We were lucky to catch up with Jessi Aylward recently and have shared our conversation below.
Alright, Jessi thanks for taking the time to share your stories and insights with us today. We’d love to hear about a project that you’ve worked on that’s meant a lot to you.
I love this question because I don’t personally believe there should only be one and so strictly so. I believe there’s different degrees of meaning, and I’m not trying to be sappy, I’m being honest. If you were to ask me this in the sense of my career my answer would be, a project I worked on for The North Face, where we created a TNF look a like to a New York Taxi (TLC), prior to Lyft/Uber being huge) and we built a custom screen that if people played with they could find easter eggs where we would take them out of the city. That is if they were willing to drop everything right then and there. We took people mountain biking, rock climbing, hiking, out in a hot air balloon, surfing, and more. It was just a lot of fun and hard work in a quick timeline. If you were to ask me about my favorite charity moment, it would be the fundraisers I raise for the dog rescue group I foster for, https://www.heartsandbonesrescue.com/. I do them once or twice a year, we bring adoptable dogs out, play games, have raffles, and drink specials at the lovely Gran Torino in Williamsburg. If you were to ask me my favorite art piece I’ve made, I’d say that I recently made a painting using three things I love: water paints, collage items from old magazines/old advertisements, and resin – which I have picked up since covid. I love my three art worlds coming to life. If someone asked me my biggest self achievement, I would say the book I wrote getting published soon! It is part about my life as a woman in advertising, starting from scratch with near to no one to help me, besides one great friend Momo who helped me get my first job! To dating in New York, dealing with ridiculous moments. I have no fear, I just want to let other women know that’s ok! And what’s my favorite project from my hobby? We’ll I would currently say I’ve recently up’d my hobby of working out by taking Aerial Classes thanks to an Aerial Yoga teacher I met at Crunch, Izzy, who saw how much I loved this artistic physical form, that she invited me to an aerial school where she also teaches, I’ve learned new ways to perform, I’m stronger than ever, and I’ve learned how to keep time and dance through a performance, I’ve never been able to do that before. I was always off beat, but I’ve found my way to connect to music and my physical body without running (I hurt my foot a few years ago and this is actually easier on my foot). And I would say everything I just listed has inspired something else in the list – that’s why I don’t think one is good enough <3.
If someone asked me my biggest self achievement, I would say the book I wrote getting published soon! Keep an eye out for it, it’s titled, And I’m only 30 — (publishing took a few years past 30 hah)
Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
What’s kind of beyond strange is “how I got into this industry”, I actually was in high school and I saw the movie, The Holiday – yes that one with Jude law, Jack Black, Cameron Diaz and the pretty british woman i always forget her name. I wanted to make movie trailers, so I joined the news show at high school, we filmed weekly and showed one skit a week, joined year book, photo club, anything I could to become her and get that house! I got an internship in NYC at a movie trailer house and I was bored, all I could do was watch like the same 5 minutes of a movie, until it became 3, and then 1.5 minutes. I was too fast paced for this. So I went back to college in Minneapolis (MCAD) and asked my professor if there was another option to do movies, but i knew my dream of independent movies was minimal due to money it takes to make and you earn very little at first. And he suggested advertising, so the next year my internship I decided would be in advertising. I then thought I wanted to be an account manager (client facing) i was so wrong – I wanted to be a producer, and as my career became more lively as did I in that role, and that’s how I became Executive Producer (contracted) at Big Spaceship and owning my own Company, Water and Air (thisiswaterandair.com). There’s a bit more to it but didn’t want to over bore you.
I constantly solve problems, and I very much enjoy Big Spaceship and a lot of places I’ve been working at since covid hit hard. People started to respect time, we worked so hard in advertising at first because we couldn’t have a life, but then one day we realized we needed to turn off, and everyone kind of did at once. It was beautiful. But everyone does there part at smaller/mid agencies which is what i love and admire. It’s work hard to play hard, play harded cuz why not, and then rest up, repeat.
Do you think there is something that non-creatives might struggle to understand about your journey as a creative? Maybe you can shed some light?
I don’t know if it’s necessarily something hard to struggle with, but I know a lot of people, non-creative or creative people wonder how I do so much, but I really think my goal and what I enjoy is being really good at a lot of things vs a professional at one or two things. I really find myself inspired between projects/works/even hours of my day.
How about pivoting – can you share the story of a time you’ve had to pivot?
I have been freelance just a bit over half my career, but full time the other nearly half. So I quite often change my direction. I try to roll with the punches, but not as “someone will guide me” as I would want! I guide myself often too much, so my roll with the punches is more about me being use to having to change things last minute. Get comfortable with the unpredictable.
Contact Info:
- Website: hottmessjess.com
- Instagram: https://www.instagram.com/hottmessjess/
- Linkedin: https://www.linkedin.com/in/jessaylward/
- Twitter: @thehottmessjess
- TikTok: @thehottmessjess
Image Credits
Photographer: Victoria Esparza https://www.instagram.com/heyvvictoria/ Art Direction Juliana Feist: https://www.instagram.com/juliananotana/ Retoucher/Editor: Dylan Boye: https://dylanboye.com/