Q&A with Milly Tamati: How Generalist World Grew From a Single Post to 30K Subscribers

I’ve been following Milly Tamati’s work for a while now — and I’m so excited to finally share this conversation with you.

If you’ve ever felt like you didn’t fit into a neat job title, or you’ve struggled to explain how all your skills connect, you’re going to love this one. Milly is the founder of Generalist World, a global community and learning platform for people with squiggly, nontraditional careers. Think: operator-types, multi-hyphenates, systems thinkers, community builders — the people who can wear a dozen hats and still see the bigger picture.

She started it not as a business, but as a way to find “a few other people like me.” Today, that small experiment has grown into 600+ paid members, a newsletter with 30,000+ readers, and one of the most intentional, engaged communities I’ve seen online. She’s done it all while living on a remote island in Scotland with 191 people(!) —and building in public every step of the way.

There’s honestly sooo much you can learn from Milly and her journey. Plus if you get to talk to her, you realize how contagious her energy and enthusiasm is. It’s clear to see why this has grown into something so special.

In this interview, we talk about:

Whether you identify as a generalist or not, you’ll learn something new here about audience-building, community design, and how to grow something sustainable online.

Let’s get into it.

I’ve shared our full conversation below, edited lightly for clarity and conciseness.

A: Generalist World is a community and learning platform for people who have nontraditional, squiggly generalist careers. It came about because I am a massive generalist. I was building companies for nine years all around the world, and I never fit into a box at work. I was always the person who was the go-to — the one who would figure it out — but I had no language for that.

About three and a half years ago, I came across the word “generalist,” and I thought, “Oh my gosh, this might be me.” But I realized the world saw it as a bad thing — there was this big stigma: specialize, pick a lane, niche down. I disagreed. I saw it differently.

The first lightbulb was just finding the word. The second lightbulb happened when I was chatting with the CEO of a mental health tech company. She wanted to hire me but didn’t know where to put me. She literally couldn’t fit me into one of the traditional tech company roles. I told her, “I actually think it’s in your best interest to not put me in a box. I don’t know what you want to do with that information, but I think it’s going to benefit you.” She ended up hiring me as the Director of Miscellaneous.

That was the moment I realized this was valuable. With the right positioning and language, CEOs and companies could see the value of generalists. But without that language, you feel misunderstood, overlooked, and undervalued.

Generalist World started because I wanted to find 2, 3, maybe 4 other people who were Director of Miscellaneous-types. And when I started talking to them, it was so obvious this was a problem. They all felt the same pain I had felt — being a generalist in a specialized world.

I wasn’t trying to start a company. I wasn’t looking to launch a business. I was happy in my job. But about three weeks in, the market pull was like nothing I’d ever felt.

I’ve built a lot of businesses before, and it’s usually a grind — you’re begging people to pay attention. This felt completely different. Every bone in my body said: run toward this. It was the perfect storm — coming out of COVID, mass layoffs, people rethinking their careers and how they spend their lives.

What started as me trying to find a handful of people has grown into over 600 paid lifetime community members, 30,000 newsletter readers, and 100,000 people who consume our content on social. And I’ve done it all from an island with 191 people.

A: I had a tiny audience. I wasn’t known. I was just starting on LinkedIn. I think my first real post was, “I’m a generalist — is anyone else here like me?”

People who’ve followed from the beginning really feel invested. I build in public. I post every single day. They feel like they’re part of the plot. And I’m very open — I share what’s going great, but also when I mess up or wish I had done something differently.

The first 50 to 100 members? It was all manual. I was on LinkedIn, looking for people who had careers that looked like mine — the same shape — and I’d message them directly. I’d say, “Hey, I’m a generalist. I don’t even know what this Generalist World thing is yet, but I think it’s important. If you think it’s important too, I’m gathering us in one space.”

I wanted to validate it, but not just with compliments. I wanted to see if people would actually pay for it. And that was hilarious because they’d say, “Pay for what? We don’t even know what it is yet!” But I was honest and transparent. I told them I didn’t know exactly what it would be, but I was going to put my full weight behind figuring it out.

In those early days, we had a $99/year membership. I wanted the price to be enough that people paused and thought, “Do I trust this?” — but not so high that it felt risky. I think we got to about 150 paid members at that early stage. The price went from $99 to $150, and even that felt big to me, because I still didn’t fully know what it would become.

And this was with barely 1,000 followers on LinkedIn, maybe not even that. It was early days. But you’d be amazed what you can do in the DMs. DMs are your friend.

I think people get discouraged or feel like they’re not big enough to use LinkedIn, but it’s just not true. If you’re a genuine person and not blasting 5,000 generic messages, people respond. My whole strategy has just been to be really honest and transparent. And it’s wild that that counts as a strategy, but it works.

A: Hmm, great question. The community has evolved so much. At first, it was just me running it and being like, I don't really know what I'm doing. And one of the first people I hired is a woman named Ece, and she is — we call her our community queen. Her name actually means queen in Turkish, so I'm like, super relevant. Just — if the shoe fits, you know?

And Ece has been the mastermind behind the GW community. She was my first hire. Community is one of the most active spaces. If anything, I think people, when they start building a community, they're like, “How do I get engagement?” And I'm like, our problem is actually the opposite. People are so engaged, it can be overwhelming. It can be super overwhelming.

So one of the first documents we made was this doc which is like, “We are a calm community.” And it set out basically the culture. A community, I think at heart, is essentially culture building. So if you can start with the culture rather than start with like, the product or the features, then the features and the product evolve. They emerge.

We have really focused on making things as community-led as possible—so, member-led. So we have members all over the world running local meetups, for example. We have members hosting our events. We have a co-working every week. We have this amazing thing called hot seats, which is basically where someone comes with a problem, a challenge that they're going through—quite specific—and everyone hops on and helps them solve it.

And the beauty is that person gets a problem solved, but everyone learns. And so now that's also community-led. We have tryouts, where if someone is wanting to try out a new presentation, a new pitch, whatever it might be—again, they hop on. It's just like this really collective atmosphere.

And I think the coolest thing about the community is that because it's a community of generalists—someone has done it. Like, someone has been there. Someone has the stories and the data, and they've made the mistakes or they've figured it out. The conversations that happen in GW is wild.

And we are, I guess, essentially like a career community. But I think we also realize that your career doesn't exist in a silo. You exist. You know, we're there for you if you got laid off, if your family is going through something, if you need support when you're traveling—all of these things come up.

And I think one of my metrics that I've really wanted to focus on since the beginning is basically creating a group of friends. That's why people come back. That's why people bring their colleagues. That's why people bring their mentees and their mentors. Because we're essentially a group of friends who are there for each other, who will go out and bat for each other, who will share opportunities, who will mention each other's names in rooms that we're not in.

But there's this little face on a Slack channel, and there's no actual connection. So we've been very intentional about actually not growing the community too fast. We limit it. We have cohorts each year, and we limit those cohorts because we are a tiny team, and we care deeply about maintaining this culture. And I think the faster you grow, it can get really shaky. The foundations can start to shake.

A: Yeah, I used to think that a generalist is something, like—I am a generalist. And I think it can be. I think by heart, by nature, I am a generalist. But the more I spend time with this concept, the more I understand it. I think being a generalist is something that you can learn. It’s an approach. It’s a way of approaching your career, but also your life.

One of the most surprising things that's happened recently is we've had loads of specialists join Generalist World. I'm like—ah, my brain breaks when that happens. But I think ultimately, we can see the world is completely changing. We can see work is completely changing. And to have one skill set is actually kind of dangerous. It's actually just a wise career strategy to have a couple of things that you're really good at.

I always say: being a generalist doesn’t mean you’re mediocre at everything. You can totally have expertise, and you can totally have specialties that you go deeper in. And I think it’s so silly to say, “Pick one thing forever.” I mean, even when I look at my last five years—I went really deep on community building. I’d never built a community before Generalist World, so I had to. By necessity, I had to go deep.

Now I’ve gone really deep on content, and that’s kind of blended into brand building—also something I hadn’t done. These skills I have? They’re not going to be the same in five or ten years. Who knows what I’ll be doing? I think it’s just reality. I don’t know why we don’t talk about it more, that your skill sets change.

One of the big things we teach is skill stacking. So you’re not starting from scratch every time. You’re building. You’re stacking these skills. And then the more concisely and effectively you can talk about that skill stack—that’s how you position yourself as someone who’s high value.

And it kind of leads perfectly into your next question, which is: what do generalists struggle with? What are the challenges?

Number one—oh my gosh—they can’t talk about what they’re good at. They can’t talk about it because no one’s taught them. They don’t fit into this prescribed box of, “I’m an engineer and I know these coding languages.” It’s very, very specific. So I’d say the number one thing people come to us for is being like, “Help. I know I have value, but I don’t really know how to communicate that.”

And what I’ve learned is—it’s not that they don’t know how to communicate it. It’s that they don’t believe it yet. So much of the work we do is around mindset and reflection. And a lot of this is the deep, crunchy work. No, it’s not a playbook. It’s the deep work where you start to really see your value.

And I think that’s where community, beyond words, is so valuable. Because people act as a mirror for each other. If I’m talking to someone, I might not see that the thing I’m doing is exceptional—because to me, it’s just normal. It doesn’t feel that wild. But in GW, this happens all the time. Someone will say, “Whoa, whoa. That’s amazing. That is a high-value skill set you have.” And people go, “Oh wow, I didn’t see it that way.”

So I would say, yeah—positioning themselves, talking about themselves—is a big challenge. I’d also say finding a role that fits their skill set is a huge challenge.

You know, we do all this work. We get people loving their value, being able to talk about themselves. They go out into the market, and it's like, “Oh gosh, everything is so specialized and so siloed.” And this is a bit of a chicken-and-egg problem, to be honest. Because to really move the needle here, we need organizations on board as well, right?

And even in the last three years, I’ve seen a massive shift in organizations bringing on these more cross-functional roles, doing things like internal talent rotations so that you’re not just stuck in the same thing and getting bored after three or five years. So I think this is another challenge.

A: Yeah, my hunch is that we're moving into an era where everyone will be an entrepreneur, even if you have a full-time job. Like, it's so insecure right now. You can't be trusting that your employer is going to be keeping you around.

So I think it just makes sense that everyone will have to lean a bit more into their entrepreneur side. And that’s why I’m so bullish on generalism. Because being a generalist means that, by definition, you have this broad skill set, you are adaptable, you’re able to connect these dots. And these are all skills—as we go into this world, which is like, I mean, it’s a one-way door with AI, right? There’s no going back. We're in. We’re on the treadmill, and we're in—for better or for worse.

And so if that’s the case, and that's a reality, then being someone who can adapt, who’s a really fast learner, who can pick up all of these skills—all of these traits of a generalist—it just makes sense.

A: Yeah, I didn’t plan on being a creator. Yeah, it kind of evolved.

I’m a writer at heart. I’ve been writing since before I could speak. It’s like my love language. I’m a writer. I’ve been described also as a ferocious reader. Like, words are my happy place.

And so when starting Generalist World, I realized that I had this message, and to get that message out, one of the fastest ways is through writing. So it started through writing. We've used beehiiv [for the newsletter] since the very early days.

And I think now when we look at people building products—it’s actually too easy. It’s so easy to launch a product. And so the thing that’s going to set you apart is being able to distribute, basically. Be able to get attention, distribute your content, and sell. Yeah, that’s it.

Anyone can become a builder now. Like, that has—of course there’s levels to it—but to get like a functional product out? And we’re still early. I can’t even imagine what it’s going to be like in a year or two.

So for me, becoming a creator was kind of the obvious choice because it meant that I owned my distribution. Of course, I post on like different platforms, but my goal is always to get people off the platforms and onto my email list. And it’s an amazing way to live anywhere in the world. To build trust.

I mean, I was just on holiday for weeks, and I came back with another 1,500 subscribers. I didn’t—I didn’t even bother scheduling posts or anything. I was just like, I’m just leaving please—I’m out.

And now it also becomes a flywheel. I’ve realized that the bigger we get, the faster we grow. Which is annoying to hear when you’re in the early days, because you’re like, oh man, just gotta grind. But you do.

I think there’s so much smoke and mirrors—being like, just do this and you’re going to become huge. But like, man, you’re going to be posting probably for years. It’s going to take longer than you think. It’s going to be harder than you think. But then you do get to this point where you’re like, wow, now I have such an asset and such leverage.

And I’d actually encourage people that if they’re like, gosh, this is taking a really long time—taking a long time just means you’re building something of value, really. To really trust you. To really, like, go out and bat for you.

And I’d say, for anyone who’s thinking about starting a company—sure, think about the problem that you’re going to solve. But also think about how you’re going to keep your message spreading. Yeah. How people are going to keep finding you. How they can spread your message for you. Because that’s going to be the ultimate differentiator.

A: Yeah, I keep shouting about this because I’m like—why is no one else doing it?

It’s like the easiest, like, it’s a criminally easy way to grow. It’s super simple. So I make TikToks. The TikTok is very specific about this quiz. It’s like: What kind of generalist archetype are you? You are either an innovator, translator, connector, or systems thinker.

People love quizzes. This is not new. People love them. Think BuzzFeed—like for years, since the internet started, people have loved a quiz.

We use ScoreApp. It’s so easy. It’s fantastic. So I make these little TikToks. They specifically drive people to those. It’s free. It takes five minutes. They get instant value.

I actually hired someone to create ours, which depends what kind of brain you are. When I started looking into it, I was like, this is not how my brain works. I know my strengths, and I know when to outsource.

So I hired someone from our community — Romero — who’s an organizational psychologist, whose brain is... this is his jam. He created it. I would recommend that, because if you create a crappy quiz—it’s like anything—if you create a crappy anything, people are going to be like, “Well, this sucks.” So make it high quality, whether that’s you or hiring someone.

So people see the TikTok. They take the quiz. It takes them five minutes. They instantly get value. We’ve had people use the results of their quiz to go and get jobs. Like, they will literally use the words from their growth roadmap in an interview.

And it just gives people — like I said at the beginning — one of the biggest challenges with generalists is they can’t talk about what they’re good at. So if we now give this... it’s on autopilot. They get it for free.

And we then use, from the quiz, we just use Zapier to send them to Beehiv. And I think our best month, I think we grew like 7,000 subscribers — maybe even more — organically. And it was just from one video that popped off.

One video popped. TikTok is beautiful because it doesn’t discriminate against old videos. You do one minute — it just keeps going. It’s not like LinkedIn, where you have like a 24-hour window. It keeps going, keeps going, keeps going.

And that’s it. And it’s so good. I mean, we have added, I think, about 22,000 subscribers using this system.

A: Yeah, we’ve had a lot of iterations and experiments. And I think the advice I would give to myself back in the day — and the thing that we’ve landed on now — is: just pick a template. And not necessarily like a design template, pick a content template.

We send our job opportunities newsletter. This is now just a template that we follow. We know that we have to find jobs for the U.S., the U.K., Asia Pacific, and remote. Social impact. These are the things we need to fill in.

Same with our podcast that we publish on a Friday. We know that we need to have the blurb about the person. We know that we need to have the takeaways. We know that we have to have the compelling things they’re going to learn. And just fill in the blanks.

I think for a long time I was trying to reinvent the wheel almost every single time, and starting from scratch. Sometimes it would take me, like, months to write an essay.

The counterpoint to this is — occasionally, I will publish an essay, and it will take me months, and it will go viral, because it’s really high quality and thought out. So that’s kind of the exception to the rule.

But if you’re promising, “We’re going to do two newsletters a week,” then make it repeatable and make it easy for your team to be able to fill in the blanks.

I’ve now kind of stepped away from a lot of the newsletter writing, and one of our team members, Emily, has really stepped up to the plate. We collaborate on it, but she’ll do most of the writing.

I also think one of my pieces of advice would be: don’t commit too much in the beginning. People are like, “We’re going to post every week,” or “twice a week,” or if you’re really wild, “every day.” I think even now in our welcome sequence I say specifically, “We will post when we have something really amazing to post.”

I’m not going to publish something that’s trash just because I said I was going to do it weekly. Again, it’s a trust-building exercise. And it really doesn’t take much for someone to hit that unsubscribe button. So make sure that the stuff you’re sending — you can stand over it and that you’re proud of it.