Launching Vocation, the AI Coach to Help Individuals Make Career Progress

Welcome to the future of education. And now here's your host, Michael Horn.

Excited to be with you, Cliff, as we talk about this new company we have given, we have created together with Bob Mesta as well called Vocation. It is based off the book job moves that we did. We had you know, decade over of research with a thousand plus individuals who had made job changes and started coaching them and so forth. Ethan Bernstein's class at the Harvard Business School, one of our co author pivotal in doing this and then you sort of look at this and you're like, hey, we could create a product out of this. And you were actually one of the early victims, if you will, of our research and tried out some of the work on you and I think it, I think it helped. But before we start to introduce what Vocation is, maybe let's tell your own personal story into this work and how you got to be here. We've been collaborators and friends for I think over a decade at this point. But why don't you tell it through your own, your own words, your personal story into this.

Yeah, no, it's so great to, to be connected again here and, and it's so fun to be building something that, that has really, when I look back, has been a passion project all along but, but now is manifested in some really, you know, powerful tools and research that we could use. But yeah, my career is pretty winding. I started out in semiconductors actually. Um, you know, when you're 18 years old and have to pick a major, you just go with what sounds interesting and, and I love math and science, studied electrical engineering, but really quickly started to find a lot of passion and energy and other things that, that frankly just didn't offer. One of which was startups and, and innovation was doing some, some venture capital work in, in undergraduate and, and working with some entrepreneurs at that, in that capacity and was dabbling with start of my own and then also education and teaching. I had never been obviously a K12 teacher, but had taught in a various different capacities and really loved just being in classrooms and thinking about how to help people learn. And so when I was struggling with unfulfillment and trying to figure out what's next, the first time, which was my first job out of undergrad, I stumbled upon your research with Clay Christianson and really just fell in love with the idea of, of how to innovate and make change in education and where that space was going, which is obviously much earlier on over a decade ago and so left engineering entirely, came to work with you as a researcher and product manager, building tools for educators and thinking about that space. And then it was during that time when Clay Christiansen asked me to be his chief of staff and help manage everything that he was involved with, obviously with the Institute, but also his teaching efforts at Harvard Business School and his consulting work and was such a remarkable opportunity to meet so many wonderful people, so many, you know, insightful leaders from all over the world, and just exposed me to, frankly, what's possible when you, when you think, you know, think big and try to help, help people at scale. And so that turned into business school and then I use that really to think about how to get back into some of the things that I enjoyed, which was startups and innovation. And so I've been at venture capital for the past several years working with early stage tech startups, usually in the AI and robotics and more deep tech space. You know, even that, that process, you know, you mentioned that I, I connected and was one of your early victims. I was navigating the transition of my own between firms, thinking about what I wanted to do. And you know, Bob Mesta, one of our co founders, said, hey, we're, we're doing some research. We're working on a process to help you think through this. And that was so impactful for me, I think, just to realize that I could focus on progress and what I needed rather than what was expected or what I should be doing or what my resume says I should do. And so when the research came out last year and I got to see the book and see the implementation of that thinking and that process, it was just a light bulb to me that there's a huge opportunity to scale those insights to job seekers everywhere who, like me, have struggled and, and tried to get through this question of what do you really want? What are you really trying to accomplish? And so it just started tinkering and prototyping and here we are now, right, building together and it's been a lot of fun.

Yeah, no, it's been a ton of fun. And so we've launched officially the new company Vocation. I'll put the link up there for those who are tuning into the live stream as well. Join vocation.com But Cliff, you sort of alluded to it, how it's helped you and so forth, and you been a part of it and you read the book and you're like, this should be a bigger product to help people talk about what the product is like, what just at its fundamental core, what is Vocation? If folks go into join vocation.com, what's their experience going to be like right now?

So we take as a starting off point really the underpinnings of the research, which, you know, many of your followers might be familiar with, which is how can we help a professional who is in the middle of a potential job change? Something's off at work, they feel like they want something new. Maybe they're starting to apply to a few roles, maybe they're networking, or maybe they're even seeking out coaches or other tools. And what we try to do is basically give you a process to work through that uncertainty, to work through that fuzziness of trying to navigate what should my next thing be, what do I really want? And so we take you through effectively the research in job moves, but in a more consolidated and focused fashion of a multi step process. Each step builds upon itself, gives you a bit more clarity and guidance and direction. Starting with what is your career quest, what is ultimately driving your desire for change, A deep dive into what gives you energy at work and what drains it. So we can really pinpoint the types of work you want to be doing. Fundamentally, we look at the themes of your career. So we try to help you understand what are the common trade offs that you've made, what, what are the constant choice or the common choices that you've made that have guided your decisions. And so that we can kind of stay on brand, stay on purpose. And then we take a user through a prototyping exercise where we look at a whole host of opportunities, some of which maybe you've never considered, some of which maybe you think I couldn't do that, but it gives us a chance to really have a job seeker wrestle with trade offs and wrestle with opportunities and put themselves in the shoes of different places to see where do I really fit. And then the last step of the process is narrowing down and guiding that process to drill down on a role that actually based on all of that discovery process makes sense for you and is going to give you the progress that you're seeking. And then once you've gone through that process, we then have a whole host of tools and resources to help you then put the plan into action. Right? So now let's go get that job and help you get the progress that we've helped you identify.

Gotcha. Okay, so that's the basic process, that's the what we've talked about, the why, because you're sort of the why like, and maybe we should make it a little bit more crisply, right? Like we see Literally millions of folks right now frozen in jobs where they're disengaged, if Gallup is to be believed, like 2/3 or 3/4. Right. Of the workforce is disengaged, 50% looking to quit. And so there's a huge amount of dissatisfaction, fear, anxiety in this place. But there's like a long, you know, standing industry cliff, right. Like of career coaches and, you know, other places you can turn. There's lots of job searching tools that are out there right now. There's tons of AI companies popping up that will take your resume and they'll adjust it for you and blitz it out to like a thousand different online postings and the like. Right. So like, why is this different from the typical career tool or the coaches that are out there and so forth?

Yeah, I mean, I think that if you've used these tools, right. And I've used some of these and, and played with a whole bunch of. Not just in building this, but also just throughout your life and even in high school, you kind of, you come across career assessments and, you know, things of that nature. I would say that the vast, vast majority of career tools are focused and still stuck, I would say, in a very traditional and narrow mindset of what a career needs to look like. And so they take as a starting point one of two things. Either, number one, what, what, what job is you looking for? So it assumes you know exactly what you want and then let's put in the tactical how to go get that job. And that could be useful, right? Particularly if you know exactly where you're going. Or they take as a starting point your resume. Right. You mentioned a lot of resume tools. And again, the resume is just a description of things that you've done. And so the best approaches are just to look at the resume and think, well, what's the logical next step? So if you've been in a certain role or industry, let's just get you a promotion in that space. Or let's look at really narrowly but obvious adjacencies to that space and that type of process in my experience. Right. For somebody that is wanting to be intentional and thoughtful about their next move, but is also uncertain. Right. It's not entirely obvious what the next thing is. Those just aren't helpful approaches. Right. Like, number one, if you look at my resume, it makes absolutely no sense. No career tool would ever have recommended leave semiconductors to go work at a nonprofit education.

Right. Like literally not linear at all.

No. Yeah, like no one would have ever recommended that. But when you do the Work of figuring out who you really are and what you really want. And if you can be intentional about that, you can find opportunities that any career, service or any coach wouldn't just completely overlook. Because that's not how people think about careers. Which is what we try to do differently is that instead of focusing on what you want and roles you're looking for, we start with who are you? And what's actually happening in your context? What are the things that are driving your desire for change? For better, for worse, what's actually happening under the hood? So that when we, we understand that, we can guide you in much more thoughtful thought ways than anything else really, really does.

So it's not even just who are you? It's like who you, who are you in this point in time with what are the forces that are acting on you in your home life and like macro.

Yeah.

In the current job, maybe you're not in the job, you know, maybe you're not working right now, whatever it is. But it's like, who are you in this moment? Is that the right way to think about it?

Yeah. I mean, just in a word, it's your context. Right. And so you could have two job seekers who are both articulating the same thing. Let's call it burnout. Right. So I'm burnt out at work. That means something completely different to two different people depending on their context. Right. And so you might dig deeper into that and figure out that for one person, it's actually they really enjoy what they do, but they fundamentally are just burned out. Like the amount of time they're spending, the sacrifices they're making, just the way that the work is implemented in their day to day life just isn't sustainable anymore. And so that's burnout and that's a different dimension of progress based on that context versus somebody who feels burned out. But you dig deeper into that and in that person's shoes, they're just not fulfilled anymore. Like they actually don't like what they're doing. It doesn't feel fulfilling, it doesn't feel purposeful. And so they feel drained every day, which manifests as burnout. But it's a completely different context, that's a completely different solution set. And so if you don't really drill down into the context and the circumstances behind your initial feelings of needing something new, you're never going to find a job that is going to bring you the progress that you actually need. You might get lucky, but statistically, which you alluded to, people don't get lucky. They end up in a job where they're just as miserable or if not more so down the line as they are now. And so we're trying to circumvent all of the trial and error that happens when people navigate through jobs or think in your words, learn, learn before switching versus learn by switching.

Yeah, yeah. And it's interesting you just brought up that example I love the burnout, like take, right? That it can mean totally different things depending on like burnout is too imprecise a word. I'll give you another example. I was having a debate with someone, one of my substack subscribers, around a post I'd written around how do we think about meaning and purpose with work, right. And one of the statements that I had made was some people like their purpose is their work, right? Like I, I, you know, I'm trying to change education and I work at a non profit, you know, focused on education change might be an example of that. And for others it's like I, I want to feel like the work that I do actually like moves the needle in some way, right. That it's having impact, but it might be different from like life purpose or how I get meaning. Right. I just want to know that I matter, right. And that I'm not just a cog that, you know, even if I showed up, called out six, six days in a row, it would, no one would notice, right? And they said, well I, for my purposes that's sort of the same thing. And I was like, I, I actually don't think it is because, you know, someone that's prioritizing the I want alignment, you know, both might be important, right? But I might have to make a trade off somewhere down the line and the person who's saying like I want purpose to be synonymous with work identity is going to be very interested in like the mission aligned. Right. Organization or something like that. And they might be okay to take a back seat on, you know, how critical the role is to day to day operations, for example, or vice versa. Right. And actually the advice, I think you'll correct me if I'm wrong from what you're learning in the data, but I think actually that distinction and burrowing underneath it actually matters quite a, quite a big deal to helping individuals find what would be that next best step and sort of that just, oh, it's meaning at work is, is maybe too simplistic an answer to say like, okay, you know, these roles are sort of equal as, as you evaluate them. What are you learning from the folks that you're coaching though, and the conversations you're actually seeing them have with the tool.

Yeah, I mean, I think that just to go back to your point about purpose, purpose or pick any category of how you find meaning in work, you call it whatever you want. The reality is that human beings are dynamic. They're dynamic, right? So I might feel like I need it. I really want to feel connected to my work and feel purpose in it in one circumstance of my life. But a few years down the road, maybe it doesn't matter as much. Maybe it's all about sustainability and family priorities or other things. And so we don't take as an assumption that there's a static definition of progress for any individual. You know, you could say that I'm a purpose aligned person and I like generally to find work that makes me feel purposeful. But that might not be true tomorrow. You know, that might not be true at the next time. You're looking for work based on whatever's happening in your life. So we, we try to be very agnostic, to quote unquote identity. And I think that's where a lot of traditional career tools and services, they try to put you in a bucket and label you as a thinker or a purpose person or a non profit. Like they try to put you in a bucket. But there's no such thing as a career bucket. There's no such thing as a career ladder. It's just you making progress through your life and figuring out what you need at a given moment. I think an example you mentioned, just some stories we've had one user speaking of labels versus progress. We had a user who had always worked in startups and viewed themselves as the zero to one founder. Right. And he was the boots on the ground, really gritty entrepreneur type. Right. Needed built companies before and so he went through the process. But when he went specifically through the career themes portion of the process where we really tried to understand why you made these choices and what's been happening and we went through a prototyping exercise with him. What he realized was that he didn't have to be the zero to one guy. He labeled himself that way. That's what he thought. That was his identity. But he started to realize that the themes that were running through his decisions were focused more on impact and helping individuals. And so what he described was a job posting that came up that he in a million years would have never considered, which was to lead like an entrepreneurship program at the local university. And he, you know, working in university, right. A lower paying generally job at a university. He felt like, I never would have touched that as an entrepreneur.

Yeah.

But when you read the job description, it completely articulated what he was finding out about himself and what he really wanted. And so when he interviewed for the job, the hiring group was like, where have you been all our lives? Like, you were exactly who we're looking for. This is your job. This is you right on paper, and we want you. He basically got hired on the spot, and now he's doing that and he's thriving. And again, once you peel back the labels you made about yourself, the assumptions you made, or the, or the progress that your resume or the world thinks you should be making, once you really just unpack it for yourself, you can be really authentic and directional about where you're trying to go.

Yeah, it's actually really interesting. Right. Because the other side is also true, which is like career boards that. Or different services that perhaps have your resume uploaded and are trying to proactively suggest you for the job. They wouldn't have found him for that role either. I know this is a different conversation for a different day, but, like, they wouldn't have found him either. Right. To suggest it to that folks or a headhunter would never have thought of him, for example, perhaps because it would look like, well, that he's just going to start his next company rather than go to a university. Thinking about entrepreneurship, it strikes me one of the things that's really, really cool about this product, and I'm super candid. I didn't think it was possible even with all the advances in AI, But I've been blown away with the work you've done in creating this, this interview that you have that historically, like, we try to teach people how to do it in the book, but like, Bob has sort of been this guru of giving this interview to really help you understand what's driving you and what caused you or is causing you to look for a switch and so forth, this interview with, with the product is like, it's. It feels incredibly personal and like you're getting to. It's not like a syncopatic AI. Right. That sometimes it can go off the rails and just overly compliment you or overly indulge you. But like, it's. It's an incredibly cool discovery process. And as you said, you're not static. So I guess I'm just curious. Like, it seems like this, this is not just a tool for one time, but this is an interview I might come back to multiple times to see. Like, gosh, I'm feeling some Unrest again at work. I'm thinking about that next step or if I can tweak my current job, can I keep sort of coming back to this tool and having that really deep AI based interview to uncover insights as they change with me, you know, dynamically? Because as you said, we're not static. Is that something that the tool will actually allow for?

Yeah. So today, today you can't run it through multiple times, but that's certainly like on a very near term. Roadmap is what we want to build, right. Is a career platform that you can have in your pocket to revisit and to stress test and to learn from whenever you need. And yeah, I mean, we've had users cry their way through some of these steps, which is remarkable to me because I think that what I'm learning right as people do this is we never set out to replace anybody. Right. We're trying to create something that's affordable and accessible as an entry point and a starting point to really wrestle through and figure out some of these thorny questions. But what I think that we're learning is that users that go through the interviewing process and just to be clear, every step of it's a five step process on the product and every step is like a 10 to 15 question interview, basically. It's not the same set of questions. It's just dynamic conversation that flows based on your responses. But I don't think that people have ever really had that type of conversation before. One, because it's not easy, but two, because most people just grunt their way through careers and through work and they find their next thing and it's fine, you know, it pays the bills. And some people are, to be clear, some people love what they do and they're super engaged and all power to you. But I would argue that most people just work, find their way through careers somewhat meanderingly and in many ways in an unfulfilled fashion. And to finally sit down with somebody that's like, let's really just unpack what the heck is going on and just ask some thoughtful questions. These aren't magic questions, but people have never actually engaged in that type of dialogue before. And it's been really neat to see people who give feedback to us that like, it's the most insightful and nuanced discussion they've ever had about their careers. And so the more that we facilitate that, the more empowering it feels to finally get stuff off your chest and finally have somebody help you work through some of these difficult questions.

One of the things that you've talked to me about is that, and I'm curious your take on this because. And I'll come back to the people piece in a moment, but I want to lean into the part you said about not putting people in boxes and like, oh, you're a nonprofit person. Right. Or you're an entrepreneur person and therefore you can't think about these other roles. One of the things going on right now, as you know, is that there's a lot of layoffs across the economy in the US Some people are attributing it to AI, some people are attributing it to more macroeconomic factors. We don't know at least half a million sort of real layoffs is in like downsizing has occurred this year. We know Amazon's about to lay off several thousand more. They've announced there's a lot of this happening in the economy. And people I think feel at the moment a sense of like, I'm hanging onto my existing job because I don't know if there'll be something else out there for me. What are you learning about sort of people, you know, through the people going through the process, being able to proactively take charge of their career and still find roles. Even as AI may be displacing certain functions, it may be changing certain job categories like that. That sort of. Because we're not the job board. Right. We're helping you navigate and figure out what's actually important to you. What, what are you learning through people's personal experiences as they've gone through the process? Or how do you think about that dislo against sort of this AI powered career coach counselor that's really going to understand what you really want and help you make trade offs?

Yeah, I mean, I think that it's first, I just want to acknowledge like it is a difficult labor market generally right now. Right. As you described. And so there's a ton of uncertainty, a ton of confusion and fear, frankly, that is AI going to take my job or who knows what's going to happen next. I think that what we've seen is that, well, two things. The first is that for some people who've gone through the product and certainly Michael, you can speak to this from your research. For a lot of people, it's not necessarily about getting a new job. Right. I have to go leave and I've got to go find something completely new in a different company. For many people, it's reframing and understanding how can I get the best out of my current situation and how can I advocate for myself and articulate what I really can do or how I can add more value in ways that haven't happened? And so we had, I'll share, I guess, two, two stories. The first is we had. We had one of our users, their company had a round of layoffs, and she was one of the ones that was spared. And so for a while, she was feeling uncertain, so she was going through the process, and then she found out she wasn't laid off, which is great. But the company, as a result of a different workforce, had to realign and reorg the team a bit. And so going through the process for herself allowed her to say, oh, these are the things that I actually want to be doing. This is what fundamentally gives me energy. Here are the types of roles or responsibilities that I want to do and I can do well. And so she was able to actually go to her manager at a time of, you know, uncertainty or reorganizing, reorganizing of the team and say, look, if we have some flexibility here, here's how I want to contribute even more, or in different ways. And that led to conversations that allow her to not just stay in the company, but really then thrive in her environment. And there's so many other stories, but I think that the reality is that if for somebody that has been laid off and now unfortunately has to go find something new and maybe on some level of time pressure, I think the reality is you're going to be better off by figuring out where it is that you want to contribute and how. So that when you go and activate your network and when you go and apply for roles, you will stand out and can articulate your goals much more clearly and in ways that are going to help you land a role that's going to add meaning and purpose to what you're trying to do.

Yeah. And it's interesting. I like those examples you just gave. One thing that occurs to me also is we found that sometimes millennials get a bad rap because they sort of ask for the sun, moon and stars when they're like, you know, whether it's control or salary or work, you know, how they express the desire to work from home, or it's a certain entitlement, shall we say, to it. And one of the things we found that I think is sort of echoing is not only like, does, you know, a reframe of their current job? But also like, they realize, actually the one thing I'm missing is, you know, the ability to do a stretch assignment in this way or the ability, right, to perhaps just like one day a week from home would make a huge difference or something. You know, it's, it's actually a smaller ask than they think it is. When they can sort of see what's driving and draining their energy and what's sort of pushing and pulling them perhaps to think about a switch and when they can express that more concretely with some evidence and data, essentially personal data behind it to the manager and it doesn't feel like a. They're asking for the sun, the moon and the stars. All of a sudden the manager's like, oh, like we can do that for you. Right? Like we, that's something we can make work. And all of a sudden it's not just a reframe, it's actually like a slight adjustment, if you will, of the job description to actually better fit you right now. And also to say like, hey, you are going to make some trade offs. Not everything's going to be perfect in any job, but are you happy making these two trade offs, say here so that you get all these perks that are actually pretty awesome about your job now and in line with the things that are really driving your energy is something we found.

Yeah, no, I think that which you said it right, there's. There is no such thing as a perfect job. And I think that often people feel like the job has to hit every single bucket of fulfillment, energy, passion, interest, whatever you want to call it. And it should hit many. Right? That's the point. That's why we do. What we do is to try to help people find more alignment with those things. But part of the process is helping you figure out, well, what if leadership matters to you and you don't have as much of it in your day to day? Are there other aspects of your life where leadership is manifest and you can feel and find that fulfillment, whether in your community, with your family, whatever it is. And you start to see your life as a function of getting your needs met versus I have to have it all met in the job. And that's also just been a big unlock. It was for me personally when I went through the process and ended up helping others is just separate what your work is versus what your life is and how can we strike a balance that makes sense for you?

Yeah. All right. As we wrap up, last thing on my mind, which is like a huge push in our book, was that ultimately job searching is a social process. Whether that's getting leads of ideas that you could do from those around you that you're Weakly connected to, to informational interviews, to so forth. I can imagine people being like, you just created an AI tool that's going to take people out of the process. It's not how I see it, but I'm cur curious, like how you would articulate how the tool connects to the real world and helps you connect with people to actually find opportunities. Because I'm still amazed, Cliff, at the number of people that think you get jobs from just like applying unmasked to things online and somehow something's gonna work. And then like, everyone's like, oh, it's broken right now with AI. And I was like, I mean, sure, but it wasn't working that way before either.

Oh, it was always broken. That's right.

Yeah, exactly. It's always been broken. It's. It's always about the people. So how does the tool bring in the people? Social capital, social network, whatever it is that actually help you find the roles. How does that all work?

Yeah, so there's a few things we do now and then there's things that we're thinking about in the future which we're not doing yet, but we would like to. The first is, you know, recognizing that a job comes from a network, you know, fundamentally. And so once you go through the process, some of the resources and the tools that we give you help you and show you how to activate that network and how to engage and how to ask in ways that allow you to have a directional and focused conversation with whoever you reach out to. I think part of the challenge with networking is that particularly when somebody is in a place of I need a new job, or, you know, it's people say, well, go network, but what does that mean? And they think, I'll reach out to my 20 contacts and ask if they have job openings. But you've been in the situation before. You've been asked for help before and so have I. And the first question anyone responds with is, how can I help? You know, and that's not a really useful directional guidance. I mean, I want to help, but I don't know where you're trying to go and what you're trying to do. And the sharper you are with me, far more focused I can be in actually finding opportunities. And so we. Part of the process is, yes, it's an AI driven tool to help you arrive at the insights. But then now let's activate your network in ways that are going to help you add value. So we have that now over time, things we're thinking about is one, building a Network of just people on the platform. So as we scale and we have hundreds or thousands of job seekers on the platform, we can say, look, if you're looking, if after you've gone through the process, what we've helped you realize is that customer success and healthcare is your calling. That's what you really want to be doing. Well, we've got five people in the network that do that, that have that job right now. We can connect you and you can start those conversations. So that's on the roadmap, something we're thinking about. And another thing is we've had some users go through the product who want to then just talk with an actual coach to kind of get back and forth and get more guidance and maybe somebody that's in the sector or in the space. And so we've started to talk with some actual coaches who coach for a living and who that is their job and can we then have them as an after effect, you know, go through the process and now you have a whole platform upon which you can really have engaged conversation with someone more focused for you. So we're thinking about lots of ways to do this. But yeah, we're not blind to the fact that AI is a tool to help you and we're very committed to not being the thousands of other job boards where AI applies to hundreds of things for you because that's just not how it happens and we want to be a bit more guided in that.

Awesome. Awesome. All right, well, this has been a great conversation. I'm so excited that join vocation.com is up live the company's vocation. He's Cliff Maxwell. Cliff, any other things folks should keep in mind as they go to check out the tool, start to use it and hopefully make more progress in their careers?

No, I would just say be prepared to be asked. If you go to the company and sign up and this first step is free, you can take the first interview for free, but be prepared to be asked some thoughtful questions. It's not going to be what do you want? And let's look at jobs together. It's going to be questions like, you know, when's the last time you really felt fulfilled? What does that mean? And you got to wrestle with these things, but the more that you can be authentic with it and, and really reflect on what you need, we can be so, so much more insightful and help you really find something that that's going to help you make progress. And so we'd love to have all you try it and really excited to help you in any way that we can.

Awesome. We'll give it a shot. Give us feedback and let us know what's working and what's not. We're going to keep tweaking and improving it. I will say you've taken what was a very cool process that we built for, made it simpler to use and still not lose the insights that I think come out of it. So huge thanks for building it. Huge thanks for all of you tuning in. I'll do better next time and figure out how to make the live feed actually work on Substack. That's my bad. I am 99% sure, but I'm thrilled this is out in the wild. Thank you again, Cliff, and we'll see you all next time.

Thanks so much.