We had the good fortune of connecting with Darryl Webster and we’ve shared our conversation below.

Hi Darryl, do you have some perspective or insight you can share with us on the question of when someone should give up versus when they should keep going?
This really is the big question, isn’t it. When do we say, “I can’t take this anymore, for once I just want to pay a bill on time.” I might be a good person to answer this question, because I did give up; twice in fact. I think my best approach to answering this question might be by sharing a bit of my personal experience. My pursuit of the arts started at 18, right after high school, I had no interest in post-secondary education, music superstardom had been the only thing on my mind since I was 14 years old. I was lucky, I came from both a musical and encouraging family, I had a positive support system from the get-go. But even with a solid group of friends and family rooting for me, the next 12 years in music didn’t result in a sustainable career. There were some exciting times: tours, a music video, some radio play even the odd payday, just enough to always keep the dream alive for another month. But more often than not, the music pursuit meant not paying rent on time, moving back home every now and then, and working retail. By 31, I felt unloved by music and completely exhausted from 3am load outs, often in snowstorms (I hadn’t moved to LA yet) and dwindling crowd numbers. I just couldn’t see how things were going to change and what was worse; I’d stopped enjoying doing the thing I loved most and in fact if I’m being completely honest here, I began to resent music. Putting the work in wasn’t paying off and I’d become languid and disinterested. So, I packed a bag and moved in with my sister in Manchester, England. While I was there my brother-in-law gave me a book on creative writing and I immediately consumed it. I took my story telling sensibilities from song writing and tried them in screenplay format. After a few months I showed two writer friends a script I’d written, one of whom lived in LA, and they both, very kindly said, “This isn’t great.” But they both mentioned there were some strengths there, they were encouraging and more importantly they both asked a key question, “Did you enjoy writing this?” I did. I really, really did. This is when LA happened. A friend who’d gone to UCLA recommended I take the Writing Program at UCLA Extension. I moved home for a few months, saved some money working the dreaded retail, even worked as a product sampler handing out free Dr. Pepper (I will never drink that stuff again), but I saved enough to finally get to Los Angeles. UCLA is where the creative lights came back on for me, my first class there felt like the first guitar lesson I ever had–Dave Ziemba from The Salads showing me what a distortion pedal could do—that was the feeling I got from my first class. I spent nearly two years in Los Angeles studying, making friends and falling in love with the city and its ambitious energy. After my final class, my short-form non-fiction teacher Norman Kolpas told me he thought I had a book in me. I thought he was nuts, I was a failed musician turned aspiring screenwriter, a book sounded like madness. So, I quit again, this time before even getting started. I returned to Canada, to a regular pay cheque and took a job managing the retail shop I’d worked at for so many years. But the creative fire had been reignited and this time it stayed lit—saying that out loud sounds cheesy, but it was true. I brought my laptop to work, I wrote articles for local newspapers, tinkered around on some of my own ideas and never forgot Norman’s urgings to write a book. One year after returning to retail, I left, I guess you could say I gave that up too, I quit again, because sometimes giving up is exciting. I took a trip around the world following supporters of a resurgent English football club and wrote a memoir. I maxed out credit cards, slept on couches, crowd-funded, but I was back in the creative pursuit. The payoff came three years after enrolling at UCLA Extension: a published book and finally a feeling of the hard work paying off. It hasn’t been a cash cow, I’ll say that, I’ve had to learn to combine different skill sets and passion projects just to keep the lights on—script editing, foreign language adaptation balanced with my own creative writing and yes, even music again! It’s funny but this whole ride took me back to where I started, reconnecting with friends and colleagues from the past who’d started a record label, I’ve somehow combined both loves, music and writing, to make a patchwork quilt of a career in the arts. How do we know whether to give up or keep going? I’m not sure I know the answer to that, everyone’s experience being so unique. But I’d start with the phrasing of the question, the “give up” part. Maybe instead of “give up” we say, “take a step back”. If you’re contemplating the question of stopping, then maybe a step back isn’t the worst idea, it might be the only way to figure out if you still love the thing you are so rigorously pursuing. And if you’ve stopped pursuing your passion with rigor, then a little break to re-asses is likely a wise idea and it doesn’t have to mean you’re quitting altogether. One more thing I’d like to acknowledge in my answer would be the role of healthcare. As a Canadian living in Los Angeles I came to understand just how much American artists and entrepreneurs risk by setting out on their own. I’ve never had to worry about the fundamental right to healthcare, I can pursue my dreams of music and writing, of working for myself without the constant worry of, “what if I get sick, how would I pay for that?” My American friends take an enormous risk when they go it alone without employer-based healthcare or the resources to get it on their own. For this reason, I have the highest respect for the American artist, and I think the question of “when to give up” for them, is too often tied to healthcare. I hope American artists, the likes of whom gave me a home, friendship, encouragement and education, get the universal healthcare they deserve. I hope they never give up.

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
I have been a recording and touring musician since I was 18 years old, first with a band called “Sunriser” and now as a solo artist known as “Old Kid” I also help adapt foreign language film and TV scripts for english-speaking audiences. I had a memoir published in 2014, called Pride In Travel (Pitch Publishing). I am a goalie coach for a rep hockey team in Toronto.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
The first night friends landed in LA, I’d take them to my favourite restaurant in the city: Masa of Echo Park. No better place on earth to get some food and drinks in, get caught up and formulate a plan for the the coming days. In the week that followed I would take them to the to the water, of course, Redondo Beach for some beers with my Manchester City friends out that way, then some more local beer and food in Hermosa. Shake off the hangover the following day with lunch at El Compadre and a Dodger game. I grew up in Toronto, our team played in a domed stadium, the unmathced beauty and sound of Dodger Stadium has never grown old on me. We’d finish the trip on a Saturday, dancing the night away to the best music night in the land and all the world—Funky Sole night at The Echo!

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
I would like to thank the arts community of Los Angeles as a whole, for welcoming me with open arms during a time when I needed a change. My friends there are people I owe a great deal to, I’ll never forget what you did for me and look forward to many more years of adventure with you.

Website: www.oldkidmusic.com
Instagram: @darrylwebster (OLD KID)
Twitter: @darrylwebster (OLD KID)
Facebook: https://www.facebook.com/darryl.webster.560
Youtube: https://www.youtube.com/channel/UC5uKsRC1zQBstwWHz6R_baA

Image Credits
Simon Willms.

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