Every factory worker and office drone has surely imagined what it would be like to turn their true passion — be it floristry, beekeeping or model trains — into a small business. Those who’ve done it caution that it can require great sacrifices, but the personal payoff is ultimately worth it.

Back in 2000, Don and Melody Legere had visions of owning a bed and breakfast. At the time, Melody was working as a clerk in fraud claims at CIBC, while Don was a production manager for a high-end desktop publishing company.

“Don was working 70 to 80 hours a week, weekends included, always under pressure,” Melody says. “I started to be very worried about him. When he was home, he was so tired and he seemed to have lost his sense of humour. Whether you realize it or not, it really affects your personality when you’re working so many hours under so much pressure, and especially as you get older.”

In January 2001, with their daughter away at university, the Legeres decided to make their B&B fantasy a reality — by selling their Toronto area home for $325,000 and buying a 2,100-square-foot, Cape Cod-style home in the tourist town of Niagara-on-the-Lake, Ont., for $265,000. After renovations and upgrades totaling an additional $50,000, they opened Silken Dreams bed and breakfast in May 2001.

Ten years later, the Legeres’ daily routine consists of fluffing and tidying the bedrooms, cleaning toilets, shopping for wine and food and preparing meals with those locally sourced ingredients. Silken Dreams is the fourth-highest-ranked B&B in the region on TripAdvisor, the trusted vacation review site, with nothing but ecstatic reviews.

“Some [B&B operators] think it’s the hardest job they’ve ever had; I think it’s the easiest one,” says Don Legere. “It’s all a question of where you’re coming from.”

Turning a hobby or long-standing fantasy into profit is an appealing endeavor. While it can offer more personal fulfilment than producing widgets, it is subject to the same hazards as any enterprise. Don and Melody Legere found success fairly easily, but not all first-time entrepreneurs have such a smooth start.

Grape expectations

Like the Legeres, Calgary couple Sally and Robert Peck had a dream — theirs involved owning a winery. It came to them during a tour of the Okanagan Valley in 1997, but it remained an abstraction until the summer of 2000, when the Calgary couple went to visit Robert’s parents in Prince Edward County, a picturesque farming region two hours east of Toronto.

By Christmas of that year, the Pecks had purchased a 48-acre property dotted with sugar maple trees near Picton, Ont., and were ready to become vintners.

Before they could open, however, they had to secure all manner of licenses, then deep-plough the field and plant grapes. And then wait for those grapes to produce a significant yield before they’d start to see any return on the investment.

Don and Melody Legere have been operating Silken Dreams Bed and Breakfast in Niagara-on-the-Lake, Ont., since 2001. (Don Legere)

The Pecks decided to move from Alberta to Picton in 2004, building a house on the property, but it wasn’t until year five — 2006 — that they had a commercial harvest, and year six before Sugarbush Winery was officially open for business.

The Pecks are what’s known as garagistes, meaning they produce small batches of premium wine out of their garage. While they don’t sell through the Liquor Control Board of Ontario, their pinots and chardonnays are available in restaurants in Toronto, Ottawa and nearby Kingston, Ont. Sally Peck reports that many people visit their store in Prince Edward County based solely on the recommendations of friends.

“We hope that one day we’ll be living comfortably off the vineyard and the winery, but it’s been a lot of work and a long haul,” she says.

Moonlighting might be necessary

One of the hitches of starting a dream business is that the transition rarely happens overnight. In fact, it can sometimes take years, raising the question of how to fund it.

To enable the Pecks to pay their field staff and acquire new equipment — all while raising a small family — Robert had to keep his day job, so to speak. A computer engineer for the telecommunications company Alcatel, Robert still spends three days a week in Ottawa, crashing at night on a friend’s couch.

“I can’t believe it’s been seven years now,” Sally Peck muses. “My kids wake up in the morning, and at about suppertime, they’ll go, ‘Where’s Dad?’ They’re so used to him disappearing for a couple of days.”

Don and Melody Legere know this arrangement only too well. Five years after she and Don became B&B owners, Melody was still commuting to Toronto to work at CIBC. She would stay over at her mother’s place Sundays to Thursdays and come home for “conjugal visits,” as she puts it, on weekends.

“I didn’t want to walk away from 30 years at a place where I had a pension and benefits,” says Melody, now 59. “That’s why I hung in.”

Of course, the extra money came in handy, too. While Melody now works full time co-managing Silken Dreams, Don still does some renovation work on the side.

Tim English was fortunate enough to be able to make a clean break from his previous career. Tired of the corporate world, he quit his job as a mergers and acquisitions lawyer for Direct Energy in 2009. Childless and unattached, the 47-year-old had the personal and financial freedom to gamble on a new business.

“I enjoyed being a lawyer, it’s a great job,” English says. “But when I’m 80 years old, sitting in my rocking chair, I don’t want to be reminiscing about that big deal I worked on.”

English had always enjoyed baking, and took continuing-education courses to better learn the art of pastry, cake decorating and chocolate-making. In sussing out business ideas, his market research revealed two important things: that chocolate, like alcohol and cigarettes, is largely recession-proof; and that North America was experiencing a renaissance in gourmet chocolate.

Tim English opened The Chocolateria confection shop in Toronto after leaving the legal profession in 2009. (Tim English)

And so in August 2010, English opened The Chocolateria, a boutique store in Toronto’s west end that specializes in truffles as well as more unusual treats like chocolate-dipped potato chips.

Working as a lawyer for so many years had given English a handsome cushion, which is why he was able to finance the business without any bank loans.

It helps that a sweet shop is a fairly cheap proposition.

“For a bakery or restaurant, you’re usually looking at a minimum of $200,000 to $250,000 to get up and running,” English says. “But for something like this, you don’t need massive ovens, you don’t need all of the kitchen equipment, you need some display cases and shelves, a sink and tables. It’s pretty basic equipment.”

English says his startup costs added up to about $20,000. Since the opening, he has purchased some additional equipment — a $20,000 ice cream-making machine, proper coolers and a tempering machine, which is key to mass-producing chocolate.

Don’t wait until retirement

Many people who romanticize a small business talk about deferring the dream until after retirement, but if the experiences of Silken Dreams, The Chocolateria and Sugarbush Winery show us anything, it’s that you shouldn’t wait until you’re 65 to try your hand at a second career. Depending on the industry, the startup costs could be too high for a pensioner. And some businesses, like winemaking, are physically gruelling.

Whatever you choose to do, you can expect to put in an exorbitant number of hours, according to the veterans.

“Our store is open seven days a week, May to November, and we staff it seven days a week, whether it’s me or my husband,” Sally Peck says.

“But having said that, I’m home for my kids, I’m here when they get off the bus.”

As English points out, if you’re creating a product or service that you absolutely love, the extra hours don’t feel nearly as onerous as the same amount of time spent in an office.

“As a lawyer, especially in the early years, an 80-hour workweek is nothing,” says English.

“If you’re an independent-minded sort, which I am, knowing that you’re in total control of what you’re doing every day puts you in a much better place psychologically than working in a big corporation, where you’re pretty much at everyone else’s beck and call.”