The Old Career Map Is Broken, Navigating Work in an Era of Constant Disruption

Sam Alvita is a career strategist, certified coach, and founder of Work Rewritten, where she helps professionals and organizations navigate the shifting rules of work with greater clarity, agency, and resilience. With over 10 years of experience spanning design, education, and coaching, Sam has worked at IDEO and currently serves as Director of Learning Design at MasterClass. A graduate of Syracuse University and the University of Pennsylvania, she holds coaching credentials from the International Coaching Federation (ACC) and IPEC. Her work sits at the intersection of career strategy, systems thinking, and learning experience design,  translating complex labor market shifts into practical frameworks that help people make smarter, more intentional career moves without panic or burnout.

Speaker Links

https://www.linkedin.com/in/sam-sloanalvita

https://substack.com/@byworkrewritten

https://www.byworkrewritten.com/

Recorded Date and Location

Date: 20/02/2026

Guest location: : Los Angeles, California, United States

Episode Description

Why do so many smart, capable people feel stuck at work,  even when they’re doing everything right? Sam Alvita, founder of Work Rewritten and Director of Learning Design at MasterClass, joins us to dismantle the outdated career playbook most professionals are still following. From broken assumptions about loyalty and stability, to the hidden structural shifts reshaping the job market, Sam delivers a grounded, research-informed framework for making better career decisions in an era of constant disruption. If you’ve ever felt like the rules of work changed without anyone telling you, this episode is your wake-up call,  and your new map.

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Transcript

1:56

Sam Alvita welcome to ProductiviTree! Thank you so much, I'm very excited to be here. Sam, you talk to capable, thoughtful people across industry who all seem to share the same frustration. Work feels harder and more fragile than it used to. Even when they're doing the right thing, it looks so. Why is that? I think there are so many different factors as to why work is changing, ranging from tech advancements to the economy to outdated models that we're following about our careers and how we should be thinking about them. So I think all of these factors combined create a tricky situation that make work feel much more challenging than it needs to. You've said that the issue is an individual effort because you recognize that resilience and effort is still there. You say that it's the underlying rules that have changed, but nobody has updated the playbook. Correct. Yes. So how I talk about this a lot in my own work is we think about careers as the career ladder. So I'm sure many of your listeners have heard this term before. So you start a career at one point, there's a predictable series of steps. You work your way from the very start all the way up this predictable ladder till the end. And that model has largely been one that's governed how people think about work, how they think about their personal development. And there have been so many studies to show that this model just quite frankly doesn't hold anymore. So people are trying to go up this ladder in this predictable way. And they're playing a game that frankly is going to be challenging to play because it's not one that's available anymore and careers are moving much more differently than the playbook that is set up for the ladder. Is the feeling of being stuck at work a rational response to structural change? Or is it more seen as personal failure? Wouldn't call it personal failure, but I will think it's a mixture of structural change and mindset that people are bringing into work. So structural changes we just talked about, there's so many different pieces of work that are moving very differently than we discussed, um and so the models and advice that people are following isn't going to work. But then in terms of how we think about it personally, there are a lot of different ways that I help my clients and through my own work think about, okay, so say this model is broken, you are going to stay stuck unless we introduce some new models, some new ways of thinking about this, some new ways of acting. And when a person can introduce these new ways of acting, these new ways of thinking, these new ways of being, they usually can move out of their stuckness quite quickly. So not a personal failure, but definitely take some personal agency to get out of these days. Sam, we have by now asserted that a lot of things have changed even if the playbook is not yet fully updated. Which are these? Which assumptions like stability, growth, and loyalty no longer hold? Yeah, so I would say even as recently as about 10 years ago, there are assumptions of stability and loyalty that did carry most careers. So for example, if someone started a job, they could reasonably assume that unless they did something really poorly or like their company was doing really badly, they would have a job in that industry, in that place for as long as they kept growing and kept working up the ladder. But in the past like, five to ten years, that has completely shifted. So I would say almost every single industry has experienced some degree of layoffs at some point. So many, many people come to me having been laid off from many jobs across, again, across many industries with massive amounts of people, right? So if you're in a company that lays off 10,000 people, 200 people at the same time, it's completely impersonal. Um, it's just whatever's happening in that industry. And then that person will have to make a change to get their new role. and I think that stability, is very tricky, right? So even the job that you could expect to carry a career for a really long period of time may not be one that will do so. and then the gap between those layoffs or changes has also increased really dramatically. So people who have great degrees, who have been in stable places, who have worked up this ladder, who have great resumes, will experience gaps between jobs ranging from two months to even a year, just because of how the job application structure is set up and some of the other pieces. And then finally, the loyalty piece that you just brought up, I think there was much more of a sense of if someone were to enter a role, they were expected to be loyal to that company because the company was providing them with a certain degree of stability, right? So living expenses were covered. They were expected to move up in certain degrees of promotion every however many months or years. And that just is not the case anymore. So someone might be loyal to a company, but they're not getting the salary that they would expect at a certain point. The promotion schedule they would have expected a point. And it's forced a lot of folks to be much less loyal. to their companies and jump around much more if they want to take full control over their own work situations. I've seen a lot of people being laid off, many of them senior leaders, they all are in this void of what do I do now, what's your advice to people that is now going through this stage of their careers, not only being laid off but also, well, the work environment as a whole, the playbook as we said has changed. Yeah, so I would say for anyone who's been laid off, the tendency of those people will be, okay, I'll get my resume together, I'll start applying for roles, I'll apply for as many roles as I need to. Again, they'll do it in the way that they did before they got that job they were just laid off from. So essentially they'll be applying, applying, applying, and they may not be getting the same results as they did previously. And they may not be able to land the role that they did previously. So I would say for anyone who's been laid off, there's a completely new playbook that they should start following that will help them regain the control and get that next great new job. So I call this RISE, so R-I-S-E, as a way to think about this as a new playbook for someone who is moving into a new space. So R is to recognize when their career is being shaped by outdated assumptions. So if they're expecting the latter to be the latter, that's probably not true. We think of it more as like a root system or a web now. So it's like, if the next available role is not available, what are you going to do instead? What new version of the role might be available? How has tech changed your role, your world? How might you learn the skills you need to learn? in order to be as competitive as possible. So that's that R. And then I, we call initiate. So that's building multiple low risk paths around their existing strengths and testing out new pathways. So for example, if one path is use resume to apply for job and that path isn't working, then what's the other path they might take? So this could look like maybe they start, as you were saying, a sub stack to share about. their knowledge in whatever pathway. Maybe they're doing different types of networking events. Maybe they're speaking on podcasts. Maybe they're doing anything to show that their value is modern uh and available to people today. S is serve. And this one's also really, really important, especially for our more senior leaders. So if they were to be laid off, they still want to make sure that they're showing their value. in the world. this could be anything from showcasing their expertise on LinkedIn. This could be helping people through a mentorship opportunity. It could just be looking like being very engaged in the community and being really helpful as they're building their next step. This is really, really key. It helps people a lot as they're thinking through their next phase. And then E is evolve. And this one is a tricky one, but it's using a repeatable practice to keep yourself relevant as work continues to change. So all of us are going to be impacted by the tech that is coming. So AI is going to change all of our jobs in some way, right? Maybe not take our job fully, but it will change it. So even thinking about like, okay, so say this is true, what might I need to do to my own work, to my own role to keep evolving so I'm relevant? And my work is relevant and everything I'm doing is relevant as the world continues to change, regardless of how I feel about AI and what it's doing to the workforce. Sam, in this unfortunately polarized world, career advice tend to sound like one extreme that is follow your passion and the other one which is more the dystopian of robots are coming everybody's gonna lose their jobs. Where are you in this spectrum of career advice at the very moment? Yeah, so I will say I'm probably right in the middle. I don't usually like to exist on either of those extremes for a number of reasons. Happy to share why. I think I can start with the robots are coming side and then we'll go to the passion side. But I mean, there's so much noise about AI and what it's going to be doing to everyone's work, how the robots are going to be replacing all of our jobs and et cetera, et cetera, et cetera. And there have been very real implications to AI already. I mean, we see it very clearly in the entry level job market right now, where I think entry level postings are down about 40 to 50 % as companies are trying to use AI to replace that entry level workforce. But at the same time, we're seeing a bit of a shift back. know IBM last week announced that they are rehiring their entry level workforce because they need. that next generation ready to go and able to continue to work at places like IBM moving forward. So I think a lot of companies are going to try a lot of different AI tools. We'll see how well that works. I think for certain industries, it's going to work, unfortunately, very well and for others less so. But I think regardless, like what I was saying before, so say AI is going to be really impacting that entry-level workforce. If someone was an entry-level worker, what they should do is not just sit there applying to the same jobs and hoping for better results. They're going to need a new strategy, potentially to pivot into something else, to think about new ways to apply their skills, potentially even get really, really good at using the AI tools that may help them land a role at the company that is potentially not hiring their role as it exists now. And I will say like, I'm not going to be the one making the prediction about where the future is heading. All I'm saying is I do think there are plenty of opportunities and a lot of really cool ways for anyone at any phase to lean into that future, regardless of what's happening. So I will say that. I don't think it's a hopeless landscape by any means. And when I coach or work with people, that's kind of how we position it. I'm like, okay, this might be happening. Sure, we can acknowledge that. What are we gonna do about it? And then on the other side, the follow your passion side. This is a really tricky one and it's something that I hear a lot in the career coaching space. And one that I have clients fairly frequently come to me being like, I don't know what my passion is. Like, how am I supposed to move forward? And I'm always like, truly don't worry about it. You don't need to know. Most people don't have their one singular passion that they're following. And frankly, I do think that it can be counterproductive advice to be searching for that passion. And I know there's a lot of other speakers in the space, such as Cal Newport, who are like, never follow that passion advice. Don't look for it. It holds you back. Think instead about how you can be of value, how you can apply your skills. We are all such... multi-hyphenate people with lots of interesting different skill sets. And usually some combination of many things is going to lead us to the most successful and most fulfilling careers. And I will say one more thing about the passion argument. Sometimes it's also oversimplified. So for example, I'm a big runner. I love running marathons. My work has absolutely nothing to do with that. I don't talk about running. don't, I mean, besides right now, obviously, but. I don't think about it, I don't talk about it, I don't need to have that passion of my life inform my work. And I think a lot of, especially younger folks, and I totally understand why, are like, I like running, I should work in the space of running. Maybe it's being a coach, maybe it's working for a brand, maybe it's doing something like that, and if that works, fantastic. But I would say it might be a slightly oversimplified version of what might be the most fulfilling long-term. Sam, as humans we need stability, we need a nest, we need a bit of a comfort zone. What in the absence of previous job stability as you said before, how does job stability look like now and in the future? Yeah, that's a great question. And also one I get frequently and how I generally answer this is don't ever rely on one single path to provide you with stability. So what this might look like is someone works at a good company, they've got good benefits now, great. Like that's providing stability for the moment. But I would always say like, be a little bit aware of if this were to change, if something were to be different about your situation. How might you make sure that you're set up for the next iteration? For certain people, think especially in the US, we're seeing a lot of this. People are starting to set up what we call portfolio careers. So they may have their day job, but they may also be doing some other type of work on the side or working on a personal project or something that gives them a more, I don't know. robust application for later would be my description of this and for certain industries like your creative folks for example they may be doing their day job and a graphic design freelance work or role on the side and that portfolio concept can be applied in a lot of different ways but I would say no one should assume stability but not it's not something to be nervous about it's not something to be anxious about it's more just always have a second plan ready to go if something were to happen. And it's always really hard when I get a client who has been laid off and they don't have their resume, they have no idea what they would do next. They haven't really explored the landscape or kept an eye on what's going on. We really have to start from step one and getting to that next role, that next stable place may take longer ideally than we would want it to. You talk about agency over optimism and clarity over certainty. What does that look like in practice when someone is deciding where to stay, leave, pivot, wait, try something new? Yeah, so I'll give an example of a client I had recently who essentially was like, there's nothing wrong with my current job, right? I am getting a paycheck. I'm doing my work every day. This particular person had been there for say five or six years. So everything was very familiar, very comfortable. But then every time the promotion cycle would come around, the company would be like, well, we don't really need... to promote you. We're good. Like everything is stable. We don't have the business need for the next layer. And then that person would stay in that exact same role for another year. And this kind of pattern of, again, very stable, but they weren't growing. They weren't gaining necessarily new skills. They were fulfilling the exact obligation that the job wanted them to fulfill. And I would say... this is where that agency piece needs to come in where it's like, that's great. If that is fulfilling and hopeful to you, fine. I'm not gonna be the person to change that. But I would say there's a lot of potential and opportunity that's being left on the table by not trying to find that next step, to try to make that next step, to try to get that next skill. And so usually when I have a client who comes to me like this and they're like, my job is doing nothing to help me. move into my own future and move into my next role, usually the conversation is, okay, we need to either have a very specific conversation with your existing work or need to look elsewhere and engage our agency to make sure that we are moving forward and doing things that help us longer term. And especially again, if they were to be laid off from that job and it looks like they've been in the exact same role for years and years and years without moving up, that is going to be an issue for their next. application cycle and may hold them back longer term. So agency, again, looks so many different ways, but that's an example of kind of how it shows up in a more quiet way, more regularly. What's the most common decision-making mistake you see smart professionals make when navigating career uncertainty? Yeah, so I think one I see a lot of is people start to make that next step, but then they get anxious and just do a lateral step immediately. say someone comes to me and they're a lawyer. This is another recent one I was working through and they're like, I hate working in law. It's very boring. It's not fulfilling to me. I don't want to do it anymore. They say, I'm gonna quit my job. I'm gonna take a few months off. I'm gonna figure out what's next and move into that. space and then that month off starts. They get anxious, they get an offer from a new company and all of a sudden they're a lawyer again. And I think it's just not having a game plan in place or some type of structure to help them navigate that next step that keeps people in similar roles, diverting to things they already know. There is a bias for the familiar, so I think it's completely normal for someone to be like, I'm just gonna do what I already know. It's safe, it's stable. I understand it, whatever, and that I think also can be really tricky and something that I think all professionals in all industries do struggle with at some point in their careers. You've said that people miss emerging opportunities because they are focused on what's being lost rather than what's being created. What is being created in the world right now that most people is overlooking? Yes, so I love this question. um I would say always there are more opportunities available to us than what we think or what we see immediately. And I would say let's take the AI example, where a lot of the news around AI is like it's taking the jobs, it's removing people's agency, it's taking creative work, it's like creating a lot of slop, whatever, however you want to call it, whatever country you're in, I know there's versions of this narrative. And I think the narrative that's not always existing and emerging in this space is like, okay, so say we can eliminate some of the more menial productivity tasks or say work is changing because of AI, what then becomes available? What are the new opportunities? So for example, healthcare may change in a really significant way, in a really positive way. And if someone were to work in the health space, how might they... lean into that space and embrace that opportunity and use it so they can have many versions of their career work on cooler projects, do many cooler things. And I would say again, there's an answer for every single industry, regardless of which one, where this may be really exciting and there are new opportunities that are coming up because of the emerging technology. And again, the news may not showcase that as an opportunity for us to. have many different careers, do many different things, push ourselves more, be able to take on new work in different ways because of this technology. Instead, it has the very negative and reductive version of it. Sam, let's wrap this up for the listeners that feel a bit stuck and confused about their career right now. What is the first practical step they can take to get unstuck? say 30 sticky notes or a piece of paper and come up with 30 different opportunities that are available to them right now. And usually most clients will be a little bit resistant to this. They'll be like, why do I need to do this? I can't think of even one opportunity. And then when we really start pushing them to brainstorm, 20, 30, 40, 50 things start coming up. And I would recommend that every single person do this really. embrace a more open view of what the future could hold for them and really cool things will start to emerge. Sam, how can people get in touch with you? How can they avail your services? Where are you? What's your social? Yeah, so you can find me on pretty much any platform at ByWorkRewritten. My website, ByWorkRewritten.com will have links to everything. I write very frequently on Substack and post on Instagram pretty frequently. So I'd say those are my two main channels, but I can be found most places you would look at ByWorkReritten. Sam, thank you so much for this very relevant and insightful conversation. My takeaway today is that everybody needs a plan B, that's clear. And also that sooner or later, the playbook is gonna be updated and careers are gonna look different than they look today. And it sounds for the likes of what you're saying that they will be a bit more fun because there will be opportunities to do different things and follow nonlinear paths, to do many different things during your career, which is something exciting for many people. Sam, all the best and thank you for being with us today. Thank you so much. Santiago. And yeah, all the best to you and your listeners as well.