When we decided to ditch your secure professional lives in Canada to roll the dice on a tourism business in Italy, one of the things we had to decide was when to tell our wider circle.

We were pretty sure our friends would be supportive, but our employers were another thing, especially in the uncertain position we were in in the late fall of 2012. We’d just told our families we’d sold our house and put a down payment on a vacation villa in the Abruzzo Region of central Italy to anchor our business.

The closing date for the property about 150 kilometres east of Rome was March 1, 2013. Beyond that, there were lots of outstanding questions.  The building needed renovations and substantial improvements. Business and residency requirements needed to be sorted out. Financial requirements needed to be confirmed, and we needed a good chunk of time to run a pre-opening marketing campaign.

We were hoping to get the business running in 2014, but that too was a moving target, and, regardless of the opening date, we needed to keep working for as long as possible to pay or renovations and to put some money in the bank.

For these reasons, I was for waiting to let our friends, co-workers and bosses know until we had more information on our plans. My wife, Lisa Grassi-Blais, wanted to let our friends know, but she agreed we should wait until we had more information because many of our friends were co-workers, and if they knew, our bosses would need to be told.

Then, without telling me, she moved things along by posting a picture of our property on Facebook and below it, she wrote something like “The future.”

Lisa has lots and lots of strong points. She’s smart, brave, sexy, funny, hardworking, and loyal. You’ll notice patience isn’t listed. When I asked her why, after we’d just “agreed” to not tell people right away in order to avoid having to tell our bosses, she did that, she played coy.

“I just thought I’d give people a hint. I didn’t say we were quitting our jobs,” she said innocently.

Lisa has hundreds of Facebook friends, including many people I work directly with, so a couple hours after posting the picture roughly 173 people had asked when, exactly, we were quitting our jobs and moving to Italy.

It was time to tell everybody, including our bosses.

After work the next day at about 5:30 p.m., I found myself in the office with only my boss left. I said before she found out from others, I needed to tell her I was leaving at some point in the future to open a business in Italy. What was interesting was that she said she knew I was probably going to be quitting soon. She said she could see that I wasn’t as passionate about the job as I had been, and that she was happy that I had a plan in place for the future. She said I had a job in her office as long as I wanted to stay. Then, she wanted to know all about what we were doing and where and said she was looking forward to coming for a vacation when we were open.

Her reaction and support put me at ease and it made the next couple years of work more enjoyable for me.

Telling Lisa’s bosses was a bit more complicated because at the time she was on leave from her prosecutor’s job working as the full-time president of the Association of Justice Counsel, a national union representing 2,700 Canadian federal lawyers.

So she told her bosses that she was coming back to work in a year or so when her term ran out in 2014, but that she didn’t know how long she would be staying. Her bosses were surprised, said they wanted to know all the details of our plans, and that they would be coming to stay with us.

In hindsight, letting our bosses know that we were leaving so early on in the process was a good thing.

It allowed us to start building word of mouth interest, and that, in turn, gave us confidence as we pursued our dream of quitting the rat race in favour of opening a tour company and inn in the beautiful Abruzzo region of Italy.

(As a side note, Lisa is still playing coy.)

Next Week: Closing the deal, Italian style.