Failure Diaries: Amy Eaton

Amy shares her journey through multiple attempts at starting her own business, and how she finally found her niche.

Dottie Omino
Fuckup Nights Toronto
9 min readAug 25, 2017

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Tell me a little bit about yourself…

My name is Amy. I’m originally from Nova Scotia. I moved to Toronto in 2009 and I live here with my partner, my baby, and our two dogs. I’ve had 3 totally different careers so far. I started out as a horse trainer [laughs]. When I realized that wasn’t what I wanted to do forever, I went to university and started working with kids — in child welfare and mental health. I did that for about 10 years, and then eventually it just got to the point where I got really burnt out and felt like it wasn’t the right place for me. I kind of always did photography on the side while I was working; I love photography, and I’ve always been really passionate about the craft. So I developed and evolved it into a thing over a really long time. And now, I own a photography business where I specialize in product and brand photography, and teach an online DIY photography course for handmade sellers.

What’s your superpower or spirit animal, and why?

I wanna say that my spirit animal is a sloth — but I feel like that’s going to come across the wrong way [laughs]. But they’re so chill, and I’m like that — I’m very laid back. I can go home, sit down, and just look out the window for hours! So yeah, if I had a superpower, it’d be being really chill!

What’s the best piece of advice you’ve ever given?

From my own personal experiences, I’ve learned how important it is to find that thing that you love, and do it. It doesn’t matter what it is. Just find it, and do it.

“Forget about what you feel like you should do or what society tells you you should do; do the thing you want to do.”

How has your background and/or upbringing influenced the way you experience failure?

My parents didn’t put a lot of pressure on me to be an uber successful person, so I didn’t necessarily have the normal perception of failure. That’s probably why I’m so passionate about finding the thing you love because they really believed in that. I remember my mother telling me very clearly — forget about what you feel like you should do or what society tells you you should do; do the thing you want to do. My parents would always tell me to try my hardest and it’d be fine. So for me, failure was not trying at all.

Has fear of failure ever held you back? Can you share a story about that?

Everyday? [Laughs] Yeah, certainly. I think fear of failure definitely stopped me from starting my own business in the past. There was never really an opportunity before where I could have safely done it — and I think that’s a realistic fear of failure. I’m all for chasing your dreams, but you still have to pay your bills. So it was a fear of not knowing whether I was going to make ends meet that held me back. Ultimately, it was more of a delay. It wasn’t the right time, and I think that now is the right time.

What’s the fuck up story you’d like to share with us today? You mentioned that it’s around your photography business?

Yeah. My first job in photography was a pet photographer — which was more of an apprenticeship thing. But then, after, I fell into the trap of going into the thing that made the most money in photography at the time. As a female photographer living in Ottawa, the money was in family and wedding photography. So I started doing that, and I denied myself finding my niche. I struggled for a really long time and I wasn’t succeeding because my heart wasn’t there; I didn’t have the passion for it. I loved photographing people, and I was pleased with my work, but it wasn’t enough for me to keep it going. So eventually that business failed — and rightfully so.

Can you walk me through the emotional and psychological effects of this experience?

It was an overwhelming experience for me. Running a business is never easy. It takes a lot of focus but, at the time, I was always looking somewhere else. I really wanted to find my niche, but I was really lost. I would be doing one thing, but I’d always have an eye on something else I could try. I tried shooting some commercial stuff, did some photography work for businesses, and even explored shooting boudoir. But it just wasn’t coming together.

So the process was a very tough one — exasperating is the feeling that comes to mind. Especially because it was such a repetitive process switching from one thing to another. And it’s a very difficult pill to swallow every time you realize that what you’re doing isn’t your thing. In the moment, it’s really depressing because you put in so much time working on it. I got to a point where I was really sad about my work as a photographer. I felt so uninspired and defeated that I decided to walk away from it and not take any more photos.

What inspired you to pick up photography again?

I ended up getting divorced, which meant that I really needed to have a stable income. So I moved to Toronto and took another job working with kids. The job turned out to be the worst I’ve ever had because I had to work with someone who had a very toxic personality. So I ended up quitting that job for my creative pursuits once and for all. When I quit, I still wasn’t sure what I would pursue, so I began by trying everything for a while. I started a t-shirt line, I tried going into marketing, I did some VA work — I even did a little bit of photography… I was just grasping at straws doing anything that could pay my bills and allowed me to be more or less self-employed.

And then I got pregnant. At the beginning of my pregnancy, I had high blood pressure and I was really worried about how that was going to affect my health and the baby’s health. I didn’t want to go on medication, so I did everything I could to minimize my stress levels. I looked at everything I was doing and thought seriously about what I both loved, and was the most realistic way for me to have a sustainable business. And it was my photography.

What made this attempt at building a photography business more successful than the others?

When I decided to focus on photography again, I wasn’t quite sure how I wanted to approach it. So I ended up in a lot of Facebook groups. The support from those groups really helped me find what I wanted to do. For one, it helped me figure out where there were needs. I’ve been part of the handmade community for a long time as an outsider because I have friends who are makers. And I know the struggle is real with their photography — they can’t find success without great photos. But it’s a really tough thing to learn; there’s so much information on the internet but it’s hard to find and it’s not directed towards them. I have a lot of love for that community — I’m in awe of their talent and have so much admiration for their work. So I just felt like that was something I really wanted to dig into and start pushing myself towards.

Another thing that helped me narrow it down was a discovery call I had with a business strategist. I really just wanted someone to help me come up with a plan for how to move my business forward. But then she had some questions for me like — who my ideal audience was, and what specific services I was going to offer. She emphasized that if I didn’t figure those things out, I couldn’t really move forward. It was a really tough call — I got off the phone and cried for a while. But she was totally right. She triggered my fear of failure, but also helped me start narrowing down what I wanted to do. I was already writing an instructional blog for makers. Plus online courses are very hot right now, and there was really no one else doing what I wanted to do. So that niche was available, and I knew that I could nail it. I knew the pain points of the community, and I already had some connections, so I just went for it.

“At the end of the day, they aren’t really “failures” as much as experiences that guide you in a different direction, or help you narrow down your options.”

Can you speak to being a solopreneur and navigating those moments of uncertainty?

Joining Facebook groups with other creative entrepreneurs was a huge part of what kept me going. Every single person there has been through or is going through the exact same thing. And everyone is there to support you when you need it. Just recently, before I launched my course, I made this wish list of services that I wanted to hire — knowing that I didn’t have the money to hire all these people. So I went on the groups and posted the list asking for help in exchange for my photography services. And I’ve had some awesome collaborations. So there’s both tangible stuff like that, and also just people willing to be there and support you.

I actually connected with a woman who runs a group for Etsy handmade sellers. I joined her group as well as a few others wanting to be where my audience is. I happened to message her once asking for permission to promote a free course in the group, and she was all for it! And now she’s my biz bestie. We talk everyday about everything, and she’s opened up her community to me entirely — so she’s a really big part of my success. The networking you can do online is really awesome right now!

How would you approach failure now that you know what you know?

There will still be that fear of failure, but I would like to think that I will welcome it with open arms. I’ll probably still cry and take days off to figure things out. But I’ve learned that it’s important to take what lessons there are from the failure, and use them to power yourself forward in a direction that’s better for you. At the end of the day, they aren’t really “failures” as much as experiences that guide you in a different direction, or help you narrow down your options.

What would you tell the younger you if you were to go back to 10 years ago?

Be super open-minded about the direction you’re headed in. And don’t box yourself into thinking that you have to be something because of you’re female, or you’re a certain age, or because that’s what everyone like you is doing. We’re getting to a point where we need to really challenge those ideas of what’s expected. You should always try to find the right fit for you. Even if it’s obscure, you should still work on it. Make it your thing.

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Dottie Omino
Fuckup Nights Toronto

Operations @Amidship. Passionate about creating user-centered products and experiences. Intersectional Feminist. Highlighting women in tech @ www.inherownway.ca