Rethinking Career Growth in the AI Era

In this episode of The Impostor Syndrome Files, we talk about building a career in a time when the rules of work are changing faster than ever. My guest this week is Sam Alvita, founder of Work Rewritten and Director of Learning Design at MasterClass.

In our conversation, we explore why today’s career paths no longer offer the same predictability they once did and why adaptability is becoming one of the most important professional skills. We discuss the shortening “skill horizon,” the importance of learning how to learn and how to think about career planning in a world where five- and ten-year plans feel increasingly unrealistic. Sam also shares why discomfort and impostor syndrome often accompany growth and how reframing uncertainty can open the door to new possibilities, creativity and career fulfillment.

Finally, we talk about proactive career management, including how to stay prepared in an unpredictable market and strengthen your network through relationship building.

About My Guest

Sam Alvita is a writer, learning design leader, and future-of-work strategist exploring how ambition, adaptability, professional identity, and career growth are evolving in the AI era.

She is the creator of Work Rewritten, a publication exploring career reinvention, leadership, AI, and the changing realities of modern work through essays, workshops, and public conversations. She also serves as the Director of Learning Design at MasterClass, she created and launched MasterClass Certificates, AI-first, multi-course learning programs developed in collaboration with organizations including Microsoft, NVIDIA, Google X, and the Navy SEALs.

Sam writes and speaks about how professionals navigate uncertainty, identity, and career growth in rapidly changing industries. She is currently writing a forthcoming book about ambition, identity, and navigating change in modern careers.

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Website: https://www.workrewritten.com

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Transcript

Kim Meninger

Welcome, Sam. It's so great to have you here. I'd love to start by inviting you to tell us a little bit about yourself.

Sam Alvita

Yeah, thank you so much, Kim. I'm excited to be here. So, my name is Sam Alvita, and I run the career strategy firm Work Rewritten. I do a lot with various clients, helping them navigate the current era of work that we're in, and then plan for the future of work that we're heading into, and then I do a lot of work as well as the director of board, director of learning design at Masterclass, so covering the same exact problems but on a much larger corporate scale with them, so that is what I do.

Kim Meninger

So, how did you get into this work? I mean, where was this always your career path, and you decided to branch out and do something more entrepreneurial on the side, or did you have any kind of twists and turns along the way that led you into this space?

Sam Alvita

Yeah, so I have been in the education space or the creative space pretty much for my entire career, and I was not originally planning directly on becoming an entrepreneur doing this full time. I actually started career coaching my friends a very long time ago, because I was good at writing resumes, like that's really what started this whole thing, and it started again very, very casually, of like, oh, this particular person was looking for their next role, I could help them out, and then I found myself really, really enjoying that work, really loving being able to step into this process with people as they figure out their next step, so I got all my formal certifications, and continued to build this entity, and then a few years ago, I would say, is when I took it to be a much larger scale, I was noticing as there were many shifts in how we were thinking about work, specifically the AI era, some of the layoffs, I work a lot with people in tech, so there were a lot of big disruptions from that particular industry that a lot of the resources that I was seeing online and a lot of the common narratives I think around the career coaching space were just not serving the needs of the people I was working with very well, so I decided I would create my own resources, which then turned into a much larger form of my business, and then the subsequent book that's coming out in 2027 about these topics. So, yeah, it just kind of grew and grew and grew, and now we're in this particular space, but yeah, started with just resumes for my friends.

Kim Meninger

Wow, that's a, that's a great story. And I mean, now I feel like it's a particularly challenging moment in history, because there's so many big changes going on, and lots of moving parts, for lack of a better term, that are affecting people's jobs, affecting the course of their careers. What do you hear from your clients, and what are the big things facing people today?

Sam Alvita

Yeah, so I would say one of the biggest things that I hear from pretty much everyone I work with is that no one feels particularly safe in their role, and I think there are level, like varying levels of severity of what that means, but I think when we think about how work looked historically, there was this career ladder, and it was relatively stable, and for people who say entered the workforce in, like, the 1950s the 1960s they really could train in one thing, enter a company. If they did work at an average to good level, they probably were pretty secure and stable throughout the entirety of their career, could move up incrementally, retire with a nice retirement package, and call it good. And I think a lot of us were trained around a similar mindset, like you went to college, you got a particular degree, or you went to a training program, you were trained in a specific thing, and there was a level of stability that carried that person throughout their career, and I would say now I know very, very few people who have not been laid off at least once in their career, and I think everyone kind of has this again at varying levels of severity, like voice in the back of their head being like at any moment my skill set could be very disrupted, or I would need to potentially do a much larger pivot into something new, I could get laid off, like the role that I am in is not as stable as maybe I was promised many years ago, and then I think for people who do feel more stable, there is also this underlying sense of it's not getting me to where I want to go, so even if they do feel like they're on a corporate path that is right. Relatively linear, they may not be moving as quickly or making the amount of money they want to be making, or whatever it is, whatever they felt like they were promised is not necessarily being delivered on. So, there's just this sense of unease that is coming into every single conversation I have, and one, two, that I hear a lot in larger scale situations at Masterclass, as well, that people just don't think that their jobs are going to look the same as they have, and they feel a need to adjust in some capacity to fit their own needs and carry themselves into the future.

Kim Meninger

It's really challenging, because we, as humans don't like that unpredictability, right? We're sort of wired for stability, and that unpredictability feels really threatening. I also think there's a way in which the fact that we're on shaky ground right now creates an opportunity for us to think differently about our careers, because a lot of people are unhappy in the work that they're doing, but they're doing it because it feels like the responsible thing to do, or you know, it's scary to make a change, and so how much of the work that you do involves like helping people imagine something new, or maybe unlock some things that they have been thinking about for a while, but just haven't felt like they could take that risk.

Sam Alvita

Yeah, I love this question, because I would say almost all of my work probably is falling into this bucket now. I think there's so much potential that every single person is sitting on, and like many of the high performers that I'm sure are your audience, and the people who come into my coaching space, do not love ambiguity. I get it, like we are trained on these external forms of validation, we have these very deeply rooted ways of thinking about work and success, and a lot of the most exciting and interesting opportunities require a certain amount of breakdown of those narratives, but then also being able to lean into something new and realize that the potential that everyone is sitting on and the potential that we all could accelerate to move into this future of work is extremely exciting, and there's a lot of opportunity in within that.

Kim Meninger

Yeah, and I think that's the part that is really helpful to remind people of, is the opportunity part of it, the exciting part of it, because it is so embedded in our operating systems to fear the unknown, right? So, to remind ourselves that actually this could be a great chance to think differently about what you do with your career.

Sam Alvita

Yeah, absolutely. And I would say we're in one of the most connected moments of history. There's more interesting technology to take advantage of. I think if someone wants to go a more entrepreneurial route or start their own thing. The barrier to entry could not be lower, and I think there's many, many exciting aspects of that that are going to carry us forward.

Kim Meninger

How do you think about the time horizon, just given the fact that AI is evolving so quickly, it has unknown implications for what the workplace is going to look like, what individual jobs are going to look like. When, when you think about helping somebody with their career path, there has to be obviously flexibility to that, because to account for that unknown. But, like, how do you think about, you know, the olden days when people say, what's your five-year plan, or what's your 10-year plan, which, you know, how do you think about planning in the age of uncertainty that we're in today?

Sam Alvita

Yeah, so I think to your point, the five and 10-year plans are extremely challenging to work with, and whenever a client comes to me requesting one of those I think we can talk about things at a much larger scale, such as, like, okay, what do you want your day-to-day life to look like? What do you want to be true for your family? What type of work do you want to be in? We can absolutely still plan in that kind of capacity, but if it's like, I want to be a senior manager at this company doing these things, I'll be like, okay, time out. I don't know if that is exactly where we want to spend our energy, and there's actually maybe better waiting for you if we don't, but I would say with all of my clients, I talk about this less from like incremental steps on a ladder perspective and much more from a skilling perspective. So say, for example, let's go back to this idea of like what worked looked like, what work looked like in the 1950s or 60s. So you'd get one skill set, maybe you'd make small tweaks to that skill set, it would carry you through your career, and then that skill horizon has just been shortening and shortening, and so in the 80s and 90s maybe. It was like 20 years, early 2010 10 to 15 years, and now we're looking at a skill horizon that's closer to about two to two and a half years for most skills, so that's concerning, right, for especially like if you're going to go to college to get a degree in something, the skill that you learned your first year will likely look very different even your fourth year before you've even entered the workforce, and I think that same kind of mindset can be applied to anyone in any career, so even like what podcasting looks like now will probably look very different in two and a half years, and that's not to say, like, oh my gosh, people are going to be cut out of various spaces, or there isn't leverage to move around. It's more like, how can I take advantage of this moment, and potentially a lot of the friction that is current might be eliminated, which is great, or maybe there's cool new opportunities to lean into different parts of your work, but again, two to two and a half years is that mindset, and I do anticipate, especially for certain skill sets, that window will continue to shorten, and we'll see what that looks like as the tools continue to evolve, but.

Kim Meninger

Yeah, well, it also makes me think about a, oh no, almost like a meta level of skills or thinking that it, that adds some flexibility to the mix, because if you go in with an expectation that you are going to be updating your skills and that things aren't going to look the same for an extended period of time, you kind of live your life accordingly, right. And so I think you could be on the lookout for what are the new skills that my career path is demanding, or what are some of these interesting new paths that are being created by the technology, right? It's like we almost train ourselves to notice things differently.

Sam Alvita

Yeah, absolutely. And I think, too, to build on that, it's a really cool opportunity to use your network differently, like to get into conversations with cool people and cool collaborations with people who may be thinking about this differently. There's a lot of fun learning to be had, and again, cool applications of the same skills you may already be good at to carry your work. So, yeah, it should be interesting.

Kim Meninger

Yeah. Well, and I also want to, I want to bring imposter syndrome into the mix here too, because that's obviously something that often emerges in times of transitioning, or when we're thinking about doing something new. I'm sure you see it a lot too in your work with people rethinking their careers, of, well, you know, I don't have what it takes to do that, or who am I to move in that direction. So, how does it show up in your world?

Sam Alvita

Yeah, so I would say anytime anyone is learning something new, there is a certain amount of discomfort that comes with that, right? Like, until you know how to do the thing, it's not there isn't an amount of ease that's carrying the process, and sometimes it can be a short period of discomfort, sometimes it's a much longer period of discomfort, and I think as we're moving into a more ambiguous space that requires more learning, more people are feeling more uncomfortable more of the time, and I always caution my clients, like, if they are feeling a certain degree of discomfort, that's not necessarily a sign to hold back or to stop trying. It's more that we need strategies to learn how to work within that discomfort, and I think I see this a lot again with people who have been really successful in the older ways of thinking about these things. Again, they've had a lot of success in, like, the more traditional pathways. If you were that, this discomfort may feel new and different, and the imposter syndrome may feel new and different than it might have recently. And I do think, yeah, there's a lot of different ways to work with the discomfort, so it does feel better, but again, that it's not evidence to step back or lean back, it's just learning how to work with it and applying different strategies, maybe than they have before.

Kim Meninger

Yeah, and I think that that is aligned with the idea of having certain expectations about what our paths look like or don't look like, and I think you're right, that that's how I've come to terms with my own experience with imposter syndrome, is that it is an unfortunate. Companion, when you are stepping out of your comfort zone, right, and it doesn't mean, like you said, it's not a signal to turn around or to stop, it's just a part of the human experience when we are out of our element and we were learning something new, and if we can name it, acknowledge it for what it is, and not let it derail us, we know from experience. Most, most people listening to this who have experienced imposter syndrome have experienced it more than once. So we know we can get to the other side, right? It's not something that we carry with us forever, permanently, in every situation that we're in. It's just a matter of being realistic about, okay, yes, I know that this is a result of the fact that I'm doing something different and new, and I'm learning, I, I'm going to be uncomfortable for a while, but this too shall pass, right?

Sam Alvita

Yes, absolutely, and, and that is exciting, right, like you're stepping into something new, and to feel energized by it as much as possible. I know it's hard to do, but I am always trying to be like, okay, this is new, it's hard for me, that's great for me. I don't want to be bored, I don't want to be comfortable. So, yeah.

Kim Meninger

Yeah, and I also think when you are in a time of tremendous change, as we are now, I mean, I'm sure that there are people who are very advanced when it comes to AI, but the majority of us are not experts, we're learning as we go, and there's something comforting, for lack of a better term, about knowing that we're kind of all in this together, and I even say to people, because people struggle with these with imposter syndrome, in particular, about certain kinds of self-doubt and perfectionism, feel this need to have like just complete expertise around everything, like be able to answer every question, to feel like they, they know all the answers, we're not gonna know all the answers. I mean, we're on a path that we can't even predict yet, and so to be able to also make peace with that and say we're all learning, right? Like that there is no one right answer to the questions that were being asked right now, and hopefully that can take some of the pressure off too.

Sam Alvita

Oh yeah, absolutely. And something I say to my clients all the time with this as well is really AI that's such its infancy that if you wanted to upskill and become an advanced practitioner, you could probably do so in a focused weekend or a focused week, like it's really like the time horizon is not like you have to invest months and take all these wild programs, like no, no, you can do a lot with the internet in like 48 hours, so it's all good, like we can all catch up quickly, and yeah, I hope that also eliminates some of the pressure that people may be feeling.

Kim Meninger

Yeah, I think that's a great point. Do you have other tips that you mentioned, kind of, how do we work within the discomfort? Do you have other tips that you would recommend people do or think about?

Sam Alvita

Yeah, I think one thing I always have my clients do is a visioning exercise of, like, okay, so say I were to work within this discomfort. What is capable, or like, what becomes possible for me on the other side of this? So say, for example, they're in a brand new role at the company, they're leading a huge team, maybe they're one of the people that has to lead this new AI initiative, and they feel like, what am I doing in this role? Like, this is not my space to just sit with it and be like, okay, yes, we are feeling the discomfort right now, 100% That doesn't mean it's scary, and if we're going to continue to face it fully, what could be true, and frame it very optimistically and expansively, and I think that kind of mindset shift takes it from this like anxiety-provoking, like, oh no, I just need to get through the day, I don't want anyone to find out what is happening, to a much like larger future-focused vision of self, of like, okay, if I lead this initiative really, really well, maybe my next major promotion is going to sit on the other side of this. Maybe I can make these particular things possible for my team. Maybe I can lead my own company eventually, whatever it ends up being. But I do think it's helpful to frame it from a much more future-focused perspective, and I think, too, just acknowledging it, like having certainty and comfort, does not necessarily mean, like, competence, or that you've solved it, and I think even hearing that is helpful for people to be like, oh, this is how I'm supposed to be feeling, okay, this is. Great, but at least it's something that I can work with and move forward with, so.

Kim Meninger

Yeah, I mean, that's something I think about a lot, is that the status quo is not necessarily good either, just because it feels comfortable, like you said, right, there are risks in not going through this, because we don't want to be left behind, either. You know, where everybody is finding their way in this new reality that we're experiencing, and the uncomfortable path forward is one part, but there's also the uncomfortable staying still, right, and, and not, not actually forging that new path. And what are the implications of that? And so, when you talk about the future, I always like to think about that too, of when we look back on our lives, it's the old cliche that we're far more likely to regret the things we didn't do than the things that we did do, and so if we can think about it in terms of like, what do I lose by not taking these chances, what do I, what do I potentially gain, really crystallizing some of that analysis in ways that don't come naturally to us, because we're always going to go to what could go wrong, right? I think can help us get through it too.

Sam Alvita

Yeah, absolutely. And I mean, I'm forgetting the exact name of the psychological phenomenon you're describing, but it's like we always think that the risk is going to be associated with more loss than gain, just psychologically, and it, the reality is the exact opposite. Usually, it's associated with much more gain than loss, and that knowing that can be helpful too. To be like, yeah, the grass may not always be greener, but it often is. So, take the chance and do the thing that would be how I would suggest it.

Kim Meninger

Yes, absolutely. And you know, you talked a lot about, or not a lot, I shouldn't say, you talked about layoffs, and I'm thinking about there's a lot of layoffs going on right now. Are there things that you think people should be thinking about maybe if they're not feeling the certainty around where things might be going within their own company right now that they can do to get ahead of the process, like maybe they're not actively thinking about a new career path or making a change, but they want to have an insurance policy against some of the things that are going on out there.

Sam Alvita

Yeah, this is a tricky conversation to have, because I don't want people to always be in like that negative mindset, like, oh, I might always get laid off feeling always anxious about that, but I do think exactly what you're talking about with the insurance policy is extremely, extremely important right now. I think just at a basic level, I always suggest that everyone always has their resume like at least loosely up to date, and it's just keeping an eye on their particular industry and the changes that are happening within it. I think what can be really tricky is when certain companies say, for example, I think Meta is about to do another huge layoff today or tomorrow, that all of these people who are in the same job function are released into the market at the same time and are competing for the same types of roles, and I think the people who are ready for that to happen and already have their ear to the ground and are prepared can kind of get ahead of some of these waves of layoffs, and some of the folks that maybe weren't thinking as proactively sometimes find themselves in much larger periods of unemployment than potentially their training would suggest that they would need and again, I do think we are going to hear about a lot more of these larger scale layoffs, and just to have a general game plan, I think, is always great, and I do find that even this game plan, again, it doesn't take hours and hours of work, it's more just like keeping your network warm, keeping that resume up to date, just keeping an eye on things can do a ton if there is going to be a larger disruption, and then, of course, keeping an eye on what potentially is happening at your own company. I think there are a lot of signs that tend to pop up when things are getting unstable, um, and some people kind of want to just push them in the background, they don't want to hear it, and I do think acknowledging it and keeping an eye is always a good idea.

Kim Meninger

Yeah, I think that you, you can't go wrong with just being a bit more proactive. I think of it as career management, it doesn't mean that you have. Be out there looking for something new, but just kind of keeping things up to date, like you said, and especially your network, and I wonder if you have thoughts on that too, because a lot of people are busy and a lot of people are really uncomfortable with reaching out to people outside of their company, even if it's just an informational interview, like, do you have thoughts on how to navigate the discomfort of networking.

Sam Alvita

Yeah, this is a question I get asked all the time. I think the word networking is something that a lot of people really dislike, and like, even me, I identify as such an extroverted person, and you put, you tell me to go network, and I'm like, can I not do that, but, but I love connecting with people, and I do think that thinking of it more as a connection is extremely helpful. It's like you always have something to give and something potentially to gain from everyone, but thinking about it more as, like, how can I connect with this person, celebrate them, their work, learn from them, and their work that makes the conversations feel much more organic and less like networking, and of course the opportunities will still come from that, but it feels less like, hey, my name is Sam, can you get me my next job? Like, that's terrible, no one wants to do that. So I feel for everyone who hates it, but the more that they can think about it as a connection and like a conversation to have with someone who could be a friend or someone who they just want to learn from. I think the more organic and easy networking will feel.

Kim Meninger

Yeah, that's a great point. I think the way we frame it is really important because networking sounds really transactional and very cold and really it is about relationship building, connecting, and I often think about too now everybody's in different places in terms of they might be making dramatic shifts in their career paths, so their current network may not be as in touch with what they're looking for, but just keeping connected with the people that you used to work with, I feel is a really good sort of low hanging fruit from a networking perspective, and even people who are not in your field anymore still have their own networks, and so there's still value to just having people out in the world who know you, who have a good experience working with you at some point, and I always like to frame those as catch-ups. Right? It's like it's so much easier to just catch up with somebody than it is to feel like, oh gosh, I'm networking with…

Sam Alvita

Yes, totally, and exactly catch up. It feels so like, okay, sure, whatever, that's easy to do. There's like a lightness to it, and I think, too, like what you were saying. I do think, like, a lot of people in your network, even if they aren't going to be the person who employs you or puts you on their specific team, they have their own networks, and so sometimes it's like a chain of people that get people to where you need to go, the person they know that you don't know, and so keeping like connections warm, even if it doesn't feel like the direct path, is often extremely valuable.

Kim Meninger

Yeah, this has been super helpful, Sam. Thank you so much for bringing your insights to us. I know you do this work for people who are interested in learning more and following you and maybe reaching out to you about your work. Where can they find you?

Sam Alvita

Yeah, so they can find me at Work Rewritten dot com I write on Substack a lot as well. So, at By Work Rewritten on Substack, and then Sam Alvita on LinkedIn, I would say, are my primary three places that are easy to find me at.

Kim Meninger

Excellent, and we'll make sure those are in the show notes as well. Thank you so much for being here.

Sam Alvita

Awesome, thank you so much, Kim. This is great.