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Episode 92

The Future of Work in the Age of AI

The career ladder was never a guarantee — but for a long time, it was a map. Now the map is gone. McKinsey estimates 375 million workers will need to switch occupational categories by 2030. The World Economic Forum says 44% of core skills will be disrupted within five years. The world of work evolved. The systems we use to evaluate careers didn’t. That gap is where capable people get stuck. In this episode, author and career coach Samantha “Sam” Sloan Alvita walks us through her four-part framework — Recognize, Initiate, Serve, Evolve — and makes the case that the professionals who come out ahead aren’t the best predictors of the future. They’re the ones who learn to read better signals, sooner.

with Sam Alvita April 16, 2026

Blog Recap

The career ladder used to be a map. Not a perfect one, but a map. You got a degree, climbed the rungs, and eventually arrived somewhere. That system is gone — and most professionals are still navigating by it. Sam Alvita is a learning designer, career coach, and author of Work Rewritten. As director of learning design at Masterclass, she built AI First certificate programs with partners including NVIDIA and Google X Moonshots, reaching tens of thousands of learners worldwide. What she shared in this episode will change how you think about the career moves you’re making right now.

The Real Crisis Isn’t Change — It’s the Map We’re Using

McKinsey estimates 375 million workers will need to switch occupational categories by 2030. The World Economic Forum puts 44% of core skills on the disruption list within five years. But Sam’s argument isn’t that change is the problem. It’s that we’re navigating massive disruption with mental models — the career ladder, the two-year rule, the prestige title — that were built for a world that no longer exists.

The Safe Choices Are Quietly Shrinking Your Options

Sam sees three patterns over and over in her coaching practice: staying too long in a stable role until skills stagnate, waiting for 100% clarity before making a move (aim for 80%, she says — that’s the sweet spot), and choosing a prestigious title over real skill growth. Every one of these feels responsible. Every one of them is a trap.

The RISE Framework for Navigating What’s Next

Recognize what mental models are actually driving your decisions. Are you living by rules of work that aren’t even true anymore?

Initiate before you’re forced to. Build options forward. Stagnation used to be a viable choice. It isn’t anymore.

Serve means having proof. Storytelling, portfolios, projects — showing the world you can carry your skills forward, not just list them on a resume.

Evolve is the ongoing commitment to realignment. The framework doesn’t end. Neither does change.

Read Signals, Not Predictions

The professionals who come out ahead won’t be the best predictors of the future. They’ll be the ones who learned to read signals sooner. Market signals (where investment is flowing), skill signals (what capabilities are becoming valuable), and organizational signals (where decision-making power is shifting) are all around you. Start with a sticky note on your desk. The habit builds fast.

Episode Transcript

Kelly Callahan-Poe: The rules of work have been rewritten and most of us are still playing by the old ones. Today’s guest has a system for getting ahead of the curve before it hits you. I’m Kelly Callahan-Poe, host of the Marketing Moms podcast. Today’s episode is called The Future of Work in the Age of AI with Sam Alvita. Sam is a learning designer, career coach, and author of Work Rewritten, a field guide for navigating careers when the old rules no longer apply. As director of learning design at Masterclass, she built AI First certificate programs with partners including NVIDIA and Google X Moonshots, reaching tens of thousands of learners worldwide. Through her coaching practice, she has guided more than 125 professionals through successful career transitions. Welcome, Sam.

Sam Alvita: Thank you so much, Kelly. Excited to be here.

Kelly: The stats from your book, Work Rewritten, are staggering. 375 million workers switching occupational categories by 2030, 44% of core skills disrupted within five years. A lot of change here. But you argue that the real crisis isn’t the change itself. What is it?

Sam: Yeah, absolutely. So as you mentioned, there’s going to be a lot of change over the next few years and 2030 sounds very far in the future, but unfortunately it is much closer upon us than we would like it to be. Again, like you said, there are gonna be many opportunities. It’s not necessarily that we are having change. It’s that we are navigating that change with mental models and systems that are not setting us up to navigate that change well. So one really common one that we think about when we think about careers is this concept of the career ladder. So in the past, someone would get a degree, that degree would last them 30 years over the course of their entire career, essentially until they retired and they’d be able to work up that ladder incrementally. They’d come in very entry level, maybe become a manager, become a director, senior director, maybe even the CEO before they retired. And unfortunately, that system just is not delivering in the same way that it used to. And the half life for these skills, as we call it, in our industry is just shrinking and shrinking. So to be able to stay at a company for 30 years with a stable skill set is almost impossible these days. Yet we are still setting up our systems of evaluation and how we’re applying to jobs, how employers are evaluating their employees to have this ladder still be in place. And that is going to be a big issue for people who are going to need to be a little bit more agile, moving around to different careers, getting different skills.

Kelly: I would like to think that the career ladder has evolved to be more of a jungle gym. And there’s this idea that when you’re on a jungle gym versus a ladder that you might take one step up, you may take a step sideways, and that might mean a lateral job move. And you might have the kid ahead of you just throw you down to the ground and you’ve got to start all over again, which could be a job loss or a family tragedy or health problems, that sort of thing. And so I feel like that should be really the model that we’re looking at because not everyone does follow the ladder. Sam, your book makes the case that the most resilient careers are built laterally through transferable skills. What does that actually require, especially in marketing where the job description keeps shifting?

Sam: Yeah, so to your point about the jungle gym, modern work is going to reward adaptability. So instead of thinking about this linear ladder where we move incrementally up in steps, instead we are going to have to take on a lot of the agency to develop our own skills, think about how we may be able to work more laterally, cross-functionally in different teams. And there’s a lot of opportunity that can come from this, right? So again, we are going to be in an era where the amount of time it’s going to take to learn new skills is going to be compressed. We are going to have a lot more tools available at our disposal. So the more experiments we can run, the more projects we can take on, the more we can apply our skills across a diverse domain of projects. Especially in marketing, I think this is extremely relevant. The better that we will be able to move around this jungle gym system that we are all going to be navigating.

Kelly: You talk about how professionals are caught between how hard they’re working and knowing what to do next. And you argue that the safe choices are quietly shrinking your options. What safe choices do you see the most?

Sam: Yeah, so in my practice I get so many people coming to me who are like I’ve made all of the right moves. I’ve done everything correctly. I did everything by the playbook and something is not working and generally what that looks like is that they’re taking on these safe choices, which unfortunately today is going to mean that they’re shrinking their options. So what that generally looks like is staying too long in stable roles. What this kind of means today is that skills will start to stagnate. So if you do the same thing for the same employer with the same skill set, there’s opportunity that’s being missed. And when you go to apply for that next job, you may not have that more diverse range of skills to work with. The second is waiting for clarity before acting. Everyone wants 100% perfect clarity to make their next move. They want to make sure the next job they’re picking is fantastic and exactly what they want. And unfortunately, that just isn’t really a thing. So usually with my clients, I tell them, let’s aim for 80% clarity. And that B range, as we call it, is a fantastic place to make choices from. I think waiting for the A or the A plus, it just isn’t going to help at a point and truly usually means that they’re going to just take a much longer time to make that decision and we’ll end up making it eventually anyways. So 80% clarity before acting is a great place to move from. And then the third one is a little bit more surprising, but this is choosing prestige over learning. And so sometimes there’s very fancy job titles that have really silo skill sets. And this can mean that you get an impressive title, but maybe your actual skill growth is weaker. So you really want to look for a job where you’re going to learn the most skills over the shortest period of time as opposed to having the most impressive title. In the world of work we’re moving into, that’s going to be extremely important to have that more diverse skill set.

Kelly: That makes sense. You have a four-part system to navigate the future of work. Can you walk us through it?

Sam: Yes, absolutely. So I call it RISE, R-I-S-E. So the R stands for recognize. So that is essentially knowing how our mental models of how we’re navigating work are serving us or not serving us. So for example, how closely are we sticking to the career ladder? Are we making any of the choices we just spoke about, like waiting for too much clarity, thinking that we need to be in specific roles for certain amounts of time? Again, I hear that you need to be in a role for a minimum of two years, otherwise an employer might think you’re disloyal. Things like that, where it’s like, how much truth is this actually grounded in? Is it better to stick out a terrible fit than to make a move? No, it’s definitely better to make a move that’s in your best interest. So things like that, just what rules of work are we living by and are they actually true today? I stands for initiate. This is great, you’ve recognized what is happening. How are you going to build as many options forward into the future for yourself? So if you have a job you dislike, you feel like your industry is probably not going to do well in this next AI era, what are you doing instead? And how are you setting yourself up for that? There are many, many tools to do this, but it does take, again, an amount of you starting this process and initiating your next steps. That’s the initiate phase. S stands for serve. So it’s great if we can do this in our heads. We think through all of our mental models, we start making these moves, but do you have proof that you’re bringing into the world of these new capabilities, why you can thrive in this new era? So this is where storytelling comes in, proof of concepts showcasing your work, whether through a portfolio or through a variety of projects, anything like that to show the world you know what you’re doing and that you’re able to carry this skill set forward. And then finally E is evolve. So that’s just constantly being in a cycle of realignment, making sure that even when you do this entire process, the world is going to continue to change. How are you going to continue to change with it moving forward? So yeah, that’s the basic four step process and there’s many different ways to think about this, but I find it helpful just even to think through in my own life — okay, recognizing where I’m at, initiating my next phase or my next change. Am I serving someone or making sure my story is out in the world and then continuing to evolve and setting up a system to remind myself to do that is really helpful.

Kelly: You say that the professionals who come out ahead aren’t the best predictors of the future. They’re the ones who got clearer signals earlier. What do you mean by that?

Sam: Yeah, so looking for signals is a really important piece of looking ahead into the future. So I’ll start with an example that is more negative, but I think resonates well with audiences as a lot of us may have been laid off in our careers before having experienced that as a concept. And usually there’s a lot of signs or signals that that is going to be happening. So there’s some funky meetings, some investment reports that aren’t going well, quarterly earnings look bad, whatever it is. And those signals compound up to a layoff. And people often feel like, oh my god, I had no idea what was going to happen. It’s like when they start really thinking about it and looking backwards, it’s like, no, there were definitely signs. It just wasn’t as obvious as our brains wanted it to be. But then if we take that exact kind of thinking and flip it, it’s like, okay, what are the really positive signals of opportunities coming in the future and how do we look for them so we can, again, make choices based to optimize for them and take advantage of those opportunities? So one are your market signals. This one’s more obvious again. This is where companies may be investing, where you hear a lot of new stories. Again, AI is a huge one right now. We all know it’s here. Doesn’t take a ton of looking to figure out what that means, but then it’s also like, okay, cool. You see this market signal. How might you optimize for that market signal? So take AI for example. Do you know the best tools in marketing? Have you tested them? Are you able to have that conversation with your boss? And again, are you maybe able to lead something in your organization related to AI implementation? That would be an example of optimizing for a market signal. We can do the same with skills. So there are always signals about which skills are becoming valuable. Again, right now we’ve got AI. Another really big one is systems thinking — how well you can navigate more complex systems and think about things at a larger scale is going to become increasingly valuable. The more cross-disciplinary work that you can take on, again, this isn’t terribly shocking, but there’s lots of little skill signals that the market’s giving for what is coming and what is going to be necessary in the future. And then finally we have organizational signals. So this is where decision-making power is shifting. One thing we’re seeing a lot of is people who are operators are starting to replace strategists. So really being able to get that work done, ship it quickly and work across a very wide range of tools and skillsets are gonna be really valuable people at the company. So again, market, skill and organizational signals, there’s a lot of ways to look for them. But even I like to tell people, truly just keep a sticky note on your desk and just see little things that your boss may be saying or a news article that may be hinting at something — you’ll start to kind of get the habit of looking for them and they become very obvious quickly.

Kelly: Got it. So in your practice, you’ve coached hundreds of professionals through career transitions from early career to executive level and people starting over. What finally makes someone take the first step and how long does real change take?

Sam: Yes, this is a great question. I would say there are a couple different reasons that people end up working with me. Stagnation being a really big one. They come in saying, I was supposed to get a promotion this year. I didn’t for whatever reason. Usually it’s due to a lack of agency. So it’s like, I did everything correctly to get that promotion. But then my company said, we don’t have a business need to promote you. So like, why would we? There’s no need for us to, so they end up staying stuck. That’s an extremely common one. Again, layoffs are becoming increasingly common. Easy one to force change, unfortunately, but it’s true, disruption can be a good catalyst for making that next step. And then the third is this identity shift. So if someone feels like I’ve been working in this particular role or this particular category and something else feels like it’s calling to me or it just doesn’t feel like it’s aligned with where I’m at with my life, my family, the goals I have for myself, that can force that change. But I think more and more people are going to be forced into periods of change than ever before. I think in past decades and past years of work, stagnation was more of an option. And I think increasingly, it’s becoming less of an option and more something we need to be more aware of and planning around. If you start to see it, that might be the time to start thinking more proactively about what is next, especially, again, as we move towards this 2030 time frame.

Kelly: Recently on LinkedIn, you posted a survey that you conducted with 360 professionals about the state of their careers. Can you tell us what you found?

Sam: Yes, absolutely. So that survey was really interesting because I think we get a lot of noise in the media about people being like, I have no idea what I want my life to look like as we move into the future. What am I even going to do? And I think quickly in the survey, I found out people have a very good sense of what they want their lives to look like. They know what skills they want to be applying. They know what type of work they want to do but increasingly they feel that the path to get from where they’re sitting now to that future vision of work is disappearing. And what I called this in the article is what I deem a career ceiling. So it’s like, if you can’t move from where you’re at to where you want to go, there’s something blocking you. And sometimes it’s our own minds. Sometimes it is actual market signals, usually some combination of the two. But there were four major patterns that came up. One was this market ceiling. So it’s like, I know exactly what type of work I want to do. The jobs just aren’t available. It feels like there’s a million applications coming in for this one role. I don’t know how to be competitive. I don’t know how to break through the AI slop that’s coming in with everyone looking very similar. What do I do to actually make that next move? It seems much less clear than it might have even three years ago. The second is this concept of the network. In the past, a lot of us went to universities where it’s like, you could just email someone from that university and they’d be like, yeah, we have this entry level, fantastic program, I’ll connect you. There was a lot you could do with your network. And now there’s less and less available in that kind of capacity. It’s like, even if you have a strong network, to be able to get the exact people you need to help you when you need that help is becoming increasingly more difficult. I think one example of this is usually at Masterclass, we post a job, usually we’re getting between 800 and 1500 applicants, which even sorting through that number of resumes as a person sorting through those resumes is wild. Like it’s really, really hard to distinguish between people — you may get 15 people trying to network with you for that role and it’s impossible to serve 15 people. So I think that concept is starting to really be felt by the job seekers who are like, again, I’ve done everything correctly. I don’t really know what to do if that’s the reality that we’re facing. The third is this stagnation ceiling. And this one is a tricky one where it’s like, I’m good where I am. What if I make a choice that makes me less comfortable, less flexible, less whatever, fill in the blank. And because of that fear of having less of something, they don’t make a move forward. So this one, again, is much more mental than it is maybe the external market, but super important to be aware of. Is the grass actually greener? I don’t know, I’m pretty good here. That thinking may really be holding you back more than maybe you think it is. And then fourth, the ceiling that’s more limited to our entrepreneurs, our freelancers, our folks that are running their own thing. They listed their ceiling as this inability to have their signal cut through the noise. So if they’re selling something, they’re competing against a lot of different content any given day. I’ve heard from people that certain social media platforms are becoming less effective just because they’re so noisy. And so it’s a matter of, how do I get my signal or my work out to the audience that I want it to be out to without spending a ton of money, a ton of time, wasting a ton of time. Again, it’s getting more difficult in a lot of ways, and I think all the people who are running their own thing are starting to feel that as a big ceiling for their own work.

Kelly: That’s a lot.

Sam: Yeah, absolutely.

Kelly: Well, thank you for sharing your future proofing insights today, Sam. We will provide links to your website, your Substack, your podcast, your upcoming book and contact information in the transcript. Don’t forget to subscribe and share and thanks for joining.

Sam: Awesome, thank you so much, Kelly.

Stay curious enough to keep growing, brave enough to follow your calling, bold enough to build the career you actually want — not the one you settled for.

UpSkilling AI FutureofWork Mid-Career Senior/Executive

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