Career Reinvention Isn't One Pivot. It's a Practice | Sam Alvita

TRANSCRIPTS Career Reinvention Isn't One Pivot. It's a Practice - Sam Alvita

[Roger]

You may think that career reinvention is a single pivot. It's not. It's many steps, and it's a practice.

[Sam]

And I feel like it is so, so important for the moment we are in now, where I think in the past, you could have a career for a very long time and not really have to unlearn or relearn. And I think now everyone in every job function is going to have to unlearn, relearn, upskill, whatever you want to call it.

[Roger]

That's Sam Alveda. She's the Director of Learning Design at Masterclass, and she runs her own career strategy practice called Work Rewritten. Today, Sam and I break down a new framework for thinking about how to reinvent your career.

We explore the learn, unlearn, and relearn cycle, and we discuss Sam's superpower for equipping people to take on big tasks like achieving a massive athletic goal, changing and reinventing their career, and everything in between. Hi, I'm Roger Kastner, and welcome to What Do You Know To Be True? These conversations are with people who are on the path to becoming more of their possible self.

Thank you for being here. Let's dive in.

[Sam]

I'm Director of Learning Design at Masterclass, so I work with a lot of different people doing a lot of different courses, learning about their superpowers as they pertain to their various professions. And then I run my own career strategy firm called Work Rewritten that is becoming a book in 2027. In summary, making sense of a lot of complexity that is facing our world right now and helping people move through it is what I spend all day doing every day.

[Roger]

So as a learning designer and executive coach, you spend a lot of time working with people who are learning new things, whether that's a new skill or discovering something about themselves. Lately, I've been seeing a lot of this Alvin Toffler quote, the writer and futurist, who's famous for saying, the illiterate of the 21st century will not be those who cannot read or write, but those who cannot learn, unlearn, and relearn. And I'm very curious, and I've been having conversations with several people, and I think you're perfect to ask this about.

How do you think about this cycle of learn, unlearn, and relearn, and how do you equip people to successfully go through that cycle of learn, unlearn, and relearn?

[Sam]

Yeah, I love this framing, and I feel like it is so, so important for the moment we are in now, where I think in the past, you could have a career for a very long time and not really have to unlearn or relearn. And I think now everyone in every job function is going to have to unlearn, relearn, upskill, whatever you want to call it. What I've seen a lot, especially in this new AI space that everyone's entering into, we are all kind of navigating this new world of what this means, how it will impact my work, my job, how the executives I'm working under are thinking, how it will impact our work or our jobs, how the world at large thinks about this.

I think no person has a full grasp on this particular moment in time. And I will say it's been really interesting working with executives or people, especially in the masterclass zone of this particular problem, because you're going in with these people who are typically the most skilled in the room or have the most expertise in the room, and they are being faced with something where they no longer have that. It's kind of like a great equalizer of there's this new thing coming, no person here knows any more about it than someone else here, and what are they going to do to unlearn potentially past versions of how work has worked?

How are they going to upskill their teams? How are they going to navigate this? And it brings out a lot of people's insecurities very, very quickly.

And I think, especially in the executive room, they might not know a ton about this, but they'll have very strong opinions about it. And I think it's been something we've been up against in some very interesting ways, I'll put it that way.

[Roger]

And what I find when someone has achieved a certain level of mastery, they are very good at looking at ways where they can learn, where they might even say, like, what can you teach me? I'm always surprised when someone asks me that. It's like, wait, no, no, no, you're the expert here.

Why are you asking me? But I think it's that innate curiosity. I also think there's a part of the unlearning where you're challenging your own assumptions when you're not afraid to question what you know, and why you know it, and why you think that, and is there a better way?

[Sam]

Yeah, I could not agree more. I do think curiosity is a very underrated form of resilience in many ways. And I forget the exact quote, but it's like, the smartest people in the room are the ones that know they know nothing.

Whatever that quote is, right? Like, if they're the ones asking the questions, they're usually the ones that are going to figure out the thing faster than those who are not.

[Roger]

Which is so interesting, because you find, you know, someone who's emerging in a certain capability, I find that there's usually a reluctance to ask, like, what can you share with me? There's a reluctance to be seen as you're new to this. Whereas those who are expert have no qualms about asking, like, what else can I learn about this?

So there's something there about the paradox of mastery.

[Sam]

When I was working with the Navy SEALs, they had this very interesting rule, I would call it, I don't even know if it's a rule that's like codified per se, but where the most senior person in the room has to speak last. So when they're debriefing something, or when they're figuring something out, like they go from the most junior in the room, to the most senior, and they force essentially the most senior person in the room to listen for however long they have to get all of that information asked, they can ask questions, of course, they're not allowed to like, not ask questions, but they aren't allowed to share their opinions about something until the end. And I was like, that is such a brilliant way of framing leadership, because to your point, they get a lot of information, they can have all their curiosities first before they're allowed to insert their opinions at the end. And yeah, it's something that I've been thinking about, like, how many organizations would benefit so tremendously from that kind of structure?

[Roger]

I'm curious about something you shared with me before we hit record around working, you know, with leaders as a coach, and you've witnessed this, this idea of the career ladder come up again, and again, as a metaphor, and you started to debunk it. And you said that successful professionals are looking at growth, not as a ladder or a set path, but as something else. Could you share with us how you how you debunk the metaphor of the career ladder and what you replace it with?

[Sam]

The career ladder is a concept that came a very long time ago, I think, like industrial revolution type era, where someone would get a specific skill set, that skill set would last them decades. For people, for example, those entering the workforce in like the 1940s, 1950s, they could reliably be trained on one very specific skill. And that skill would last them the entirety of their career.

And then they would retire, maybe with, again, very minor tweaks to that skill, maybe some light up leveling, but for the by and large majority of their career, they could really follow the same trajectory. In doing so, they could use that same skill to work up that corporate ladder in a very reliable way. And we've seen the shortening life of skills since then.

So you get to 1980s, 1990s, you're looking more at like a 10 to 15 year skill range. And we keep working up this chain. And the college graduates that are graduating today, their skills are estimated to last between six months and two and a half years, they spent more time in college, learning the skill than that skill is going to last.

That paradigm and how that fits does not fit on the corporate ladder in any way. And we, as professionals cannot enter into any company and expect that company to carry us from the very beginning of our careers, all the way to the end with a retirement package. And I don't think most people are thinking about it like that either.

So that there in and of itself, we already have a break in that ladder structure. Instead, I think about it as a web kind of concept, or I've used a couple different metaphors like web or root system, portfolio, the most successful people that I know today, including those that work in major corporate environments, typically are not handing over all their power to those corporate environments. So they may not just be interviewing for jobs and seeing where things shake out, they usually have other things going on.

There are people that really are investing in their personal brands, other projects they're interested in, they might be collaborating with people on the side, consulting, doing all types of things to really diversify their footprint and their impact, and also be able to communicate their value in ways that spans more than just their particular job function. And there are so many ways to think about that. And I think when people hear this concept, just at first, it sounds like so much work.

Like I don't want to be an entrepreneur, I don't want to be a solopreneur. That's fine. You don't need to be.

I think it's more just like how might you bring your skills outside of your job capacity and be able to think about yourself as more multifaceted than potentially the very specific role you're in at any given time.

[Roger]

And I love the image of the web. Because when I think of a ladder, when you think of a ladder, and you fall off a ladder, there's only one place to go. Well, there's two places to go, there's the ground, and then there's urgent care.

But the idea of the web is like, if you were to fall, you're going to get caught. Like there's a safety net there that's already there that we might not be thinking about when we're thinking about the ladder and the next rung to climb. And as I'm working with people who are in the midst of a transition, whether voluntary or involuntary, the thing that not only gives them a sense of agency and being able to take action, but the thing that ultimately finds them their next thing is their network, and the sense of creating connections and nurturing connections.

And the more you do that, that very much makes me think about you are creating your web that is there to help support you and to catch dinner. I might be taking the metaphor too far.

[Sam]

Hey, I like it. I think it lands. But yeah, I do think the network could not be more important.

And I think people oversimplify this concept of the network slightly in terms of like, I have these transactional relationships where if something happens to me, I have people that can back me up, which I mean, is true, right? It's just like how we show up for other people, how deeply our connections are tied to other people. I mean, I think all of our careers are very intricately linked to the people we've worked closely with.

And I mean, my network has absolutely gotten me new opportunities. I can make an assumption that yours might have as well. But I think it's a really important thing to be investing in and connecting authentically and deeply with people, regardless of whether or not you're looking for a job is always a really good thing.

[Roger]

You know, the Navy SEALs are having a little bit of a moment that they're being held up as, and probably rightly so, as sort of the epitome of what great teams look like. And I'm fascinated by this idea and actually heard a Navy SEAL talk about this, how there's so much literature out there and there's so much, you know, social posts and so much thought leadership out there about leadership and such a dearth of information about being a good teammate. And yet we know our superpower, our learning, even our healing and our growth happens in relationship with other people.

So I'm really curious to learn anything that you might've learned from the SEALs about what it takes to be a great teammate.

[Sam]

This is something that has been very top of mind for me lately. And I feel like a lot of the executives that I'm working with are often evaluated on very specific metrics that have to do with themselves. For example, are they meeting whatever budget goal with their team?

Are they showing up with X type of presence? And again, this very, I would say, I wouldn't call it self-centered version of leadership intentionally, but I think it's how they're evaluated just based on how leadership has been talked about in the past. The Navy SEALs in contrast have a version of leadership where they are evaluated based on how well they skill the people below them.

Ideally leaders are thinking about themselves as like, how can I prepare my team to be even more competent and capable at my job than I am? And it's very focused on this type of servant leadership to bring their teammates up the ranks in whatever way, to bring their capabilities up the ranks in whatever way. And it's a very simple concept when you really think about it.

That's exactly what should be happening. And I'm also a very firm believer. The stronger the whole organization is, the better everyone does.

I just think it's so rare for organizations these days to be thinking in that type of way. And I don't know, at least off the top of my head, any other organization that evaluates their leadership based on how they're skilling their team. And I think that is a major gap that could be capitalized on and one that I would encourage many leaders to take advantage of if they have the opportunity to do so.

[Roger]

I mean, maybe it's also just a leftover of an old way of thinking, an old way of organizing work that no longer fits the modern workplace. I'm curious from your experience when it comes to building teams where people are in it for the team, what have you seen to be like the two or three things? Or if you're working with a leader who's just forming a new team, what are those one, two, three things you would want them to focus on to create a team environment that people are fully engaged and fully participating and not showing up as individuals?

[Sam]

One really big thing that comes to mind is how the leader of that entire team is behaving. Partially what we've already discussed in terms of how focused are they on your growth as a person, but I think also having deep trust in their own team. My current manager is very hands-off in terms of like she is never micromanaging anyone and is much more like, if you need me, come find me for this, but instead we're going to focus on these things and I trust you to have everything you have inside of you to do your job really well and to do what you need to do.

Trusting the team capabilities and really focusing on building the team and focusing on their growth, that's really important. For example, at Masterclass, our teams work super well because all of us have very, very specific lanes, but then we know enough about each other's work to be able to be really strong assistants to those people. For example, when I'm doing a class, I always work with the producer and I do a lot of the writing and interviewing of people and making sure that the learning and all the things we've talked about, the complexities broken down, we're teaching the right thing.

Then when we go on set, they are doing all the making it beautiful, talking to the people live. I have absolutely no business doing visual design of any sort. On set, my job, and I know my job is just to be the best possible support system for that producer.

Then afterwards, when we're doing other types of things, breaking down complexity and talking through how this course is really going to come to life, the roles kind of reverse. I think being able to go in and out of that leadership and owning your lane into these really supportive modes of working is really, really helpful in building, I feel like a very strong team environment that works really well. I'm curious if you have thoughts on that and if that's applicable past just the creative space.

[Roger]

Something you said that really stands out is this awareness of what other people's work is, where their skills are, not only what they're talented in, but what is the job. What is the work that they're doing and how are they doing it so you can assist, but not get in the way. The work that you do at Masterclass, I'm fascinated by.

I'm curious, when I talk to someone who is fully in their mastery, they're deep in their superpower. When I ask them, what are the building blocks? How did you develop this thing?

Sometimes they can't answer that. They're so good at what they do and it comes naturally, but they can't share it. Oftentimes in sports, the great player becomes the coach and they're a horrible coach because they can't explain it.

Recently, you shared with me that you've experienced that many people carry a version of themselves that they deeply want to become, but they quickly dismiss it before they even get to say it out loud and definitely before they take action. What happens when someone finally gives themselves the permission to name the possibility or dream that they've ruled out?

[Sam]

I think this is a great question because all of us are living some version of an identity out in the world that we were either told or it was some part of the narrative that we faced when we were brought up. People from our community who go to this school or start in this job need to stay in this very particular lane and do these very particular things. I found with every single person I've ever worked with, there's some part of that identity that is holding them back in some capacity or in more extreme cases, they want to have a very, very different identity maybe than the one that they are currently living out.

Once we start breaking that down, you realize there's so much more potential under the surface than maybe what they present originally. I will say it is not easy work to go from some very particular role, some very particular job function, break that down, and then pivot into this newer updated version of themselves that feels more true and aligned. It takes a lot of very deep work.

I think I feel very privileged to be able to walk with people as they do that and some of the outcomes on the other end have been really, really exciting and awesome for the people I work with. It's been great.

[Roger]

Why do you find it really difficult for people? I totally agree it is difficult, but would love to hear why you think it is. What are the major things that get in people's way to make that transformation?

[Sam]

I think there are so many different narratives that come up. For example, people feel that they have a responsibility to live out some degrees. Say they paid X amount of money to become whatever they chose to become in college degrees, maybe a master's degree, and then all of a sudden they're like, this does not fit me at all.

Am I throwing away that money? Is there some cost that I'm up against? Is this just how work is?

Is this just how I'm supposed to live? I think there's narrative after narrative that keeps them in that place. Then I think, too, there's a component of this that is just what people think is challenging.

For example, when I started submitting my book proposal to agents, I was hearing over and over from people in my own life, not authors, who were like, oh, publishing is really, really hard. I wouldn't spend the time doing that. People don't get those types of narratives, which I'm really good at ignoring certain things.

I'm like, oh, whatever. I'm just going to do it anyways. What do I have to lose?

But I think there's a lot that people are up against with the narratives that surround them. I think it is hard to be like, I'm just going to do whatever I'm going to do anyways, or I'm going to try it anyways, or I'm going to spend the time to do this thing that might be hard, might go nowhere, and maybe it will go somewhere. I think to get people to lean into that is harder than it appears often.

[Roger]

You've designed learning programs, so some really big names, IDEO, Masterclass, and you also coach people through their own reinventions. I'm really curious about what has designing and equipping other people's growth taught you about your own growth?

[Sam]

This concept has spanned my entire career from the very beginning up through what I do now. I will say my answer will change based on the experience. I'll start from the beginning, if that's okay, and walk you through maybe this answer as it would change.

I started my career in Teach for America right out of college. I was working in classrooms with students. I think my perception of education and how people learn was very informed by that 90s, early 2000s learning model of the teacher is the expert, and they give the information to someone in whatever form they see fit.

It is the learner's obligation to take that information and do what they will with it. That concept was completely blown up for me immediately entering the classroom, to be like, actually, the onus that is placed on teachers to be the expert, sure, that still holds true, but it's so much more about how you communicate the information, how you meet the people who are in front of you where they're at, how you see their individual talents. I think in these higher stakes education environments, this one-way stream of information from teacher to student, it doesn't really work that well.

That was something that informed so much of my work going forward. I need to meet the people that I'm working with where they're at, communicate information in ways that is relevant and accessible to them, and bring a lot more creativity into the room, potentially, than what I might have originally thought I would have needed to do. I think with every single role I've had since that point, the stakes get upped and the complexity gets up.

I went from that classroom to this charter school in Silicon Valley that was like, we're going to push the boundaries of education by doing various things in design thinking and computer science and all these different things. How do you bring this type of model to new information? Went from there to working with incarcerated students, teaching them tech tools.

Again, you up the complexity with many, many components of that. On to IDEO, where they would give us courses. For example, I actually did a course called Managing Complexity or something along those lines, which they were like, you're going to teach about complexity as a concept.

That's going to be the course you make. Taking some of the biggest problems we're facing and being like, okay, if I'm an executive who is facing some major sustainability challenge or wants to make my company circular, how do I actually do that and bring my team along? It's wild to be thinking about information in that kind of way and to be at that scale.

Now at MasterClass, we do a lot with AI and emerging tech and trying to figure out the world and the future that we are heading into to the best of our ability and talk about these concepts that can be very technical, can be very complicated in ways that feel very accessible and exciting and actionable. That's exactly what I do with a lot of my day-to-day coaching as well is work with these executives or people who are looking for their next job who seem to be up against these very large systems and be like, okay, yes, the job market is really bad. Yes, we are entering this future where tech is going to make things very unstable for certain people.

What do we have the capacity to do to break it down, do as small a piece as possible and move forward as quickly as possible? That is really how I think about everything now.

[Roger]

What have you found when you're working with people who are being identified as having a certain level of mastery? How often do you find that they can explain what are the building blocks and how often do you have to work with them to pull that out of them?

[Sam]

Yeah, this is a great question. I'm laughing a little bit because I would say every single person I've ever worked with who is at a certain level of mastery needs it pulled out of them. I think that's in many ways not surprising because if they've reached the very, very top of their careers, there are so many things that would have had to have happened between the beginning and going all the way to the end.

Take, for example, if you're working with a very strong designer or someone who has a really strong visual sense and you ask them, how did you become this top interior designer? They're going to have a very, very hard time answering that question. They might say something like, oh, I went to college at this particular art school or I traveled to this place and saw these cool patterns at this place and was drawn to it, but a lot of it has to do with taste and passion trying a lot of things and being committed to this craft for many, many years.

The real meat of this expertise is less like, what did your teacher teach you in this college class? How did you stay committed to this craft? What does building this craft look like?

How are you identifying and addressing your weak points? What's something you've always been good at? Even sometimes asking that question of what have you always been good at can clear up a lot of complexity because they're like, oh, yeah, it's just something that is natural and innate to me.

Okay, great. We can fill in the blanks elsewhere and we can figure out how to fill that in for people who might not have that innate sense, but I do think some of these people are just very naturally talented in what it is that they do in the first place, but there's also a lot of depth in building the craft, taking the classes, applying this craft over very, very long periods of time.

[Roger]

Which I think this is where your superpower of breaking things down into bite-sized chunks so people can take action is super helpful. I'm really curious, what or who inspired you to have that superpower in the first place?

[Sam]

I've been a competitive runner for a very long time and coaches of competitive runners, they never are like, oh, you are aiming for this time. We'll just keep doing workouts and hope that you get there. It's usually this extremely prescriptive we're going to do this exact thing over this period of time, ideally achieve that result, often achieve that result.

Maybe you don't, pivot, you do it again, but it's very prescriptive. I think for anyone who's run a marathon before, especially people that maybe don't run a lot and want to run a marathon, it sounds really daunting, right? You start like, oh, I can run three miles a comfortably.

How on earth am I going to run 26 miles? That is a huge jump. If you talk to anyone who has run a marathon, they'll be like, oh, you totally can.

All you have to do is get a good plan, you'll figure it out. Often they do. I think this concept of getting a really good plan and figuring it out is underrated, I will say.

If you are that three mile person, you want to run a marathon for 16 and 20 weeks long. It'll have on Monday, you're doing this, on Tuesday, you're doing this, on Wednesday, you're doing this. All of a sudden that momentum builds, builds, builds, you get to the end, you successfully do the thing.

I do think there are a lot of problems in life and a lot of situations that appear very complex at this large scale that when given, if someone is given a 20-week plan, become much less complex very quickly. I think I am very

[Sam]

I think I am very driven by this idea of like, if someone wants to do something really hard, how do we make them that 20 week plan? And oftentimes they realize, oh, it's actually not that hard. It's just a lot of different little things that I have to do and put together.

[Roger]

I love that example because I have, I've run a couple marathons, but it's been a few years since I've done that. And just when you said 26 miles, my brain said 26.2. And then thinking about, oh, that's the distance from where I live to the airport. That's a long, that's a stupid distance.

Who would ever do? Oh yeah, I did that. And you're right.

The idea of, okay, no, it's not that you're gonna go run 26.2 miles tomorrow, but you're gonna go run three. And then the next day it's three, and the next day it's three, and the next day it's three. And then you're gonna start introducing hills, and then you're gonna introduce track workout, and then maybe Saturday you're gonna go for six, and then bop, bop, bop, bop, bop.

It's those little bite-sized chunks that you talk about. That's such a great, I was gonna say, yeah, of course running a marathon is a great metaphor, because it's true.

[Sam]

Something that I am very curious about, and I know you'll have insights about, is this concept of unlearning. Specifically, like if you've ever had to unlearn something about your own growth, or it's something that you're bringing into your own coaching practice, this concept of unlearning.

[Roger]

It's where I really am spending a lot of time trying to figure out, like, what does this mean? The thing I wanna say about unlearning and relearning comes down to the sense of community, which we were talking about a moment ago when it comes to networking. And what I have had to think about in this pathway to becoming more of our possible selves is not necessarily being in teams or communities for what it gives to me, what it does for me, but ultimately being parts of teams and communities for what I can give to them, what I can put into it.

Because what I'm learning about what it takes to be a great teammate is that it's not necessarily what I get from being in the safety of the pack, of being in the herd, of being accepted and what that feels like as a human being, but more like my superpower, my fulfillment only happens in relationship with others. And I think it's the same thing, the value of being a good teammate is what you learn by being in service and relationship with other people.

[Sam]

Yeah, I love that framing too. I mean, it also makes it way more fun to be on teams, right? When it's like you're just thinking about your teammates and their growth and how well they can do, I think it makes everyone better and makes the day really fun too, so.

[Roger]

But there's a sense of commitment. I'm sure you've had this experience as well where you're part of a team, but it's really just a collection of individuals. There's not a common goal, there's not a shared vision that's pulling people together.

When I do some reading or watch, there's a documentary recently about Navy SEALs in dealing with PTSD. One of the SEALs was talking about this idea of like, oh, my team guy brain turns on. And it was really that sense of mindset of commitment to one another.

I think I've experienced that just a few times in my life and I miss that, I kind of long for it, but I've probably been on more teams that I think fit into that description of a group of individuals versus something that brings people together more than the team name or the uniform we're wearing.

[Sam]

I would say, I don't know the exact percentage, but the people that I'm coaching, I would say probably 80 to 90% describe their teams more as that collection of individuals. And then you have those special organizations that are that special 10 to 20% on the other side where it's people who are set up to help each other succeed. And I do feel very lucky in my work at MasterClass that I would say we are very much in the 10 to 20%.

I think partially it's how our work is structured and the type of work we do, but also I love my colleagues. And I think because we live in so many different kind of creative worlds and we have to rely on each other really deeply, it creates this very, very strong team dynamic that has been awesome. So I'm like, how do we get more people in those types of roles?

Yeah.

[Roger]

When did you first discover that the superpower is a superpower?

[Sam]

Very early on in my teaching career, but not while I was teaching, it was actually in working with friends in my life who were dealing with various things that I felt like I was able to talk to them and help them in different ways than I would have been able to prior to this skillset coming online. And not like bossing them around and be like, you need to do X, Y, Z and make this plan and blah, blah, blah more just like thinking through problems in different ways than potentially the conversations that they were having in other spaces. And I think even the coaching skillset as it's brought up, it benefits me a lot in my life when I'm not coaching and I'm not trying to coach either.

It's more just like how I listen, how I'm thinking about the deeper parts of various problems, how I show up for the people in my life. And if they were to ask for my advice to be able to maybe give a different perspective than they might hear in other places.

[Roger]

Do you give advice?

[Sam]

When asked, and I guess on my sub stack all the time just because I have a captive audience, but I try not to if, yeah, I don't wanna ever be that person giving unsolicited advice but it does happen of course.

[Roger]

That advice monster that pops up for young coaches and I think for humans, cause we wanna help. But yeah, as Anne Lamont says, our help is the sunny side of control.

[Sam]

Yes, a hundred percent. And I agree with you fully. I will say there are parts of my coaching practice that are very like cut and dry.

And those are the parts that my clients also want advice where it's like, if I'm looking at someone's resume, I'm like, do this, do this, do this. And it works. So there's not like, but I would say that's a little bit different versus like them working through some of their big blocks.

[Roger]

Yeah, when they're not an expert at writing resumes. And there's always times where we have something that we could offer and do that coachy offer of, I'm gonna, can I offer something? You can accept, reject or modify, but yeah, making sure that you're signaling that, hey, you get to choose.

I'm not saying this is perfect for you but it's something that would help. And yeah, things like you can take off that objective statement of your resume and, oh, you might wanna remove the year that you graduated college. Those kinds of tips I think is always helpful to give with the best intention and receipt as such.

[Sam]

Yeah, absolutely. But people are experts in their own lives and I'm not going to pretend to be the expert in their life.

[Roger]

So once you've discovered your superpower, what have you found to be one of the most difficult challenges you've had with it?

[Sam]

People often conflate the relationship between something being simple, so simplicity and ease. There is nothing easy about marathon training. It's more just that you've made it simple.

You're building every day, there's steps you can take, it's very actionable, but that doesn't make it easy. And I think in the culture that we all live in now, people really like easy things. I mean, who doesn't, right?

Like I want things to not be hard all the time. When I'm working with someone who's looking for a certain degree of ease, there's a lot that we have to do around facing discomfort, like thinking through some of the other elements that even though we have made something simple, it doesn't necessarily mean we're like good to go and off to the races. Usually there are other blocks that we have to work through to help make it actionable in other capacities.

[Roger]

So in this moment, Sam, what do you know to be true about your superpower of breaking things down into bite-sized chunks so people can take action?

[Sam]

I know that I'm going to keep doing it. It is an evolving craft that I hopefully even five, 10 years from now will be even better at than I am now. And I just encourage anyone if they're facing anything that is big or challenging, that there might be some easier, smaller pieces that they can act on quickly that will create a lot of momentum for them.

[Roger]

One of the things I learned in my coaching program is the focus on what's the next right step. They're not paying for coaching because it's something that they already feel like they're capable of doing. It's something that they want, but there's something else that's getting in the way and they need to unpack that.

And I have found that you only unpack it by actually taking action, by doing that little thing, things start to reveal themselves by taking action and your path will change. You might change that 16 week marathon plan. You might get rid of those hills because you don't like it or the track workout.

Oh, I hated the track workout. Or you might invite friends to come meet you at 5 a.m. at the track because it's a lot more fun to suffer together. As you take action, you learn and you grow through that action.

[Sam]

Yeah, absolutely. And there's always ways to make things more fun, I would say.

[Roger]

So what did you believe early on about your superpower that you've come to learn is not true?

[Sam]

Not everything is quite so methodical. And if you wanna do really big things, you're gonna have to work on some of the more annoying things unrelated to those big things that a lot of us don't really want to work on. So that's, yeah, just part of the deal.

And I mean, everyone's on their own journey with this, myself included.

[Roger]

So what's next for you and your superpower of breaking down things into bite-sized chunks so people can take action?

[Sam]

I am still working on expanding work, rewritten my career strategy firm and bringing this book to life. And I think this entire experience has been really fun and interesting because the thesis of my book is like living itself out in real time with the world that we're in. Meaning I also have to pivot a lot and I also have to work through complexity a lot, but I am hoping that I can give people another tool that they can use to navigate the world as we are facing it now.

In 2027, we'll have this product out in the world and I'm very excited for it to reach the people that need it and would benefit from it and that I still get the opportunity to learn and grow alongside them as I also figure out this very complex world that we're in.

[Roger]

So if a listener wanted to follow you or ask you a question, where do you wanna point them to?

[Sam]

Yeah, they can find me at workrewritten.com or on Substack at byworkrewritten or on LinkedIn, just my name, Sam Alveda. I also am on Instagram at byworkrewritten. I need to post more frequently than I do, but they can find me there and send me a DM and I'll answer.

[Roger]

Well, Sam, thank you so much for coming and sharing about your superpower and your experiences, helping to not only design learning experiences for other people, but then also the work that you do as a coach in helping people reinvent their careers and making that pivot to be more of their possible self. It's such a unique perspective that you have as being an educator and being someone who enables people, whether it's from learning or reflecting on their own experiences and then focusing it back on what's the next two or three things you can go do that helps them start them on that different path that they wanna do, but they're so scared to do. So thank you for sharing that with us.

[Sam]

Thank you so much. Yeah, it's been great talking to you, Roger, and learning alongside you in this conversation. I always appreciate that as well.

[Roger]

Thank you. Take care. Bye-bye.

Bye. Thank you all for being in conversation with us and thank you, Sam, for coming and sharing what you know about career reinvention and exploring the learn, unlearn and relearn cycle with me. What Do You Know To Be True is a Three Blue Pens production and I'm your host, Roger Kastner.

We are recording on the ancient lands of the Duwamish and Suquamish people. If you wanna continue this conversation on career reinvention and identity, check out this conversation with Sylvia Taylor. And if you wanna learn more about breaking big goals into little experiments, check out this conversation with Wynne Leone.