Lindsey Lerner, partner at Generalist World and host of Generally Curious, has navigated a “squiggly” career path; her journey highlights how seemingly unrelated skills can combine into unique career strengths. At Generalist World, she helps others embrace strategic flexibility, discover their unique value, and turn eclectic experiences into spiky, impactful careers. Whether through frameworks like the “4 Cs” or crafting a one-liner that captures your value, Lindsey’s work empowers people to thrive in today’s complex, collaborative world.
Notes from the Show
Lindsey Lerner, partner at Generalist World and host of Generally Curious, has followed what she calls a “squiggly” career path. From photography to touring management to a role with NYC Football Club (and many more), her diverse experiences reveal how eclectic skills can become powerful career assets. Today, she helps others do the same.
Generalist vs. Specialist
At Generalist World, Lindsey champions the idea that tackling complex problems requires multifaceted perspectives. Generalists bring value by stacking specialties and adapting across fields, offering flexibility that’s essential in today’s economy. Being a generalist isn’t about being scattered—it’s about being strategically flexible.
Discovering Unique Value
Lindsey uses the 4 Cs framework to help people uncover their unique value. The key is understanding what you’re naturally good at, the abilities that enhance those strengths, and the environments where your talents shine. Emotional intelligence ties it all together, creating a personalized strategy for career growth. Through programs like the Unboxed course, Lindsey guides individuals in distilling these insights into a clear, compelling message about what makes them stand out.
Networking and Relationships
Lindsey emphasizes that networking isn’t about being extroverted but about fostering connections that matter. Diversity of relationships, ideas, and collaborations fuels innovation. Whether at conferences or in everyday interactions, preparation and authenticity are essential.
Thriving with Your Skills
Success starts with reflection. Identify what excites you most and focus your energy there, saying no to what doesn’t align. When presenting your value, skip the fluff—clearly articulate how you help, who you serve, and the results you’ve delivered. It’s about proving your impact, not just talking about it.
What’s Inside:
What makes a generalist and a specialist different?
How to define your unique skills.
Creating a career with what excites you.
Crafting a one-liner to meet and win clients.
Mentioned in this Episode:
Transcribed by AI Susan Tatum 0:38
Hello everybody, and welcome back to stop the noise. Today, I'm talking with Lindsey Lerner, who is a partner at Generalist World, and we've got, I think, a really good topic today, because it's going to be generalists versus specialists, and when you do what and what the difference is. And then there's also some other wonderful things we'll get into. Lindsey You have the most intriguing background. So first of all, welcome. And then secondly, how did it lead you to where you are now?
Lindsey Lerner 1:07
Yeah, absolutely I appreciate. I'll take that as an honor you know.
Susan Tatum 1:14
absolutely
Lindsey Lerner 1:15
my squiggly path started out originally. I From the time I was a little kid. Honestly, Susan, I thought I was going to be a photographer. That was it. That's all I wanted to do. And I had my own photography business in high school. You know, a lot of my friends were working at fast food chains, and I thought, well, that's, that's nice, but if someone is going to pay me 1000 bucks to shoot their wedding, I think I'm gonna, I'm gonna go and do that, which, in hindsight, the people who trusted me to shoot their weddings at 15 questionable. But hey, we made it up. We survived. And then when I got to art school, I was like this, it wasn't it wasn't everything. It wasn't just about photography. It was much more about people, which then led me down the path to anthropology, which anthropology led me to the music industry? Because I start, I studied anthropology at a university that was primarily business focused, and so that, I think being swimming in that water impacted me quite a bit. And then that intersection of art and business has really become the driving force between or behind all of the projects that I've worked on thus far. And so when I started out in music, I had a company called level exchange, who's a production and co working space for artists in and around New England. I grew up in Rhode Island, and through that, we worked really, really closely with city and state government, looking at music really through the lens of economic development, and looking at it through the lens of nighttime economy and how to grow it. And so it became a way to empower entire community of artists who had been looked over historically and ended up shutting that down. But through that, ended up becoming a tour manager, and I did that as a moonlighting gig for about a decade, and learned a lot you know about, about travel, about technology, about logistics, about what to do when everything hits the fan, and how to how to solve it. And eventually, through that, I ended up getting starting my own, inadvertently starting my own freelancing business, because I was helping other people start up their own businesses and get their whether it was consulting firms off the ground or their travel tech companies off the ground, anything really, anything that was growing, anything that was building, I was excited about and then my squiggly path led me to Millie, who is the founder of of generalist world about a year and a half two years ago, and ever since then, we we hit it off, and we've been off to the races. And now generalist world is a media and a membership platform for leaders with non linear careers.
Susan Tatum 3:32
Well, that's the first time I've heard of that. When you and I talked the previous conversation that we had and we so the the listeners that know me know that I I'm pretty much a talk about specialists and advise people to specialize as much as as possible in order to break through all the noise that's out there. And so and then when you and I were talking, you have a your idea of a generalist was different from because I was thinking of the general generalist is the person who says, Well, I can help anybody with money.
Lindsey Lerner 4:05
Totally, totally, totally,
Susan Tatum 4:06
tell us what. How you define a Gen that generalist?
Lindsey Lerner 4:10
For sure. I could definitely do that to me generalists are more it's more about problem solving, I think is at at the heart of it. And I think we really need to bust the myth of generalist versus specialists, and overall, the myth that generalists are, you know, folks who just couldn't pick a lane, they couldn't make a choice. You know, the jack of all trades, master of none trope that I think a lot of folks fall into. I think that the truth is, is that really, when you think about it, most of the innovative, quote unquote, solutions come from those of us who see patterns across industries that others miss, and we refer to it internally and on the LinkedIn universe as spiky careers. And it's not about being mediocre about that many things. It's really about being strategic in the way that you stack your skills and you stack your experiences that then creates a really, really unique value. When was the last time you know a complex problem was solved by looking at it through just one lens?
Susan Tatum 5:07
three totally
Lindsey Lerner 5:08
Yeah, the real and the real magic is when you can translate between specialists. You can spot connections that maybe they they don't see, and then you're able to pull solutions from unexpected places. And to me, that's not being unfocused. That's really about being strategically adaptable, and neither path is inherently better or worse. It's really about what lights you up at the end of the day.
Susan Tatum 5:26
So how do you I completely agree, and so there's two thoughts going through my mind. One is that you talked about you just mentioned the experience and the exposure to all these different things and the expertise that that gives you and what I'm seeing, and I want to hear what you're seeing in the marketplace, because now we've got more consultants than we have problems that people are willing to pay to solve, so it's becoming a buyer's market. And what I think and expertise where, not too long ago, that was the thing that got you the business. You know, the person that had the greatest expertise is going to get, to get, well, now there's too many options. There's too many experts out there So expertise totally important, because you're not going to get, you're not even going to get it to the table if you don't have that expertise. What makes you different, and you
Lindsey Lerner 6:22
totally
Susan Tatum 6:23
is the insights that you have been able to derive, or that you formed based on that experience and expertise
Lindsey Lerner 6:32
Exactly, exactly. And that's what we've been talking about within the generalist world ecosystem, as rather than, I think historically, a lot of folks thought about the career ladder. Whether you're a consultant or you're working within a company, there is some sort of hierarchy and something that you're attempting to climb upward. And we know that the career ladder is is dead. It's been knocked over. It's been burned down like it's a little bit it's more than a little bit irrelevant at this point. And we've
Susan Tatum 6:56
counted on, I would say
Lindsey Lerner 7:00
correct. We've been thinking about it more as a career flywheel. And so to your point, as consultants, as somebody who has expertise in various different domains, you then have to take whatever project you worked on with client x, and then you have to spin that story to get you in with client y, which then gets you to the next client. And so it's very much taking the momentum approach in that way, and folks are doing that, both as entrepreneurs, as entrepreneurs, and anywhere and in between on that spectrum.
Susan Tatum 7:30
That's really interesting. And it answers the question, a question that I just jotted down here to to ask you. So what I see is business owners, people. So we, any consultant, knows you've got this framework, you can solve this problem across any industry. It doesn't really matter, but the buyers tend to think that they are extremely unique. And you know, in my problem, you know you've got to have banking experience, so you've got to have this, or you got to have that, of course. What then can you share with us? What? How do you get prospects, potential clients, to understand the value of that cross industry experience
Lindsey Lerner 8:09
totally i the framework that I use for that is, we call it skill stacking, and it boils down to the four C's, which are core skills, complementary skills, compassion skills and context skills. And so the you have to go through the there's a obviously go through the framework to identify them. And so your core skill are your natural talent that feels effortless, what is so easy to you that other people are like, Oh my gosh. How do you do that? It's usually invisible to you because it's so natural. And it's typically that thing that others consistently praise you for and or notice, and it's really, it's the foundation that everything else builds upon. Like, for me, I just, I love people, I love hanging out, I love chatting, whereas somebody who's more introverted is like, oh my gosh, how do you do that? Oh no, I don't know. So to me, like, I don't think about it as a skill, but in reality, it is. Then the next part of that is the complimentary skill. So you're thinking about that through the lens of what, what are the skills that amplify your core strengths? What are the skills that create unexpected value combinations? And what is it that really makes your offering unique and it multiplies the value rather than just adding it right? And that that next level is the compassion skill, which, again, a lot of people, I think, take this for granted. But I think across the board, many consultants are good at this. This is your emotional intelligence advantage. It's how you're able to navigate different human dynamics. You're able to translate between different groups. To your point about it doesn't matter what the you know, what industry it is, it's a problem. I'm gonna solve it. And it's really, really getting into the weeds to understand what the unstated needs are. Because, as you know, as a consultant, every time you get into an organization, what they think they need versus what they actually need can sometimes be very, very different things. And then the last part of it is the context skill. And this is where your specific skill set creates the most impact. So is there a specific environment that you personally thrive in? Is it a specific industry? Is it situations in which you excel what think about it as your optimal playing field, essentially? And the magic happens when you stack all four of those so it's Core Plus complimentary, plus compassion plus context equals your unique value proposition. So for example, perhaps somebody their core skill is pattern recognition. A complimentary skill to that would be data visualization. Maybe you're really, really good at mocking up different, you know, graphs and charts. And the compassion piece, the emotional intelligence piece, comes into when you're thinking about like really putting yourself in someone else's shoes to make a really complex idea super, super simple, and then the context might be, you know, my background high growth startups. So that skill stack then creates a person who can spot trends in a super, super messy startup with the data and communicate insights so that the teams actually use them. And so that's the process that we typically take folks through, especially generalists who have a very diverse skill set, we take them through that framework, and then at the end, they're able to very, very clearly convey their value.
Susan Tatum 11:10
Are you focusing on solving the same problem, the same type of problem, you know? What would basically we say it's a, you know, the end of the day, it's the same problem, sure, across a bunch of different places where that problem might reside.
Lindsey Lerner 11:26
I think it depends on the person like for me, I like to get involved in many different industries and solve many different problems. I don't necessarily want to solve the same problem across the board, but that's my own, my own issue. There are some cases in which the common thread throughout my entire career has been community in some way, shape or form, whether it has been the music studio or on a tour bus or now with the generalist world community, you know, we have 650 paid members within our community, and so it's all about people. And I never really thought about that as a skill until I had a handful of people on the outside come to me and say, hey, I want to build a community. Could you teach me how to do that? I was like, Oh, I do know how to do that. There are systems and procedures in place in order to do that. And so that's one example of I have a couple of clients who are looking for community building, and so I'm able to go and do that across you know, one's a seven to nine figure CEO coach. The other is generalist world. Another is a community for community builders here in New York City. So that, to your point, is similar?
Susan Tatum 12:29
Well, yeah, no, I think that's a perfect example. And you talked about how you realized that this is what people were asking you for inside generalist world is it sounds like that's something that you help people figure out about themselves, or, yeah, because it comes from other, it comes from the outside
Lindsey Lerner 12:48
totally. And I think that's the that's the most beautiful part of the community, is the peer to peer connection. Is being able to hop on, you know, quick, as you can call either one to one or a handful of people, and we're all able to assist each other in doing them. And then the course that we just recently launched, called unboxed, goes through a lot of these frameworks as well, but it's a much more lengthy and much more deep process. And it also goes into not only your stack of skills that you can stack and restack in order to solve X, Y and Z, but also goes through a one liner framework as well, which I know a lot of folks have one liners. Some people call it an elevator pitch. Some people whatever you want to call it a way to talk about yourself. I think the nuance for having one lot, a one liner as a generalist is you have, ironically, many one liners. So I have different one liners depending on who I'm talking to. So I have a one liner for when I'm talking to music industry people, in case there's an opportunity and something that I'm excited about, that I want to do. I have a one liner for when I'm talking about travel tech. I have experience in that if I'm trying to land a gig in that arena. And then I have a one that is more tailored now towards community, community building.
Susan Tatum 13:58
So do you do you tend to pick Do you see companies that you or people that you want to work with and reach out to them, to get conversation with them? Are you at a point in your career where people are just coming to you?
Lindsey Lerner 14:11
Historically, I would say it was mostly doing outreach, finding companies that were that I thought values aligned and or doing projects that seemed really interesting, that I thought that I could add value in a unique way, and rather than I've never applied to anything and gotten it. It's always been through some sort of either word of mouth or very, very direct communication in terms of, Hey, I saw you posted, you know, XYZ, on LinkedIn, the project seems really cool. Have you thought about X, Y, Z, here's the way that I think that I could help, and typically that's open the doors now to your point of being a little bit later in my career. Now, a lot of it has come down to putting out content that I'm really, really, really excited about, and that's done all of the lead generation that plus going to very strategic conferences, has been a game changer. And by strategic, I mean intentionally putting myself in rooms where my unique experience is going to stick out. So I spend a lot of time going to conferences that are mostly male dominated, that are mostly in tech, that are like it's intentional, and going in with more of my anthropologist hat, more of an observer hat, to go through and survey and figure out what is going on, and then insert myself where I would like to rather than going to a conference, you know, a generalist conference. Not that those exist yet, but I wouldn't stick out there,
Susan Tatum 15:41
sticking with the these conferences that you're going to, and you're getting the lay of the land, and then you're jumping in the middle of it. Do you think that requires a bit of a extrovert or just a well prepared introvert,
Lindsey Lerner 15:53
a well prepared introvert? And I think, I think that's where the the one liner framework helped me a ton. Because I used to think, you know, and historically, like, I've done so many pitch competitions and business plan competitions and startup B things where they want you to have, like, you just say the thing and you repeat it over and over and over again. And that doesn't work, especially for generalists. So once I gave myself the space to be able to have those different iterations of that one liner. Then it became it became simple, because no matter who I was talking to, I'm able to be I'm prepared, so I'm therefore quick on my feet so that I can convey the message that that person needs to hear.
Susan Tatum 16:31
So for your content, because what I'm thinking, so to me, I just in my head, I think of marketing is one to many, and business development or sales as being one to one
Lindsey Lerner 16:42
interesting
Susan Tatum 16:43
and you talked about your content, and if are some of this posting on LinkedIn?
Lindsey Lerner 16:48
yeah.
Susan Tatum 16:49
So how do you appeal to multiple target audiences in a situation like that? Because that that's kind of one to many.
Lindsey Lerner 16:57
Totally, totally, yeah. I appreciate your definition of it. I haven't thought about it in that, in that way, I talk to everyone like they're my best friend, because I think that they could be. I think that ever I come from it, from that perspective, really believing that we have more in common than not. And so when I'm sharing on on LinkedIn, I am talking directly to the people who are in my DMs or in my inbox asking questions about anything that has to do with being a generalist and or anything that has to do with solving problems and then that, I think to me, my main belief forever has been that diversity is what drives everyone's favorite buzzword innovation. Yeah, and so the more diverse that you can have in your experiences and the people that you hang out with and the people that you engage with in the work that you do, the more creative, and therefore the more innovative you will be. And so if you go through any of my LinkedIn posts, you can see very easily there's a plethora of people who are all different races, some of them, you can tell because of their, you know, LinkedIn bios, you can tell they're not only like their race, their gender, their religious views, their political views. You can see the diversity of that spectrum, but then you can also see the diversity of the industries that they are in. And the common ground is that everyone at more of a person level, wants to be seen, heard and understood, and so if we can meet in that way, then the game on.
Susan Tatum 18:27
So, so now you're at a point where that that stuff you're doing on LinkedIn is creating a good flow of people that are coming into you and asking about doing business with you.
18:36
Yes.
Susan Tatum 18:37
How long did it take to do that? Be honest/
Lindsey Lerner 18:40
a long time, I think honestly, it was, it wasn't until the last year that it has been consistent, and I think that has been because of a lot of the internal work that that I've done, as well as finding the right people and right collaborators to work with, and that started to shift and make the difference
Susan Tatum 19:00
and how long were you working at it before that?
Lindsey Lerner 19:04
I think I never had a career strategy, ever. I never said I want other than when I was a kid and I said I wanted to be a photographer. I never set out to have any sort of title. It was very much so I was going about in the wild, navigating life, and as I met people and they told me their problems, I stood up businesses around their problems. So when I was working, I met musicians, they told me that that they were getting screwed over. I started a business to help them prevent that. And then, when I was a tour manager, I saw a lot of terrible things happen on the road. I tour managed primarily for black and brown men, and I always got treated very nicely, and the people that I was on the road with got treated very poorly, and that deeply frustrated me. And so I had built an app in really great timing, January of 2020 to get it to travel tech. And so that didn't go so well, but I learned a lot, you know, through that process. And. And then after that, I noticed that people were struggling with deepening their connections during travel, and started a travel card game that was conversation cards for a deeper travel experience. And then so on and so forth and so now with with generalist world, it's really the just big coming together of every single thing that I think I've ever done into this one concentrated focus, which I think has allowed more of a springboard in in that way.
Susan Tatum 20:29
Yeah, how does somebody know whether they should be a specialist or a generalist?
Lindsey Lerner 20:34
I still have a hard time in terms of of putting them in opposition to each other. I think it's much more about and it's funny, because obviously, like, I helped run a community of more than 650 generalists who proudly wear the badge of honor of being a generalist. But my pushback to that is that being a generalist or a specialist isn't so much the identity portion of it. It's more of the lens in which you're viewing the world. So for many generalists, I would argue that they are simply stacking specialties that we have. I can think of six different people within the community that are PhDs, which, on paper would tell you they are a specialist
Susan Tatum 21:14
pretty much, yeah
Lindsey Lerner 21:15
but the reality is, it's the approach in which they're taking to things. So like for one, one guy that I'm thinking of, Shern. He is a PhD. He lives out in Australia, and he is a professor, but he and he's a scientist, and he, like I said, he has his PhD, but it's much more about the way in which he approaches problems, teaching all of those things. It's more how much are you allowing your perhaps personal life to bleed into your professional life, and I see more often than not, myself included, I'm constantly taking different things that I'm learning and I'm integrating them into my work. I learn more from my eight year old daughter than I do from some of the consulting clients, and I take those lessons and apply them across the board.
Susan Tatum 21:58
Interesting. That's good. Okay, so that was kind of a non answer
Lindsey Lerner 22:02
to answer your actual question. I think, honestly, it's more about doing more of the deeper reflective work around, what are you genuinely excited about? And if you can follow that, you typically what I've seen inside of generalists world outside of generalists world in life in general, when you are able to follow something that you are genuinely enthusiastic about, you are then able to figure out whatever it is the path that works for you. And so the more in alignment you are, the better off you'll be. If you're, you know, if you're a consultant and you're sick of solving the same exact problem, eventually it catches up with you. And there's a comes a point at which it's not worth the money, and you see, that's, that's where people get burned out and they get tired.
Susan Tatum 22:45
That's true. Yeah, that's true. But I think, I really think you're with you when you talk about stacking specialties, is, that's the that's the key, right there is that there they are. You are a special you're a special specialist in building communities. Your special is specialized in helping consultants build their businesses
Lindsey Lerner 23:06
totally
Susan Tatum 23:07
bands, road, managing whatever you decide you want to
Lindsey Lerner 23:11
a 100% 100% the generalist component comes into when you start to translate skills from one specific area or arena to another. So when people like one, people don't ever really know what a tour manager does. Tour managers are everything from the driver to the babysitter to the parent to the accountant to bodyguard, like you do everything. And so when I say tour manager, people are like, some people are like, Oh my gosh, you know, sex, drugs and rock and roll. They think it's this, like, flashy thing. Other people are like, Oh, that's really cool. You know, who did you manage? Would I know them? Whatever? They don't actually know what it looks like day to day. But now the reality is, is when, anytime, whether I'm parenting, I think I'm a decent parent because of my tour managing skills. So, like, that's part of it, but it's also when it comes to business, there is nothing that I have not seen, knock on wood, that I don't think that I cannot handle because of tour managing. And so it's that, that translation of those skills that allows me to do other things,
Susan Tatum 24:12
confidence through exposure. Huh?
Lindsey Lerner 24:15
a 100% it's about the we have a generalist world member, Peter who has a great quote. He said, "I don't have I don't need confidence I have evidence." And I love that.
Susan Tatum 24:24
That's good, that's very good, that's very good. Well, I could obviously sit here and ask you keep talking me forever, but we're up against our time. So two things, one is, do you what kind of tips might you give the listeners if they are struggling, and hopefully we've made them feel better about they don't really have to choose between a generalist and a specialist. But what sort of tips? Because I do see this, that when I'm when I'm trying to say, let's let's focus, basically, is what it is. Let's focus on a target market, a service a problem that you're solving, and there's a great, great discomfort in doing that, and I even do it myself. Sometimes. When I'm trying to say when I'm when I'm trying to get more focused, there's fear that if I focus here, I'm going to lose an opportunity there. So what kind of advice might you have for people that are in that, in that situation,
Lindsey Lerner 25:22
in those situations, and I struggle with that too. I mean, there's, there's so many opportunities, but at the end of the day, obviously you have to make a choice, and that means saying yes to one thing means you're saying no to a lot of other things. But I think again, it comes back to that alignment. If you actually sit and get quiet and you're like, you know, here's my here's my opportunities. And you take a minute and you actually reflect, you're like, typically, one rises to the surface more than the others. And then I think it's also, it's about conveying the story. If you take a minute and you look back at all the projects you've done as a consultant, you think about your entire portfolio, and then you reflect on of all of these projects, which one was I most excited about which and and then decipher, was it the project? Was it the client? Was it the people that you got to work with, like, what was it about the thing that you did, the portfolio piece that you did that was actually really, really pants on fire, exciting. And then tell that story. And when you tell that story, then people are attracted to that, and they think, Oh, well, if you did that for those people, maybe you could help me do that. And that's where I've seen a lot of the inbound comes from. And I think the last thing I'll leave you with is more is the framework for that one liner that we talked about. And it's as simple as I help who achieve what through how. And then the the icing on the cake is when you say, like, when I insert your proof there. And most people stop at the beginning. They're like, I help tech startups clarify their market position through strategic storytelling. And you're like, Okay, you just used a bunch of buzzwords that are kind of fluffy and kind of irrelevant and not really helpful. But if you insert the proof of that portfolio piece that you are so enthusiastic about, that's how you end up being able to have great clients.
Susan Tatum 27:07
That makes it real, that last part, as opposed to the fluff that's what everybody else is saying.
Lindsey Lerner 27:13
Yeah, exactly. And that's the thing, that's the thing most people post on LinkedIn, and they're just yelling, repeating out whatever chat GPT, you know, tells you about tech or consulting, about health care, about it, or AI or whatever, like tell your story. And when you tell your story, people are like, oh, I want to work with that person. That's what differentiate to your point.
Susan Tatum 27:31
I like it. So Lindsey, how people that want to know more about generalist world know more about you? What? How to really what's the best way to follow up?
Lindsey Lerner 27:39
Yes, the easiest thing is to go to generalist.world. That's our website. You'll find every, every bit of information there if you want to find me live on LinkedIn.
Susan Tatum 27:48
alright, and we'll put the links in the show notes too.
Lindsey Lerner 27:52
Yeah, that sounds great.
Susan Tatum 27:54
Thank you. Thank you so much for being here.
Lindsey Lerner 27:55
This was great. I appreciate it Susan.
Susan Tatum 27:56
it's been fun and it's been informative. So I appreciate you being here and have a great day.
Lindsey Lerner 28:03
Thank You too. Bye. You.
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