work coming from happy clients.
As the years passed, his small business grew into a thriving operation. He hired help when needed, adjusted his workload to fit his lifestyle, and never lost sight of why he started: to live simply and work with integrity.
Today, Simon earns around $150,000 a year, runs his own schedule, and still feels that sense of satisfaction that comes from seeing a freshly painted wall and a happy customer. His business has brought in over a million dollars since he first began — and it all started from the moment he got fired.
Lesson
Simon’s journey is proof that losing your job doesn’t mean losing your direction — sometimes it’s just life rerouting you to something better. By choosing authenticity over prestige, he built a business that matched his values and gave him freedom on his own terms.
He didn’t just change careers; he reinvented his life. And sometimes, the best opportunities show up right after everything falls apart.
Inspired by a true story originally featured on Side Hustle School by Chris Guillebeau. This rewritten version is independently produced and fully original.