Career Skills & Transitions with Dan Brockwell, Co-Founder at Earlywork

Lucy Wark: So welcome Dan Brockwell, founder of Earlywork and doer of many other things. I might actually just ask my first question because I think it allows you to tell us a little bit about yourself. 

What is your career story so far?

Dan Brockwell: Career story? What's happened so far? A couple of things, a couple of things.

My background originally started off studying biology and finance at UNSW in Sydney. I picked it roughly based on my two favorite high school subjects. And then stumbled into a startup called Tilt, which was a social payment startup, which was my first professional role in uni. I had cold messaged the country manager because I was trying to build a similar product and then saw he was trying to do it, I was like, 'well, hey, that's pretty cool'. I ended up joining them as a growth intern in my first year of uni. They got acquired by Airbnb a couple months into my internship. I lost my job and I was like, 'holy shit, startup are awesome!'.

And so from then on, I switched up my degree. I was like, 'okay, yeah, tech's the future'. I want to learn how to build shit. I want to learn how to sell shit. Let me switch into computer science and marketing. That's probably the closest map to it at uni. And then just spent the rest of my time at university, not too much on the lectures, more on just internships. So just working out what problems I wanted to work on and what role I want to play in those problems.

So I tested out UX design, web design, marketing, sales, project management, operations, big tech companies, small tech companies, social enterprises, a bit of a mix throughout university. I was like, 'Hey, I think there's something really powerful about the product management skill set'. You know, I think it combines the fact I'm interested in the technical stuff, the business stuff and the design stuff and thought, okay, in Australia, where can I go learn that skill?

Atlassian is one of the few companies that had a dedicated, structured program around product management. And so joined Atlassian as Associate Product Manager in 2020. I spent a year there. Not too long. The reason being, coming to the end of university, I saw a bunch of friends who were going into consulting, banking law, and hating it.

I was in tech, loving it. I was like, 'guys, what are you doing with all these jobs in tech?' And friends asked me, 'hey, Dan, what's product management? What's customer success? What's growth?' I just realized the universities were failing to teach students about the fastest growing industry in Australia and what roles are in it.

And so I launched a newsletter to curate jobs for friends. That soon turned into a community, which is now Australia's largest early career tech community. From there, I went full time, spent a year fucking up and failing and now building a school to help people get their first jobs in tech.

Lucy Wark: Amazing.

Oh my God, there are so many things I want to dive deeper into there. What I might do is I might actually ask a few more of the questions we've talked about, because I think some of the things that I'd love to hear from you are going to come out through that.

You've clearly been quite thoughtful about the way that you want your career to unfold.

What ingredients, like skills, attitudes were most important for you early in your career? 

Dan Brockwell: Proactivity is probably the single most important one; like don't wait for the job listing, make the job listing. If you want an opportunity, go and message that person, go and apply for that job, go and refer someone to a company, go and pitch yourself, send a video.

I think like the majority of startups I got into in uni didn't have a formal job listing for that job. It came because I either sent a cold email or I referred a bunch of friends, then hit them up on LinkedIn or I applied for a job that wasn't actually the real job and used it to have a conversation with the team because I liked them.

So I think that's probably like the single most important trait and probably alongside that I'd say curiosity. And so I think when I generally made the better career decisions is when I authentically followed my curiosity in terms of, 'Hey, what problems am I generally curious about?' Where do I think I might find an environment I can thrive in? Being self reflective, what are generally my career goals? What's important to me. And then what are the skills I'm good at? What am I not good at, what am I shit at? What would I like to develop? What are the things that drain and energize me. So I think

proactivity and curiosity, if you've got that combination, you will go very far and you might not get it right the first time, but if you're curious, you'll keep trying all the things and proactive is like, you won't be afraid to give it a shot.

Yeah, probably the final piece I would maybe call out there is the resilience piece.

I think especially early on, everyone's like, 'yeah, I want to do strategy. I want to product. I want to product growth strategy'. Realistically, starting off as a junior, you may not have those skills and you've got to be able to almost choose the grunt work that best resonates with you. As in, starting off in junior role, not everything is going to be pretty and sexy and high level. Find the thing to you that feels like play, that to others feels like work, out of the possible subset of junior roles that are out there.

Lucy Wark: I love that so much because you probably now have had the experience of both being the person who's choosing that work and of managing someone who has come in and taken ownership of an area of the business or taken ownership of a piece of work and just gotten shit done and you fall in love with that staff member so quickly.

So what's the biggest career transition that you've made and what helped you take that step? 

Dan Brockwell: The biggest career transition? I'm trying to think about how you quantify that. Like, probably it's going from an employee to a founder. That is a huge career decision. Like, going from Atlassian, which was a company of 8,000 people, to starting my own small business, which was three co-founders.

That's probably the biggest material transition I made because all of a sudden you go from having a manager to not having a manager. You go from having a product that's got customers to working out, 'Oh, what is the product?' You go from having a very clear revenue model to going like, 'fuck, how are we going to make money?'

I think in making that transition, I had two co founders around me, which is incredible for support. But we were all coming from bigger company environments. We'd worked in startups before, but I think starting your own thing comes with a new level of ambiguity.

I think number one (that helped me), is obviously

speaking to people who've been in that position and it's not because they have all the answers, but because if you speak to a sufficient sample size of them, you start to see the patterns

like generally in early stage businesses, what seems to work well and what doesn't seem to work well, and there will always be exceptions and your own lived experience, you'll learn a lot of things that maybe conflict what others have told you.

But I think number one is like speaking to founders who've been there, done that, especially founders I used to work for, like getting advice from them on the journey.

Number two as well from a lifestyle perspective, and this took me a little while, but I think especially as a founder, it's now like 'oh, it's not like a contract where it says nine to five, it's like, what are your hours? Who decides that? Oh, it's me? Oh, do I do it all, I really like it, do I do it all the time? Oh no shit, probably not.'

I think a big piece is if you love what you do, I think it's totally fine to work more than five days a week. I think it's totally fine to work nine to five. With the caveat that I think like sleep is the best drug, try and keep your sleep, good exercise, social stuff, et cetera.

And so I think being really intentional about blocking off time for non-work things is super, super important. As in, I think as a founder, it's a marathon, not a sprint. And so something that really helped me in making the transition eventually, in a healthy way, was going like, 'hey, I'm going to spend this time on dance, or I'm going to spend this time, like, book it in with friends, have like a recurring catch-up.'

And I think that gave me the time to switch off and the time to engage with a part of my brain and my body that's quite different.

Lucy Wark: Yeah, I have a version of that that's like a therapist.

Dan Brockwell: 100%. Yeah, plus one for that. I mean, because being a founder, like it probably is more stressful than the average job.

Some would almost call it irrational to become a founder. But I think the highs are really high. It's a lot of fun, but yeah, being intentional about what is your support system? And that can be a therapist, it can be friends, it can be family, it can be co-founders, and different people might be good at different things, but I think it is a journey that will have like some lows and so being intentional about support system and that environment that allows you to almost be like a shock absorber, like, 'Hey, if hard things happen, you've got good people in your corner.'

Lucy Wark: Absolutely. I think particularly being a startup founder has a really interesting psychological challenge to it, which is like, you know, statistically,  that a majority of startups fail or don't reach their goals. While at the same time like I think these is a lot of pressure to live up to like the visionary founder archetype or to like project a confidence that, you know, early on in the journey of a business you may well not have yet. If you're on the pathway to finding product market fit, you might not yet have convinced yourself that it's there. And I think it's a really interesting one to kind of sit between those pressures. And it's also something people's identities get mixed in. Personal identities get mixed a lot more with their professional identities as well. Whereas in a lot of jobs, you can sort of be like, 'here's how I think of myself, and then over here is like the thing I do for money.'

Dan Brockwell: Yeah, it's interesting. So many good points there. There's some nuggets there. Two things I want to call out: number one, there's that piece around like, a friend of mine, Joe Harris, often describes this as, Diversify your self esteem and it kind of ties with what I said before, where it's like, okay, you know, for me, for instance, like being a co-founder of Earlywork is a big part of my personal identity.

It's not just a personal identity because it genuinely corresponds to a lot of my core values about helping people find things that are meaningful to them in their work. I think it has such a big impact on happiness. So I proudly fly that flag. I've got several Earlywork tattoos. So I'm pretty deep in. At the same time, it's like, I think sometimes in life like your work channel may not be going as well. And what you want is other channels in life where like you can switch and things are going well. So like it could be something creative, It could be something in terms of like physical exercise. I think I find often like having spaces or places where you can switch off from having to be in founder mode, work mode is a good way to get around that. You touched on something else there. There were so many good nuggets and I feel like I forgot.

Lucy Wark: Mixing personal and professional, like I think the fact that startups fail.

Dan Brockwell: Yes, this one. This one I have a lot of thoughts on. It's like - Why? Okay, that's like a very high level statistic (start-ups failing). It gets thrown around a lot and there's some truth to it. But it's like, okay, why does a startup fail? And I think at the end of the day, there are like really only two reasons.

It's either the founders give up or they run out of money. Everything else ultimately, usually can be traced to one of those two routes. The run out of money one, it's something to think about. Like people say startup, like they mean a Canva or Atlassian. I think like there's also very sensible service based businesses where you could be doing consulting work, advisory work, recruiting, where you can bring in quite reliable revenue.

And so even with Earlywork, I was at a point when I was working at Atlassian where I thought, okay, after a year of Atlassian, I'm going to go full time at Earlywork. And even if we don't have a business model, I'm just going to bootstrap and do some recruiting work. I had high conviction based on the strength of the community we built and the brand around that, that there were ways to keep that business afloat. Even if we didn't yet have a clear model that was absolutely smacking it.

I think a lot of startups fail because they try to do the hyper sexy scalable things straight away. And sometimes you've got to do something that's just like, you know, maybe it doesn't look quite like the thing you want at the end, but you do it to get you off the ground.

I talked to a lot of founders who've done service based work, advisory work, things that aren't very scalable, even if they want to build a scalable company. So that's just kind of the caveat. All like, you know,Start ups failing. And then, what I think is it 90 percent of startups failing or is it 90 percent of products failing?

Because you can also pivot. Yeah, Earlywork, the first iteration before we even launched a community. We were testing no win, no fee career coaching where we would coach people on how to get a job and they would only pay if they got a job, had no good structure or system around it, like crashed, but we learned a lot of good lessons, but you can say, okay, did the startup fail?

It's like, well, yes the model failed, but the team kept going and under the core brand, under the core idea and thesis, problem, we launched a community. We did a jobs board, shut that down. We did a talent search engine. Shut that down. We tried running a paid community. We shut that down. So I almost think it's like, it's not 90% fail.

I think it's more like 90 percent of ideas or products fail. And I think as a founding team, if you stay together and you know, and whether you've raised funding, if you're bootstrapping with service based work, if you've got cash reserves, one of those three things, usually then you can keep having a crack at it.

Lucy Wark: Yeah, I love that. I think it's a really good call out to almost say look like we hear that stat a lot, like 90 percent of venture backed startups fail. And often what that means is much more that's from a venture capitalist portfolio point of view, we've been on each of these with the thesis being grow to a billion dollar valuation plus Company and the failure is defined as did they grow this thing to the billion dollar plus company we thought they were going to grow it to. That's a very different threshold.

Dan Brockwell: And in that regard, just flipping that around, it's also important just to be self reflective in what success in that business looks like for you, because that's not necessarily the same as what success looks like for a venture capital investor. Or someone else you might be trying to hire, like

when you have a really good definition of what success looks like for you, it makes all other business decisions a lot easier.

Lucy Wark: one thing that I just want to build on that and then we should move on to the next question. One thing that I found really, really helpful, and this was kind of the first topic I worked on my therapist, when we started working on Normal, was separating out really distinctly, like I want to become better and better at the process and craft of building companies, from the specific results of the company that I'm building.

Like, I think I'm very happy attaching identity to a thing where I have a lot of control. And where I will take pride from becoming better and better at doing this. But I don't necessarily, like, I know the odds and I know my job is to make the best rational decisions I can with those odds for the company I'm building, but I don't necessarily control everything about the market that I'm building in et cetera, et cetera. I think that's been like a helpful distinction for me over time to think about.

Dan Brockwell: Big vibe. I think it's always about like, there's a big piece around like detaching the outcome, which is so hard in an industry where it's like, Oh, outcomes matter, not outputs. Like that's the whole mantra of tech. It's like, 'Oh, fuck all the outcomes of that'. Then like, what the fuck does that mean to me? If I've put all my time into it.

What I've found is from a happiness and well being perspective, if you are working on problems you give a shit about, with people you love, I think you're able to take those failures in an environment that's still positive, very healthy, very rewarding. It doesn't mean it's easy, it doesn't mean it doesn't hurt, like it still could feel like a punch. 

There are some startups where it's like, you know, if you're working at a company that's going really well, sometimes maybe not the answer to the problem, or maybe, you're not a huge fan of your co workers, but it's easy to work at a company that's going well.

It's hard to work at a company that's not going well. And so I'd say, like a big thing there just in terms of founder wellbeing, is being intentional, like, 'Hey, have I selected a problem that like really pisses me off?' 'Is this something I could honestly work on for 10 years?'

I've seen a lot of founders actually come to a authentic self reflection in very hard times where they realize like, wait, when the going gets tough, I actually don't care that much about this. Which is a good honest point to come to, but ideally you want to find that earlier before you commit a lot of time and money to it.

Lucy Wark: Yeah, definitely. I've also seen founders who are quite successful, who are like almost extremely problem agnostic, but just obsessed with the craft of company building. Like I think someone who people often cite is like Didier from CultureAmp as just being like, kind of could have been a lot of different problems, but just loved the discipline of like company building.

Dan Brockwell: Yeah. Interesting. There is a fun element there. And every founder is different. It's funny. It's a personal thing. I think for me. The problem outweighs like the founder role. It's like, I'd rather be a non founder on a problem I think is really important, to being a founder on a problem that I don't think is important, but that's also like a very personal decision.

So it's like, don't be like, Oh, this has to be your career framework. It's more like, I recognize that because I just found that's what gives me energy.

So how have you built your own professional toolkit over time?

Dan Brockwell: Number one was just try a lot of different jobs. Like, I think I knew quite early on that I wanted to create things. I love building things. And so I knew I wanted to start my own business in some way, shape or form. So coming back to that early career journey, part of the reason I tested out lots of roles,  part of it was to learn what I liked. Part of it was also to be able to see a problem through a certain lens and have a baseline ability in that area, such that if I meet a professional from that area, let's say I'm hiring a designer, okay, I've done design before, I'm not a pro, but I know the language to speak in. I know the questions to ask.

So that was kind of an important baseline to have threshold toolkit. And in particular, I think, as a founder, what really helped was spending time working at other early stage startups. When you're working very closely with founders, you start to see what toolkit is relevant because Id also contend,

a lot of people in their careers, they're very focused on learning, but it's not just about how much you learn. It's also about the relevance of that learning to your goals, which is a factor I think a lot of young people underweight

like they go into a grad program because, Oh, there's so much learning. But wait, what, learning are you getting? Now, as a founder, in how I think about building my professional toolkit, I have kind of like two to three, actually, now I'm down to one professional development goal that I do per quarter as a founder, and we have accountability, my, myself and my two co founders. The three to us, like helping each other get better in certain areas. And I think we used to focus on weaknesses and now it's actually more doubling down on strengths where it's like 'Hey, I want to become really good at this because I think it'll help the business.' Here is like the asynchronous content, the advisors and the practices I'm going to do to get better at that.

So I think, yeah, now in developing that, that's a key part. A lot of it as a founder is just learning by doing. As a founder, your toolkit will be developed by doing the things that are important to the survival and growth of the business. Like, a lot of it, candidly, is ad hoc. But that said, I think a lot of founders underweight this, like a lot of founders are like anti, like they hear anything as like a consultant, they're like, Oh, no, it couldn't be useful.

I do think it's very powerful early in your journey to bring in more senior advisors to give you candid feedback on things, whether that's just very high level ideation or whether it's very nitty gritty stuff. Like before we went full time on Earlywork, we had something called stages.

Where I recognized as a business, we're all young founders. We don't know much. Let's bring in like three people who are a bit more experienced who can hopefully be a sounding board to us and show us the ropes and at the time we brought in Justin Teo who's head of International at Eucalyptus, Steve Solomon, who's in the investment team at TDM and then Lucy Tan from SquarePeg. So we had like these like three folks who are a couple steps ahead of us career wise and they were calling out blind spots as we were kind of progressing as a community thinking about how to build a business model around it. And even now I've certainly recognized the power of working with, like we've had an advisor for design, there's an ad hoc short term thing, another one for even like for capital raising I've got, you know one or two I'm working with on sales and sales operations.

So it's like, there are two ways at the end of the day to learn. I know I've ranted a lot. There are two ways to learn something real. Number one is do it. And like hit your face on the pavement and keep doing it. And then number two is like spend high touch time with someone who has deep expertise in that domain and ideally get them giving feedback on your work, shadowing you, you shadowing them, sort of a two way learning process with that person.

It's like learn by doing or learn by expertise. 

Lucy Wark: awesome. I think I have a similar version of that. That's like, mentally, I have learning curves across a bunch of domains. And then I'm like, okay, do I need to be at a level where I'm executing it myself or holding someone accountable and briefing them for execution or just knowing enough about what good looks like to find the right thing?

Dan Brockwell: there's a quote from a book where I think it's from the founder of Wix, who I think I heard speak in Israel. It may not be this founder, but I think it is. And he said something like

as a CEO or as a founder, you want to be a brown belt in everything. Like you're not going to be an expert in everything, but you need to be good enough that you could pose a challenge to the expert in that area.

Because otherwise, if like you hire someone and you don't know anything about that domain, like imagine a founder who's like never sold, just hiring someone to do their sales for them. You actually won't have the literacy to be able to like challenge them on whether things are going well, whether things are not going well.

And so from a founder, professional perspective, our thesis is always like nail, then scale; learn how to do an area well ourselves, and then hire someone that over time can take on that area and make it even better than what we had made it.

Lucy Wark: Yeah, which I think it sits in contrast to a lot of like classic teaching that's like, you know, hands off, find the right person for the seat, just give autonomy.

Dan Brockwell: Like don't get me wrong, I love the thesis of hire smart people and get out of their way. You need to know what you're hiring them for. You need to know the area well and ensure that the function actually even makes sense.Because otherwise you're hiring someone for an area that doesn't make sense. 

What's the best career advice you've ever received?

Dan Brockwell: It's, it's almost more life advice than career advice, but I'd say it's probably

keep your own voice in the game.

I got this advice when I was in university from a guy who was a Fulbright scholar from Argentina, had traveled the world, randomly ended up in Byron Bay. And the reason why I think that advice was so important for me to hear at the age I was at, it was two things:

Number one, as a young employee, you're often concerned with, you know, looking like the noob, or like getting things wrong, or being afraid to challenge your managers. And when I reflect on the times in my career where I've actually like learned the most, it's oftentimes when I've come into a system, working with people who are more senior, realizing something wasn't quite right, and I called it out or challenged it or push it a better solution. I think when you're coming in as a young employee, you've got different perspectives, often to the old execs you work with and that's a competitive advantage.

Like that's something you can genuinely bring as value. And

you should be confident that even if you don't know everything about the domain, even a fresh set of eyes will see a problem in a different way.

And the other piece of why that advice was so important is because it also kind of led me to really reflect on the power of authorship, where it's like, you know, oftentimes you're gonna be working in a certain industry, in a certain company and there's a huge advantage from, you know, creating content or you know, like speaking or kind of discussing or going to events around the area that you're passionate about.

And so you'll see a kind of a lot of that as you get, you know, further along in your career, you'll oftentimes have moments where you're invited to speak or write or you practically do that. And I think that advice has been really important because It's helped me in the way that I'm building my company now, stay authentic to what I believe.

And sometimes that's different from, you know, the other startup I worked at. Sometimes it's different from other founders in tech. Sometimes it's different from what my managers in big tech told me. Sometimes it's even different from my co-founders. I think when I have kept my own voice, when I've tried to be clear about what is Dan's perspective versus what is Earlywork's perspective, or what is, like, the perspective of founders in Australia, or Gen Z in Australia, keeping honest to that, and not being afraid to share that with peers and managers is one of the things I think made a massive difference to my career.

Lucy Wark: I love that. Thank you for sharing that. I have two more questions.

What's one thing you wish you knew when you started your career?

Dan Brockwell: Titles don't mean shit. I think in uni I very much fell into like insecure overachiever trap of like seeing a really flashy title and thinking, like, 'Oh, if I have that title, that's like a, a good role. It's respectable. Like I'm smart. I should be at that role or it's like product or strategy.'

And you start to realize like, I used to probably over index on the role, the title of the job and then the logo of the company, right? And in uni, I got a few big tech internship and whatnot, and I realized the jobs that made me happiest didn't always correspond with that.

And instead focusing too much on the title, realistically, companies hire someone with a certain title, but what you actually do day to day can be so different to the title and change so much. I think the more important constants to focus on  are work on a problem. Again, it's like the problem you work on or the industry.

You either need to be like, it needs to piss you off, be passionate about it, or just think that it's like a growing industry. Like be bullish on it from like a more investor mindset. And the other one is just like the people you work with. And in particular, the manager. Like, I think I would take a job with just whatever title, if it's with an amazing manager on an amazing problem space.

If had I known that earlier, I'm happy with where I ended up, but I think I would have probably gotten some awesome learning earlier that took me a little longer to get.

Lucy Wark: absolutely. I second that one hardly. And finally

What's one resource that's helped you in your journey?

Dan Brockwell: the 80,000 hours careers guide.

For those who don't know, it's generally just like such an incredible not for profit; they focus on this question of how do we get people to maximize the positive impact they can make in their careers? Reading 80,000 hours hugely shaped not just the roles I spent my time on, but even like the company that I've built now.

And so, like, I'm indebted to the work that they've done. Yeah, we definitely recommend anyone check that. And to be clear, it's not like you have to exactly agree with their assessment of, oh, these are the most important problems, but the sorts of questions it poses, the sorts of frameworks it gives you for thinking about impact in a career context, I think are incredibly insightful for someone who wants to choose a career where they'll wake up in 10 years and be happy that they chose that career.

Lucy Wark: that's a really great point. I actually weirdly nearly took a job being an effective altruism, like investment analyst or whatever back in the day and had a, I think maybe a similar issue where I was like, look, I don't wholly feel aligned with the philosophical underpinnings of how people do like course selection...

Dan Brockwell: yeah, there's a very healthy debate that needs to happen there, but to me, it's less about the precision. It's like, do they choose the exact top fields correctly? And it's more like accuracy.

It's like, broadly speaking, I think there's some good directions there about problems that are probably going to be a pretty important part of the future.

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This interview transcript has been edited for length and clarity.