Hear It Live is a closer look at a song and its writer/performer. Hear “Sometimes I Wonder (How I Got This Far)” when Zachary Lucky performs Friday in Regina.

The artist

Guitar-playing country singer-songwriter Zachary Lucky grew up in Saskatoon, spent some time in Regina, and now lives in Orillia, Ont. with his partner and two young daughters. As a touring musician, he’s following in the footsteps of his grandfather, Smilin’ Johnnie Lucky, a country musician who toured Canada far and wide.

The song

It was summer 2018, and Zachary Lucky was spending a lot of time performing in Saskatchewan. He was staying in Regina with his friend, pedal steel player Ian Cameron, and “out of nowhere” Winnipeg singer-songwriter Richard Inman happened by.

They stayed up too late catching up, and over coffee the next morning ended up writing a song together, “Sometimes I Wonder (How I Got This Far).”

“Naturally there was a guitar or two sitting around and the song came very naturally. It felt more like a conversation than a song,” Lucky said by phone, while trying not to wake his sleeping daughter, and conscious of bread baking in the oven.

“I think it really stemmed from the conversation we were having, talking about why it is we do what we do as songwriters, why we travel around the countryside, leaving our families behind and playing these guitars in bars and staying up too late and doing all those long drives.”

After writing two verses, Lucky got stuck.

“I said, ‘OK Rich, your turn,’ and I gave him the guitar and the pen and the paper and — I’m not sure if you’re familiar with Richard’s music or not, but he wrote a verse and he played it for me and sang it, and it was just way too sad. Richard is just a master of writing just heartbreaking songs. I said, ‘OK, make it a little less sad.’”

Zachary Lucky performs at a GrassRoots Regina show on Nov. 22, 2019.

Tom Wood /


The words

Their conversation about families at home is reflected in the lyrics — “I never thought I’d be the kind to leave you there alone / Minutes turn to hours every time I go.”

Also reflected are the chance encounters with fellow musicians during frequent tours — “We’re seeing friends that we never see / It’s better than drinking alone.”

And, it’s the music that fuels them — “It’s the way these guitars ring in an empty bar.”

“I think it’s a song that at least anybody else who does this can definitely relate to,” said Lucky.

He began touring years ago for “wanderlust.” Growing up on the Prairies, “I think it’s a pretty common feeling to feel like you want to get away. … When you’re young, it’s easy to not see the beauty that is there.”

Now, it’s about making a living, but also about “getting out there and seeing friends that you don’t always get to see when you’re at home.”

Plus, “being on the road really fills the tank” for songwriting ideas.

“Somebody put it to me once how being on the road, it’s like living 1,000 lives, because for 24 hours you get to be this one person and then you go to another town and you’re a totally different person, and you’re hanging out with different people and experiencing different things and being a part of their lives,” said Lucky.

Listen now

Lucky’s new album, Midwestern — named for the region he grew up in — is available on streaming services.

On the recording, “Sometimes I Wonder (How I Got This Far)” includes Inman’s vocals, fiddle by John Showman and pedal steel by Kevin Neal.

Hear it live

During his current tour, Lucky is joined by Mitch Thomson on upright bass and Miles Zurawell on dobro.

“It’s gonna be a bit of a stripped down, acoustic style show. And it’s going to be a little folk, a little country and a little bluegrass, somewhere in the middle.”

Lucky performs in Saskatoon on Thursday, Nov. 21, 8 p.m. at The Bassment, joined by Inman. Tickets start at $20.

Lucky performs in Regina on Friday, Nov. 22, 8 p.m. at The Exchange (presented by GrassRoots Regina). Tickets are $20 at the door and through grassrootsregina.com. Lexy Desjarlais opens the show.

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