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Career Skills with Alex Brogan, Entrepreneur, Creator & Founder at Faster Than Normal - pt.1

career skills & transitions


What's your career story so far? 


Alex Brogan: Yeah, absolutely. So in many ways, yeah, I've had a traditional and non traditional career that have coexisted. I started my career at Goldman at 20 years old, which in hindsight was quite young as I've come to realize in terms of the learning that's, that's occurred since that point in time, I spent Two years at Goldman and going into that, I had a good feeling that that wasn't going to be my long term career.


I think the early experience started to validate that quite quite quickly and I very much didn't aspire to be growing up and to be the sort of leaders in the organization in a lot of ways. And so for me, it made a lot of sense to, to jump out. And my. Immediate pathway was was into startups.


So I joined actually a growth marketing agency called Ammo in Perth W. A. And the idea behind that move was really Building a skillset that I thought was going to be useful in the startup arena, I think, above and beyond a sort of general finance skillset and after approximately nine, nine months, I jumped into a venture backed startup called Zipline in a sales role and that evolved into a account executive role and later a head of go to market role, which took me to America, which is an incredible experience.


And now I'm working entirely on my own projects as of six months ago. So The non traditional career part is very much what I've been doing on the content creation side, which I started two years ago now in 2022. And the thinking behind that was knowing that I was very likely to go Into a sort of business building mode or capacity in the future, but not necessarily knowing what I wanted to work on specifically.


And I saw the audience building content creation journey as something which could be very productive to that. And so, yeah, that's sort of transpired over the last two years and has been an incredible journey in its own right. And A lot of learnings and yeah, right now I'm sort of 80 percent focused on that and thinking about what's next as well, which is a bit of an open question, but I've got a few ideas.


Lucy Wark: Yeah, awesome. And for those who may not know you as well, I'll, I'll just give a quick like plug to that, which is like Alex writes really awesome productivity and let me not reduce it to productivity, but a lot of like really cool learnings about productivity and life and strategy on LinkedIn has about 60, 000 people reading your newsletter.


Nearly 200, 000 following it on LinkedIn. So I think a lot of people really resonate with what you do. Have I missed anything important there? Please feel free to


Alex Brogan: very kind. Read a fine. Yeah, that's, that's awesome.


Lucy Wark: Yeah. Awesome. So you started out in. Banking, you went into growth marketing and then into sales and then into being a LinkedIn creator. A lot of awesome transitions there.




What ingredients like skills or attitudes have been most important early on in your career?


Alex Brogan: Yeah, it's a really great question. I think in a traditional career perspective, something I observed very quickly at Goldman was the sort of concept of imposter syndrome, which I'm sure we'll touch on a little bit more in this conversation, but I think A large manifestation of imposter syndrome ends up being a reluctance to ask questions that help you do your job in a better way.


And it's somewhat paradoxical that the, the smartest people often are the ones who ask the least questions because they think that they very much have to have it all figured out. And so I think Realizing early on that asking questions actually is a very positive thing that shows you're thinking about the work actively and understanding what the instructions that you've been given is, is really something that Is so productive yet.


I feel far too underused. And so I'd say that that that's a big one. I think a second one is actually communication and the concept of that being a very large part of the job, i. e. how you communicate, how quickly you communicate is important. Fundamental to a lot of the work that you do and also managing sort of expectations of the people around you.


And I think far too often there's a tendency to not see that as part of the job and sort of entertain more. Not sloppy, but yeah, sort of lazy communication practices, which ultimately is, is something to avoid in my view. So I think those, those two things, I certainly didn't crack them early on in my career, but I learned, I learned pretty quickly that those are going to be very useful and yeah.


Try and try and use them a lot this day and the non traditional side I suspect we'll, we'll dive into a little bit more, but ultimately I think the learning piece and sort of believing that you're able to learn anything with, with the right application is, is what that sort of pathway boils down to in a lot of ways.

So, awesome.


Lucy Wark: Yeah, I think that that's fantastic. I also, I really resonate with the communication one there. And one thing that it just brings up for me is something that we see a lot in negotiation. So I teach negotiation as well, and like one of the things that we see a lot there is either people not thinking consciously about communication or coming even with a perception that to think consciously about how you communicate is somehow manipulative or inauthentic.


And I think it's really valuable to reframe that and actually be like, this is a skill and a muscle, like the way that you show up. Should be deliberate that doesn't translate to inauthentic and managing it as actively as you would manage anything that matters in your role makes sense. Like I, that to me is like a really useful shift in what you're saying there. So I love that.




What's the biggest career transition you've made? What helped you take that step?


Alex Brogan: Yeah, so definitely leaving. I think, yeah, I think it, In many ways, it was the hardest decision I've ever made, but also the easiest. And I'll unpack that. What I mean by that specifically is Goldman for me, it was definitely a mimetic choice in the sense that during university, I looked at what sort of the smartest people were doing to get the most optionality.


And. It felt like a very safe option in, in many senses, but I quickly realized that, you know, being in that environment was not going to be for me and I felt a large part of my sort of personality and being actually subverted in, in that, in that environment, which, which we can get into to further, I'm sure, but in essence, I realized pretty quickly that even more quickly than I thought I would realize that that wasn't going to be the environment that I wanted to stay in.


And so there was a large amount of sunk cost fallacy and, you know, ego sort of attached to this role of going to Goldman Sachs and being like the youngest graduate and, and so on and so forth. And that was hard to step away from in many ways. But at the same time, the way that I rationalized it and the way that I Made it feel a lot easier was actually just some very simple frameworks Which I'd love to share and one of those being this concept of fear setting I think in general in modern society there's a tendency to far overestimate the scope of risks that exist and This is like a really ingrained behavior from an evolutionary perspective.


We're hardwired to be very aware of the risks in the environment and respond to those risks such that we can survive. It turns out that the suite of risks in modern society, certainly a first world country as well, in, in most cases, the suite of risks is very, very low. And ultimately the. The lowest case sort of scenario, especially after going to university or going to a grad organization is still very, very high.


And so I think. Coming at it from a mindset of even in the worst case scenario, I'm going to be very okay in making this decision. And I've got a full suite of options I can pursue if it doesn't go the way that I intended to go is like a really useful framework. And basically fear setting is predicting in advance what those worst case scenarios are and coming up with ways that you can prevent or mitigate those worst case scenarios from Coming to fruition.


And in my case, that was just getting really cognizant that even if I left Goldman Sachs and it didn't work out for whatever reason that I could probably go and get another, another job in the investment bank, like very, very quickly. And therefore I'd be in the same spot as I was before. And so in reality.


The upside was infinite and the downside was very, very little. It was an asymmetric type opportunity to pursue. So that was one, one where I rationalized that. I think the other two big things were just regret minimization and thinking in thinking in decades rather than than years, ultimately it was a very uncomfortable decision to make in.


The short term, but knowing on a 10, 15, 20 year time horizon that it was going to be something I looked back on and said, that was a good decision because you weren't actually passionate about it. And actually being passionate about what you're doing is very important to longterm success because that allows you to put more curiosity and energy into the work and ultimately have more material success in the end.


So that was the way that the way that I rationalized it. I think it was, I think it was quite effective. But yeah, still, still very much playing out. And yeah, it was it was hard and easy in those ways.


Lucy Wark: ... So I think just to just to catch up folks who might have missed like a final bit there. On the recording you were saying like Using a regret minimization framework, thinking in decades and sort of reflecting from that perspective instead of thinking short term.


So I think we pretty much caught it, but anything you want to add, just to make sure it's reserved for history, preserved for history,


Alex Brogan: I think it's well implanted. But, yeah, I think with these decisions, it's so important to just zoom out as much as possible and consider that the weight of, you know, Regret when you're older is often so much heavier to bear than the short term cost of making the hard decision to step in the direction of something that is going to be far better for you.


And I think it's, it's ultimately really hard to do that and to build the courage to do that when you're on a traditional path. But. I would say, seek out people who have done it before, speak to them, understand the steps that they've taken, and, and, and ultimately mitigate your risk in doing so, so that it does become that asymmetric scenario where if it works out, great, you're off to the races, if it doesn't, you're still in the same spot, and then there's, there's nothing to lose.


Lucy Wark: Yeah. Awesome. And I was just reflecting that I think particularly for people who are contemplating like a career change, that step of diversifying your social circle or diversifying your peer set that you're comparing yourself to, or diversifying your role model set is so powerful because so often What you don't have visibility over is that you might be in like a triangle shaped organization where everyone at the levels above you has made Like has opted into the decision to stay and so what you see as the world is actually like People who have continued to opt into that decision for their own reasons and there's this entire world of people who have gone off and done other work who you're probably not getting exposure to


Alex Brogan: Such a good point Lucy and to to add into that like jumping out for the first time was extremely lonely to be honest Because We didn't have that sort of inbuilt community that you can tap into and ultimately people that really understood.


You and what you wanted to do. And so, yeah, that's, that's been absolutely massive and such an accelerant just finding that, that community. It's really good point.


Lucy Wark: Yeah, definitely. And sometimes it can even be parasocial community as well. Like I think finding people who. You like, and like listening to on the internet can be so valuable. And finding them in real life is great as well.




What are your favourite career frameworks? Obviously you've shared a few there, but any others that you want to add? 


Alex Brogan: Yeah. If anyone hasn't noticed by now, I do like my frameworks, but yes, there's three, I've whittled it down to three.


And I think those are explore and exploit, seeing your career as a product, and as far as Explore as Exploit goes, I think what's crazy to me is that so many people will make their decision on what they want to be doing with their life when they're 17 years old. If you think of a career or your life in general as a sort of, you know video game almost.


It's a, it's a map. And when you're 17 years old, you probably only explored 5 percent or 10 percent of that map. And it turns out that the decisions you can make get better and better with more information the more information that you have. And so, I think seeing the, coming at it from the perspective of the first decision I made on what I wanted to do may well not be right.


And it's up to me to actually keep exploring until I've found something that I am confident Is the thing that I can work on for a long period of time in the future. Ultimately, that's sort of the explore phase of getting as much information as possible. And sometimes that means a very how to describe it.


Zigzag pathway of trying different things, but. That time spent at the front of your career is so valuable in the back half of your career, which really, in many senses, kind of only starts when you're, in my view, 30 years old, when you can really, like, get into your career and, and, and focus on the job. the exploit phase, which isn't the greatest terminology, but that is to say that you can use all of the information you've gathered and the skills that you've gathered to go deep on, on one opportunity.


And so I think that for me was, was really helpful in, in rationalizing the decision to sample from disparate areas and really understand what, what I was going to enjoy the most. I think the second one, which I've come to Believe in more and more as probably the, in general prescriptions on something I love, but if there was one prescription for how to not go wrong in building a career, I think that is to think of building a career as building a product and that product has.


Five to six key components, that being skills, knowledge, personal relationships, capital, and your brand. And ultimately those coexist and they interact with each other. Focusing on All elements of those is important. I think skills and knowledge tend to come first and will reinforce or allow you to get more of the other elements being personal relationships or capital and brand as well.


Those things are really built on having some knowledge and having some skills that people will come to you for that you can share with the world and that you can provide value with. So. All of these are fundamentally really important. I think the great thing about them as well is that they compound. So the earlier you start building them, and the more you focus on each of them, they just keep compounding, and they're compounding and reinforcing each other, and I think it is, it can be a bit of a failure mode to, to not focus on one of those sort of elements of the product for me, an area that I didn't focus on enough.


And. I think to the point earlier around when I jumped out of of Goldman was actually building personal relationships in a lot of different different areas and building that community and being really intentional about building that community as well. And so that was a bit of a smack in the face moment where where I said.


Wow, I've been doing this sort of nowhere near the level that I should be doing it and I've sort of paid for it. So career is a product. And the last one is just inversion. And that is to say, ultimately, if I fast forward to the very end, what do I, what do I want my career to look like? Even more important than that, what do I want my life to look like and how can I build a career such that it serves that end purpose of living the life that I want?


Lucy Wark: Awesome. Yeah. I actually often think about the career life intersection as rather than like work life balance or something, a concept like that. One I really love is like, people have different relationships to their career, all of which are totally legitimate. Like, and one of those relationships is like, fulfill me.


And you're like, you're looking for identity and self expression and like deep connection, emotional connection, period. One is like fund me where you're like, I just want this to like help. with the rest of my life. And the other one is like fit around me, which is like, I actually like, I have a series of other priorities that I want to do.


Like I need it to like balance or fit with those. But being able to kind of first define like where you want the role you want paid work to play in your life and can be really useful. Cause I think our generation, if anything, Probably imbibes the view or millennials imbibed the view that your career should be self expressive of your values and should say something about you.


And you should like love your career. And Gen Z have probably gone the other way with like snail girl trends and quiet quitting and sort of almost like anti capitalist reactions to paid work. And so it's, it's really interesting to just be like, Potentially this is more a matter of choice than dogma around how you should relate to your career.


Hey, I'm also conscious of time because you have really good answers. Do you have more time to keep going? I'll stop adding my builds onto the Alex show.


Alex Brogan: Super insightful and things that, yeah. A very worth hearing. So, okay,


Lucy Wark: I'll do a quick build failure modes that you've observed that lead to regret. Everyone's got them. Everyone's got them.


Alex Brogan: Oh, yeah. Oh, yeah I mean for me for me the ones that i've observed that were most relevant to me I think two two brackets. One is ego traps and The ego trap the ego traps that i've observed I really come as a result of I think youth and ultimately The path of psychological development that occurs from childhood to teen to later years.


And there's sort of three aspects to this which I tend to see in the areas that I've been in. There's a mimetic desire, this hill climbing analogy, and the spotlight. And these are all actually, when you boil it down related to ego, mimetic desire is related to ego in the sense that we make mimetic choices because if we do go wrong on that path, we have a very easy out by saying, that's what everyone else was doing.


And so you avoid a situation where you're putting your ego on the chopping block, so to speak. And I think. As I did, I made a decision to go to Goldman Sachs, which was in hindsight, a mimetic choice. And actually leaving Goldman was the first non mimetic choice I had probably made in my entire life. And, and that is in part I think the maturity aspect in part I'm sure other things, but fundamentally I think revisiting why you made the decisions that you made in the first place is so, so important.


The second one, which I really grappled with when I left Goldman was, and actually soon after leaving Goldman was. My ego really struggled for like six months of I'm no longer working at Goldman and this is this is quite hard I don't have I was in status limbo in the sense that I couldn't attach my name to anything that I was so used to Attaching my name to and in school and university and into the first job as well.


We always have a status We have the status of Being a high school student and then the university student and then a worker at Goldman Sachs or whatever organization that you have. And to me, this actually manifested when I was making my decision on, on what to do next, deep down, I knew that I wanted to go into startups to be an operator.


That's where I saw myself going. That was my intuition, but the sort of lure of venture capital became very, very enticing after jumping out and sort of saying, Hmm, this is harder than I thought. It's taking more time than I thought. Maybe I could just go to venture capital and that would feel better. And, and the analogy that I'm talking about here is is hill climbing, which is essentially saying there's a local maximum.


And a global maximum. And you can think of them as two different hills. And when I was at Goldman, I was on top of this hill over here, but it turns out that that hill was actually the lower hill of the two in the valley. And there was this alluring hill in the middle, which was venture capital, which I could have sort of stepped down and or even caught a bridge across to, to that here in the middle.


But it turned out that I actually had to. And this is still playing out by the way, but I had to go right to the bottom, make the long walk to like the bottom of the hill, this big hill over here, hopefully, and, and start walking up and yeah, that, that sort of manifested for me in starting an entry level sales role, a, a startup called, called Zipline, like, like, I don't know who does that.


It was like hard. In many ways, but I'm also extremely thankful for it because now I feel confident in that domain. I built a skill set that I know is useful in the domain that I'm in now. And how I see this very often is actually folks sort of coming from the McKinsey's, Goldman's, et cetera, looking for roles in startups and thinking about, Oh, I can go into a chief of staff role, or I can go into a strategy role.


Fundamentally, when you think about a startup. As in sort of Maslow's hierarchy, you have the sort of self actualization phase at the very top is like strategy or in some respects, chief of staff, I think chief of staff is very different because you can get very good operational experience. But at the bottom of the period is actual product sales, marketing, the real foundations.


And I think just realizing that, like once you've made the decision. Once you realize you're not in the domain that you want to be, don't try and shortcut the steps to not building the relevant skills in that domain and really focus on that. I think the last one is not to go too much on. No, no, no,


 The spotlight, the spotlight effect. And I think this is another manifestation of ego in the sense that when we're younger, we think the world revolves around us and we think that everyone is thinking of us when we're making these decisions. And I found from from my perspective, that was something that made it very hard to.


Make the decision of going and doing something non traditional. I, what will they think of me? What will I look like? I'll look dumb if this doesn't turn out, but it turns out no one's actually thinking about you anyway. They're actually just doing their own thing. So if that's the case,


Lucy Wark: Can't begin to express how much they don't fucking care. Right?


Alex Brogan: Yeah. It's so fundamental. I think that the last thing I'll say on this list before I wrap up is this other bracket, which is just. I am a big believer in general. And I think it was another way that I rationalized the decision. The decisions that I made was the precedent that you set early on for the types of decisions that you will make is the precedent that you will take with you for the rest of your career.


In other words, the. Chains of habit are too light to be felt until they're too strong to be broken And I think as it relates to Korea if you do settle for something that you know in your heart Isn't going to help you self actualize The longer you leave that The more likely you are to probably stay in that mode for the rest of your career.


And so I think being very clear on the precedent and the standard that you will set for yourself on on what you'll accept is important. At least it was it was for me.


Lucy Wark: Oh, I I would underline everything you just said. And a couple of things that might also be useful as just actual builds, I said, I wasn't going to do it, but I'm going to do it.


Was if anyone wants to look up mimetic desire look up Renee Gerard or Luke Burgess's recent book. So Gerard would be the very original and Luke Burgess is like the. more approachable way into it, but essentially the idea that we make decisions because other people value things rather than because we value them.


And I was going to say like, I think that that idea of yourself as a person product that you were talking about earlier and even I think coming into the loss of identity that comes with leaving like a high status employer or a perceived high status employer really resonates and It reminded me of a really helpful concept that I Heard first from Jessie Wu.


I'm not sure if it's someone else's originally. But the concept of owned and borrowed career capital and so the notion of like A lot of the time we make the mistake of building our careers within employers where essentially we are, we are like building relationships and credibility upwards.


But we don't think at all about like horizontally or externally building career capital. And so we actually can't take like, yes, you can take that credential with you, but you actually can't take very much of that with you. And the idea of being able to build. An audience or more of a brand that you're known for or more resources or more opportunity flow for yourself that comes from a more well balanced set of things, I think is really powerful.


She speaks about this better than I do. But a great concept to actually go and like dive into a little bit more, like owned, portable, monetizable. Yeah,


Alex Brogan: I love that Lucy. There's actually, it reminds me of a really good article by Paul Graham, one of many. That's sweet. The linear and it actually speaks about


Lucy Wark: links at the bottom of this.


Alex Brogan: Oh yeah, it's going to be great. It speaks about this concept of in the past. The way that people exactly this, the way that people would get credibility was through organizations, but now with the cost and accessibility to things like personal media, you can actually earn your own credibility and you can do it quite quickly if you're willing to, and I think that separation is, is very much going to be a theme of, yeah, the next 50 years.


And so it's so worth thinking about.


Lucy Wark: Yeah. And I think a lot of people like, for example, view somewhere like LinkedIn as a tax. It's like, this is a tax I have to pay to be part of the modern workforce and view it very defensively as like, I guess I have to update, or I guess I have to go on here when I get a job, as opposed to, I think, viewing it more proactively or as a place where you can like build opportunity flow for yourself.


And I suspect that that shift is, it's already, like, I think we're already starting to see the beginning of it. But I suspect that shift is going to be quite profound, particularly as people get more confident with the notion of being micro creators on that platform in their own right as well. And finding like a way that they're comfortable speaking publicly too.


Yeah, so that should be super interesting.



This interview transcript has been edited for length and clarity.



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