She’s sent postcards to herself for over 40 years. Here’s what she’s learned

Debra Dolan was 21 and on her first solo trip when she first sent a postcard to herself.

It was 1979, and Dolan, who grew up in central Canada, was visiting Vancouver for the first time. She was immediately blown away by the city’s vibrancy, and the beauty of the surrounding region.

“It was the first time I’d ever really seen mountains and the ocean such as this,” she tells CNN Travel today.

Dolan wanted to capture the joy she felt when she looked out at the towering Vancouver skyline and the nearby soaring mountains. But although she was usually a keen diarist, Dolan was swept up in the excitement of the trip, and found she barely had a spare moment.

“I thought, ‘I don’t have time to write in my journal.’ And I didn’t travel with a camera,” Dolan recalls. “So when we went to Whistler, or Vancouver Island, or saw places in Vancouver, I decided, ‘I’ll just send a postcard to myself.’”

On the back of each card, Dolan scribbled a paragraph or two about her impressions, thoughts and feelings, and then mailed it to her home address, signing off each dispatch with a single heart.

Some 10 days later, Dolan returned home to a stack of postcards from herself. Receiving them, recalls Dolan, was “an absolute joy.”

Dolan had grown up writing letters to various pen pals, but there was something different about writing to herself – knowing the contents were for her eyes only. She already sensed the postcards would serve as time capsules of a place and a moment.

And the trip to Vancouver was significant in more ways than one – it also awakened Dolan’s love of travel. As a kid, she’d only ever gone on camping trips in Canada with her parents – the family hadn’t traveled much outside of their province, let alone overseas.

“But after I’d come to Vancouver, I realized, ‘Well, it’s easy to travel. And it’s easy to travel solo. I don’t have to be nervous about this,’” says Dolan.

She pushed back the pressure she felt to get on the corporate ladder and kickstart her career and decided exploring the world was her first priority.

“I felt brave and courageous. And I wanted to be unusual,” says Dolan. “Next thing I knew, I just decided to hitchhike across Canada.”

From there, Dolan traveled on to Australia. Then she stayed on the road for months on end, traveling the globe.

“I went traveling for almost three years,” Dolan recalls.

On these adventures in the early 1980s, twentysomething Dolan kept travel journals, but she also continued her new habit of sending postcards to herself.

She mailed these dispatches to her parents’ house in Canada, sometimes sealed in envelopes so she could keep some of her thoughts and adventures private, away from any prying parental eyes.

Over 40 years later, Dolan is still an avid traveler. And she’s still a keen postcard writer. Over the decades, she’s sent hundreds of postcards to herself from trips across the world. Amazingly, they’ve all arrived – albeit sometimes over a year delayed –  and Dolan’s kept them all as memories of a life well traveled.

“They really tell me about – not only where I’ve been, but who I was that day,” says Dolan, who says looking over the postcard collection also makes her “realize the longevity” of her efforts, as well as inspiring her to reflect on “the experiences that I’ve been able to have.”

“I made it a core value to incorporate traveling into my life as a young person, I really did,” adds Dolan. “I felt the most free traveling, I felt the most independent traveling, I felt most myself traveling, my most grateful, always, traveling. And I think that’s what the postcards capture.”

A life in postcards

Today, Dolan is 64 and lives in Vancouver, the city which first awakened her love of travel. She spent her career working in administration, always saving up for her next adventure.

Dolan’s postcards used to be scattered around her home, but as her travel slowed down in recent years – first following an accident, then due to the pandemic – Dolan found herself in a reflective mood and decided to compile all her postcards into one place.

“So I purposefully took them out of journals, took them out of drawers – there were things in different places – to put them in one spot,” says Dolan. “I remember it was really overwhelming for me to see them, it was a very personal experience.”

Some of the postcards, now over 40 years old, were discolored and fading. Many contained descriptions of thoughts and emotions once felt intently, now almost forgotten. Most of the cards were emblazoned with photos, others were illustrations, or replications of famous paintings or artworks.

Dolan’s always enjoyed the process of choosing the postcards as much as she enjoys writing and receiving them. She explains she’s deliberate and considered with her postcard picks.

“For instance, from the Rijksmuseum in Amsterdam, you might send an overall postcard of Amsterdam to a friend or a family member, but to yourself, you’re sending the picture, or the painting or the portrait that you saw there that moved you, or that you spent extra time with,” says Dolan.

Given the choice, Dolan prefers to buy her cards from independent stores and museum gift shops – although whatever vendor she chooses, Dolan’s noticed that postcards have a tendency to depict an imagined ideal of a destination, rather than its reality.

“You go, ‘Really? That’s not what it looks like. This is so stylized. This is so photoshopped. This is not what it looks like – or maybe once, on a nice day, but this isn’t how it looks for me.’”

That’s one of the reasons why Dolan sometimes opts for illustrated cards.

“An artist gives you a different rendering of it, or an interpretation – whether it’s abstract, or just their emotions come through in it,” she says.

Sometimes Dolan will have a predetermined idea of what she wants her chosen postcard to look like, and will hunt around the destination until she finds the perfect realization of her vision.

“I knew that when I was in Vienna, and I was there at Christmas, it had to be a postcard that showed snow and the beautiful lanterns that are lit outside the Opera House,” recalls Dolan. “It couldn’t be anything else.”

Other times, Dolan stumbles across the postcards when she least expects it. She recalls a visit to Helsinki, Finland, calling into a beautiful hotel. In the glamorous bathroom was a writing desk, pens and free souvenir postcards.

The moment felt serendipitous.

“I guess this is an invitation for me to write,” Dolan recalls thinking.

Dolan’s always sent her postcards mid-trip, she never “cheats” and posts them once she’s back home in Canada. She says hunting out the post office, buying stamps and finding a mailbox is all part of the process.

“I love the whole postmark piece too, and the date stamp,” says Dolan.

While walking the Camino de Santiago in 2008, Dolan made an exception and opted for letters over postcards, figuring purchasing cards while en route might be tricky. Before embarking on the trail, she bought airmail paper, envelopes and stamps and then enjoyed searching for rural post boxes en route.

“They all arrived – not in order, but they all arrived,” says Dolan.

Charting time and adventures

Looking back at her postcards over the decades, Dolan also notices how her handwriting has morphed, how her choice of language has evolved and how her travel habits have changed – nowadays, she often opts for slightly more luxurious options than the backpacking that characterized her early travels.

Somewhere along the line, Dolan also switched from being known as Debbie to Debra, so how she addressed the postcards also changed.

But the writing of the postcards has remained constant – and so has Dolan’s sign-off of choice.

“I have always ended my postcards with a heart,” she says. “I don’t know if that’s just love for myself, or love for the experience of this, or that appreciation of that moment, that time.”

Sometimes, Dolan will write her messages horizontally, other times she’ll flip the postcard 180 degrees and write vertically, to squeeze in as much as possible.

A message on the back of one of her postcards, dispatched from Fiji when she was 25, was written in a circle. Rediscovering this card recently, Dolan was baffled. Then she cross-referenced the date in her travel journal and found her answer:

“I had a quarter hit of LSD on the beach,” recalls Dolan.

Some of the postcards invite wince-inducing memories – unrequited crushes on fellow hostel dwellers, for example – “some of them you just want to rip up” – or embarrassing moments.

And while Dolan is grateful for all her travel experiences, there have been times she’s felt lonely, sad, or out of sorts on the road, and she’s expressed those more complicated emotions on the postcards too.

Capturing the moment

Dolan remains committed to traveling without a camera – and while she has a smartphone she uses in her day-to-day life in Vancouver, she always leaves it at home on her travels.

That said, her partner, who often accompanies her on trips nowadays, always has a cell phone in his back pocket. But while the couple enjoy taking the odd photo or two mid-vacation, Dolan’s postcards remain her favorite mementos from any trip.

For Dolan, the postcards to herself capture a moment, and epitomize the importance of living in the present.

“Those special moments in your life that are uniquely yours, they’re only yours. We may all see the same thing on our travels. We may all do the same thing – we go to the Coliseum in Rome, because that’s what you do. But our experience of that day is all different or that hour or that moment is all very, very unique,” says Dolan.

“I think that that’s the thing that the postcards capture. They might have sold 10,000 of that image. But each one of us who wrote on the back of it, wherever it went in the world, is different.”

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