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Shemina Jiwani: It's not a straight line to CEO

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Shemina Jiwani: It's not a straight line to CEO

Shamina Jawani’s career journey is a powerful testament to the unpredictability and flexibility of professional paths. Starting in marketing, she made a bold pivot into real estate and hospitality, where she developed transferable skills in leadership, communication, and empathy. This experience not only deepened her understanding of diverse industries but also prepared her for a return to the payments sector, where she eventually became CEO. Her path was driven not by a rigid plan but by personal evolution, including a desire for new challenges, family life, and better work-life balance. She credits her success to adaptability, self-awareness, and empathy—both in managing teams and in navigating personal transitions. Shamina emphasizes that career progression is rarely linear, and that moments of uncertainty or risk are often essential for growth. She highlights the importance of transferring skills across industries, honoring one’s current life stage, and seeking support through networks, especially for women. Ultimately, her story challenges the notion of a "straight-line" career and instead celebrates serendipity, personal evolution, and the courage to pivot when needed. For young professionals, her journey offers a vital message: embrace uncertainty, trust your process, and prioritize what truly matters—like balance, growth, and fulfillment—over rigid expectations.

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Welcome to the unexpected career podcast, where we share stories of real people and the twists and turns they have taken along their career journey. I am Megan Dunford and as someone who found myself in the payments industry largely by accident, I'm fascinated by how people's careers unfold and how they've gotten to where they are today. It's also why I'm passionate about reducing the pressure on young people about going to university, what to take in school, and on getting that right first job. Today I'm speaking with Shamina Jawani, CEO of Ascendant, and my very first manager in the payments industry. Thank you for doing this. I'm really excited. I'm a little nervous about my life, but I feel like we'll just chat and it'll be fine. Yeah, that's generally how it goes. Alright, so let's get into it. I always start with the very beginning of when you were a small child, like what did you want to be when you grew up? So I think the first thing I wanted to be was a teacher that I can remember, and then I wanted to be an advertising executive because I loved the Coca-Cola commercials. And so I wanted the polar bear commercials that were on air, and I thought that they were so neat, and then they had all the merchandise, and I thought it was still amazing that they pulled all of this together. So honestly, that's what kind of drove me to doing marketing in university. I always knew I wanted to do business. There was no doubt in my mind that I was doing doctor or science or anything like that. I don't even think I took physics in high school because I had no desire to do anything in science. It was always going to be something in like advertising marketing somewhere around there. That's amazing. So it's also really cool because it clearly fueled your decision of what to take in university. That doesn't always happen where people are like, oh, I've seen this thing, and I'm going to see what that means, and that's what I'm going to take in school. Yeah, it actually even made me go, okay, I want to go to Miguel because they had immediate entry into commerce and to business and all the other schools, most of the other schools anyways, you've had to take a couple of years and then get into it. And I was like, no, because if I don't get in after a couple of years, I'm going to be devastated. I'm just going to waste my life. So I literally was like, okay, I'm going here because I get in right away. I was always curious about that decision to go to Miguel because obviously it's on the other side of the country from where you grew up. I always wanted to go ahead and family that had gone there and I had a couple of friends that I'd visited at times and I just love the idea of being in Montreal and in the center of downtown and not having to fully speak French to be functional there. I think beyond that it was just like, I know I'm going away from home and so why not go somewhere that I actually really would want to be and again the program to kind of drove a lot of that decision too. Yeah, that's amazing because the university has such a great opportunity beyond the academic side but to figure out who we are and get out of the shadow of other people or expectations or whatever it might be and learn how to be a grownup. Doing laundry and figuring out what to eat is that it's part and you know studying without having a deadline. I think that was like a real big wake up call for me in my first semester as most kids like, oh God, I have to do this all year and I can't just cram with the last minute. So it was good life less than more than school and like functional. 100% that's how I think of the university as well. So you took marketing at McGill. What was first job after school? How did you choose it? How did you make that decision? First of all, I come from an Indian family which if you know anything about that means marketing is too soft. So I also do the double major marketing and finance. So I'd have some hard and some soft. But my heart was in marketing. So I applied for jobs like proctor and gamble and craft. And then on the flip side, I also interviewed with Goldman Sachs and investment banking and honestly that world just terrified me because I didn't love it enough to do the hours that part of it. And with proctor and gamble, I think there was like a couple of spots for the entire country. And so I went to the final round and I didn't get it and I was devastated and literally was like, I wanted to do with my life. And my brother and I was working at a company called Thomas Cook financial which at that point everybody only knew Thomas Cook for travelers checks and the travel keys, but they had a fine hand. And so he said, well, we're looking for people. Why don't you just come and hang out and just, you know, shadow us for a day and see if it's something you'd want to do. And so I went there and it was a Friday afternoon. And they had it was called California Friday or something like that and people had Corona's on their desk and they were throwing a football around and everybody genuinely liked each other. And it was one play almost like an extension of university. And so I'm like, you know what, I'm just going to try it and I'll do this while I look for other true consumer marketing opportunities. And so I started there in 2020, I believe turn 2020, 2000, 25 years ago. And I got into this international payments industry and I'm still here 25, 26 years later. It's amazing. What a day to shadow. How many? You know, it's interesting because it was like all of a sudden the job was important, but it was more like, I want to be here if I had to be somewhere for eight hours. And it's not like cash and consumer products that I thought I had. It's amazing. I'm going to like these people and I'm going to enjoy. And I didn't realize it at the time, but now I know how important that is and how important it is to like where you're going every day for work and actually enjoy the people you work with. That's so true because to your point, you're at work eight hours a day. You spend more time at work than any other thing you do in your life, really. And ideally you get to enjoy it. And what an opportunity to shadow at all. Let alone that it was a Friday where people were relaxed and having fun. But just to even get to shadow and get a feel for what the place was like and what it would be like to work there. Because the technical side is something you can generally learn. Like that's usually not we think it's the biggest obstacle, but it's not the biggest obstacle. It's what is the environment like? What are the people I work with? What's the culture? I don't know if you found this, but even now when I'm hiring people, it's really, it's about aptitude and it's about, you know, the desire and the effort. In the technical stuff we can teach, right? So like I've hired people that have philosophy degrees. I've hired people that come from science. I don't really care what the background is. It's really like, hey, do you have that earns to learn? Are you a good person? Are you going to jump in when someone needs you? That stuff is so much more important in my mind now than a university degree in some specific section or our faculty. Yeah, 100% and it's that, I think he is the word aptitude, but like willingness to learn and be part of the team and grow within the role makes such a huge difference. And when you're starting your career, you ideally are looking for places that have room for that growth as well and that you'll be able to thrive in it. And that environment is different for different people, but finding that environment is game changing. What we're saying, it's not lost on me that I landed in a really good place that then did offer me all these stepping stones to grow. And I also think I realized early in my career that your job is your job, but there's so many other things that you can kind of get your nose into that will help you grow throughout your career. And maybe not even through your career, but just in life, there's different sort of scenarios that you can put yourself into like nobody really wants to do certain things. And if you get yourself waged in that, you become an expert in that and all of a sudden all these other things sort of come from that. I think we've both done that, right? Like there's lots of things in what we do that's complicated and I mean, I would say boring. And it's not the line light that sales could be or that driving that, but without what we do at times and without some of those projects, those clients can't be on board it. And I think those sort of projects have helped us jump up in our career. Yeah, for sure. So willingness to say yes. Because a lot of the times, you're just like, I don't know if I can do this. And I think about back in my career, I know I've stopped myself from doing some of this. Even today, I have stopped myself from doing things because the imposter syndrome kind of kicks in and I'm like, I don't know if I can do this. Yeah, yeah, that's a good point. It's like, even if you don't feel ready, say yes, like do it before you're ready. Because somebody else will inevitably say yes, and they may not be anyone qualified that you, they just may have the confidence, right? I'm 100%. She's not many times. So tell me a little bit about what you're doing now and then that journey to get there. I started as just like an account manager at Thomas Cook. And then I moved into more of the financial institution, like key accounts. And then Thomas Cook got purchased by Travel X and life just changed and that full culture that I logged sort of evaporated overnight. And so a bunch of people from Thomas Cook joined another company called Custom House. And so I joined as well. And we were in charge of the US market, and we didn't really want the US market, so then it kind of just grew and I got to do a global role which involved me traveling to Australia and the UK and Italy and it was a phenomenal role for me at that one in my life. But it was this global exposure, try to say, hey, we want to replicate what we're doing here. Totally different markets, so we're going to have to adjust and figure that all out. But it was probably one of the most eye-opening roles for me and when you talk about, like, who am I? I think I was maybe late 20s going to all these places and telling people, hey, this is what we do and this is what I think you should do. It was kind of surreal in a way. But again, we just kind of did it and we did so much fun through that whole process and then we got ready to be acquired again by Western Union. And at that point, I think what I realized about myself is I'm a generalist. I love having my hands in seven different pockets and I really enjoyed getting exposure to different things. I didn't like the specialty side of it and with the acquisition coming, we were making each role sort of narrow and scope and I was getting really bored. And so at that time, my dad's a commercial contractor and he was building this resort in the Rocky Mountains. Most people will know where math is, but just outside of BAMF and the developer hands in trouble. And so we kind of took over on the development. And so my dad said, hey, you know, if you're bored, do you want to come here and start working on managing the resort and selling out some of the condo units? And at that point, I was like, I don't know what I'm thinking, but sure. And I did it. And so it involved me moving there and doing something completely outside of my comfort zone. But also realizing that like everything we're doing is transferable. You can't go from polar opposite industries from hospitality to international payments. And like everything that I did, yes, I had to learn some nuances and a new system and whatever, but all those skills transferred super quickly and super easily. And I think they were a big portion as to why I was able to do that. And seamlessly into that role. But I will say it was the hardest few years in my life hospitality is next level in terms of hours that you're putting in dealing with some really, really difficult people and expectations. But it was it was fun. It was something different. And I met my husband in Canmore. So I was super happy about that. He may not be as cute but I am. But yeah, essentially for me as moved to Canmore, got married, hadn't got pregnant, which was a hard road for me. And so when I got pregnant, I realized I couldn't keep going at this sort of pace. And I wanted to move back to Toronto. And so I reached out to my old boss, a couple of my old bosses. And I got a couple of decent job opportunities. And I took the one where I am right now and ascendant. And essentially, I was just coming to fill in for an account manager that was going the way on medical leave. So I did that, but I learned the system. I got back into how do we service the customer and what are we doing. And then he came back and they said, well, hey, why don't you manage this team? And I said, okay, cool. So I started managing this team. And then it was like, well, we have this problem child. Do you want to take this on? Okay. So I started managing the payment operations. And then it was, you know, sales. And then it just kept growing. And we started doing really well on the sales side. And so I evolved into a CEO role at ascendant. And the CEO role was huge. It was beyond what your typical CEO role is because it's all of that plus sales and marketing and relation management. And then I also had development like product development prioritization under me. So it was a big role. And it was, it was great. It exposed me to so much. And it was totally in line with my, I like my hands and different baskets. And it was super fun. And then I think from there last January, I became CEO of the company after we got some private equity ownership. So that's where I've been for the last year is CEO CEO of the company again, super fun. A whole other level of dimension of responsibility and accountability, but it's great because ultimately the buck stops with you. And so you get to have some of that decision making that I didn't have in the past. It sounds like a wild journey because the step away from payments and going into essentially real estate construction hospitality, this whole other world and not just one piece of the world, multi pieces of that world feels like completely on paper. It feels a bit crazy, but as you said, the skills are transferable. And I would say even the stuff I learned just by having a corporation and the tax pieces and the lawyer in the contracts, all of that is transferred right back over to the ascendant side as well. I don't think I would have been as prepared to be CEO or even CEO if I didn't have that experience as well. So it's really interesting to me because I don't know, I feel like it was a blessing and also expose me to the house hard. You really have to work hard in that space. And you kind of got me a little more regimented in my approach to things because you just couldn't do it all. I love that. Like the transfer will back or the new skills you learn as well. And I think it's so interesting because so many of us and I am guilty of this to it can be really hard or scary to step out of the industry. It's like this is all I know even changing companies can feel like that even if you're in the same industry. But that can be the necessary change that will ultimately get you to the next level, which is maybe a level you're not even seeing right now, but that's the random puzzle piece. And the other thing that I thought was super interesting of when you did decide to come back to payments, arguably you went into a role that was way below your capability and way more junior than what you had been doing before in either industry. But it was ultimately the opening of a door that led you to now being CEO of that company. Well, I guess I don't want to romanticize it too much. I was also three months pregnant knowing that hey, in six months, I'm going to be taking a year off and that's not easy for any employer in my situation. I also felt like hey, I can do this and I also want to see if I like it again and if I want to do it. So for me, it was win win for a Senate. They had this sort of six month stint and I made it a six month stint and I also didn't know if I wanted to do this again for a career. And so it all kind of worked out in that realm, but I think the other thing I'll say is, you know, sometimes when you take that leap and you go to a different industry, even if it doesn't work out or even if it's awful, it doesn't preclude you for coming back to the industry. So I don't know. I always just view risks as like, hey, if they don't work out, it's not like the end of the world. You're not stuck somewhere. You can always come back. You can always do jobs. And honestly, most of the time when you're working somewhere, people will vouch for you. Right, if you're doing all those people will take you back. And that's what I found, you know, is that I didn't feel as panicked because I did have people that I could go back to and say, hey, looking to come back and I did have people that were interested in finding roles for me. That's very true. You can always go back. No decision. Very rarely. There are some decisions in life. But most decisions in life, you're not locking yourself onto one way, set a train tracks. Like you can always go back. You can always pivot. Take a different turn. You just keep making the next decision with what the information you have now. And I think the other thing you were saying about how you came back. Yes, there were some personal circumstance about it. But also you kind of did an experiment of like, yes, I can go back to this because this is where I came from, but I'm not 100% sure I want to. And this is a way for me to reengage with the industry, see if it's something interesting. Do I like it? Do I want to come back to it? Because every industry company team, there's pros and cons to them. So it's a way to evaluate. Wait, is this actually what I want to do? And is it the right fit? And I would also say that my requirements changed as my career went on, right? In my 20s or even as a young kid, you know, what I'd be saying, oh my God, CEO, that's amazing, right? Like, cool, that's what we all want to be. But as time went on in my career, like, when I got pregnant, what I really valued was challenging my brain, but I also wanted some flexibility. I also wanted some trust for my employer to know, hey, I'm going to get the job done. I can do it. You don't have to worry about that. You know, but different, you know, or I may have to run out for appointments or school stuff or whatever. And so that part also, at that point in my career, meant a lot to me. And so to have people that knew me and knew my work product was super important for me to come back into the industry, because I wanted people that trusted who I was so that I could be afforded some of that flexibility that I needed to be more. Yeah, I think that's a really good point. What's important and what we need to or want to prioritize or even what we want from our career. evolves and changes as we go through different life stages and milestones, but also just as we learn things I think too. So I think that's also a good point of each decision we make based on right now and the information we have. It again doesn't have to be forever. You're going to evolve and something that might be really great right now isn't necessarily great forever. And vice versa. I think we can get stuck really quickly. This is what I know. This is what I have. It's easy. What I also feel like there's so much out there and that risk can pay off. And there is, you know, I think we think in that moment that it's the biggest deal in the world because it's our existence today. But at the end of the day, sometimes those risks are exactly what you need to get yourself to where you want to go. And sometimes you don't really know at this point where that is. And that's why I say I don't know that everything I've done has deliberately led me to this role. I really do. I think, like I said, my younger self would be like, yes, this is where we wanted to be. But all the way through this journey, I can tell you that hasn't been the ultimate goal for me. I like that you said deliver it in there somewhere because yeah, even if that's a vague idea of where we want to go or something we're thinking about when we're young, we're not always deliberately making those choices. And even if you had a deliberate plan, it's not really how life works out. There is a lot of serendipity, but if you're getting skills and open to opportunities and also honoring where you are, actually that's usually where the magic eventually comes from. I also think it's just big, good people. When you're a good person and you work around good people, I feel like that's a big part. And I know a lot of what you talk about with some of your guests is like, hey, what did you want to be in university? And that's the part that I kind of it doesn't really matter background. What I think is really more like I said is the aptitude, but it's also being a good person and being reliable and jumping in when when people are needing something like I've been really lucky to have really good people around me. And some of my work colleagues are some of my best friends in the world and I feel from my perspective that you have to have those strong sort of relationships and those will give you the confidence to figure out what that next move is or what is it that you want to do. And I think we've talked about having a personal board of directors and it really helps as you're trying to figure out what that next step is is just thinking through and having someone that is not meant to be in your company or a mentor or a sponsor. It's just the pattern of people that know you, that know your goals, that know your situation and that you trust to bounce these ideas off of you because I think from that perspective when I think about the unexpected turns of my career, I probably wouldn't have been able to make them without those people there to help me talk through or walk through those decisions. Also, let me realize that they're not as big as I think they are because I think we'd build this all up in our head a lot. Yeah, so true. That opportunity to talk things through out loud with people as you said that know your situation beyond just work like the bigger picture is so helpful in getting that outside perspective from people who really know you that way can be so helpful. That's a key, especially for women, I think having that group, whether it's a couple of people or it's larger of women who aren't facing similar challenges, whether it's different industries or same industry is game changing for sure. Yeah, I do think just a woman on the woman piece for a second. I think that's been some of the biggest challenge for me because whether it's in my group of friends or in the company, most of the executives are men and for me it's been really challenging to navigate being a wife, being a mother, being a CEO or an ambitious woman and so oftentimes I kind of need to kick in the butt to say it's okay, right? It's okay that I might miss, I don't know, some dancer side olds because I'm doing this because also it's okay for me to miss that last dinner at a conference because I don't go driving home to get to my daughter's Halloween costume. So I feel like there's not a lot of that out there and I think that's a piece that has been super helpful to me with other women that are juggling all of the things and then I think just mentally I think I've seen this across all of my friends that are women that are ambitious, we do need that extra sort of confidence boost that our other friends can give us or that our other colleagues can give us, whereas I don't think my male colleagues need it. In fact, I think they're the ones, you know, rushing to the top of the list and where come like, oh, do we have all of the things and can I do this, can I not do this? So I feel like that has become a lot clearer to me as I evolve through my career is that I have to get over that piece oftentimes that I can do some of the things balance is balance, not at all times, it is throughout a long period of time you can have balance. So I will make sure I go to something for the kids, but I'll also make sure I'm at this work event and I try and balance that out. And ultimately, you're the hardest critic of yourself and you have to just sort of get over the fact that other people are judging you and if they are, oh well, kind of thing. And that's harder. Yeah, for sure. And to your point, having people in your life who are in a similar situation can help just remind us of, wait, like it is okay. And I can't remember I'm going to have to look it up now, but there is, I think it's an author that she talks about juggling and some balls are rubber and some are glass. And the important thing is knowing which ones are glass. And sometimes that's a family thing, sometimes it's a work thing. But some balls you have to let drop, but just drop the rubber ones and not the ones with their glass. Yeah, I'm lucky because one of the mentors I have right now, he is two times, three times CEO, just super smart, but over this last couple of years, his first roles are family and health and then work. And that's super important for me and it's almost given me license to take a deep breath and slow down on the work side because the first two have to happen before the third one can happen, so that's it's just something that I can't believe I have to tell myself, but I do have to remind myself of those things. For sure. So your career has been like as you're saying before, on paper looks quite varied and unexpected in terms of you were definitely in a path in payments and then you stepped out and then you came back, but did this experiment of starting in a more junior role to test if you really wanted to be back and have then just taken on more and more in and are now CEO. When you look back on the journey, are there common threads that you see that carry throughout? I would say one of the biggest things is communication. I've realized how important it is to be able to clearly communicate not only what you're doing, but if there's a set of deliverables and bringing people together, I think across all the different pieces and why I kept going in that progression was I was able to communicate effectively to everybody as to what was going on and then I think the biggest thing is people skills, right? I mean, it's not just people skills, but it's empathy for people. Well, I always say today, do you think someone was trying to screw up? Do you think someone is actively trying to make a mistake or do something bad? And the answer is always no. So for me, if you're going to bring together a team, you have to understand what everybody's skills are, what they can drive from the team and then it's about communicating these are the roles maybe on the team or whatever, but then being very empathetic and giving them the feedback in that moment. And I think that served me pretty well throughout my career, even when I started at Thomas Cook. I remember those days where we were a team of three and one of the guys had it a child at home and I would volunteer to stay I'll stay late because you've got the child or, you know, I don't celebrate Easter so I'll do this. You go and that would work back and forth and I feel like all the types of things are what actually instill that trust and I don't think a good team works when out that trust. And so I think that is easily probably has gone through the entire stretch since I've started the course. I also think that I've always had fun doing what I'm doing. You know, the minute I stopped having fun is the minute I would actually look for something else. I think it's super important that for me anyways that I'm actually enjoying what I'm doing and that I'm stretching and what I'm doing. As soon as that goes away, don't have any desire to do it and then I'm quickly looking for the next thing. And as you said, right from the beginning, we spend eight hours of our day at work. So if we're not having fun and we're not being stretched, what is the point? What is the point? And I think, and this is where empathy comes in, is there are people that are okay with that? There are people that are totally fine with coming in and doing eight hours and doing what they do really well, but this is their focus. This and they're like, they are not interested in going to the next road. They are interested in staying in their lane and having that stability. And I think acknowledging that everybody's different and having empathy for people like that is, is right, right? It's really, you have to come from all different Texas skills and motivations. And I think once you can figure out what everyone's piece is in the puzzle, it makes a huge difference. That's so true, not everyone wants to climb the ladder. And they're happy coming in and doing their job and that being and going home and leaving it behind. And so I think that's a really good point. And it can be hard to accept that in each other and to your point, like that's where empathy comes in. But a business needs both kinds of people. If everyone's trying to get up the ladder, there's not a lot of stability. And you start to lose things potentially, like trust. We all come from a place where we want all types of different people. We need all types of skillsets. I think at the end of the day, those people that are eternally loyal, they bring so many skills to the table, that sometimes it's hard for you not to understand why they're not ambitious because they could be doing more with that X level. And I've been in meetings where people are like, well, if they're not ambitious, you probably don't want them. And I totally disagree with that. I think there are people that are really comfortable in what they know, continue to excel at what they know. And if they don't want to do more, I think that's totally fine. And you don't have to look at them through your lens, since you're 100%. You alluded to it earlier. But what do you think 15-year-old, 16-year-old Chimino would think about what you're doing now? I think she'd say it's pretty kick ass. I look at things through my daughter's eyes and she'll tell people, oh, you know, my mom manages 100 people and she's super proud of it. So I get super proud when I see it through her eyes. I think I always knew I wanted to be a leader of a company and CEO would be really cool. I think that my 15-year-old self would not recognize how many different things have to happen for you to get in that role. Some of it is just like you said, serendipity, luck, but a lot of it is preparation, hard work, learning to deal with a whole bunch of different types of people. And I would say, I think looking back, I think that person, that 15-year-old was like, yeah, this is what I want to do. Just making polar rare commercials instead of writing international payment company pencil. Yeah, and it's not like one more young. We think it's a straight line. Whether we're interested in that or not, we think it's like, oh, it's just the spline climbing up and it's straightforward and it is totally not. Now, an or shouldn't be. I guess that's the advice I would give. When you're in it, you think that moment is everything and I totally get it because I was in all those moments. I can't wait to say it now, but those moments are just little blips in time and it's that whole journey that's going to get there and you're going to go all over the place like we're talking about. But nothing is the end of the world and you're just you're constantly evolving and everything is changing as time goes on. Like, you know, just with my kids being a little bit older, I have just that much more flexibility than I didn't have say five years ago and so that's even changed the realm of what I can do and what I want to do. Go ahead and forward. I also really value my time way more than I ever did in my 20s. Now, for me, I want to be in bed. I might each myself. I want to be in bed at a decent time. I have a certain amount of hours outside of my work time to split between me being healthy. The kids, activities, you know, social things with my friends. All of these things have a very small window and so my time now has become the brometer value for me. It's not about my career title. It's not about the money. It's not about any of that stuff anymore. It's really about the value of time for me. I think that's really, I mean, I heard a couple pieces of advice, but one of them is that journey. When you zoom way out and have hindsight, you can see how it looks maybe more of that straight line, but actually when you zoom in, it is very up and down. I think there's a meme from Adam Grant that's like that and it is very up and down and, you know, when you're at those little peaks or little troughs, it's just remembering this is just a moment and it's part of a bigger story and a bigger picture. But the other thing I've heard too is just again about the journey, how your priorities in that journey evolve and so when you're young and I'm going to speak for myself here, the time thing wasn't as important to me and I was happy to put in the extra hours at work and I may be partly because lucky enough to work summer that I was having fun, I felt valued, you know, so then the effort feels worth it, but that that evolves and changes over time. So, you know, I think that's the other, to me, a piece of advice in there of honoring where you are in both ways in terms of what your priorities are, but it's just a moment within a wider journey. Yeah, and I think it's really easy for us to forget that piece in those moments because we may have started in a role where things were very different and we may be in a different spot now and I think it's okay to rewire yourself and have those tough conversations and I was talking to somebody recently at our company and I was saying how when we adopted our son from Morocco and when we had to adopt him, I literally knew I had to be in Morocco or a period of time and I was honestly in knots just trying to figure out how am I going to do this and whatever and literally my husband's like just go ask if you can work from there and this is pre-COVID and I'm like there's no way nobody does this, there's no way know how and I did and luckily for me, my boss was like yeah, we eat you to work, we can't afford for you to be gone for six months but if you can work from there and we can figure this out absolutely and so even two years when I started in this role, I didn't have any of those needs and those needs evolved as I was in this role and sometimes we have this story built at our own hand that we can't evolve within the role. I said I was going to do this so they're probably going to do this and I have to do this exactly the same way in this state role and I think that's something that I learnt along the way is you can evolve within your role, you can set new expectations, you can alter what your deliverables look like just by having some of those conversations as well. I don't know that we're wired that way, I think sometimes somebody has to give us a good kick to realize that we're good at what we do and you can ask to change the roles of engagement as you need. That's amazing. Giving ourselves permission to evolve in the role and if you don't ask the answer is no because you haven't even asked the question. I think lip side of that about evolution is also recognizing when you evolve the role might have been giving you something before and it might have been a really great fit. If it isn't willing to evolve with you but you have to ask and do what you know try to to make that change. If it's not going to work it's okay to then make a different decision and be like this thing was amazing. It's not the right fit anymore and I'm going to speak for myself again but sometimes the hardest thing to let go of like I had so much fulfillment from this it was so fun. I still love the people but the role itself maybe isn't the fit anymore and I've evolved within it as far as I can. Absolutely and I think you're good at it. I think that's the piece that people also forget. You may be asking for something else or you may be changing or you may say it's time for me to move on. Like at the end of the day and I'm speaking for you right now is you are really good in your role and you were like this is as far as I can go and as far as I can learn and same thing with me I felt like before I went to go live in Alberta for the resort property it was like I don't see where I go from here. I don't see where I'm going to learn something more or I'm going to love the people I'm working with that much more and hit this plateau what it was like okay I have two choices I can sit here and be that eight to five and hope for something to open up or I start to figure something else out for myself and I think the other piece was I think I am good at when I do there and even with that I'm not hitting other opportunities in fact the role is kind of shrinking, wide perspective shrinking. You know I think to your point it's just also about recognizing when it's okay to start looking for other things and also widening the scope of what you're looking for because going back to what I said at the very beginning a lot of what you learn is transferable and a lot of what people should be looking for and are looking for now is the ability for people to grow in that role that it doesn't really matter what your background is do you have the ability to take on do you have the ability to work with people do you have the ability to analyze things do you have the ability to accumulate effectively like those are all very general skills that can be applied across tons of different industries I think there's a misconception and you touched on it before of people need to be specialists but actually well for a lot of us that's not that exciting like the generalist being involved in a bunch of things is more fulfilling and more challenging, but on the other side, like, businesses need generalists. And I think it's what you were saying too, about like, there are people who are going to be ambitious, and then they're going to be people who are happy with their role, and they just work their eight to five, and that's it. And you need both those kinds of people. A business also needs specialists in generalists, because the generalists help tie it all together. And so many of those skills are the ones are transferable. And actually, I would argue a lot of specialist skills are quite transferable as well. But I think there's a miss perception, sometimes, that we place for cells, usually, like, I think the reality of the world isn't necessarily like this, that those skills are less valuable. Or it's hard to recognize that them as skills. Like I look at job descriptions, and they can be pretty precise as to what they're looking for. And you kind of can talk with yourself, right? You can say, oh, well, I don't really have all this in-depth knowledge on, you know, this system or this process. I know the system works with our overall strategy. I know how it works in the realm of communicating with a whole bunch of different departments. But I would talk myself out of applying for that role, because I didn't have that in-depth knowledge of that system. And I think that's where that needs to change is that all of that can be acquired. And I think that's the crux of it. And I think that's a big underlying theme of your podcast is people get to very unexplained places in their career. And the majority of you are really impressive, and they're very capable. They just have an underlying set of skills that can be applied in a whole broad set of circumstances. And that's why I think this podcast is super interesting, because it gives you that like, hey, I've got a whole bunch of generalist skills, even if I'm a specialist, that like, hey, if I was to go out of my specialty or to another company, even, and I think that's the piece that when you're in it, you don't really stop and take a step back and notice that you have a lot of underlying skills that are almost or as important that more important than the specialty that you're in. Yeah, 100%. So we've done like a lot of looking backwards. When you look forwards, what's your vision for the future for what's next, it could be very short term, it could be long term, it could be both. So I'm in the spin in this role for a year, just over a year. And I like it, and I enjoy what I'm doing. So I do want to stay here, we've just scratched the surface. And I think there's so much more and I think the payment space and the technology space is moving at rapid pace and you add an AI and it's like, my boy, so we're exciting, it's super interesting. You know, if you ask me what I was, and even now I'll say I'm on a freedom 55 plan, I'd love to, and when I say freedom 55, I don't think I'm ever going to retire fully, like I want my brain to still work, but ideally in the end, or in 10, 15, 20, whenever that happens, if I would love to move away from like the day to day operations and had some more flexibility in my life, I love to golf. I want to be around for my kids through high school. I had kids late. So being around for high school, being able to travel, just having that flexibility. But I also really like my brain going. So whether that's sitting on a bunch of nonprofit boards, maybe for profit boards, you know, being introduced to the private equity world, seeing how some of my skills could transfer within that world would also be interesting. But right now, I'm just focused on really doing more or kind of keeping up with where the industry is right now. Yeah, that's amazing. And it definitely is a very exciting time and a lot of transformation happening in the industry in North America right now. So definitely very exciting time. And yeah, no shortage of new things to learn and opportunities to look into. Well, when your 11 year old daughter is showing you new tricks and how she made an app in 20 minutes, it's Holy Crow. I have a lot to do to keep up with what's happening. And I think that's the exciting part right now. Yeah, sounds exciting and a little bit scary. All at the same time, I think everything is anything that's exciting has a little bit of fear associated to it for read. Yeah, yeah, that's true. Someone I used to work with said once about an opportunity they had at work for a different role. They're like, well, it scared me a little bit. And that's how I knew it was the right one. So I think it's if it's not a little bit scary, then there isn't that challenge the thrill world to the thrill, right? Yeah, for sure, amazing. Thank you so much for sharing your journey. But even more than your journey, the amazing insights from your journey. And I always love and excuse to talk about things like being a generalist and the virtues in that, but also the importance of empathy and understanding the different needs of people on the team. In terms of hiring, but also on how you manage the team and trying to remember to not look through our own lenses, when we evaluate people. So thank you so much. I really, really appreciate it. Anytime. I love your podcast. I'm really doing something interesting to see how everybody has this weird roller coaster journey and how it literally isn't even like to miss. It's like all over the place. It's amazing. Thank you. I think it's cool because even people who think they have a really straight behind journey. Actually, once you start talking about it, it's not like even people I know have been in the same company for 20 years. Once you actually start talking about the things they've navigated within that company, it's like, yeah, it wasn't. It's not a straight line for most people. No, I think there's someone's value in that because I think right now, there's so many people that are trying to find that straight on and are almost looking for permission to take them wrong. That's a little bit outside of the norm. And I guess the last thing I'll say is I think everything also starts with yourself. And I think oftentimes we're so hard on ourselves and we feel like we have to have all the answers and be perfect in all of the things. And so sometimes it's just it's okay to sit in. I don't know. And we're going to take a shot at this and we're going to see how it goes. And we'll figure it out. That's an amazing reminder because we speak to ourselves in a way that we would never speak to our friends or our co-workers or people on our team. So you're right. That's a really important place to start is with ourselves. It was so lovely to chat with Shamina about her career journey. And a few things that I am taking away from our conversation are first transferable skills. In the middle of a successful career and payments, Shamina took a major pivot into real estate development and hospitality, where she learned how transferable her skills really were. She also credits this move for giving her new skills that helped her be ready for the COO and then the CEO role when she came back to payments. Second, honor where you are. One thing I was struck by in Shamina's journey were the risk she took to honor where she was. The pivot out of payments was because she felt she had plateaued and wanted a new challenge. Her road back to payments started because she wanted to move back to Toronto as she started her family. And she took a junior role as temporary cover to re familiarize herself and see if she truly wanted to be back and to afford herself the flexibility. From the outside, these seemed like really risky decisions, but they paid off because she was honoring where she was in that time period. Third, empathy and understanding. Shamina spoke a lot about having empathy for people's different ambitions, their intentions, what might be going on in their lives, which is so important as a manager and a leader. And I love how she also brought it back at the end of our conversation about having empathy for yourself too. And I also think it's so important to role model that like Shamina does for her team and her mentor does for her. I also think this is where the power of having a personal board of directors or tribe comes in, especially for women. Lastly, Shamina's advice about not putting too much meaning into a single moment as it's just one in a longer journey is so true. As she says, he will always be evolving and everything is always changing. It's actually one of my inspirations for the podcast. We put so much pressure on each decision in our careers, but things don't happen in the straight line you hope them to. Thank you for listening to the unexpected career podcast. Please follow share and rate on your favorite podcast provider. The unexpected career podcast is produced, edited and hosted by me, Megan Dunford. See you next week.

Podcast Summary

Key Points:

  1. Shamina Jawani’s career journey reflects a nonlinear path, including a major pivot from marketing to real estate and hospitality, demonstrating the transferability of core skills across industries.
  2. She returned to the payments industry through a temporary, junior role, using it as a deliberate experiment to reassess her passion and evaluate whether she wanted to re-enter the field.
  3. Empathy, communication, and trust in teams—especially recognizing different motivations and life priorities—were central to her success as a leader and manager.
  4. Shamina emphasizes that personal growth and career evolution are not linear; instead, they involve constant adaptation, risk-taking, and reevaluation as life and priorities shift.
  5. Her experience highlights that foundational skills like adaptability, collaboration, and emotional intelligence are more valuable than specialized knowledge or formal degrees.
  6. She values flexibility and work-life balance, especially as a mother, and sees time as a more important metric than titles or salary.
  7. The journey underscores that career plateaus are not failures but opportunities to explore new paths and rediscover purpose.
  8. Shamina advocates for self-compassion and the importance of having a support network—particularly women in similar situations—when making bold career decisions.

Summary:

Shamina Jawani’s career journey is a powerful testament to the unpredictability and flexibility of professional paths. Starting in marketing, she made a bold pivot into real estate and hospitality, where she developed transferable skills in leadership, communication, and empathy. This experience not only deepened her understanding of diverse industries but also prepared her for a return to the payments sector, where she eventually became CEO.

Her path was driven not by a rigid plan but by personal evolution, including a desire for new challenges, family life, and better work-life balance. She credits her success to adaptability, self-awareness, and empathy—both in managing teams and in navigating personal transitions. Shamina emphasizes that career progression is rarely linear, and that moments of uncertainty or risk are often essential for growth.

She highlights the importance of transferring skills across industries, honoring one’s current life stage, and seeking support through networks, especially for women. Ultimately, her story challenges the notion of a "straight-line" career and instead celebrates serendipity, personal evolution, and the courage to pivot when needed. For young professionals, her journey offers a vital message: embrace uncertainty, trust your process, and prioritize what truly matters—like balance, growth, and fulfillment—over rigid expectations.

FAQs

Shamina emphasizes transferable skills like communication, empathy, teamwork, and the ability to learn quickly. She believes these generalist abilities are more valuable than specialized knowledge and can be applied across industries such as payments, hospitality, and real estate.

She started at Thomas Cook Financial after a shadowing day, where she felt a strong connection to the culture and team. This led her to begin a career in consumer marketing, which eventually evolved into the international payments industry.

Yes, she left the payments industry to work in real estate development and hospitality, which she found challenging but highly rewarding. This experience helped her develop new skills that later supported her return to and growth in payments.

She returned after becoming a parent and wanting more flexibility in her life. She took a temporary, junior role to assess whether she still wanted to be in payments and to rebuild her confidence in the industry.

Empathy is central to her approach—she understands different people’s motivations, work styles, and life situations. She believes in recognizing that not everyone wants to climb the ladder, and that both stable, grounded roles and ambitious ones are valuable to a company.

Her career involved unexpected pivots, such as moving from marketing to hospitality, and then returning to payments with a new perspective. She emphasizes that career progress is rarely a straight line and is shaped by personal growth, risk, and serendipity.

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