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Uprising: Making the Impossible Possible with Jess Shortt


The Shortstop digital director on working from Halifax, the industry’s need for better teaching systems, and why ‘Where in the World is Carmen Sandiego’ played a pivotal role in the work she does today, writes LBB’s Josh Neufeldt

Uprising: Making the Impossible Possible with Jess Shortt

As an old boss of hers once joked, “No one should ever say ‘it’s not possible to do this’ around Jess Shortt. If you do, she’ll immediately start looking for a way.”  

There might not be a better statement to represent the ethos of the now digital director of Shortstop. Creative, dedicated, and always seeking to learn something new - either for future use, or just for the sake of it - Jess is always trying to innovate and prove that the unthinkable is only seemingly impossible. 

The reason for this? The 1985 video game, ‘Where in the World is Carmen Sandiego’, which she says was critical in helping develop her global perspective and gumshoe nature. “I love solving puzzles and getting the answers, so ‘Carmen Sandiego’ was right up my alley. It was all about detective work, which is engaging other people and hearing out what they know and what their viewpoint is, in order to piece together the answer.”

To this day, Jess affirms that the lessons learned in-game translated perfectly to her working life. “It taught me that I don’t have all the answers, and that I need to look outside myself (‘investigate’, if we’re keeping with the theme) if I want to find them,” she says. “It's a blessing and curse - the need to know all the things and answer all the questions and not leave a question unanswered - but I think it’s what makes me good at what I do.” 

There’s a bit more to Jess’ story, however. Growing up in a small town, she describes herself as a shy, introverted kid who spent a lot of time watching people to absorb what was going on, and reading. In the case of the latter, voracious doesn’t even begin to describe it, unless by ‘voracious’ one means, “regularly having the librarian override the system to check out more books.”

“I would read everything I could get my hands on, whether it was books, encyclopaedias or the newspaper,” she says. “I had binders stuffed with clippings and house floor plans from newspapers, entries copied from the encyclopaedias along with my own fiction writing, stored with no real regard to order.”  

And, this would only grow stronger once Jess’ mom introduced her to computers. Although this was during the era of dial-up, well before a computer was a common household item, Jess would spend hours upon hours scouring the web for more information about anything and everything (assuming she wasn’t playing ‘Carmen Sandiego’, of course). 

It was here that the first inkling of her future career would emerge. Although Jess notes that she didn’t have anything specific in mind when thinking of what her adult life would look like, she knew two things. Firstly, she didn’t want to end up at a desk, filling out spreadsheets. And secondly, she enjoyed developing websites - reading all the HTML guides she could find and playing around in Paint Shop Pro whenever she could. 

“It never really occurred to me that I could get paid for making websites, or that the brains behind the Gushers ads I was super fond of at the time were paid to do that,” she says. “So, instead, I actually went into university with the intention of becoming an architect.”

That didn’t quite pan out. Because the program required two years of general studies first, Jess opted into the computer science program to pass the time before officially starting. However, a single course in web development was exciting enough to sell her on a change of direction. “I’m not so sure that computer science itself really translates to what I do day-to-day now, but it really gave me the foundation for making websites and the digital comfort zone to use as a launching pad to other areas of the industry,” she adds. 

Specifically, Jess started out as a developer, albeit one who was constantly worried about a future of repetition - tasked with doing the same thing over and over again. “It stressed me out a lot when I was in the early days of my career, working at companies with a focused product,” she says. “I kept thinking that there was only so much you could do with one thing, and so I messaged an advertising agency without really knowing what I was getting into. I liked that they were working on so many different projects and I was lucky that they decided to take a chance on a junior developer.” 

The jump came with its own unique set of challenges, however. Jess recalls that in the early days of her career, she was left alone more than not, which forced her to figure out what she was doing by herself, in an era when digital tool adoption was just catching on. “I’m independent almost to a fault, and that really helped me in the early days,” she notes. “The biggest takeaway for me was that no one else can learn things for me.”

This was certainly true of Jess’ first professional project, in which she was assigned the task of creating recruitment ads for a local university via Flash. “I hadn’t worked with Flash before and I also didn’t know how to build ads, so most of what I remember was feeling totally lost and trying to prove my worth at the same time,” she says. “As such, I felt very accomplished when I finished something like 40 different executions of the ad, came up with a page template for displaying them to the client, and they were accepted by the ad distributor in one go.” 

The same theme can also be seen in the project that, according to Jess, changed her career. While at her first agency, she found herself responsible for animating a video for the Bruce MacKinnon exhibition at the Art Gallery of Nova Scotia, despite having very little experience in that realm. In fact, she still vividly remembers one interaction in which, when asked if she could do it, she responded “Of course I can” while simultaneously googling how to use After Effects. 

“The team had so few notes on the work in progress that I felt like I was doing something right, even though I was learning as I went,” she continues. “That was a turning point because it gave me the confidence and the voice to take on new projects outside of my comfort zone, and allowed me the chance to advocate for myself in areas I was interested in and wanted to work with (which was just about everything).”

Since that point, Jess has been able to stick her fingers into just about every part of the process - from strategy to design, and data analytics to writing SEO content. And, while she’s quick to express that she’s been blessed with some great leadership that trusted in her ability, there’s also no denying that she’s had to stand up for herself and her abilities on numerous occasions. In particular, as a female web developer in a generally male-dominated industry, Jess has had to consciously learn to be assertive, and how to say things in a way that leaves no questions. 

“It was something I had to learn quickly,” she adds. “There have been many times it hasn’t worked, no matter how confidently something has been said, but another lesson was learning to pick which battles to fight and which ones to let run their course anyway.” 

But nevertheless, Jess has remained undaunted. In fact, she wouldn’t even call any of these things her biggest challenge. Rather, she would give that title to the difficult task of learning to get go of a project. “The idea that other people will see it and have comments on it is the hardest part of making anything,” she says. “I used to have a tendency to hoard something I was working on until the very end because until it was perfect, no one could comment on what was wrong with it. It’s something I’ve tried very, very hard to undo over the past few years, because I know how much creativity can come from collaboration, and how much getting other people’s perspectives can change how I think about a part of a project and how it can change the project itself.”

In turn, this can make time management a point of difficulty. Specifically, she highlights the fact that it can be very tricky to juggle multiple projects and timelines simultaneously, but that learning the art of it has been exciting - and has been for most of her career - something which reflects Jess’ overall mentality of finding joy in the challenge. 

“My absolute favourite part of what I do is that every project is a new challenge in an entirely different way, and most of the time, is pulling me out of my comfort zone,” she says. “There’s always something in every project that is completely new among the familiar, and that keeps things fresh and interesting, although sometimes also frustrating.” 

However, the way ‘new’ is approached, Jess believes, sometimes needs to be done better. Specifically, the lack of support and guidance for new starters is something she'd like to see changed, especially given her own experience. “It’s frustrating to have been through it, and to see and hear about other people going through the exact same thing,” Jess continues. “My introduction to the industry is coloured by feeling alone and lost and not feeling like there was anyone to ask to get answers, and I know I’m not alone in that.”

To this end, Jess thinks that advertising might do well to pick up some of the values of computer science. As she puts it, “When you’re helping someone with a code problem, the ideal way to approach it is to guide them towards the answer, have them explain how they think it works, and ask questions that make them consider the solution without giving them the whole answer.”

Comparatively, she adds that in advertising, there’s a general “grit your teeth, get through it and come out the other side better off” view which is super prevalent - ironically so, considering advertising should be a space where collaboration and learning from each other is prioritised. “A lot of people start in the industry and they’re given very little to go on. Yes, some are people who have the ability to figure it out, but if you’re a little shy or don’t know who to ask questions to, or even how to ask, you get left behind.”

It’s for this reason that Jess hopes to see strong mentorship develop alongside the movement towards genuine and sincere advertising - another matter she is equally passionate about. “I’m really excited about the push towards honesty and authenticity in advertising, including the push towards diversity and inclusion,” she says. “Hopefully, we begin to see a clear delineation between companies who are just ticking boxes for profit’s sake, and ones that are actually authentic and genuine about what they’re representing. I believe this goes hand in hand with companies thinking about a sustainable future, and being invested in it.”

For her, she’s found this in, perhaps, an unexpected place. Where much of Canada’s advertising is run from Toronto, Montreal and Vancouver, Jess’ location on the east coast might be considered a rarity within the national scene. But, given her background as a web developer, she never really understood the idea of being limited in location, especially given the potential of the internet. 

“I’m currently based in Halifax, and I’ve found people here to be generally nice, very welcoming and willing to talk about the things they’re interested in and try new things,” she says. “I’ve also lived in Toronto while doing an internship, and never found Halifax to be missing what those bigger cities have… Except for the trust in the local talent to make things that work. Halifax is a growing city and has the potential to be an advertising hub. There’s great work that’s come out of here and there are award winning agencies here.”

Additionally, she believes that the regional municipality is the perfect place to pursue creative hobbies - of which she has many - both in and outside of work. “For a city of this size, it definitely feels like there’s a lot of opportunity to get weird with whatever personal interests or creative outlet you’re looking for,” Jess continues. “I’ve also accidentally taken on a lot of hobbies that have a creative aspect to them, and I’m in the learning stage of a lot of those right now. Between playing the piano, learning new languages, playing baseball and volleyball, drawing and writing, it’s definitely a good way to take a break from work without completely shutting my brain off.”

Not included in that list, but perhaps the most important of the bunch, is Jess’ pastime of coaching a girls baseball team filled with 10-12 year olds. It’s fun, rewarding, and something that, she notes, usually comes up pretty quickly in conversations with pretty much anyone she talks to. Moreover, it also reflects Jess’ belief that inspiration and strong viewpoints can come from anywhere, regardless of age. 

“It’s been an extremely rewarding experience that I’ve learned so much from. [The girls] have such interesting, hilarious perspectives and they’re not afraid to try and fail - something I find admirable, and try to apply to my own work. I love the idea that if you’re the smartest person in the room, you’re in the wrong room… and since I’ve never felt like the smartest person in a room it’s always been an educational experience.”

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Shortstop, Wed, 19 Apr 2023 17:06:25 GMT