Andrew Montgomery is a Digital Product + UX Designer born and raised in Jamaica, but currently working in Toronto, though he considers himself a citizen of the world. He’s seen two sides to the story of technology. Coming from a place with limited access, to a hub of innovation, He always questioned how to bridge the gap. Then he discovered user experience design.

He believes that access to technology is a right, not a privilege,and this guides his design decisions. He aims to help make the world more equitable through his work.

As a creative thinker and problem solver,  he enjoys straddling the line of marrying human needs with business goals. Creating great products comes from understanding the people using them. Humans willingly incorporate useful and enjoyable experiences into their daily life.

When not designing, He’s teaching kids code, in the mountains skiing, playing soccer or travelling the world. Experiencing different cultures heavily influences the way I solve problems.

16 countries and counting.


Show Notes

Katherine Ann Byam 0:00
I don’t think it’s typical to have people that look like you in design, why is that?

Andrew Montgomery 0:05
A big question? I think one of the reasons is that it may be cultural. So we could get into like imperialism and all these other stuff. But I feel like culturally black people and Caribbean people, and a lot of African friends as well, who experienced the same thing. They’re pushed towards traditional careers, whether it’s by their parents or teachers, or just what they think society will deem as an appropriate career path. So that’s one of the reasons why in terms of non traditional careers, we don’t see as many people that look like us. For me, I was, I was fortunate because my parents, they always encouraged like thinking outside, outside of the box. They’re both entrepreneurs. So I had the cultural angle of like, what is perceived to be a good career from the outside. But like at home, I was encouraged to basically, quote, unquote, follow your dreams. And always think about, like non traditional ways of generating income.

Katherine Ann Byam 1:02
My name is Katherine Ann Byam, and I’m your host. What’s your purpose? And how does it integrate with sustaining life itself? For some of us this question is a deep ache that we spend a lifetime trying to find, perhaps shifting direction as we learn and grow from one path to another. For many of us our children give us a clear definition, providing for them becomes our reason for being. For others, it’s about enjoying the present moment; ever so fleeting, and ever so beautiful. For still others it can be financial, status, contribution or impact. In this podcast, my guest and I will share with you tips, ideas and methods on how to build a career that integrates with who you are and the life you want to lead. We will explore the social foundation on which to build your transition and an ecological ceiling, above which we need not climb, so that we live not just for ourselves, but for our collective ability to thrive. Welcome to The Purpose Driven career podcast: Do What Matters.

Andrew Montgomery is a digital product and UX designer born and raised in Jamaica, but currently working in Toronto, though he considers himself a citizen of the world. I love this, we’re going to talk about this for sure. He’s seen two sides to the story of technology coming from a place with limited access to a hub of innovation, he always questioned how to bridge the gap. Then he discovered user experience design, he believes that access to technology is a right, not a privilege. And this guides his design decisions. He aims to help make the world more equitable through his work. Andrew, absolute, welcome to the show.

Andrew Montgomery 2:41
Thanks Katherine for having me, excited to be here.

Katherine Ann Byam 2:43
Excited to have you as well. And it’s so great to find a fellow Caribbean person who’s kicking it, if I can say that on YouTube, sorry, in his role and in his job, and it’s such a pleasure to sort of celebrate that positive story. So I’m really, really pleased to have you on the show. So what inspired you to get into design specifically?

Andrew Montgomery 3:03
Honestly, I think from a very young age, I just had an interest in it. My dad was always into like construction. So I really believe it’s probably genetic. I was designing from a young age in like different forms, so at a computer from an early age, my sister and I used to just print stuff, I used to design flyers in high school in Jamaica, I did technical drawing my undergrad degrees in architecture. Later in life, I got involved in like web design, web development. And that’s actually how I got into product design specifically, like through doing web development, I was looking to kind of formalise my web development education. So I started looking for like boot camps and stuff like that. And Brain Station, which is a boot camp in Toronto started sending me like marketing information. There was a marketing information, there were links to like the different programmes that they were offering. And I saw UI design, I saw UX design, I saw product management, and also web development was really interested in at the time, but the design portion like really stood out to me. So I started doing my research, because I’ve never heard about this. And I ended up going to one of the info sessions that they had. And that’s when a bell kind of went off in my head. And I was like, this is what I’m going to pursue. And that’s actually how I ended up in product design specifically, but all throughout my life, I was around design. And I was always like, mostly interested in design, even though I didn’t necessarily know what specific road I would go down. Initially, it was the architecture road and then life happened. I was kind of basically just figuring my life out and figuring out where I stood, and I think product design specifically aligned with like all my interests. So that’s why I kind of ended up here.

Katherine Ann Byam 4:42
How long ago was that?

Andrew Montgomery 4:44
I’d say probably about three four years ago when I first heard about user experience design ever, but even when I got introduced to it, I was kind of like procrastinating. So I didn’t actually dive in until probably three years ago.

Katherine Ann Byam 4:59
It’s interesting because I think this discovery story of finding your passion, it takes a little bit of time to kind of grab onto it, because we’re clouded with the things that we should be, and we should do. And the expectations of us from our cultures or from, from our colour or for whatever it is, and, and suddenly you just say no, okay, I want this, I’m gonna go for this. I don’t think it’s typical to have people that look like you in design, why is that?

Andrew Montgomery 5:28
A big question? I think one of the reasons is that it may be cultural. So we could get into like imperialism and all these other stuff. But I feel like culturally black people and Caribbean people, and a lot of African friends as well, who experienced the same thing. They’re pushed towards traditional careers, whether by their parents or teachers, or just what they think society will deem as an appropriate career path. So that’s one of the reasons why in terms of non traditional careers, we don’t see as many people that look like us. For me, I was fortunate because my parents, they always encouraged like thinking outside, outside of the box. They’re both entrepreneurs. So I had the cultural angle of like, what is perceived to be a good career from the outside. But like, at home, I was encouraged to basically, quote, unquote, follow your dreams. And always think about, like non traditional ways of generating income, my dynamic was a bit different. And then I think through those, those cultural like pressures to go into fields like law, and medicine and stuff like that representation is something that’s big when you’re looking to dive into a career. So if you’re not seeing people like you in that space, you might not necessarily be encouraged to go into that space, or you don’t know what avenue to take. And then a lot of the things like Google and YouTube, and these are newer technologies, they’re fairly recent. So coming up to like, these times, they weren’t necessarily places where you could go and learn about things on your own. So I think those are some of the reasons why we don’t necessarily see people like us. And then we’ll get into all other stuff like systematic racism and like people saying that there’s not enough of our pipeline and stuff like that. But I think the concepts I mentioned earlier, are some of the main reasons.

Katherine Ann Byam 7:09
Yeah, we’re gonna come to that. But I think I want to touch on something before we even get into that. But what does success look like in a product design career to you? And I say to you, because I think that that brings another dimension to the thing as well.

Andrew Montgomery 7:25
So for me, it’s about working in, in spaces that I want to work in, but that’ll have an impact on the people that I want to have an impact on. So specifically, like I worked on a lot of ed tech platforms, or I’m working on products that are focused on people that from my background, so one of the products that we’re working on is a learning management platform that tailors learning lessons to specific learning archetypes. So it’s focused on underprivileged kids. And another one is there’s another learning management system where it’s basically centralising all the lessons digitally, which is not necessarily a thing in the Caribbean. So being able to work on products that have impact on people that look like me, being able to work on great teams. So product design, and UX design, specifically, are very, very collaborative. It’s a very collaborative space. So liking the people that you work with is a very, very big thing, working for companies that you want to work for, whether it’s full time or contracting or freelancing. So it’s working on things that you want to work on with the people that you want to work on, that have the impact that you’d like them to have, and being able to see the results of your work and people actually using the things that you’re designing and building.

Katherine Ann Byam 8:37
Yeah, no, I absolutely agree with that. Actually, as you said it, I remember my cousin actually, she’s, she’s a phenomenal talent at drawing. And one of her passions in creating artwork, and basically texts for kids and stuff, is that we have all of these, especially from the Caribbean, we have all of these stories of things that mean nothing to us. So we’ll talk about grapes. And we’ll talk about I don’t know, whatever else strawberries, but we don’t even have those things in the Caribbean. So she wants to talk about things like avocados and things that are more traditional to the Caribbean. And her caricatures and drawings represent something that is more akin to the real story of growing up Caribbean, and not the textbooks. We’ve had all our lives. So I think it’s interesting that you’re doing this in the learning space.

Andrew Montgomery 9:26
That was just one of my inspirations coming in, I did, I like to say I’m pretty self aware. So I know what my interests are and what I like working on. I know how I like to work. So when I was deciding if it was like one of the right career paths for me working on things that are dear to me was definitely on top of the list, being able to, so being from the Caribbean, like there’s a lot of great designers doing like graphic design, or like different forms of design. They’re not necessarily as lucrative as product design, and a lot of them have not been introduced to the concept at all. But, there’s a lot of it’s not the same thing, but there’s a lot of transferable skills, so, as a representative from the Caribbean, being able to introduce some of these people to some of those things was also also pretty important to me. So going back to what you said, not having things that are representative of us, I think being able to kind of expose my people to the vast array of possibilities out there to align with their skills was was pretty important to me.

Katherine Ann Byam 10:20
Yeah, no, that’s really powerful. The other the other area that I find that Caribbean designers do very well is in fashion. So I have like, in the UK, I’ve met so many or I’ve seen amplified the stories of so many women in fashion, who’ve come from the Caribbean who talk about that, that legacy and, and being mixed cultures themselves, they’re able to carry the story easier. So that’s, that’s really been a success story, at least from the Trinidad Diaspora perspective. So let’s, let’s get into now, this the challenges you face, sort of doing this role that you’re doing to be as a black Caribbean man in Canada, and I think, I think I don’t know, because I haven’t lived there, I’ve only visited. I think that it’s easier to be a black man from the Caribbean in Canada than it is to be that in the UK, or in the US. But tell me what your thoughts are.

Andrew Montgomery 11:14
So it’s true. I agree. I’ve never lived in, in the UK, but like I follow UK culture heavily. So in terms of music, film, and I have friends in the UK, not just from general reading and stuff, I think everybody has their struggles as a black person in whatever country they’re living in. So for example, like I can compared to the states and I know some, somewhat in the UK in terms of like police brutality and stuff like that, if I’m driving on the road, and I get pulled over by a police, I don’t necessarily fear for my life. But there might be another other black person from a different upbringing that had that same experience that somebody in the UK has. So I can only speak from my personal experience, but I’ve had generally positive encounters with like law enforcement in Toronto, I’ve had bad encounters as well, which I know, are specifically due to race, but not I don’t think it’s as ingrained in my brain and I’m in contact with law enforcement here, I think there’s a lot of so the issues that we deal with are very similar, but it may be more overt in places like the UK and the States than in Canada, it’s more covert. So we can argue whether that’s a good or a bad thing, what I like to know and see what I’m dealing with. But there are definitely challenges. And from a different lens. The one of the challenges, like growing up in the Caribbean is the lack of, educational and just in general, it’s a regimented environment. So for example, if I’m going to a job interview, I have both my ears pierced, right, and I’ve never taken on my earrings for an interview here, since I’ve had a beard, I’ve never shaved my beard. In the Caribbean, there’s this facade that you need to look a certain way, and behave a certain way and act a certain way if you’re going for a traditional job interview. So I think that’s more positive here. But in terms of like the experiences, I think I still struggle with being a black person in, in a Western society. So I’ll be on teams where I’m the only black person or if there’s any other black person, they’re far removed, there’s a lot more people from other races in senior roles. But that’s rare. Whether or not this is in my head or not like wondering if people think your ideas are valid, because it’s whether you’re black, or you’re Caribbean, that’s definitely a struggle. So I think all of us deal with or struggle in different, in different ways. And whether or not it’s worse or better. That’s, I don’t really know. But the fact that it exists is obviously, is obviously a problem. But by being here, I’m trying to kind of address that problem. I mean, open the pipeline for other people to be able to exist in a society where they, where they want to work.

Katherine Ann Byam 13:43
Yeah, I agree with that. I mean, it’s difficult to compare, I also agree with that, my experience here is that it’s not as it’s not as overt as you might think. It’s it’s very covert, but it’s very known as well. So, so I would say that Brexit is one of the things that has sort of opened the door, basically, for people to be more open about how they feel about things, which, as you say, good or bad. It’s a fact that, that it is it is a lot more open, that you can, that you can see things like you can see people’s impressions, and they have justifications for everything, right? So that’s, that’s always something that you have to kind of process I would say and, and definitely, I would say that, especially in the corporate setting, having that, I basically have like for for minority status is here, so I’m female in black in from the Caribbean, and I’m just a general outsider. So, so all of those things do tend to have a weight in how you’re evaluated and stuff like this. And I don’t know if it feels that way in places like design because I like to think of design people as being a lot more forward thinking as really embracing diversity more because it produces the innovation, and they embrace that idea a lot more. What are your thoughts on that?

Andrew Montgomery 15:06
So I think I would like to think that statistically, studies have shown that if you have more diversityin jobs, whether it’s racially diverse, ethnically diverse, diverse by age, gender diverse, that you produce better products, because you have representation from different groups, and you’re building products for generally building products for many different groups of people, but the reality is everybody comes with their own lived experience. And that plays out in, in hiring or whether they take people’s decisions seriously, working with others and stuff like that. So if you’re coming in to, and like I mentioned, there are a lot of people in power are generally white males, right. So that design is probably more forward than a lot of other like fields or industries. But it’s still have some of the same, the same issues that other industries, I think in tech and design, specifically, their numbers, people, and they understand that working to let people feel welcome and welcomed in a space allows them to be more productive. So it’s not necessarily that they’re like, less racist, or less, whatever, whatever the word you want to use is, I think they understand that this is what helps you to make better products, and if we make better products it’,s better for productivity for our company. So we need to incorporate these things into our company. It’s not necessarily like a moral decision. It’s it’s more of like a bottom line decision, so if someone has a company, and they know that this is going to give them the best output, then that’s what they’re going to do. But as I said, people come with their their different lived experiences, and all those biases play out, and whatever. It’s just a microcosm of the wider society. Right. So it’s less so in this field, but it does still exist. It’s still playable.

Katherine Ann Byam 16:51
Yeah, what has been your greatest sort of achievement in your career so far, and why?

Andrew Montgomery 16:57
Oh, I’m working at a great company, right now, so, coming in I didn’t think I’d necessarily be at a company of this magnitude, so quickly, even though like imposter syndrome is real. So I know, like, I’m a very hard worker, I’m always trying to learn and grow. But it comes back to like, all those realities that I’ve experienced, kind of making it downplay, or not understanding how talented you are as an individual. So I think working at the company I’m working for is one of my greatest achievements to date. And also, as I mentioned earlier, was working on two products that are basically dear to me. So being able to work on products to kind of expose, first of all, to expose them to learning pathways that are relevant to them. So like the education system in North America, if you’re not going to private school, you might not get the education or the or the attention paid to you that you need to. So being able to help facilitate, facilitate that in both of those products I work on two of my, my successes.

Katherine Ann Byam 17:57
And what could you learn from any failures that you’ve had in your time and kind of what can you take away and learn from the things that didn’t work out the way you expected to?

Andrew Montgomery 18:07
I like to phrase things as more of a learning experiences, I don’t really think of anything as a failure. So I try to learn from whatever situation I’m in and make myself better. I think one of the things, one of my greatest learnings is just learning on understanding my work on being in the field specifically. So when I started out freelancing, I didn’t really know what to expect. I was definitely undervaluing myself. But it was also mainly to develop a body of work that I could present to people and say, this is what I can do. So going through that phase, during my freelancing journey, I learned a lot of lessons. I learned how to optimise process, I learned how to deal with like different stakeholders at different, with different levels of understanding of design, I learned always to charge what you’re worth, and don’t feel bad for that. One of the biggest lessons in terms of that is what money is not all things, but to live comfortably in the world, you need to have money, everything costs money. So if you really, ultimately want to be happy, you want to just have great experiences that costs money. So not undervaluing myself on understanding that as a designer, I’m operating within the context of the wider world and then not having any regrets for expecting or demanding what you think you’re worth. Because at the end of the day, you still need to live on everybody wants to live a comfortable life. So I think that’s one of the most important lessons.

Katherine Ann Byam 19:21
Yeah, I totally hear you on that, brethren. That whole issue of what to charge and making sure that you’re getting that that money side, right. It’s the biggest challenge for all freelancers, especially when you’re still looking to build your reputation. So yeah, I totally I totally feel that what sort of advice would you give to someone getting into freelancing today in terms of cracking that challenge, how to break through that challenge, what to do first?

Andrew Montgomery 19:49
In terms of freelancing specifically, in order to get better at your craft, you have to be doing work and I don’t like to advocate for people doing free work, but I’d say learn the craft. Ensure you’re on top of your game where that is concerned also making sure that design and freelancing is right for you. So Google ‘what it takes to be a freelancer’, and the same way we do a lot of whiteboarding design, right? Of, everything, all the qualities that you think you have, where you want to get to, like outline, all these things and and make sure that it’s right for you. Learn business concepts; so just basic entrepreneurial concepts, basic bookkeeping skills, understand what your expenses are. And then that will kind of help you to to situate yourself and understand what you need to charge. And also, like, do research and see what other people are charging at different levels of design, so and then have conversations with other people. So you can kind of understand where you are in the design field. I think a lot of us feel bad for negotiating when, when money is concerned, because you don’t want to lose a job. But you also want to get paid, right? So don’t feel bad for doing what’s best for you to live in what’s predominantly a capitalist society?

Katherine Ann Byam 20:54
Yeah, that’s interesting, because I, I’ve definitely had that challenge of challenging someone, and having them walk away from the conversation altogether. But I think that’s another lesson learned, which is you have to do it. If somebody is not willing to have that conversation with you. They’re not willing, they’re not the right people for you to work with ever.

Andrew Montgomery 21:13
Yeah, I’ve had experiences where I’ve done work, like as a favour for other people, it’s you have to set boundaries, anything I do, I always go above and beyond and make sure I’m doing the best work. Because it’s a reflection of me, but you when you undercharge one, it’s always going to be in the back of your head, especially if you’re not having a great relationship with the person you’re working with. You might be thinking, I’m not even charging what I’m supposed to charge them, they have all these tips, all these descisions, all these. So being, making sure you, you’re charging what you’re supposed to charge, being transparent about what this whatever package you’re charging entails. And one thing that I think all freelancers need to do as well is, once you have that set package, make sure there’s a conversation about any add ons, and okay, this is what I’m going to give you and anything extra is you’re gonna have to pay this for it. So having that transparency and understanding between the people and an understanding that what you’re providing is of great value to the people that you’re providing it to. So if they don’t want to pay for that value, then just, just cut the conversation short, and it’s always better to not get into an agreement that’s going to be very hostile than making compromises on your end, and then having a negative relationship with the person that you’re working towards. And ultimately, people understand the value that you’re bringing as a product designer, UX designer, if they can afford to, and if they think that the work that you’re going to provide for them is valuable, then they’ll they’ll be willing to pay for our if they’re not, then they probably just don’t understand the value of what you’re giving to them.

Katherine Ann Byam 22:38
Yeah, absolutely. One other question that I want to touch on. I work with a number of sustainable entrepreneurs people both in service and in product. But I have a theory. And I would love to chat through it with a designer. But I have a theory that products today need to have an element of service and an element of UX. And I wanted to know your thoughts and perspective on that

Andrew Montgomery 23:02
Any product that’s been built has a user experience, you can technically design a user experience, you can design a product, and a person has an experience with that product. And the methodologies used across all fields of designer are pretty similar. So it’s about understanding what the problem is that you’re trying to solve, understanding the people that are going to be using those products, talking to them to get an understanding, if you have data you can extract to understand the problem a bit more, do that. And then build or design a product that’s custom that addresses the needs of the people that you’re designing it for, like if, if I don’t know what your problem is then I’m just making assumptions, and I can’t really truly design something that that’s meant to solve your problem. So design in general is just understanding a problem, understanding the people that you’re solving the problem for, and then trying to address that problem through design, a lot of the design challenges that I’ve heard for like interviewing for different companies and stuff, they’re always these ambiguous problems that seem to be like purely physical, and then you have to come up with a digital solution. So that has made me think about how I can integrate random stuff, incorporating whatever level of digital input into physical products and experiences is a plus. And I think like as a product designer, you’re supposed to always be thinking about the holistic experience and how that fits into the person’s day to day life. Right. So we do a lot of user journey mapping. And that’s thinking about things outside of the specific product is thinking about the context that a person will be using the product in and what leads them up to using that product and what happens with them after using that product. So generally, you’re supposed to be thinking about a whole the holistic experience, which is very similar to service design.

Katherine Ann Byam 24:37
Yeah, no, it’s really interesting, really, really interesting conversation. All right, so I’m gonna bring it to a close today. Any final words you want to give to inspire our youth back in the Caribbean about what they can be doing? I know for sure that a lot of people have written to me in the last year particularly during COVID, to find out how they can come to the UK how they can come to Canada, how they can get opportunities and stuff. But in reality, they can do this, just as we were talking about digitalising the experiences, they can sit where they are, and get opportunities anyway. Any thoughts or reflections on that?

Andrew Montgomery 25:09
Yeah, I would say to young people, we’re in the age of the internet, basically, information is out there. And you can connect with people by not actually being physically around them. So I’d say whatever your passion is, just type that into Google search. If you’re passionate about design, there’s a lot of design forums where you can connect with other people. So Twitter, on Behance, dribble, LinkedIn, go and explore all the Internet has to offer. And once you do that, you’ll see names come up. If you’re interested in product design, specifically, type in black product designers, there’s a bunch of forums where you’ll see these people and don’t be afraid to reach out to them. So one thing that I think is important is having coaches and mentors somebody that can guide you through the process, who was been through the process. So all in all, do your research, put yourself out there, the internet is at your hands. And don’t be afraid to reach out to me or any other any other product designer, me specifically, I don’t say no to people who reach out to me, if I have the time, I’ll give you my time, especially if you’re from the Caribbean. If you’re a designer, I’ll be more than happy to kind of help you guide you through the process or direct you to somebody who can and reach out to people as potential coaches and mentors to help you. A lot of us growing up we never had all these tools at our disposal. So basically the world is your oyster on major connections and do the research that you need to do to kind of get where you want to go.

Katherine Ann Byam 26:30
I love that and what handles can they reach you at if they want to connect.

Andrew Montgomery 26:34
So I’m on Twitter or my my Instagram. It’s designr, so designer without the last e, Drew. So that’s my handle on Twitter. That’s my handle on Co-Host, so you can reach out to me there.

Katherine Ann Byam 26:51
Thanks so much for joining us.

Andrew Montgomery 26:52
Thank you, Katherine.

Katherine Ann Byam 26:56
This episode was brought to you today by the Courageous Career Club. Have you picked up your own copy of; Do What Matters: The Purpose Driven Career Transition Guidebook. To find out how you can get your copy, as well as resources that go alongside it, visit my website, www Katherine Ann or engage with me on the socials. I’m looking forward to hearing from you.