A boomer quits sleepwalking through life … and travels

Since travel is such a big part of many retired baby boomers’ lives, we like this story sent to us by Gorham, Maine artist and blogger Terrilynn Dubreuil. It wasn’t easy — sometimes it seemed downright scary — but she just took a big trip, and a big leap.

Two years ago I was fed up with sleepwalking through my life. What woke me up?

It could have been a lot of things. My 60th birthday. Finalizing a divorce after 26 years of marriage. Living in the “empty nest.” I realized I had been giving my all for family, friends, students, and my teaching job. But for me? I had lost myself.


Terrilynn Dubreuil

Thankfully I am still healthy and active. So when I hit 60, I left my teaching job, not waiting for “retirement” age, I greatly simplified my living situation, and after organizing a few basic, leave-behind items, I “took off.” Off to find myself! The new me, the now me, just myself, a single woman, at this later point in my life.

Today, after these last two-and-a-half years, it is a full and (mostly) exciting voyage. That said, it is challenging and disconcerting to travel alone in a new country where I do not speak the language. I endured it first when I was seventeen, in Ecuador, but then I was more supple and able to adjust faster to the challenges. It is a bit trickier today.

Today the country is Italy.

San Gimignano - the village of towers - an Italian hill town in Tuscany, southwest of Florence. Encircled by 13th-century walls, its old town centers on Piazza della Cisterna, a triangular square lined with medieval houses.

San Gimignano – the village of towers – an Italian hill town in Tuscany, southwest of Florence. Encircled by 13th-century walls, its old town centers on Piazza della Cisterna, a triangular square lined with medieval houses.

I have made a list of Italian words, hoping they will be useful, but I have used so few. Yesterday the man at the train station told me he spoke English. Not well, and definitely not well enough. He proceeded to sell me a Rome-to-San Gimignano ticket — that’s in Tuscany — but he totally neglected to offer me a way to get from Civitavecchia to Rome – a fact I did not realize until later. Thankfully I was at the station a half-hour early and on the train … but now I am wondering about making the 9AM train in Rome that he assigned me.

While on the train I have a chance to ponder.


I ponder the things that still pop up and worry me. Things that bother me more now than when I was young and emotionally flexible. Things like, “I am not going to make the 9AM train in Rome,” or, “Oh, no! My debit cards are not functioning and I’m almost out of cash,” or, “My bank account is limited and I should be producing more income and not spending so much.” Anxious thoughts that intrude and try ruin everything.

But the deep, deep inner me is not concerned. I have survived. I will survive. Things will work out for me. They always have. And they continue to. So why do I doubt?

Terrilynn Dubreuil

Terrilynn Dubreuil

When I finally do arrive in Rome, I have, of course, missed the 9AM train. Deep breath, then I figure out how to catch the next train and, with a bit of effort, to stay focused on “It will work out.” Which of course, it does. I arrive at my destination, San Gimignano. A bit later than originally planned, but I arrive.

My reward for surviving? For the next few days I delight in exploring this amazing, medieval town.

Leave a Reply

8 Comments on "A boomer quits sleepwalking through life … and travels"

Notify of
Sort by:   newest | oldest | most voted

Terrilynn’s blog is a delight to the senses as she crafts sentences, posts delightful pictures and her beautiful works of art.


Very inspiring, Terrilynn!


Terrilynn, we are so proud of you back in Portland, Maine, we have loved your blogs and beautiful photos along your journey. A lovely 60 year old woman doing her thing. Congrats on the article!


What an inspiring journey. I biked to Belgium from Holland at 18 way back in 1972 and feared nothing. Now at my present age, I would love to see the world again, but in a more comfortable way!


It’s time to wake up and smell the pizza! Enjoy your life!


I hear you! I’ve been caught up in the silly little worries about what could go wrong when travelling. And occasionally things have gone wrong and I’ve discovered, yet again, it’s not the end of the world.
PS Love St Gigmingano but if you get the chance go visit Volterra — a Roman Amphitheatre, a museum stuff with Etruscan artefacts and more alabaster than you can poke a stick at.


You are enjoying a well deserved journey. Have you written an article about tips for traveling solo for women over 50?


Thank you all for your wonderful comments. I thoroughly enjoyed them all. (More blog entries, of course, and artwork at my website: travelingartista.com).