In the end, my wife and my decision to quit our professional careers to open and inn and boutique tour company in Italy came down to four factors:

1.    We wanted to do it;

2.    We felt we should give it a shot;

3. We were willing to do what to took to do it right; and

4.    We knew we could re-start our careers if we failed.

For about a year, my wife Lisa Grassi-Blais and I had been secretly exploring the possibility of moving to the wonderful and diverse Abruzzo region of Italy to open a tourism business, and in early October 2012 it was time to decide if we were just playing around.

So we added up the pluses and minuses.

We’d found the perfect place to set up a business running small-group, customized tours of Abruzzo. It was the right building in the right place. Property = plus.

We’d crunched the numbers. If we saved carefully and things stayed on budget, we could afford the property and the renovations it would need without much, or any, borrowing. Capital start-costs = plus.

We would be mostly cashing equity from our house in Canada and plowing it into real estate in Italy. Research showed that Italian real estate was more volatile than Canada’s, but it was still real estate, one of the most secure investments you can make, anywhere. Still it could take a while to cash the investment if the business failed. Investment = neither plus nor minus.

We were both making good money, especially Lisa, and our jobs were secure. So we would be forfeiting guaranteed salaries in favour of unknown profits. We were pretty confident we could market our business idea, but the financial professionals said we shouldn’t give up the guaranteed income. Revenue potential = minus.

I was three years into a new career as a municipal bureaucrat after 14 years as a journalist. I’d enjoyed my time with the City of Ottawa, but I couldn’t see myself becoming a lifer, and I really didn’t know of any other shirt-and-tie job I might be interested in. Lisa was eight months into a two-year term as head of a union representing 2,700 federal lawyers, and she was pretty tired of her regular job prosecuting drug charges. Timing = plus.

We were both 44. We had no kids. Our parents were still alive, and they were healthy and mostly independent. Also the business would be seasonal, so we could visit Canada often after getting things rolling. Family circumstances = plus.

We knew getting a business started in Italy would be a challenge, but we would be ditching the stress and frustration associated with slaving away at jobs we aren’t interested in doing anymore in favour of being our own bosses and serving guest with lots of time off in the off season. Lifestyle = plus.

For us, the pluses outweighed the minuses.

So we posed two questions to ourselves. What if we didn’t do this? And what if we do it and it doesn’t work.

On the first question, we both felt it would be tough for us knowing we could have done something cool but decided not to in order to cash a steady paycheck.

On the second question, the worst case was we couldn’t get the business launched or we launched it and it failed. In that case, we could put our Italy investment up for sale and go back to Canada to whatever job we could get.

Even under that scenario, we would be doing something we wanted to do by embarking on an adventure in a place we loved. We would be taking a big bite out of life, and, even it failed we would know we tried.

It would be a lot of work. It would be risky. It would be trying at times. But we felt if we committed to doing the things needed to do it right, it was the right decision.

The final decision came as we were having an after dinner glass of wine in the kitchen of our house in Ottawa.

The last question was: were we willing to do whatever was needed to give ourselves the best shot at success in Italy? Were we willing to let this the property we liked go couldn't get a good deal? Were we willing to work longer in Canada? Were we willing to do outside work in Italy while the company got up and running? Would we commit to learning the language and all the things we would need to learn to run the business properly? Were we willing to confront obstacles together and work through disagreements?

The answers were yes all around. We committed to each other that there would be no shortcuts, and that we would do whatever was necessary.

“I want to do this. I think we can do this,” Lisa said. “What do you think?”

“It feels absolutely right,” I said.

“Let’s do it,” Lisa said.

We clinked glasses, and that was it.

The next day we contacted our Canadian and Italian real estate agents and got things moving toward setting up an inn and tour company in the beautiful and authentic Italian region of Abruzzo.

Next Blog: Negotiating the villa purchase.