I’ve Seen This Before
In this episode of the Impostor Syndrome Files, we explore how to manage self-doubt and recognize opportunities during periods of technological change. My guest this week is Yoli Chisholm, a digital marketing leader who has navigated several major technology transitions throughout her career. Drawing on those experiences, Yoli offers a reassuring perspective on the uncertainty many of us feel about AI.
Yoli shares how building a career without a college degree left her questioning whether she belonged, even as she advanced into senior leadership roles. She reflects on the unexpected doors that opened during times of uncertainty and how learning by doing helped her build confidence. We also discuss how remembering challenges we’ve already navigated can help us approach new ones with greater perspective.
In our conversation, we explore the pressure to keep up with AI and the fear that our experience will become less valuable. Yoli shares what helped her move past her initial resistance and see opportunities for growth. We also discuss practical ways to learn without becoming overwhelmed and recognize the value of what we already know.
About My Guest
Yoli Chisholm is an award-winning Marketing Executive recognized as a “Digital Innovator”. In 20 years as a business professional, she has cultivated a multifaceted career as a Revenue Marketer, Corporate Career Anthropologist, Entrepreneur, and Speaker who writes about these areas including her book on navigating corporations - Crushing Corporate.
Whether she is talking to students or professionals about their career development, small businesses, startups, or seasoned marketers about building their businesses, Yoli fuses a message of proven performance principles and disciplined risk-taking. Playing a leading role in every digital marketing transformation since the commercialization of the internet Yoli has earned a reputation as a very early adopter of new technology. She has a passion for the impact of culture as a lever to optimize business performance and speaks on the topic in her TEDx talk “Are you a strong Tree?” As the Author of Crushing Corporate Vol. 1 & Vol. 2, Yoli brings to her writing a point view on intrapreneurship and entrepreneurship having experienced different corporate cultures at 10+ corporations including Microsoft, Sprinklr, eBay, Lavalife, and consulting with startups globally US, Canada, Switzerland, UAE to working for the Danish Embassy in Africa over a 20-year career span.
A business “backbone builder” with deep B2B marketing innovation roots. Seeking to motivate in ways that deliver measurable transformation to organizations and people striving to excel. Yoli is now the Founder of Borderlessself.com.
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Connect with Yoli:
Website: www.Borderlessself.com
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Transcript
Kim Meninger
Welcome, Yoli. It's so wonderful to have you here today. I would love to start by inviting you to tell us a little bit about yourself.
Yoli Chisholm
Thank you so much, Kim. It's an honor to be here. So my name's Yoli Chisholm. I've been a digital marketer for over 20 years. I'm 54, and I would say I've I have made the journey up the career ladder in a pretty initially not a traditional way, but once I was became a marketing coordinator, I kind of have gone up the, the ladder, and in the last five years, have been in that scary zone of transitioning from a VP to a CMO, and, and trying to get my my my chops as as a CMO, having been a number two for a very long time. I've worked in in tech, worked at some companies like Microsoft and eBay and Sprinklr, and I've also worked globally and you know made some of these transitions. Just to step back a little bit. I I initially migrated to Canada from Kenya with my family as a refugee, and then you know spent my college years in in Toronto and got into tech, and, and, and I did so in the late '90s. So you know, have seen a few of these technological transitions. You know, I started out in the secretarial pool. So I'll just leave that there. And so it's definitely been been a journey from a career standpoint, and, and now you know at 55, you know the reason why I was really excited to be on your podcast is because you know imposter syndrome has definitely been a part of of my journey, and, and so happy to talk about it.
Kim Meninger
Thank you for sharing that. And you have a really impressive career story. So obviously, imposter syndrome hasn't stopped you. It's been it's been a companion, but it hasn't kept you from growing. So can you talk a little bit about how it has shown up for you over the years?
Yoli Chisholm
Yeah, you know the first the first thing is that I am a college dropout, so I originally was a dance student and got into York University to take a fine arts degree, but midway through, I realized that this was not going to be something that I was going to be able to make a career out of for a number of reasons, and I, I kind of made my peace with that, but it, it, it meant that I had to drop out, and I started working, you know, in retail, and, and and wasn't quite sure what I was going to do in terms of a career. However, I ended up in retail, working for a retailer and consumer packaged goods, I, I had done a typing test and got a temp job, you know, getting into the secretarial pool, and working for a CMO, and she was amazing, and she literally said to me, she was gonna teach me what she knew. So I got very lucky, you know, in that I, I, I found a woman who was you know at the prime of her of her career, and she saw something in me and was was willing to to mentor me, and but as you imagine, you know, I was surrounded by peers who, some of who you know had been formally trained, and, and so there was always that that question of you know do I do I deserve to be here can I keep up, but I will say that I, I always say that you know technology changed my life because at each. Transition. Nobody knows what's going on, you know, and, and so I would just encourage people, especially like the time that we're at right now, you know. I've been through that a few times, and I remember when the first computer came into the, the office, and you know, our secretarial jobs changed, and then I also remember when the internet, you know, started to become a thing. And those moments, they they kind of reset the, the bar, for lack of a better way of saying it. It's just that, like, it's an opportunity for you to like, kind of leapfrog. I didn't recognize it then, but looking back is when I'm like, oh man, I've made some of the biggest moves when, when there's been a lot of uncertainty, and I would say you know that transition from from offline to online, you know it. I answered an ad in the back of a newspaper. The Canadian government wanted people to learn HTML, and you know I was still working offline, and I, I remember, you know, making that decision that I was going to quit my job, that job that had given me that start, but I was going to take this HTML course, and it was like a six month thing, and so I don't want to go on too long, but so that's how imposter syndrome has kind of shown up because I didn't have a degree, and then over the years it's just been okay. I'm gonna have to learn by doing, you know, and, and, and so that's one of the things I just you know in the online space you can be much more of a practitioner, you know. There's so much that you can just learn on the side while you're doing your job, and so that's why I really feel like technology has really been been the thing that changed my life.
Kim Meninger
That's such a timely message, given where we are right now with AI and the changing world around us. And I think it's such an important reminder that nobody knows what's coming next. Everybody, you're right about it resetting things because now we're sort of all figuring this out together, and everybody brings a different angle to it based on their experience and their point of view. But there, nobody has you know deep expertise in and can predict what's going to happen next, and so it does create opportunity for everybody.
Yoli Chisholm
Yeah, absolutely, and I think that you know, even when I made that transition to the online space, what I had done offline wasn't a waste, and that's one thing that I think people should keep in mind now. It's like you know, you can't put your head in the sand about AI. It's here. It's happening. You know, and if you've still got a lot of runway left in your career, you really need to adapt. But it doesn't mean what you've been doing goes to waste. It's like, really, now you have an opportunity to kind of stack AI on top of what you've already the experience you already had. So back to that original job, you know, was it was in retail. I took the course, the internet course. I ended up getting an internet publishing certificate, and the first job I got after that was at an e-commerce company, and so they wanted the retail experience, but somebody who had now had the, the technical skills. So both things ended up being, you know, valuable. So, like right now, if you're looking at your career and like, oh, AI is going to take over. Well, maybe you, you know, maybe there's a long runway of of training the AI in your discipline. Maybe there's a long runway of, you know, supervising the AI. You know, but in your discipline. You know, I, I've recently done some AI training work, and it was using my domain expertise as a marketer, and initially I was actually resistant to AI, and but then I realized, oh no! I've seen this. I've seen this before. I've seen this pattern before. It’s not as scary as you think. But nobody knows what's going to happen. And usually, what happens is a whole new set of jobs, a whole new set of ways of working. And that's what I'm seeing, and I believe that to be true. I believe that's going to be true in with this era as well.
Kim Meninger
You said something really important just now, and you said I've seen this before, and I think that has relevance to a lot of what we're talking about. Because oftentimes, when we feel anxious and we're going through a change, we tend to become laser focused on what's unique about this moment, as opposed to zooming out and recognizing we've been here before, we've we've navigated similar challenges, right? And and I think that perspective can be really valuable when we feel stuck or when we feel really overwhelmed.
Yoli Chisholm
Yeah, 100% If anybody is listening right now, believe me, this time is when everybody says, "Oh, this time's going to be different, maybe, but there's going to be a lot that's been like exactly what's happened before. You know, I was in the secretarial pool when the typewriters went away. We adapted. You know, executives learned to type their own memos, but then the whole set of work expanded. You know, and a lot of us moved into new roles. You know, that were more complex, and and new roles were created with completely new job titles, and then the same thing with the internet. You know, oh, you know, people aren't gonna put their credit cards online. Oh, the internet is just the for the darkest, you know, regions of the of of industry. No, until it became completely mainstream, and, and the other thing we forget is is how long it takes. It feels like it's super fast, but the, the, the internet it took a long time for people to adapt it, adopt it, you know. And it took a long like when you think about some of these companies, like Facebook is now over 15 years old. Like you think about it, it's, it's, it's fast, but it's not as fast as you think, you know. So, so I really encourage people to to just think that there are patterns. There is a history to how technology adoption happens, and at the end of the day, I wouldn't bet against humans. Like we are so creative and adaptable, and, and we're going to figure out amazing things to do with with this tech the same way we figured out amazing things to build with the internet, you know. And and I've worked in some of these companies, and I know how long it takes. I know how like the challenges they're gonna have with like regulations and like governance and putting checks and balances into place and, and making sure that people still feel valued. Like these are not things that are just gonna be thrown out the window. You know, they we still and the other thing is, at the end of the day, companies want to grow and they want to make money, and most of the time that growth requires like the creative thinking of human beings. You know, so yeah. I mean, I don't. I wouldn't want to pretend to have answers. All I can just tell you is like, you know, internet, social media, mobile phone, like big data. These were all like massive, massive trends, and there was all kinds of like, you know, you know, big headlines about it, and we adapted, and, and, and I believe the same will be true.
Kim Meninger
That’s a really lifting message. I think it's it's comforting to hear you say that because I think we we tend to focus on what the potential losses are as opposed to what the potential gains are. And I wonder if you can speak a little bit to people who may be thinking about what is a potential opportunity right now, but they're not quite sure how to break free from where they've been. So there's that maybe that that wanting to take advantage of the change that's coming, but maybe they feel locked into well, I've been doing this for such a long time, or I don't know if I have the right skills, or you know the, the self doubt that creeps in when we're thinking about making a change.
Yoli Chisholm
Yeah, I mean I have to admit, like you know I was most recently working for an organization where you know the CEO was on the AI bandwagon, and it felt super. It felt super aggressive, and initially I was like, I want to resist. And particularly in marketing, where you're like, you know, it's the human connection. It's, it's, you know, it's the best practices. Until I realized right now you have to admit when you think about the full scope of your work. There's always things that you're like, wish we could do this better, or you know, we've been doing it this way. We we we there's still gaps or holes in the places that we're we're blind where we don't have enough information. Well, that's where I think you should focus on in terms of how do we leverage AI. That's what that's what helped me, kind of get over my resistance. Was like, oh man, are there areas that I've always wanted to fix that now I can? You know, is there a like, you know, even just being able to move faster within these large enterprise organizations? You've got a window of time right now, where where a lot of executives are open to that, you know they're open to you know relooking at these best practices. They're open to blurring the lines between roles and departments because now you can do something with the technology that maybe you wouldn't have been able to do. For me, what it was was I was in the marketing department, always reliant on engineering teams to get things done. Right, always reliant on them to to do the experiences that we want to build, to make the changes that we want to to make in, in the product, and now wow! Like there's a lot you can do without waiting for engineering. You know, you can build it, you can prototype it, bring it to engineering. You can use it to build your business case. You can, you know. So, if you're looking, so so that's how I would look at it now as a, as a professional that's kind of thinking, okay, how can I convince myself, and then how can I look for opportunities within the organization? It's look at those areas where you're like, why are we still doing it this way? Why have we always done it? Why I wish we could fix this. Ask: Is, is this something that you could you could get AI to do? Not with the with the thought that okay, am I going to talk myself out of a job? But but you know, is there a way I could make make you know what we're doing better? I know it's easier said than done, and I know it feels scary. But what, what what has been more true has been that you, you fix the things that are inefficient, and you find that you're able to do the things that you know maybe where your time would be best suited. That's not just talk, like I think that that is, is going to be proving to be true.
Kim Meninger
Yeah. You know. Yeah. Well, and I also think, again, thinking bigger picture. Of course, it's scary because it's unknown. But what's scarier to me is being left behind.
Yoli Chisholm
Yeah, yeah.
Kim Meninger
I mean, not want to miss out.
Yoli Chisholm
And yeah, because because that does you know that does happen, right? If you are, you know, you know, going to be slow to adopt or a little bit stubborn or reluctant, and for me, at the end of the day, that was that was the, the reality. It's like Yoli, you still got another 10 years, maybe you know, in your career. Are what are you gonna do? Like, are you gonna just you know be in denial, or are you gonna try and figure this out, you know. And what I what I've what I've always tried to do again because of the chip on my shoulder of not having a degree was always having something on the side, like a side project where I can experiment with these new new technologies or new things that are happening, so you're not necessarily putting yourself up for scrutiny within the organization, but find a way to to test some things in a safe environment that's sort of within your control, so whether it's standing up a website and, and then you know testing the AI to to for you to kind of learn, that's actually that's what I felt was a more comfortable way for me rather than being with the whole capacity of people within the org who are sucking up to the executives, trying to, you know, trying to create these projects that that are are because there's a lot of projects that are going nowhere. Trust me. There's a lot project people are like you know, it's it is kind of cool to be able to build a website in you know in minutes, and but at the end of the day, you know, especially if you're in a large enterprise organization, you know it it's going to require a lot more substance, and so so my point is more like learn in a safe environment that's within your control, and then you can you can come to to the organization with, with a little bit more confidence. That's, that's what, that's what helps me, you know. I'll have a, a business on the side, and it's maybe not a business that I'm like looking to make money, but I'm using the infrastructure to kind of learn, and it's, it's within my control. That's how I experimented with with some of these LLMs, the other thing that I've, and this is the last thing I'll say because I could ramble on about this is, is make a bet on one LLM. You know, like just because it's because if you listen to all the talk out there, and if you're on Twitter, you're just going to be overwhelmed. You know. Make make a bet on one of them, and just go deep with one of them because they're all competing. And as you know, with tech, right? Everything ends up being somewhat on par, right? Like they're all kind of like, oh, we came out with this one, but they're all so so focus on one, right? Like, and this is another patent recognition, right? Like I was around when there was MSN, AOL, Excite, right? The portal wars, the same thing with the cloud wars, the whole like, they all end up building the same thing, right? That's true. Go to. It's true. Just bet on one. Go deep on one. Like you know. You know. Fingers crossed that you bet on the right one because because I remember when there was like Word Perfect and then Word, and it's like so. If you bet on Microsoft stack, so it's like so. I, I, I'm kind of like watching where the money's going. So I'm like, okay, if Microsoft's betting on chat on OpenAI, then I'm gonna, I'm gonna go deep on OpenAI. You know, if, if Amazon's investing in, you know, so that's kind of how I would do. I would make that decision because they're not gonna let it fail, and, and you might as well become. Expert in one, or at least comfortable, like a pro user in, in one.
Kim Meninger
Yeah, that's a really great point because it can be very overwhelming, and I think there's a way in which we we become self critical when we think I should be doing more. I should know this. I should know that.
Yoli Chisholm
Yeah, yeah, and, and the truth is, with software and with with technology, like we end up using a fraction of it. You know, we end up using like the core features. So just figure out like what's what's the foundational stuff I really need to know. You know that's how I'm thinking about it. The same way, you know, when you think about office products, right? Like PowerPoint, Excel, Word-you know-everybody adopted had to at some point adopt all of that tech, but we all got to you to know to know it to a certain kind of basic level, right? There's only some of us that became Excel experts or you know PowerPoint whizzes and it's and I so I think about this tech the same way. It's like how can you become competent, like a, a good like a power user without overwhelming yourself?
Kim Meninger
Yeah, that's such a great I think a, a great transferable point too. It applies to technology, but applies to so many other things too, where we just put so much pressure on ourselves and feel like I should know everything, and if I don't, then I'm not good enough. When really, it's more practical than that. It's like, what do I need to know do my my work as effectively and efficiently as possible? Right. There's a like you said a lot that we're not going to need to know, and if we need something at some point, there will be people out there that are whizzes in those areas that can support us.
Yoli Chisholm
Yeah, yeah. I mean, and think about this is kind of how I also rationalize like, you know, should I get should I go get a degree and get my MBA? You know, and it's like, well, you know, I've worked with people who have MBAs, and yeah, they, you know, they've been super smart in certain areas, but in certain areas, I've been more experienced, you know, and so it's it's it's all at the end of the day, you know, it's the doing, right? Nobody's giving us a test at work, like it's like it's the doing.
Kim Meninger
Yeah, exactly. I was thinking about that when you were talking earlier too, around the, the, the way you leveraged your retail experience when you went into the, the next job, and that is a degree in of it in and of itself, right? As the example that you get, and so we've become really attached to this one way of thinking about, you know, academic credentialing, when in actuality, describing so much of it is learned on the job. And if you think about how many people who got their degrees in certain subjects years ago, and how many advancements have been made since then that they never studied while they were there.
Yoli Chisholm
Yeah, that's so so true. One of the things that really helped me realize this was, you know, because of because of my background, not having a degree, when I when I moved from Canada to the U.S. so I worked in Seattle for a while, and then I worked in New York for a while. And with each of those moves, I had to do like a what they call an attestation, which is like if you don't have a degree, can you prove that you have X amount of experience? And then we'll look at your years of experience and equate it to, you know, is it the equivalent of one year university or two years university? It's it's really interesting, but that's how some of these countries do that, where it's like, hey, you know, if there's somebody who has a lot of experience, but they don't have a degree. Is there a way we can we can look at the work experience they've had and equate it to a certain level of you know accreditation? So that's kind of. But it helped me kind of value my experience in a different way.
Kim Meninger
Interesting, yeah. I know it's just funny to think about because I went to a liberal arts college, studied psychology, never took any business courses, never took any tech courses, right? So like, oh yes.
Yoli Chisholm
And we’ve probably worked with a lot of people who are not doing anything in their, in their degree, and, and funnily enough, I think it's, it's, it's a lot of the liberal degrees or liberal folks that were on that side that are going to fare better in this AI world.
Kim Meninger
Yeah, yeah, you're absolutely right. I agree with you. Wow, Yoli, this has been such a great, uplifting conversation. I really appreciate the positive, the, the positive energy that you've brought to this discussion because I think there is a lot of nervousness naturally around this, and I think you've given us some really great ways to think about it to embrace rather than resist.
Yoli Chisholm
Do we have any other choice? I know that we have.
Kim Meninger
You’re absolutely right. So for people listening who want to stay connected to you, where can they find you?
Yoli Chisholm
So I'm at I'm on LinkedIn at you know LinkedIn dot and, and Yoli Chisholm and then I'm also at Borderless Self dot com which is my website and my app and at Borderless Self and all the socials.
Kim Meninger
Excellent! I will make sure those are in the show notes and thank you so much for being here.
Yoli Chisholm
Thank you so much for having me, Kim. I really enjoyed the conversation.
