#75 Storytellers I Admire: Amy Shio

How to show up authentically, even online



Have you ever wondered what it’s like to live out part of your life on the internet? AND To have people interested in it? Many years ago when I was still a reporter, I went to a glitzy fashion event in Toronto and was lucky enough to meet Amy Shio. Over the years I have followed her online as she evolved from investment banker to stylist and blogger to style inspiration and now, “person of interest”—that is what her bio says and if (and when) you follow her you’ll quickly understand why.

Amy aka @lesbest makes the internet, specifically social media, a better place. She is an expert in the medium whose inclusion in your feed adds a bit of lightness, a lot of inspiration, and a whole new perspective on how you may choose to share your story with the world particularly your sartorial story. I was lucky enough to sit down with her sipping green juice and chocolate smoothies at a juice bar in her colourful Kensington market neighbourhood in Toronto. We chatted about purpose, authenticity, and forging your own path as upbeat music from all over the world played in the background and cars drove by on the narrow street beside us. It was a lesson in defining yourself in terms beyond just what you DO how you are productive each day we can all benefit from.

The conversation was an inspiration to me and I thought would be a great way to continue to dive into a new year here in this Adventure in Storytelling. It’s another long one, so grab a cuppa and dive in to what it means to tell stories as a person of interest on the internet.

Quick Reminder before we dive in: I have a free storytelling webinar coming up this Thursday January 13, 2022 at 12pm ET and I don’t want you to miss it. It’s called Storytelling 101: Finding Your Unique Voice and Sharing it With the World. I’d love for you join. It’s a great way to dive into your story as you head into the new year. There will be a recording sent out following if you can’t make it at the time. You can sign up for the webinar here.

Amy Shio also known as @LesBest

NB: This interview has been edited and condensed for brevity, but I tried to leave as much with you as possible so you get a real lens into another perspective and experience of life. It’s long so I’d encourage you to grab a cuppa when you have a bit of time and dive into the world of one storyteller for a bit. Enjoy and let me know what you think in the comments.

Chantaie: So, the first question I always start with is, "What's your story?" And you can interpret that however you want and share whatever feels right to you.

Amy Shio: What's my story? To me, I feel like it's such an interesting question because within our lives we have so many different stories. So, I'm so confused as to which one I even want to start with or how each chapter equals the person I am today. But I would say that my story is that I'm a first-generation East-African-South-Asian-Canadian, who was born and raised in Rexdale. That's important to me because it adds a layer to who I am and how I grew up. I'm the daughter of two immigrant parents who moved to Canada and started their own businesses. My mom just wanted the best for my brother and I and so pushed us into completing post-secondary education as many immigrant parents do; checking off the boxes of a doctor, a lawyer, a businessperson, somebody that didn't have to work a regular mall job or a nine to five or a factory job. That was important to them because they had their own business—all of our family’s stores were in malls, so their hours were nine to nine. What that even equals for me is that my brother and I basically self-parented after school at home or went to the store to work.

I ended up getting my undergrad in communications and business. The next layer, which is super interesting, was the double cohort. I graduated in the grade 12 cohort of Ontario’s Double Cohort year [when they eliminated grade 13 and twice the number of kids left high school in the same year]. So, getting jobs was a really funny time when we all graduated. Obviously getting into university was hard, but getting a job was really hard. I had always wanted to work on the communication side of my degree and not the business side, but as life would have it, I ended up getting a job in a mail room at an investment banking firm. They knew that I had the degree in business and communications, and I ended up moving up and working there for 10 years. I became a VP in investment banking and managed a team by the time I left.

But during that same time Twitter was launched and then Instagram. I was posting my outfits on the internet and then I created my persona, Les Best. It was honestly just to curate things that I deemed Les Best and had nothing to do with anything, but it was like, oh, find these really interesting. So, I'd just be like, this is what I found, or this is how you can spice up an outfit. And I guess I ended up realizing that it was my passion. It was a cool way to have an outlet while also working in finance. I started styling wives of people that worked in investment banking and hence became a stylist on the side. And then I started working with a really cool celebrity, styling her. That led to a lot more things.

I started working on my art on this side and I realized that a lot of what I was doing brought me more joy than work. I kept saying my investment banking job was just my job, I took off my bear suit and became Amy. But when you work in a job for 12 hours a day, that is really you. Parts of me were getting really crusty and jaded and I realized that if I didn't pursue trying to be a full-time artist, I wouldn't do justice to the person inside that was really trying to shine through. So, I ended up quitting after 10 years and trying my hand at just being an artist and doing all the things and seeing what made me the most happy. And here I am. I call myself a person of interest because I feel like there are many layers to me.

I don't think that I necessarily need to put myself in a box the way that society makes people. To have to say what you are, and you're only defined by the things that you do. And that makes me really happy. And so, I get to have really fun conversations with people like you, but I get to go paint and get paid for it. I get to model and get paid for it. I get to have unique experiences. And my community, I'd say, that follows me on social, they're very mighty and they're really devoted and understand the layers that equal me. Growing up in Rexdale and being a tomboy, also having immigrant parents and, but then having a job that I really didn't really enjoy and then thriving and being really happy and positive in the ways that I am, really resonate with them and show little girls like me that don't have a role model, of women like me that it is possible. I don't know. The story's still going. We're still rolling.

I love that. I was going to ask you to define what you do if you had to say, ‘the thing,’ but I’m going to leave person of interest as the thing. When you think about the work that you do and the world that you live in or the many worlds that you live in, how would you define a story in that context? What would you say makes a good story?

AS: I think a good story, honestly just boils down to authenticity and including the raw parts of a story. Even if they're not the most comfortable to digest and swallow. I think that that's really what telling a good story is. Even in going back to an Instagram moment, no one really cares about glossy photos. People like seeing raw and they like seeing the real stuff that really happens with people. I really do think that just being raw and authentic as much as you possibly can, without obviously hurting your mental health or hurting someone else, is the telling of a good story.

So, I want to dive into that a little bit. Your persona, Les Best, and the world or the life that you live on the internet or social media specifically. So, talk to me a bit more about what that's like for you and how you approach it in a way that allows you to tell authentic stories.

AS: I think that the really interesting part about me is that first, the life that I live on the internet is really the authentic life I live in real life. If we're in Kensington Market recording this today, this is what I will share. I'm not going to share something that isn't really true to my life.

And how do you stay true to that notion of authenticity?

AS: The way that I personally stay true to it, and I think that this is super key for anyone that's in this space, is not to take themselves too seriously. At the end of the day, when people buy into their own bullshit of, I am higher than thou or cooler than thou, that it's not sustainable. It really isn't. I don't ever go into a space thinking someone knows me. I don't ever walk in and expect anything from anybody. I really do feel like I am... I don't know, I'm just Amy. And that's it. That's why if I changed my name now maybe my name on Instagram would be Amy and not Les Best. At the time, having a fun name was the whole point of having a handle. And therefore, I created one around my blog, but Les Best and Amy are synonymous with each other, they're the same. What I'm wearing right now will be what you'll see on the internet. You won't see something else. What I put on the internet, therefore, and when I have those over-the-top outfits, I absolutely wore them. And if I'm having a night out, I won't post in real time only because I do like enjoying a moment. We've been together and I haven't taken my phone out once. You may do a job on the internet, but that doesn't mean that your life is dictated around the internet. And I think it's what I said. It's not buying into the bullshit of what the internet thinks you should be doing.

A taste of Amy’s instafeed

Right. Is there bullshit that you think the internet thinks you should be doing in the context of the work that you do?

AS: Yeah. I think that you're meant to share a lot. It's like in any industry. If you're a writer, what are your fellow colleagues doing? And then you're like, ‘All right. Well, why am I not doing that?’ It's carving out a little space for yourself to be like, ‘I'm not doing that because it’s just not me and that's okay. And maybe that's why I'm getting paid to do the things I'm doing.’ So, it's reminding yourself that it's okay to live in a certain silo; of not having to be cookie cutter. Especially in a creative field. It's not like I'm a doctor and I need to do surgery in a very specific way. That's the beauty of being an artist and being able to find your own path and figure it out on your own. And I think it's always just a constant reminder to slap yourself in your own face just to be like, ‘No, you're doing what you're doing authentically for yourself, you don't have to copy each other.’

But that takes time. It takes time to develop that. I don't think that if I were to speak to you when I was 22, I would have said what I just said. I would've been like, ‘oh my God, I haven't done an unboxing story but I got that same gift so now I need to unbox, so the internet knows that I also got the same thing.’ Whereas it's just so different now for me, I don't feel that that is a true marker of my success.

Awesome. Okay. So, the next question is usually when did you decide or realize that you were a storyteller? But I’ve found that it's important to ask people first, do you consider yourself a storyteller?

AS: (pause) I do. I do consider myself a storyteller. It depends on where the story's going to land and who I'm speaking to. I got the honour of speaking to the grade 12 graduating class of my high school. And it was super important for me to go back to where I came from and be reminded of little Amy and just figuring out how little Amy would navigate in a big city. To the kids that grew up in my neighbourhood, the idea of Downtown Toronto is so foreign and it's only 25 minutes away. So, in those moments, it's important for me to share my story and tell these kids how I got from a place where we thought that we would never be able to leave to seeing people like me do the things that I do and telling them that a lot of it has to do with being a good person and never knowing where your blessings will come from.

Do you see storytelling as a tool for inspiration?

AS: Sometimes.

In what way?

AS: Even with just talking to kids from my neighbourhood. I didn't have anyone that I knew that, not even did what I did, but even moved away to university. Nobody in my family did that. I think that it can be inspirational, but I also think it depends how we approach it. Because I don't think that all positive stories are inspirational; sometimes they’re detrimental.

Okay. Say more, say more.

AS: I guess it's the way in which you do it. It could be tacky sometimes. I believe in bad energy, in evil eye kind of stuff. So, then it's like, ‘Well, who the hell does she think she is, talking about all this?’ That's why the granular details in a story matter, because it's not like I just came from Rexdale, came to Toronto and boom, I'm Amy. There was a lot of blood, sweat, and tears behind the person that I am, even in becoming an artist and telling immigrant parents that you're going to leave a six-figure job to go and paint and do things that make no sense to them. But it can be detrimental if you're just giving the glossy details of your experiences. I think that's why in storytelling it’s important to have those raw moments, it's important to say things that might not be digestible. Things are hard, but they're reality.

Thanks for sharing that. As you were talking, my brain was like, "I really want her to tell me what she does." Where I was like, "Define it." But I actually also don't want you to put yourself in a box. What I do want to understand though, is when you say you're an artist and you think about your art, what are you thinking about? What's in your brain when you're referring to that part of what you do?

AS: Like when I say I, Amy, am an artist, what am I thinking?

Yeah. What's the reference in your head?

AS: Okay, so you're asking me this question in a different manner, but in my head, I still feel like the question is, "What do you do?" And I can't even define that because if you were to shadow me for a day, you'd be like, "Okay, so you go for a run and then you respond to some emails and then you maybe pitch an idea to a client and maybe you film a reel, then maybe you go paint in the basement. Then you decide to cook, and you have Les Best Cookbook as a part of your Instagram, so you decide to make a meal." This is so weird, but I feel like I'm getting paid to just be Amy.

That's awesome.

AS: And that's why it's really difficult now, going from a perspective of ‘I worked in a bank, and I did deals for big oil companies; I sat at a desk and I sent out press releases and filled allocations.’ Where that is a defined job, I feel like I just live my life and I get paid to live my life. And I feel like people, I'm not going to say the word inspired, but are intrigued by what I do and therefore follow me in those spaces. And they like me for different reasons. So, there'll be the mom that likes me for the cooking, but then there'll be somebody that's really into fashion that will like me for that. And then I've posted a lot about being a Pisces. So, the sensitivity group will come around for that. I can't really say what that equals because today, I don't feel like painting. But that doesn't mean that I'm not going to create art while I'm making food. We're in Kensington Market right now. I'm going to go to the market, and I have an idea of what I'm going to make for dinner and likely will share that on the internet. Maybe not depending on my energy. But I feel like that's a big part of it. And then what ends up happening is that people in PR follow me and they're like, ‘Oh, she cooks, let's send her X, let's do a partnership with X because this makes sense.’ ‘Oh, she and her husband like to go for cocktails. Okay.’ Now there's an alcohol brand. ‘Maybe this would be interesting, because her followers clearly pay attention to what she eats drinks and stuff.’ And then it's a fashion moment or a beauty moment. So, I just naturally share things that I really like and I think that's what the difference of my entire approach is about. If I like a mascara from a drug store, I will say that. And that equals authenticity to my followers rather than every single thing being sponsored or paid.

That's why I can't really define it because I think I just do things authentically and jobs come to me. I was reading something about, Human Design, it's a personality system.

I'm a Projector. I know exactly the system you’re talking about.

AS: But basically, the energy that I have, and it's not to say that I'm lazy, but jobs and opportunities come to me. But they come to me because of the person that I am. So, I mean if I had another energy and I was pitching jobs, I'd probably be a millionaire by now. But I'm just not, and I'm lucky enough to have the right eyes on me, I think.

So, you've talked a little bit about the different types of followers that you have. When you think about yourself in the context of sharing stories and being a storyteller, who's the audience that you're thinking about or who's your audience, in your opinion? Or who do you create for? Is a better way to ask that question.

AS: Myself. I definitely create for myself. I create things authentically because I like wearing them. I like eating them. I like drinking them. I like the style of them. So, a hundred times out of a hundred, I'm not doing something because the internet thinks that it's cool right now or the internet thinks this is the trend and so I need to all of a sudden find bell bottom pants. Pretty sure I probably didn't throw away my first pair of bell bottom pants and therefore I have them. But I definitely generate for myself and hope that there will be people like me that like that. Yeah. I don't really have an audience that I'm thinking about that is my target.

I love that. So, who's a storyteller that you admire when you think about your world and the types of stories you're exposed to? And when I say your world that literally means your world, everything, not just the internet. Who's a storyteller that's doing things that are really interesting to you right now?

AS: Oh my gosh, Lena Waithe.

Yeah, okay. Tell me more.

AS: She is just so authentic with the stories that she wants to tell for her audience. She has a very specific eye. She has a very engaged audience and she knows that there was, for the longest time in Hollywood, not producers and writers that were Black that were telling stories for that community. And then to layer on top of that, being a queer female. None of those stories were ever really told in the mainstream. And so, I feel like everything that she's doing is for her community and is the epitome of storytelling, through lived experiences. And for me, I find her storytelling (LOUD car horn and ongoing rumble of a motorcycle) to be incredible. I just feel moved by it. So, I feel like it's people that really are the opposite of me—they have a specific eye and they know who they want to talk to and they know who their audience is that I admire.

Awesome. So why do you think stories matter in general? Do stories matter? You can tell me they don't.

AS: Do stories matter? Yeah. Of course stories matter, and that's why it's so important to talk to different people from different walks of life and different backgrounds, and ethnicities. It matters because first of all, it opens people's eyes up to somebody that they would've never been able to see. Your community that reads your stuff may not have ever known who I was before this and may either find me interesting or not. I feel like that allows people to form an opinion.

[things get really loud on the streets around us, but we keep going]

AS: Garbage Day in the market.

Yeah. Let’s keep going when this guy turns his motorcycle off. Okay. You were saying something about creating meaning through storytelling because I was asking why stories matter. They help people understand or form an opinion.

AS: I think we're lucky enough to both live in a city, but a lot of times, not everyone lives in a big city to have exposure to people like you and me. And we're siloed, even. I can see it with some of my family that lives in the suburbs. Their opinions are all the same, the people that they hang out with are pretty much the same. They're fed the same news and have the same opinions and aren't exposed to other things, and therefore would never see anything outside of maybe a Netflix or something that would actually show them another story. I think that's why stories matter regardless of what medium it comes from. I think that's why it's important to have this exposure. My husband always reminds me that you think that everyone around you is similar until you leave, because he's not from Canada. He always just tests me on things that I say, and he'll be like, ‘Well, not everyone is.’ It’s easy to forget.

Like when I am in Kensington Market, I just feel like everyone's the same. Everyone's a little bit all over the place. And a little hippie. But you leave and go to London or Rexdale and that's not the case. So therefore, exposing people to new things and showing them that your friends can be from all different backgrounds and not just the same community is important. I don't know. Does that make sense?

That was very cohesive. I know, you have a look on your face that you’re not quite sure.

AS: I'm not trying to bring race into it, but at the same time, in my mind, it's everyone hangs out with their own in the suburbs. It's just a fact. Whereas here you may be comfortable with what looks like you, but you may be more energetically connected with just different people. And I think that's where you get different stories here, just through friendships, that you don't really get that in a smaller town or a suburb.

Right. Right. And is there a story that you're thinking about sharing or that you're just excited about coming up in the future?

AS: I don't know. I think the next layer of...My brand or the next layer of what I would want to do in life is acts of service. That's what I'm excited about. I feel like I'm the happiest when I have moments of give back. I'm just trying to navigate what that feels like to me because I want it to be authentic. I always feel the most happy, even when I was younger, when I volunteer. Sometimes you have to grow up and you have to pay rent and pay the bills. And therefore, you are a little disconnected from what your purpose is. And so, I think I'm uncovering another part of me, which is about fulfilling my life's purpose.

That's awesome. Do you know what it is yet?

AS: Yeah, there are parts of it. You know that feeling of, ‘if I say it out loud, it's real?’ I'm too nervous to say it out loud because I don't have it perfect, it doesn't need to be perfect, but it's just not cohesive in my head right now. But I know that that's where the next trajectory of my life should lead me.

That's exciting. That's really exciting. Those are all the questions we have, partly because that's all the time we have. Is there anything that you wanted to mention or that you thought we’d talked about that hasn't come up that you wanted to throw out there?

AS: No. I'm so bad at this stuff because I just get so shy or nervous. What about you? Is there anything that you need me to fill in the blanks for?

No, no, no. I was going to ask you more about fashion and your perspective on that from a storytelling perspective. Unless you have something to add there. Do you think of fashion as personal style specifically as storytelling and what are the things you think about?

AS: Oh my God. Yeah. Okay. So personal style and storytelling. I dress based on mood and I'm not that person who picks her clothes out the night before and looks at the weather. It's just however I'm feeling in that moment, I will wear. Funny enough, last week somebody asked me if I had to describe my style what would it be. I said I go from a stripper to a grandma. From zero to 100. That is my idea of style because it should be mood based. If you're feeling sexy one day, then you wear something that exudes sexy to you. But if you're feeling conservative and like a classy little lady, then that's where you go. I love just being in the market and seeing people's style. Certain people have uniforms and literally they'll just wear a black shirt and denim and they look so incredible.

But with my style, I just have something to say all the time and therefore, being a little more introverted—I would describe myself as, an introverted extrovert—It's my way of being able to speak to the world without having to speak to the world. Even just in the last two years wearing masks, your expression goes away from your face and therefore what you wear can show joy or show the ability to just blend in, which is also okay. But I found even last year with the pandemic and everyone's walking around outside, you pay more attention to people's outerwear. I could go on with this for days.

Go for it.

AS: But in the pandemic, I decided that I was not going to buy sweatpants and a hoodie because in my mind history is defined by clothing. If you look at different eras, we remember what people wore. When we lived through Y2K, we didn't think it was a big deal because it was just Y2K. But you look back at that now because we're 20 years removed from that and you're like, ‘Holy shit, that was a movement.’ Similar to the eighties and the seventies and the sixties. The twenties, I feel like were such an elegant, cool time. So, I was thinking of that in the same way with this whole sweatpant movement during the pandemic. And I was like, I will not be a part of that story, although I understand it for comfort and I understand it for all of these things. It was one thing that I did not feel like letting go of and therefore during the entire time, I always dressed up, even to have dinners at home.

My husband and I would get ready for cocktail hour. And wear shoes in the house (I know, blasphemy for Brown and Black people lol) just to be like, "We're putting on some shoes and have an entire outfit and are doing a thing." I think that kept both of us, I'm not going to say that kept our marriage spicy or anything, but it reminded us to still continue to try. Not just for each other, but for ourselves because it felt nice to put on makeup. It felt nice to do your hair. It felt nice to do certain things and not fall into a rut of not doing those things.

So, I find that so interesting because a lot of my friends, and just people in my world, I've talked with them about the fact that I don't know how to dress anymore. I don't know who I am anymore. I don't know what clothes are. Dressing used to be part of my identity." And I'm not alone in that. I'm wondering if you've seen that or experienced that or have any thoughts on that.

AS: Who were you dressing for before? Were you dressing for yourself or were you dressing for the gaze?" Whether it's the male gaze or the female gaze or the them gaze, who's gaze were you dressing for? Because I understand that, and I know that a lot of people's fast fashion purchases dropped during this time. So, I think the immediate question to me when that was happening for people is, who were you dressing for? And maybe it's a little bit of a recalibration of self to either say, "Yeah, I was dressing for my colleagues and I like getting accolades from other people," and/or a renewed sense of "Holy shit, I should be just dressing for myself." And that's what it feels like.

But yeah, I know a few people that were in that space and I'm not saying that it's easy for everybody, especially with parents that have children at home and their first thing is to ensure that they're fed and taken care of.

Yeah. Awesome. Thank you for sharing that.

AS: You're welcome.

That is revelatory. I needed that. I should pay you for that insight. Thank you so much for doing this interview as well. I really appreciate it.

AS: Yeah, of course. Thanks for asking me. I read your email and I was like, what an honour. It's so nice for you to consider me as someone that you want to speak to and place on your platform. And I think it's because I said that I don't buy into my own bullshit, that's why it sometimes makes me nervous or make me wonder why do you want to talk to me? I don't know. I have nothing important to say. Look, I'm just Amy that lives my life. I don't have these big, extra contrived moments.

I hear that. As somebody who's…

[The conversation continues beyond the recording].

Chantaie Allick

Writer|Strategist|Storyteller

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January 2022Chantaie AllickComment