Poet? Potter? Doula?
How Milly built a 60,000-person community by pulling a number out of her ass
…and other career advice nobody asked for but everyone needs
A poet a potter and a doula walk into the bar. It’s all one person. Meet Milly. She’s none of those things (yet) and she figured out a way to change the world. Here’s a list of my favorite things we talked about:
→ How she went from wanting to marry the neighbor on her farm to realizing the world is very very big
→ How she grew a community from 300 to 60,000 by coming up with an idea, being honest about that idea, and charging for that idea (bing, bang, boom)
→ Advice to generalists looking to navigate this weird weird world
Millie: The first version of Generalist World was really as simple as that. I think I had, like, 300 followers on LinkedIn at the time, and I was just like: is anyone else here? Generalist? Raise your hand. And there were a few very early believers — I still remember hopping on calls with them and seeing their eyes light up when I said, are you also a generalist? Could this be a thing?
We realized very quickly there was just no space for us. Every community, you had to mold. I could go into product, I could put that hat on. I could go into founders, I could put that hat on. But I was like, what if I don't want to put any of those hats on? What if I just wanna be me and not apologize for being broad and having a diverse skill set?
So the first version of Generalist World was built on a handful of people — maybe 100 in the early days. My first 100 customers. And I was very honest. I was like, guys, I don't even know what this is. I had never built a community. All I know is that I want to hang out with you.
I was like, here's a Stripe link. It's $100. I pulled that number out of my butt — it was more just like, would people pay anything to be a part of this? And those first 100 members, we still have inside Generalist World. They're the OGs. They're the foundation of everything that's to come. And I got quite lucky — those first 100 just happened to be freaking phenomenal. Really community-minded, really collaborative.
Kallie: I love that you just pulled the number out of your ass. You're like, it's $100, we're just gonna roll with it. Because it's so true — so many businesses do this. They don't say that, of course. They're like, pricing strategy, whatever. But we're all doing it one way or another. You were just testing the market, and it turns out the market wanted it. I can see 41,207 people have taken your free test.
I actually found you because I was doing a weird career newsletter — kind of career coaching for, I think my tagline is, "for people who hate their job or wanna have a job to hate." People who are switching roles, figuring out what they want. And this really spoke to me. I saw an Instagram video about it and I was like, yo, this is perfect.
So when you were applying for jobs as a generalist — how did you position your resume?
Millie: There are a couple of different ways to get your foot in the door depending on the kind of role you're going for. The thing that's worked best for me and for lots of people in our community is having an in — what I think of as the side door. The featured roles on our job board are ones where I have direct relationships with the companies. You wanna work at Gamma? I know people there. You wanna work at Sendia? I know the founder. So there's a side door where you're not just on a list of a thousand other people sending a CV.
How I got my Director of Miscellaneous job was through cold outreach. I decided on the industry I wanted to work in — or more, what problem I wanted to solve. At that point in my life I was really drawn to mental health. I was like, I would love to work in this space, but I don't want to train as a therapist. What else can I do? So I started with the problem, found 20 or 30 companies I thought were cool, and instead of doing a spray-and-pray generic template, I was DMing the founders. Hey — here's what I really like about your company. And from what I can see from the outside, here's what's missing. If we could have a conversation, I'd love to walk you through two or three things I think could really improve your growth or conversion.
And the job board itself — it's built on Claude. Claude Code built it for me.
Kallie: Wait, really?
Millie: The premise is: we have this newsletter, 60,000 people read it every week, but everything was behind the email. I was like, what if I just took those jobs and made them public? Which is why some of them are done manually — it's actually just a Notion doc, a database of jobs, and Claude publishes them directly to WordPress. The thing I haven't figured out yet is how to handle expired listings, because jobs can sometimes be live for twelve hours.
Kallie: Yeah, that's the hard part — how do you flag a role as closed? Because the company might fill it and never update the page.
Millie: Exactly. There's a feature on the roadmap — and when I say roadmap, I mean my brain's to-do list — where people can flag a listing and say, hey, this is closed now. But the reason it blew up was honestly just one silly TikTok I did from my hotel room after a long conference day. I was like, I am so sick of shitty job boards. Woke up in the morning and within the first week, 500,000 people had seen it. If that isn't a signal from the market that people are so over boring, rigid, traditional jobs...
The job board is not perfect. I am completely hacking it together. But people are getting jobs from it, and people are now submitting roles to it too. It works enough for now.
Kallie: And I saw on LinkedIn you're commenting on people's posts, adding the link — you're including that for free?
Millie: Yeah. People tell me I'm everywhere. How are you everywhere? And I'm like — you just have to comment. You get the illusion of being everywhere. And it's a little cheeky because I'm totally self-promoting, but hopefully in a helpful way. Everyone who sees those comments, that could be thousands of people visiting the link.
Kallie: Okay, you were just in New York — tell me everything. What was the vibe?
Millie: It was so intense. Because I live on this little island — I have a very quiet, very simple life. I spend a lot of days watching the birds. So when I go anywhere, I try to pack it in. New York came about because I got asked to keynote at a conference in Columbus, Ohio — which is its own whole amazingness, one of the coolest summits I've ever been to. And because it's all the way in the States, I was like, okay, let's do as many events as we can. We have a huge Generalist World network in New York. We ended up running nine events in eight days. Brought hundreds of people together — everything from a picnic in Central Park to a giant meetup at a bar in Brooklyn.
How I think about trips like this: when I get one opportunity, how can I make it exponentially cooler — not just for me, but for all these people in my life? So the first thing I did was secretly pitch my teammate Aja, who had never been to the US, to the conference as a speaker. She didn't even know I did it. I DMed her one morning like, do you wanna be a US speaker? Let's go to America. Then I pitched Gamma to sponsor a full-day workshop and looped in our friend Lindsay, who's the best facilitator I know. One opportunity turns into nine, ten different events. Other people get to travel, put new things on their resume.
Kallie: That's the through line for generalists, right? Instead of just doing the one thing, you zoom out and you're like, oh, this would be fun, and this would be fun, and this would be fun. It's lighter. Less rigid.
Millie: Yeah. We have this line between a few of us: call it work. We just wanna create this kind of work where we're like, I suppose — call it work. We're getting paid for it, but it doesn't feel like work because it feels fun and collaborative. Not for me. More power to people who love that nine-to-five structure. Heck no from me.
Kallie: And for the companies on the job board — are they expecting generalist-style resumes? Like, what if my resume is all over the place? Head of Content, then Project Manager, then something else?
Millie: The big dream would be to change the way companies hire entirely — let's not even have CVs. But I'm aware I'm one person. For the job board itself, a bunch of those companies have no idea they're on there. They'll just see from their tracking: the heck is Generalist World? Why are all these great applications coming through? But for the featured roles, I have direct relationships with those companies. They're more bought into the generalist ethos. Gamma's CEO has gone on stage and specifically said, we are hiring generalists. We are a company of generalists. I try to spend my finite energy working with people who already get it.
The world is also starting to see this shift. With AI, it feels like sand is being swept out from beneath our feet. And it's becoming clear that being full-stack, multi-passionate, multidisciplinary is a massive advantage. That's where I'm putting my money.
Kallie: Totally. And I think about this historically too — doctors used to be creatives and astronomers and all of these things in one. Then they started specializing. Now you have to go to a specific foot doctor and they can't see the whole picture. The same thing happened in careers. At one point it was a benefit to be really niche. But roles change so quickly now — you might have one job title and two years later that role doesn't exist anymore.
What were you like as a kid? Like, did you know you'd end up here?
Millie: I grew up on a farm in New Zealand. My worldview was very small. My dream was probably to marry the neighbor and have a bigger farm. I didn't grow up with role models of women working. So it was really only when I left New Zealand at 20 and started traveling that I was like, oh my gosh — there are all of these options out here. And I think that's what inspired this weird, squiggly journey. I just have missed the gene where people say, I have to do the one thing. That's just never been an option for me.
Kallie: I love that. You didn't even know until you left. And now it's almost a bigger-fish-bigger-pond thing — you're growing to the size of your imagination.
What's your role now? Like, how do you introduce yourself?
Millie: My role has changed a lot. Year one, I was hardcore chief community builder. And this is one of the misconceptions about generalists — people think we can't have specialisms. Of course you can. I just don't want to do the same one for forty years. Think of it like a spike: you go really deep, figure it out, then move.
Today my role is a mix of partnerships, sales — I'm the only salesperson at Generalist World, selling memberships and sponsorships — and being the evangelist for generalism. Even though I've been talking about this since 2022, every day someone new finds it and says, I can't believe I never found this. And I'm like, me too, girl.
I also have a system now where I get something cranking, get it working, and then hire someone to take it from one to ten — honestly, better than me. I did that with community. Now I have a community lead. Same with the newsletter — I got it going, and now we have Mildred, who writes it ten times better than I did. I'm excellent at zero to something, and I love handing it to someone else after that.
Kallie: Take it away, baby. I love this. And yeah, people are looking for weird jobs — I was just writing a newsletter about how to use your talents to find a role. A lot of people are still stuck in: I studied communications, so I need to go into internal PR. But what if you play video games all day? What if you're the friend everyone comes to for advice? What if you can spend hours making jewelry? Those are skills that translate.
Millie: Absolutely. And it's so cheesy and so true — the more time you spend actually understanding your strengths, not just what you put on your CV... I used to write "detail-oriented" on my CV. And now I'm like, that is the most self-unaware thing I could have written. Because I am not detail-oriented. I am chaotic. I am creative. That's my power.
Kallie: Yes! No founder needs another detail-oriented person. They need that person because they're the one setting the crazy, explosive idea. They need someone to make sure there are no typos in the email. And how do you find that in yourself?
Millie: Ask your coworkers. Ask your partner. Ask your best friend. Getting a variety of responses — not just professional ones — gives you a much fuller picture. Or sit down, quiet room, pen and paper, and ask yourself: what do people come to me for? When do I completely lose track of time? And on the flip side: what's in my calendar that makes my stomach drop? For me, it's checking details on spreadsheets. I'm like, okay, I need a cup of tea. But podcasts? Green light. I love this.
And then community. People come into Generalist World with wild imposter syndrome, but they are so talented. They've had this wide, amazing array of experiences, but because it's not traditional, they feel unconfident. And then they come in, and others can mirror back: are you kidding me? You've done all these things. You could do this with your eyes closed. There's something about being too close to yourself where you can't see it. Having someone hand you a mirror — that's really valuable.
Kallie: And what you said about Generalist World — you're really creating a space for the misfits. Do you remember that Christmas movie, the Island of Misfit Toys? All these little broken toys on an island — cool and different and interesting, but they don't fit anywhere else. That's what this sounds like. A space where you can be vulnerable in your search. You don't have to be polished.
Millie: It's not only okay — we need that. Cognitive diversity. And what I see is this deep craving for these kinds of spaces. It's a direct reaction to algorithms, constant ads, socials built on polarizing opinions. When I sent out a testimonial request recently — first time in a year — the word that kept coming up was human. Almost every single one had it. And so to have a space where it's not performative, where you can say I don't know, or I'm going through a really shit time right now — that's just immensely valuable.
Kallie: And work is such a defining part of people's lives. We spend more time at work than with almost anyone else. When we lose that sense of identity, it becomes a core question of who we even are. So this goes beyond career coaching — it's almost therapeutic.
You mentioned an essay?
Millie: Post-Productivity. Took nine months to write. Went bananas when I published. It's not the doomsday AI rhetoric — it's asking: who are you when you're not working? What actually brings you meaning? Because when AI takes care of all the things that make us productive, and it already can do it a hundred times better and a thousand times cheaper — then what? If we've tied all our worth to being productive, uh-oh.
Kallie: I think about this all the time. Most of my life I tied my self-worth to productivity — to how I was seen at work. I'm 37 now. It took a long time to realize: that's not about me. I started seeing a coach, and she had this framework called data vs. drama. What gives you meaning outside of work? The friends I have who are the most attached to work are the ones crying on Sundays. Too stressed to go to a comedy show. They're drowning in it, and then it feeds itself.
Millie: The way I've realized it works: if I can't let good feedback — real praise — settle in my body, then I also can't let the bad feedback settle in my body. If I do one, I have to do the other. So when amazing praise comes in, I let myself swim in it, but I don't internalize it. I am not better or worse because of this external thing. Swim in it — but don't let it settle into your cells.
Kallie: That's very Buddhist of you. And I think about happiness too — it's not something we talk enough about in the context of work. If we're not happy, how does that show up everywhere else? I always think about that Mother Teresa quote — you want to save the world, go home and be nice to your family. This idea of impact being domestic, local. And I think generalism is almost saying: you don't have to want crazy, lofty goals. You can be happy watching the birds. You can be happy marrying the neighbor and having the farm. It doesn't have to be tied to one clean path.
Millie: And I don't even know if happiness is the goal. It's not static. What I'm optimizing for is a regulated nervous system. One of the first documents I ever wrote for Generalist World — the first one we send new members — is our stance: we are a calm community. And consistently, the feedback is: what a relief. What a breath of fresh air. Everywhere else is like, go go perform engage. And I'm like: life happens.
Happiness is great. And it's often the byproduct of a regulated nervous system.
Kallie: And there's a core belief running through all of this — acceptance of instability. Accepting yourself and how you show up in the world.
Millie: We think we can plan our way through life. We can't. Every day is going to have some ambiguity to it. The more we can be a little floaty in that ambiguity — nothing is certain, you don't know what's around the corner — the better. And this is where I'm so bullish on generalists. It's an approach to life: I can reinvent myself. I can reincarnate. I can pivot. I can start again. We had someone in our community recently say, does anyone just want to quit knowledge work and open a café? The response was wild. We're all going to open cafés.
Kallie: The thing about the café fantasy though — it's hard. Like, once you're doing inventory at 2am, you will want to go right back to knowledge work.
Millie: There is no easy path. Life is hard. Choose your hard. The grass is always greener.
Kallie: Okay — what's your escapist fantasy? You're leaving Generalist World, quitting the internet, shutting the computer forever. What's the thing?
Millie: Poet, potter, doula. That's my fantasy. I've said it for ten years and it's kind of starting to manifest — next week I'm going to England to learn how to build cob houses, which is essentially pottery houses. I write poetry every day. And I've been present at three births. Not officially. I kind of insert myself when it's happening.
I'm half-joking, but I've said it so many times it's becoming real. And I think I'm just never going to be one thing. I know this about myself.
Kallie: I think they're all the same, though. Poet, potter, doula — they're all creating from nothing. Different mediums, but it's all about birth.
Millie: I love that. I hadn't seen that pattern. What's yours?
Kallie: Well — I'm already a poet. And we actually help authors publish their poetry.
Millie: Get out of town. Are you kidding me?
Kallie: [holds up books] We design, edit — we do it for people who really care about their work but maybe aren't "poets" by training. One of our authors is a neuroscientist. Another just lives her life and wrote poetry — we did a Japanese hand-binding for her. It's really fun.
And then jewelry is my new thing. I've been making pieces in wax and getting them cast in silver. So: jeweler, cloud photographer — like, the clouds, not clowns — and official letter writer. I would love to just write letters to people all day. Those are my three.
Millie: That is such a great question, and I don't think you ask it every time.
Kallie: I don't — I don't really have guests. I just started a random website to help my friends find jobs and now I interview people randomly.
Millie: I love that.
Kallie: And the last question — the weirdest one. Can you tell me a joke?
Millie: Yes. Oh — wait. Okay. Did you hear what she said? Did you hear what she said about you? No. Shit. I got it wrong.
Kallie: Wait, I already like it.
Millie: Okay, the punchline's gone. It's like... did you hear what that owl said about you? And then the person goes, who? It's something like that. It was my favorite joke for three days and now it's just... gone.
Kallie: Oh my god. I love this. I mean — who remembers jokes? The only ones I remember are ones I cannot repeat on camera. Okay, and finally — do you have anything to say to someone watching or listening who feels like the world is completely broken and they'll never find a job?
Millie: I get it. When you open the news and you're like, oh god. I counteract that by looking closer around me. It's really easy to get caught up in big, horrifying headlines — and they are horrifying, not taking away from that. But when you're stuck in them, you lose the ability to make change on a small scale. So: keep looking around you and look for the light that is local to you. I promise you it is there.
As for the job market — it is wonky. I've never seen it like this. And it's really not you. It's them. And you have agency. You are not chained to a single path just because you thought you were going in one direction. You are absolutely allowed to change. To zig-zag, start again, go open the coffee shop.
The last thing I'll say is: look after each other. It is a wonky, scary world out there at times. And the more we can find our people, be in community, know we're supported and have people rooting for us — it's just even more important in times like this.
Kallie: I love this, Millie — poet, potter, doula. Thank you so much. It's been my pleasure.
Millie: Thank you. This was great.