It’s Time to Go - JT’s Tales From The Trail, Rambler Cafe Blog

It’s Time to Go - JT’s Tales From The Trail

Jill Thomas is a rambler, traveler, and storyteller with a big laugh who thinks its funny how life leads you right where you need to be, however the roundabout path.

I am going through a big transition right now, which might be typical of the time in life when we slow down our careers and plan for what comes next. It’s both scary and exciting. My hubby Stormy and I have sole our home in Pensacola, Florida, and plan on living in Canada in our home on Salt Spring Island for 5 months of the year traveling the world the rest of time until we tire of it. 

I arrived in Pensacola for the first time 13 years ago. When I arrived at my hotel on Pensacola Beach, I called Stormy and said, “This is the most beautiful beach I’ve ever seen,” to which he responded, “bullshit,” but later conceded it was true.

I came to create a Facebook Page for a sports bar located in the lobby of a beachfront resort hotel, which at the time was under construction. The owner wanted to pull out all the stops to compete with a popular local sports bar called Sidelines and I convinced him I was his secret weapon.

It turned out that no bar can compete with Sidelines regarding wings and football. However, at the time, Sidelines was bragging about their fried beans on their streetside sign, and I thought, how hard could it be to out-compete a bar that grandstands about fried beans? Turns out they're fried beans are delicious as are most other foods that southerners batter and fry!

At the time, we lived on Salt Spring Island, a tiny island on the West Coast of Canada, where we owned two restaurants and raised our kids. It seems nonsensical now that one might travel 2,962 miles from a tiny island on Canada’s West Coast to the Florida Panhandle to animate a Facebook Page for a sports bar in a beach hotel. But there were some odd forces at work in the world.

Most importantly, Web 2.0 had recently enabled people to publish content on the internet without knowing how to write code. This fact exploded my brain, so I launched a food blog and used our restaurant to learn how to leverage social media for marketing.

I can be charismatic and determined in equal measure, when I’m obsessed with a new idea, so I managed to convince a Pensacola tycoon, who was visiting Salt Spring Island, that I was a genius. So this is how I found myself as far away from home as it is possible to get without changing continents, talking to folks wearing starchy-pressed casual business attire in bland hotel meeting rooms about Facebook.

It was the beginning of a journey that transformed my life in many interesting and beautiful ways, and it will be heartbreaking to leave. However, to travel like Stormy and I want to, we need to be less encumbered. 

I would love to hear about a big mid-life and beyond transition you are experiencing in the comments!

READ MORE > JT'S Tales From The Trail


1 comment


  • Laura Carolina

    Best wishes for your new lifestyle of travelling half the year or so and being “settled” the other half. I retired at 55 and downsized to a small apartment and travelled up to seven months a year for several years. Since 2017 I have been home-free, travelling 10 or so months a year and returning to Victoria BC for a month or two in the spring. I plan to carry on as long as I’m enjoying it. (I was a Pender Islander for 17 years, so greetings to you fellow Gulf Islanders!)
    The world awaits… :-)


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