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Canada’s Luckiest Student: What’s It Really Like to Win?

Written by Connor Briggs-Morris
Canada's Luckiest Student winners

Want to be the next winner of Canada’s Luckiest Student? Find out what you could expect from some of the students who won.

(Students in Canada can enter the current round of Canada’s Luckiest Student right here.)

Just the thought of winning over $50,000 in student prizes in Canada’s Luckiest Student can be overwhelming. And why wouldn’t it be? This is a life-changing sum of money that can open up educational and career opportunities that may not have existed for the winner.

So we asked three recent winners what winning Canada’s Luckiest Student is really like.

We caught up with Tori Watson (Sheridan College, Winner of Canada’s Luckiest Student 5 in 2017), Omar Steele (University of Guelph-Humber, Winner of Canada’s Luckiest Student 6 in 2018), and Ben Westmore (Churchill High School, Winner of Canada’s Luckiest Student 7 in 2019) to talk about why they decided to enter Canada’s Luckiest Student, what it was like to win, and their advice on how you could be next.

In case you had any doubt, it’s all legit, and one Canadian student is going to win it again this year. Maybe it will be you.

Canada's Luckiest Student winner Tori Watson
Tori Watson, at the reveal of Canada’s Luckiest Student 5.

How did you hear about Student Life Network?

Tori: I first learned about Student Life Network in the first year of my undergrad at Queen’s. My then-future housemate Michelle is a CIBC customer and I believe she mentioned it in a passing conversation. I believe at the time some high school friends were also posting about CLS on Facebook.

Ben: I’ve also seen ads for it on Instagram. It just kind of pops up sometimes.

“It never really felt like work and the chance was just too tempting to turn away from”

Tori Watson on why she entered

What convinced you to enter Canada’s Luckiest Student?

Tori: It just felt like something that I had to take a shot at! The contest itself is pretty engaging and interesting. It was easy to take a couple of moments in my day to answer the questions, share the posts, etc. It never really felt like work and the chance was just too tempting to turn away from when I knew it could really help me. I have joined every year of my post-secondary journey and it almost has become a tradition to enter.

Ben: One time I was looking for scholarships. I was looking pretty early and I came across Canada’s Luckiest Student, and I’d heard of Student Life Network, so I knew it was reputable and it was legitimate. So I was like, “What’s the point in not applying?” Because you just enter your name, and it’s really easy to enter. And the prizes, like, who wouldn’t want the prizes for how easy it is?

Canada's Luckiest Student winner Ben Westmore
Ben Westmore, winner of Canada’s Luckiest Student 7 taking a minute to call his parents.

How did you find out that you won?

Tori: The Student Life Network team, in cahoots with my family and friends, surprised me at The Den, a restaurant on Sheridan’s Davis Campus where I was completing my ECE program at the time. SLN had been dropping hints about the winner for a couple of weeks I think and had narrowed it down to a Sheridan student before the actual reveal. I almost didn’t go to the party that night since I commute by transit and it becomes more difficult to get home to Orangeville the later you stay in Brampton since there’s a limited bus schedule. Looking back to the night before, my mom and dad really pushed me to go to the reveal party- my dad even offered to come pick me up after, which wasn’t too common since he has such a busy work schedule! It really should have tipped me off in retrospect!

Omar: I just remember being in the movie theatre, not thinking anything of it, because I remember that day I actually was not feeling great. I didn’t want to go, but my mom convinced me to go to the movies. So I remember Stephen [Sills, SLN Co-Founder] was doing the games and I was getting hyped. And when he brought me down to play the basketball game, I was not expecting like at all them to announce the winner. And when they reveal to me the billboard and I read it, my whole body just went into shock.

Ben: My teacher just told us the week prior that Student Life Network was coming in because they’re doing a thing where they’re going to classes across Canada and just shooting this documentary-type thing about scholarships and how to enter and all that stuff, so I thought it was completely normal. Yeah, it was Steve [Sills, SLN Co-Founder] that was giving the presentation. But then he said he was going to take some of us out one-on-one to talk to us, and then he chose me to talk to. And I was like, “Okay, whatever. I’m sitting in the front row. It’s like normal that he chose me to talk to first.”
​So then Steve and I went to a room down the hallway, and he asked me questions about myself and what I want to do in the future and things like that. And after a while, I was starting to get a bit skeptical because he’d been talking to me for around 10 minutes, and I was wondering how he’s going to talk to multiple people if he’s talking to me for so long. But I was like, “Oh, whatever, maybe he just has a lot of questions.” But then he walked me back down the hallway to bring me back to get someone else, as he said. But then before we went into the room, he looked at me and said, “Ben, your class has a surprise for you. Enjoy it!”

“I kind of had an idea then, and I got all shaky and I was like…I couldn’t believe it was actually happening.”

Ben Westmore on realizing he had won.

What was your reaction to winning?

Tori: I honestly was in complete shock. It didn’t seem real, it was dreamlike. My mind went completely blank, I teared up a little- my mom was a little disappointed that I didn’t cry more. She thought for sure there would be more waterworks, but like I mentioned, I was too shocked to do much more than smile! I also remember being extremely nervous about all the cameras and lights, I am pretty shy so that was a new experience! Overall, it was an amazing rush of happiness and confusion!

Omar: I was just completely surprised, to be honest. I was not expecting that at all. And I started this freaking out. I mean I couldn’t really speak, it was just so unreal. The moment that this picture in my head, every time just this brings back such an amazing moment of my life that I am just so thankful for everything. Everyone for actually you working to get that all sorted out. And is this an unbelievable, unbelievable moment.

Ben: I kind of had an idea then, and I got all shaky and I was like … I couldn’t believe it was actually happening. So I went in and they shot off the confetti guns or whatever, and my whole class was there congratulating me. And then there was the big check and everything. But yeah, at first I didn’t really … because it was just like … I hadn’t expected it at all until we were right outside the door. So it just kind of hit me, and I was like … I didn’t know how to react, but I think I handled it all right, afterwards. But, yeah, I was pretty happy.

Canada's Luckiest Student winner Omar Steele
Canada’s Luckiest Student 6 winner Omar Steele with his $40,000 cheque from CIBC.

Which prize in your bundle did you appreciate the most?

Tori: SLN are masters at making amazing gift bundles for the CLS contests. I am not going to lie; the $20,000 dollars was huge for me as a student who is putting myself through post-secondary on my own. As many students in Canada know, tuition and textbooks are so expensive. Recent cuts to OSAP and education in general just continue to make problems for those of us trying to obtain degrees. Even with my luck of winning CLS5, I still will finish my post-secondary journey this year in debt. But winning that money has lightened that load considerably! Other than the money, I loved both my trips! My friend and I had a blast in Costa Rica, it’s a trip I will never forget.

Omar: Actually, I would say the cash. Because I mean…​I was able to help my mom and take care of my student loans and also pay for my future education. So that was obviously the most useful in that sense. But from an experience perspective, the Contiki trip to Europe was the most memorable, because I got to experience so much different culture, so much different countries and meet so many great people that, who I have become great friends with. Even though they are 12, 15 hours away from where I am, we still talk every day.

Ben: ​I’d say the $20,000 was pretty nice, from CIBC​… because that’s going to help a lot with … If I go to a university like UBC, that’s a big part of it, just paying. So, that’ll help a lot. So I think that’s what I’m happiest about, yeah.

“To say it in simple terms, the past 12 months, or 13 months to be exact, have just been the most amazing experiences, moments I’ve had in my entire life. Being able to travel, being able to help my mom, being able to just enjoy life for that moment”

Omar on how things have gone after winning

What has life been like since winning?

Tori: Life has been pretty good since winning, my family and I keep chugging along. I finished my ECE program at Sheridan the year after winning, so I am fully registered ECE now! I am currently in my last year at York University for teaching, specifically Primary/Junior grades and I am excited to finally be moving into the working world soon!

Omar: To say it in simple terms, the past 12 months, or 13 months to be exact, have just been the most amazing experiences, moments I’ve had in my entire life. Being able to travel, being able to help my mom, being able to just enjoy life for that moment, I’m just so grateful for everyone at Student Life Network.

I’m just so grateful because my life has absolutely changed for the best. I mean, last year I graduated from the university, and to be honest, I was very nervous because I had so much student debt but I also wanted to continue, well my education, and I just didn’t know where I would get the money from. And this happened in that moment, just really lit like a light in my life and just was able to help me progress and to continue my future without having to worry about financial struggles, not going to stop. So I’m super grateful for everything and the past year, it’s been the most amazing time I’ve had in my entire life.

Ben: The biggest effect it’s had, really, is that I got to go on my first trip this summer that was part of the prize. So I went to Costa Rica for three weeks and that was a big part of my summer. So, that’s the most direct effect it’s had on me. But yeah, the money’s definitely nice.

Canada's Luckiest Student winner Ben Westmore
This could be you.

What advice do you have to other SLN members who have entered CLS?

Tori: My advice would be to take every chance or opportunity presented to you! Also, take full advantage of Zombie weekends/events!!! They are game changers where you can make up those ballots that you potentially missed when life or school was putting you through the wringer! I would also suggest working together- there were times when I couldn’t solve something and even my Googling didn’t help me, but friendly members of the SLN fam would either nudge me in the right direction or share their answers. It’s more fun to work together than against each other, students should stick together

Omar: ​First of all, don’t give up. I mean, I remember when I first started university and it was always looking for different places where I can enter a contest to win a fellowship. And I’ve been entered a network for the past four years and I every entry that was possible, I entered it. It doesn’t matter if it was like in someone’s Facebook or Twitter repeating something. I was doing that it just to increase my entires, I believe I had crazy but over 2000 entries and I thought there’s a kind of a meter at the top that says like the average 25 in a weakness based committed and never even when I never won the first three times I never give up.
So that’s one thing you guys just keep in mind, just don’t give up and keep on going and be thankful for whoever wins because you know it’s something that’s, yeah, I’m just saying don’t give up and just keep going.

Ben: What I did, really, was just whenever I had some free time, I’d go on the site. Usually, it was at work because when I work at the community centre, there’s not a whole lot to do there, to be honest. That’s mostly the summer. So I went on the Student Life Network site, and I did their riddles and the things you could do to get extra entries, like going onto sites and signing up for things, just anything that would improve my chances. Even though I did a lot of those, I didn’t really expect that I’d win. So obviously, since the chances are so low of anyone that enters winning, don’t get your hopes up too high. And then especially if you don’t get your hopes up too high, it’ll be that much better when you win.


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*Opinions expressed are those of the author, and not necessarily those of Student Life Network or their partners.