8 min 4 sec

Wine Expert Loses Job; Becomes House Painter Earning $150,000/Year

After rejecting the extravagant spending associated with the high-end wine industry, an Alberta man looks to get back to his roots and ends up transitioning to something completely new.
Customer Service International Low-Tech Service Transition Story

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What It's About

A transition story about a wine expert who leaves the wine industry in lieu of living a more intentional life.

Business Model
Skills Required
Business Savvy & Coordination
Profit Potential

Words of Wisdom

Before Simon jumped in with both feet, he decided to conduct some “market research”—the old-fashioned way—by picking up the phone and calling to see if there was any demand for his business. When his research led to landing actual work before his business was even officially set-up, Simon knew he was onto something and, in January of 2005, he launched a window washing and painting business serving the painting needs of Vancouver Island.

If you're not sure who your audience is, do some cold calling to see if your service would be something that people would want. The worst that can happen is that they say no, but it could also end up landing you your first clients like Simon!

Fun Fact

Sometimes your biggest mistakes turn out alright in the end. Simon was painting a summer cottage in rural British Columbia, and everything was going smoothly until the last day when he was cleaning up. The family showed up for the weekend and as Simon was breaking down the scaffolding a can of paint fell off and splashed everywhere—the floor, the table, the couch, the dog, literally everywhere.

Instead of running out the door and driving away like he wanted to, he did everything he could to fix it. He cleaned the furniture, got the dog shampooed, offered to replace the couch and touched up the paint. In the end, his efforts paid off! He got more work from the family, a great referral, and was paid in full.

Notes from Chris

Episode 173

Like all of us, Simon Kuhl’s story starts years ago. But for this episode, we’ll just jump back to when he was 25 and climbing to the top rung of the wine industry in Alberta, Canada. He was working with some amazing people, learning a lot, and drinking a number of amazing wines. For all intents and purposes, he set himself up to have a thriving career in the wine industry.

But just a couple years in, he was burnt out and disillusioned with the extravagance of the industry. He could no longer find the motivation to move up in an industry that promoted such luxury. He wanted a simpler life, more authenticity in his interactions, and a sense of accomplishment in his work day.

So he quit. Simon and his wife, Deborah, moved to British Columbia where he got a low-paying job at a winery. Then, six months after starting his new job, he got fired. Yep, you heard that right, he got fired.

After the shock and disorientation wore off, he discovered that he qualified for an intense 3-week business plan workshop, and this led to the development of his very successful painting service, Sombrio Painting. As Simon put it, “It turns out getting fired was the best thing that could have happened to me.”


  • Sombrio Painting: Learn more about Simon and his transitionary painting business on his website. Check out all of those glowing testimonials!
  • Weebly: The platform that Simon used to create his website for Sombrio Painting

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


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Quote of the Day
"Defining your success is so important and the experience of creating a business is an incredible learning experience. While it is a difficult road, easiness is not the objective—growth is. Sure, it can be scary to not have a regular guaranteed income, but the trade off is invigorating because there are no limits to what you can do!"
—Simon Kuhl #SideHustleSchool

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To infinity and beyond,

Chris Guillebeau