The Iteration Point
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The Iteration Point
Portfolio Careers and AI: How to Stay Relevant When Everything Changes
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Shara Karasic has been working on the internet since the 1990s, back when you could learn HTML in a week and there were only 20 websites to look at. Today, she has what she calls a portfolio career - working on about five different things at once, from advising a Gen Z fintech startup in Ghana to running an AI education company for non-technical people.
In this conversation, Shara talks about why portfolio careers might be the future of work, the opportunity cost of being in a corporate job that doesn't let you learn AI, and why taste is becoming one of the most important career assets. We discuss how algorithms are making everything look the same, why the ability to synthesize across domains matters more than deep expertise in one thing, and why being scrappy and adaptable might be the best survival strategy in a world where AI can rebuild your business model in three days.
Whether you're feeling stuck in a traditional career path, curious about AI but don't know where to start, or just trying to figure out how to stay relevant when the rate of change keeps accelerating, this conversation will give you a different way to think about building a career that can flex with constant change.
Connect with Shara:
- Substack: https://sharakarasic.substack.com/
Welcome to the Iteration Point. I'm Michael Atkins. There's an idea that career success means climbing a ladder, working at one company and moving up over time. But what if the future of work looks completely different? What if the most resilient career isn't a ladder at all, but a portfolio? My guest today is Sarah Karasek. She's been working on the internet since the 90s. She's built a portfolio career, doing about five different things at once, each one enriching the others. Through her career, she's seen a lot of changes, and now she's watching AI reshape everything again. A piece of advice she offers, if you're in a corporate job that doesn't let you learn AI, there's an opportunity cost, and you may be falling behind. In this conversation, we talk about why taste is becoming one of the most important career skills, why algorithms are making everything look the same, and why the ability to synthesize across domains might matter more than the deep expertise in any single thing. This is a conversation about adaptation, about building a career that conflicts with constant change, and about why being scrappy might be the best survival strategy we've got. Let's jump in. And Shara, if you could introduce yourself to the audience, I'm uh excited to talk to you.
SPEAKER_00Great. I'm Shara Karasik. I've been working on the internet since actually the 90s. So I have a very broad view of it. And I I would say I definitely have a portfolio career now. The one through line that integrates everything is kind of translating technology and culture and connecting people. But I'm working on a variety of things in the past few years.
SPEAKER_01Yeah. So when you say a portfolio career, that's really what do you mean by that? What's a what's a portfolio career mean to you?
SPEAKER_00So it literally means that um I'm doing about five different things.
SPEAKER_01Yeah.
SPEAKER_00And at first I I was kind of, you know, just doing what was easy and in front of me and was an obvious fit for me. But now I look at it like each thing I'm doing really enriches the other. So for example, I advise startups in Ghana. So I'm working with a startup called EXO, which is an AI financial assistant. So, you know, getting very deep into Gen Z culture in Africa and then also AI, and you know, have tested out chatbots and creating my own chatbot. I I taught myself dialogue flow, et cetera. Um, and then in the in the last few months, started a company for AI education for non-technical people. Okay, so we are having a workshop next week. And so all of the AI learning I did for the startup is is playing into that. And now I'm taking some of my new learnings with vibe coding and all that back into the startup and my work with our new CTO. So it's very interesting how it plays into each other.
SPEAKER_01Right. So you so instead of like one specific defined role at a company, you're leveraging your knowledge and expertise and learnings as you're working through with these new technologies and applying them in various ways, right, to the next problem that you're seeing or the next opportunity. How's that how's that working out in terms of your satisfaction, your compensation? How is that all kind of tied together compared to what many people would consider standard job where you just go to your job and you do your job and you know go home at the end of the day? Compare, contrast that for me a little bit.
SPEAKER_00So I honestly feel that for me it's a much better personality fit to work on more than one thing. Honestly, get bored working on just one thing, but also I'm a synthesizer. I have that kind of personality where I'm always naturally working across domains and in some corporate environments that's discouraged, or you're stepping on someone else's territory. And I always like to look at the big picture. So with a portfolio career, I can not only apply learnings from different domains, um I can work on different things that um I feel like they all play into each other and and help each other. And in fact, I I mean, the way I got into the internet in the whole in the first place was I was traveling, I wasn't sure what I wanted to do. So I would do temp jobs in San Francisco and I worked for a tax attorney who was kind of an early internet person, and he would bring me into his office and show me Netscape, and we look at the 20 sites that were up. And so he wanted to do one of the first attorney websites. So I helped him with it. And I wrote a tax fairy tale for his website and drew a picture of a um a tax profit. And he had some guys do the HTML, and then he handed me some instructions for HTML, and he said, You should learn this, you'll make more money. And I looked at, I bought a book, Learn HTML in a week. And then I did. And then my next job was for the first kids site called Cyber Kids. And so being open and looking at different opportunities and open to learning got me into this in the first place.
SPEAKER_01Yeah. Now it seems like that the economy is shifting in such a dramatic way that maybe we're gonna see a lot more people having to be scrappy, right? Like you have to try and do new things and reinvent yourself a little bit, learn the new technologies, right? With AI. Like, what can we do as an individual to bring more value to the world around us, create new tools, whatever it is, right? Like see a need, go make that tool. And it seems like that's kind of a aspect of having a portfolio career that maybe really will resonate with people.
SPEAKER_00Yes. And I mean, I have to mention that uh I forget where I read this recently, but there's an opportunity cost now to being in a corporate job that doesn't let you learn AI. You know, for the last six months or so, I've been diving into various AI tools, cursor and cloud code, looking into open claw. And yeah, it takes some time to kind of figure out all of the tools and the landscape. Um, the tools for promoting your business, doing websites, GEO. I mean, there's just a lot of learning. And so anyone who's not doing that now is going to be behind. So it's kind of risky to have certain full-time jobs if if they're not the right one. I could see that.
SPEAKER_01Yeah. That's similar to you. I've been working on Cloud Code as the avenue for app creation and doing some vod coding myself. That's uh that's a really good point, though. And we've both been in the situation where you're working for the corporate organization and you're putting everything into it. And at the end of the day, the last thing you want to do is spend another couple hours looking at a screen and your brain is already wiped out because you've put all of your mental energy into fixing other people's problems, right? Are useful and I can be really passionate about the problems that I'm solving at my job too. But that doesn't, it's a just an opportunity cost to do this stuff that uh wouldn't otherwise have the time and capacity for.
SPEAKER_00Yeah, no, I I remember having a 6 a.m. meeting that was to prep for a 7 a.m. meeting two days from that 6 a.m. meeting. And yeah, so my brain would be fried at the end of the day. I wanted to write my memoir and all this, and I couldn't do it. And so I also think an important thing about a portfolio career and having creative interests is um the idea of taste. So Paul Graham and others, there's a whole article in the New Yorker about how taste is becoming one of the most important aspects of a career because AI can do everything else, basically.
SPEAKER_01Yeah.
SPEAKER_00You can't cultivate a taste by following an algorithm. I don't I don't know if you've read the book Filter World, but but it talks about how all our tastes are getting really narrowed through algorithms. And so if you look on Instagram, pictures of cafes all around the world now kind of look the same. They have a white wall and they have plants and a a wooden counter, which is nice, but they all look the same.
SPEAKER_01It's fine, right? It's it's it's the same thing with like the millennial gray housing stock that, you know, if I go to open houses around town, yeah, all the houses that they were building were in gray tones. And it's fine, but it's boring, right? Like there's no individuality there. And I think that what is what you're saying, right? Is that there's that narrowing that's that is happening because the algorithms are bringing certain images and certain fashions essentially into the spotlight, and it's ignoring all the other stuff that's out there that's actually probably more interesting.
SPEAKER_00Right, right. And and having a portfolio career and a portfolio life, because not all of the pieces are career.
SPEAKER_01Yeah, yeah.
SPEAKER_00I feel like helps to improve taste. So time spent going to museums, reading, reading real books, knowing history, recognizing patterns, and not just following whatever's on Instagram or TikTok, but developing your own taste through an active life and and doing a lot of different things, understanding different cultures and cultural differences, et cetera.
SPEAKER_01Yeah, it's a renaissance approach to living, right? Like being that artist that was also the inventor and scientist and the author and all those, all those kind of various skills that make us well-rounded human beings. It's pretty myopic without that, right? If you're if you're very focused on your little sphere and you block out the stuff that's outside of that, better or for worse, that reinforcement of those that that bubble, right, does not broaden our thinking. It doesn't broaden our horizons. Yes, yes, it doesn't get you out in the world and experience different cultures and understand that the uniqueness that exists and also that we're all people, right? And there's a commonality that you don't necessarily get that way.
SPEAKER_00Yes. And since you brought that up, so one of the things I do as part of my portfolio career is digital strategy for a nonprofit called Tomorrow's Women. And they bring together Palestinian and Israeli young women to meet each other, learn leadership skills, learn each other's stories. And I wouldn't have been able to do that if I still had a full-time job. And so one of the things that's wonderful is being able to add meaning to your life besides just making money. I mean, after a benefit we had in in Santa Fe in September, the young women were all in the kitchen, kind of uh cleaning up, putting food away, and then they were blasting music from their various cultures and dancing together. And I videoed their feet because a lot of them had to be kind of private about what they were doing. Sure. But it gives you hope when you you realize there are pockets of people who are trying to connect across all of this to vision.
SPEAKER_01I agree. I love that. That's that's so powerful because if yeah, if you're just looking at a bunch of feet dancing, right? It's that's great because everybody's just having a great time and connecting, and we have more in common than we have in terms of differences, right? Wow, that's really cool. So are you organizing events throughout the US? Is it a global kind of coming together? How does what does that look like?
SPEAKER_00So traditionally for the last 23 years, there were camps in Santa Fe, New Mexico, because that was just such a separate place. It kind of put people into a different mind state. But now it's super hard to get visas to the US. So we've now been having events in Switzerland, which is kind of perfect, right?
SPEAKER_01It's neutral. The neutral territory.
SPEAKER_00And then next year there's going to be an event in Northern Ireland, actually, with experienced peacemakers in Northern Ireland leading workshops. Because I mean they figured it out. So uh it's a hard problem.
SPEAKER_01Yeah, no, but that's fantastic. I mean, it's that's just I think that's great. So you're you're involved in a lot of things, right, as part of this with your portfolio career. Walk walk me through some more. I'm I'm super fascinated by this.
SPEAKER_00What else I've done in the last three years or what I'm doing today.
SPEAKER_01Sure, whatever you want to talk about. I mean, it sounds like you've got a lot of irons in the fire, right?
SPEAKER_00Sure, great. Well, I'm involved in a startup, uh a financial AI financial assistant startup uh based in West Africa. So that's targeting Gen Z in Ghana. I was a technology volunteer in Ghana in 2001. I have had a very married life. So so that's very interesting. We just hired a CTO who used to work at Wikipedia and she lives in Ghana. And you know, I'm very happy that we have a female CTO. So we're we're building our MVP right now. That's exciting. And then, you know, I'm living in Los Angeles while working remotely, obviously, for them. And I also just started idea toaudience.com, which is AI training for non-technical people. So uh we're doing a workshop at Blank Spaces in Venice, California on Saturday.
SPEAKER_01Oh, so an in-person workshop for people to sign up for?
SPEAKER_00Yes, a class for people to sign up for. And, you know, it's really interesting to take this mountain of content about AI and you know, kind of figure out for people what are the tools that you should learn or you need to use. That's been quite a project. So I'm really excited about that because I feel like that plays into everything else I've done. You know, I love educating people.
SPEAKER_01Yeah. So there's a very community-minded approach to an in-person workshop like that, right? Where these are people that are in your local community. I love having that option of an in-person place to come and connect with real humans because it's a different kind of learning that you do when you're surrounded by other people and collaboration that can happen when that all comes together.
SPEAKER_00Yeah, yeah. I I I love it too. I taught kids how to code for years in LA, Coder Dojo, Los Angeles. So now teaching adults, it's a little easier in some ways and harder in other ways. Yeah. And then we'll create an online version. I also outsourcing like everyone else, have a team of great developers in Ghana and Nigeria. You know, if if if we need to build out AI workflows for people. So so that was an example of my life coming together, this experience in Africa.
SPEAKER_01Yeah.
SPEAKER_00And now working on AI education and consulting. And then I have a team of really talented people in in Ghana and Nigeria, which is great.
SPEAKER_01That's awesome. Wow. That's that's really cool.
SPEAKER_00And then one other thing that I I mean I might as well talk about. So I try to connect everything in my Substack, which is called all over the place.
SPEAKER_01Okay. That sounds uh very appropriately named. No, I think that's exactly.
SPEAKER_00So it's SharaKarazic.substack.com. So I try to connect all the things I'm doing and write about some of my insights on that substack. Cool.
SPEAKER_01I love that. That's great. Well, you've got uh oodles of talent for for one. I know that firsthand. And having the uh kind of broad reach, I think, that you're aiming for and being able to have lets you have a big impact and and not being so closed-minded and I would say kind of hyper focused on one thing lets you make those connections to be able to learn from new technology or a connection that you're making in one area. So your education background, right? Teaching kids to code led to being able to do workshops in AI, right? It's all built on our our past, our history, our experiences.
SPEAKER_00Yeah, and and I was an English major, which now apparently is wonderful for the age of AI, right? You can write good prompts.
SPEAKER_01Yeah, I like that. So, what your experience with AI, what advice would you give to people that because it's still new enough, there's people out there that are maybe have been resistant to getting into it at this point. What how would you overcome their objections? How would you suggest someone get started if they're curious?
SPEAKER_00I would say pick one of the LLMs and um use it consistently. For example, even with ChatGPT, once it knew more about all the projects I was working on, it became really good at helping me organize my day and prioritizing my day and creating systems. Um, it became much more helpful over time. It was not that helpful for me originally, but I felt like, well, I have to learn it, so I have to keep using it. And now it's really genius because it will see patterns that even I haven't seen yet. So that is really interesting. But then I would also look at what you're already doing and how AI can enhance that. So, for example, with podcasting, the script has AI built into it called Underlord. And you could take a half-hour clip and you could say, pull out the best clips for social, and it will do a pretty good job of that. I mean, you have to kind of look at what it's done. So look at the AI plugins to your existing tools and learn those. And then don't be scared of vibe coding. You know, lovable tends to be the easiest platform for people who aren't technical. You might not build a startup, a monetizable startup right away, but try making a little game, you know, or or something just to realize that you have the power to do this.
SPEAKER_01I've been toying with it as well. And what I've noticed is you don't have to let the technology scare you away from developing an idea. And because I've done scripting and worked in different languages through my career, but I'm not a software developer per se, right? Building a whole application and the whole stack of technology that you need in order to run the application is very complicated. Yes. So the AI coding, vibe coding revolution that we're seeing, I think, is simplifying that so you can get your creative vision to a point where you're at least prototyping it.
SPEAKER_00Yes.
SPEAKER_01Right. And then at the point where you have something in your hands where you can play with it, that's when it's really exciting, right? And you could potentially then go get investment to go build it out and scale it up and make it into something more market-based at that point.
SPEAKER_00Yeah. And one suggestion that my son, who's getting his master's in computer science right now at Johns Hopkins, he he said to me when I was talking about vibe coding an MVP for EXO, and he said, Mom, start with Figma Make. So I went into Figma Make, and I'm telling you, less than 10 minutes, I had a wonderful mobile prototype that looks really good. So I can show investors or people at a conference, I can quickly show them that before we have our actual MVP. Right. But the great the hardest thing was to actually figure out how to import our logo. It was some somehow weirdly complicated, but everything else was amazing. And people see it, they they kind of understand our concept. And the other thing I would suggest people to try who aren't that technical, Claude and ChatGPT, they connect to your Gmail. And I mean, the privacy thing's a little weird, but it's so helpful. I mean, I will say to Claude, um, I I tagged a bunch of vibe coding posts I found on Twitter that I didn't have time to read. And I emailed them to myself and I labeled them vibe coding. And then I just asked Claude to read them all, summarize what were the top tools mentioned, what were the main points. So that saved me a ton of time. But you, you know, there are a variety of ways you you can get help with your email through those tools now without building anything.
SPEAKER_01Yeah. I think it's still in its infancy in a lot of ways in terms of how is this going to be useful? I think we're just scratching the surface and trying to understand how to make it more useful and leverage that. I think there's a lot of potential for good. I'd like to get your perspective on what this might do to that could potentially be negative, some negative implications. We're certainly seeing a lot of layoffs, and part of that's attributed to AI. I think that probably some of these companies will regret, regret letting go such a large portion of their workforce.
SPEAKER_00That's one really obviously negative effect. And for someone like me who's seen a lot of these cycles and been in the industry for a long time, then I feel like, okay, well, then I have to become an expert and hold the reins instead of just being swept away by it. I have to be one of those people who does a lot of different things so I can cultivate taste and discretion to create really good AI products. What's going to happen is they're going to be a ton of generic products, right? I mean, I already could see a versal website, you know, that just looks a certain way. Some of the LinkedIn posts I see are just so obviously written by ChatGPT.
SPEAKER_01Agree completely. They'll have the same format. They all they're very easy to spot at this point.
SPEAKER_00Exactly. Um, so so that that and then privacy obviously is an issue in people dumping their whole life into these systems and not really worrying or thinking about that. And then also I worry about younger people and their learning because they can just so easily find out stuff or get stuff done by Chat GPT. And at least at our age, we've already learned the stuff. So it's helping us add on to that. So I do worry about the thinking of young people.
SPEAKER_01Critical thinking skills, right? You develop those by being out in the world.
SPEAKER_00But that being said, I mean, the the time AI saves. So, for example, in my vibe coding project that I did recently, there was literally an extra bracket. And and that was the kind of stuff that I hated about programming. It just seemed like such a waste of time for me. So the fact that now AI can QA itself and find the missing bracket. Human doesn't have to do that. I mean, that's really freeing.
SPEAKER_01It's true. Yeah, you're right. Because I've been in those situations as well. And it'll take you an hour combing through the code, looking for the outliers and trying to understand where you went wrong.
SPEAKER_00I was just checking out this book, Flux, by April Rin. She lives in Portland. But she talks basically about how change is inevitable and we all need to have portfolio careers, you know, and just sort of be in the forefront of change instead of letting it gobsmack us. I mean, I think in general, those of us who understand the overarching concepts, you know, the details are going to keep changing. But if we understand more of the systems and how things can be architected and the connections between things, then we'll stay at the forefront rather than focusing on one little thing. My brother is a a CPO, and you know, he said some of his engineers are embracing the new technologies, and then others are really attached to their, you know, 15 years of knowledge uh of how to code and code the exact way they they want, but they're gonna be swept away, honestly. Yeah. You know, if if if you're too attached to any one way of doing things as opposed to learning the concepts.
SPEAKER_01Having that having a flexible approach to learning and to your job will probably suit you well as this pace of change continues to evolve, I think. It's an interesting world we're living in for sure. And I appreciate you coming on and taking some time to chat and just, you know, catching up a little bit. It's been great.
SPEAKER_00It's wonderful. Thank you, Michael. This has been great.
SPEAKER_01Share is working on several things right now, and the best way to connect with her is through her Substack at sharecarassic.substack.com. That's sort of her central hub. One thing Shara said that really resonated. Paul Graham and others have written about how taste is becoming one of the most important career assets because AI can do everything else, but you can't cultivate taste by following an algorithm. The abilities to synthesize across different domains, to see connections that others miss, to develop genuine taste rather than algorithmic taste, these might be the things that keep us relevant as AI handles more and more of the technical work. Sarah also mentioned a book called Flux by April Rin about how change is inevitable and we all need portfolio careers. We need to be at the forefront of change rather than letting it dobsmack us. I think that's a good note to end on. Thanks for listening to The Iteration Point. New episodes drop every Tuesday. If this conversation made you think differently about your career, it follow and share it with someone who's trying to figure out what comes next in an AI powered world. If you've built your own portfolio career where you're thinking about it, visit the iterationpoint.com. I want to hear your story. I'm Michael Atkins. See you next time.