Career Advice: Kara Answers Listeners’ Questions

21:39I love when people go back to school. I took an accounting course, of all things, at University of Pennsylvania at the Wharton School one year because I wasn't as good as I could be being a reporter and not understanding, you know, spreadsheets. I really wanted to learn about spreadsheets, and I did that. I feel like recently I thought I should go to school again because school is wasted on the young in a lot of ways. So it's great you're doing that. That's the key part. The second part is really doing a lot of research and what's happening around the space and try to get in on a startup of some kind.

22:06There's all kinds of areas. You know, my son is in engineering and climate. There's so much stuff happening and so much interesting innovation to happen, that there's lots of opportunities. So you should sort of target areas you're interested in. I'm very interested in nuclear issues right now and how to create that. And a lot of people are frightened of it, but I think it's really interesting. My son was working on a fusion startup. Now he's working in advanced manufacturing to try to, it's climate focused because it's trying to be more efficient. So there's all kinds of directions you could go, but I would first get this training and then look around and really do some research into startups.

22:42That's where I'd begin and then just get yourself in there. And if that doesn't work, get yourself in somewhere else. Even at 52, you can change jobs. It's, you know, it's not for the young necessarily to do that. I've changed, I recently changed my job again. I keep doing it. I just did a TV show. I didn't know anything about television on a topic I thought was interesting. So I think you could do it at any time in your life. Up next, Victoria Zunich has a question about turning her side job into more of a profession. Hi, Kara. Thanks for doing this. My name is Vicki, and I consider myself a re-emerging journalist.

23:19I have a day job, and what I want to do is work on some investigative-type stories. This is not a get-rich plan, but it is something that I would like to be fairly compensated for. I'm presuming that as I develop the story ideas, I'll be reading other outlets, and I'll get ideas for where I want to pitch them. What else do you think I should be thinking about at this stage? Thank you. Well, you're talking about investigative reporting, which is really hard to do on your own, although people do it. And I often think I'm not an investigative reporter. I've done investigative pieces, but that's not what I do.

23:55I'm so in awe for investigative reporters and what they do. But it's a tough job because, one, you have to be legally protected. You have to have the support of an organization, which very much helps. And it's really a team sport at most newspapers that I've seen. There's this image of a crusading investigative reporter, but they are backed by researchers. They're backed by the organization. I was privy to it when I worked at the Washington Post and also the Wall Street Journal. And it's a real slog. What I do is I try to start smaller, I guess, maybe a smaller investigative process and let it build.

24:29I just had a great interview with Theo Baker, who did that at Stanford, and he managed to get the head of Stanford out of his job because of stuff he'd found. And so I would start small and with story after story after story rather than start big. I used to say to people who work for me, let's not try to boil the ocean today. Let's start with a tiny little thing and a tiny little thing and a tiny little thing. And as you become an expert in the area that you're talking about, and you will over time, then you can really go for the big swings and then find the outlet you think would like it the most.

25:02And sometimes some of the bigger places do take freelance, although mostly it's career people who work there. But good luck. It's a great thing to do. The next question comes from Kara Stevens. She has a question about moving from the public sector to the private sector mid-career. Hi, Kara. I'm Kara from Central Ohio. I've been a school counselor in public education for over 20 years. I spent two decades doing what most companies now will pay consultants six figures to attempt. I've been building trust with resistant stakeholders, teenagers, de-escalating crisis situations in real time, navigating bureaucratic systems while really moving the needle for individuals.

25:57I've chaired nonprofit boards. I've worked with our family court system. I've even founded a grassroots advocacy organization in my own community. So I'm pivoting into the private sector from the public sector. I'm looking for something related to ed tech, public affairs, mediation, instructional design. And the question I keep running into is, how do I make the market see me for what I actually am, which is a seasoned and highly educated professional, and not see me as an entry-level career changer? Wow, it sounds like you have enormous experience, and I would think private sectors would find that valuable.

26:52It sounds like you have a lot of skills, whether it's ed tech, public affairs, mediation, all this stuff. I would begin with the people you've worked with and find out if there are companies that are affiliated with the things you were doing in your public job. Same thing with your nonprofit boards. There's probably people on those boards who have some ideas. The same thing with your family court system. Find out from where you've worked, where there's opportunities, where there's companies that are working on that stuff. Someone with all these kind of skills are very valuable to the private sector.

27:23And one of the things you have to sell yourself on is that you're not a public sector. I mean, people like trash public sector people. I find that ridiculous. I find them to be some of the best workers. And it's such a trope that they're not as good as private sector people. It's just not true. But one of the things that's really important, and it sounds like you have the skill, is an incredible ability to network and understand. And maybe start thinking of people you've worked with that might give you an idea. One of the things I do when I was thinking about leaving places, I talk to everybody.

27:53I talk to everyone. And often it comes from a strange place, a tip or an idea or something that occurs to me. But you've got to follow it up. And unfortunately, when you're making these shifts, you need to be dogged in terms of calling people and calling people and calling people. And you absolutely have to get used to rejection, unfortunately. It's really hard to make a shift. And then once you get in there, it does make it easier. I would suggest maybe starting off doing some consulting because then people don't have to hire you right away, but maybe you could work on contract. And once someone's really good, when you have them on contract, most people want to keep them.

28:28Although, honestly, a lot of people, more people are working on contract permanently because then they get to pick and choose their things. So, again, I would start off much smaller, maybe do a contract here and there, and then prove yourself to people and prove your usefulness. up next bruce hackney has a question about how to market your skills to employers hello kara swisher this is bruce i live in new york city and i'm 62 years old and i've been unemployed for 14 16 months so i decided to do something very un-62 year old which is to ask artificial intelligence to get some idea of a question to ask you.

29:11So the question was, what career advice should a 62-year-old gay man who's been unemployed for 16 months was previously employed as an office operations manager and a freelance project manager for a live events production company as an artist liaison and gallery director at several contemporary art galleries in New York City, and as an unpaged manager of the estate of a dead Swiss gay photographer, ask Kara Swisher. And my artificial intelligence said, what a rich and unconventional career history. And they said, why this works well to ask you is you've been outspoken about ageism in tech and media.

29:54You value people who've built unconventional paths. You don't respond well to self-pity, but you respect directness and self-awareness, and you're likely to give a blunt, useful answer rather than a generic one. So that's my question. I'm 62 years old. I have a genuinely varied career across operations, live events, contemporary art, and I've been out of traditional employment for over a year. How do I reframe what looks like a scattered resume into a compelling narrative, especially when ageism is real and I'm not trying to pretend I'm 40. First of all, stop asking AI questions. All they did was just vomit up me at me.

30:37I just can't stand when people ask AI questions. I know Scott does it all the time, so I apologize. But I think you already know, and you say this at the end, how do you reframe what is a scattered resume? I think the way you reframe it is you're a can-do person. It sounds like if you've been an operations manager, freelance project manager, it means you had to solve problems. And so that's the way I would do it as I'm here to solve your problems. And, you know, especially operationally, I think one of the things where a lot of companies fall down is operationally. And I think that there's a creativity to being operational in a lot of ways.

31:08I think what you have to do is sort of sell yourself as someone who can, you know, wherever you're put, you can fix the problem, create a system, because that isn't really, I do know a lot of people who have a hard time finding very competent people who can do just operations and don't want to do something else, by the way. I think that's another thing you can tell yourself if you're 62, you don't want to run the company, you don't want to do this, you just want to be someone who's going to make things go smoother. And I can tell you a lot of people who have high output careers really value that as a person.

31:41So I would say I wouldn't worry about your age as much as putting the message out that you can get things done. And you can use tech skills and stuff like that. You have those skills. and I hope you get a job.

31:56Kara Swisher:Next, we have a question from Dorothy Novak. She worries about pigeonholing herself in a changing industry. Hi, Kara. I'm seeking career advice. So I work in public media, and as you know, things are really, really rough, really rough right now. And to make it harder, I'm on the TV side instead of I'm not in the radio side. So it kind of feels right now like we're on a sinking ship. And I hate that feeling because I love what I do. I love our mission. I love our supporters. I love it. But I'm in my mid-50s. I'm a single mom. Where do I go from here? Thanks a lot. Bye. I don't think public television is sinking ship.

32:46You've got to stop using the term sinking ship Because public television has been astonishing for people and the kind of output that it's had has been amazing. Again, another area that gets pilloried in ways they don't deserve because of the stuff that public television has given us over the years compared with what it's taken. It's just so much more additive to this world. That said, it's unfortunately been caught in a political vice grip for a long time. This is not a recent thing. And I think in this country, at least, compared to other countries which value public television, although there's stuff happening at the BBC, there's this and that, you know, everywhere across the world, there's been contractions in this area, I'm sorry to say, especially because public television probably didn't act as quickly as it should have with the advent of all manner of different innovative technologies.

33:34And so doing what you're doing, there's going to be fewer people, and there's just no two ways around it. I talk to a lot of these people who run these stations, and as much as they'd like to keep people employed, they're not going to be able to do it on the funding they're getting, especially as the government cuts it down. So it's not a sinking ship. It's an underfunded ship. So I do think it's going to be around. It's just going to be a lot smaller. I hate to say that in this country because we don't value that. I don't know what to do. If you've lived in this, there's other media businesses, but they're contracting too, and that's the issue.

34:05And it is very hard to enter a media business pretty far into your career. I don't know. I think what you should do is try to hold on to your job as long as you can. There's going to be cuts. There's no two ways about it. And then sort of assess what part of your job you like doing the best and what you're the best at. Be honest with yourself on that one. And then try to figure out where you might fit into a production company that makes things or any manner of things you might not have thought of, you might think about podcasting a growing era. Because that's video now, by the way. All podcasts are like, look at me, I have a face for radio.

34:40Public radio, too. And so I think it's really important to try to figure out where you might fit in in maybe the newer things that are growing, like podcasting. But it is tough. There's no two ways about it. And I hope you find something. We'll be back in a minute.

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36:16Kara Swisher:Support for this show comes from Fetch Pet Insurance. Cats are special little creatures. So are dogs. I have both. I love my cats and dogs. And my cat's name right now is Lovely, and she means a lot to me. And she's really quite narcissistic, but I enjoy it. She's been pretty healthy throughout her life, but I've had other cats who have gotten sick at the end. And I do think about what's going to happen in the next years ahead because she could get sick, have a health issue. And with previous pets I've had, the bills that racked up were enormous, and I never got pet insurance. And I think it's really important going forward to do that because these are big surprises.

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38:59A lot of you are sending questions about AI, of course, and how to adapt to its arrival in the workplace. So let's get to some of those. Hi, Kara. My name is Carolyn Champa. I'm a longtime listener and reader. I am a librarian. I'm originally from Minnesota, but right now I work at an overseas military library serving soldiers and their families. I also have a family, six and a four-year-old. We also love K-pop demon hunters. So here's the thing. Career advice. Thanks for doing this. I am a librarian, but I've done cybersecurity work, and I honestly hated it. Hated it. What I love is the human side of information.

39:36I love connecting people to what they need to learn. I love putting books in hands. I love programming. But I'm watching AI reshape everything we're doing, and I feel like I'm in a good place to help bridge it responsibly. So here's the question. Where are the most realistic entry points for someone with both technical experience and a really deep sense of public service? Last thing, if you ever need a personal librarian, I'm available. I love a librarian I have to say librarians have changed my life more than almost anybody teachers and librarians I had a wonderful woman when I was growing up who really helped me I read a lot and was really just guided in beautiful ways by librarians so what a great job I also worked when I worked at the Washington Post I made friends with the archive librarians at the Post where I did pictures and stuff like that I always thought they knew more than any reporter it was always my feeling so I always went to them for questions because I knew they'd know the answer compared to other people.

40:34Information science is really undergoing a change because of AI, but it doesn't mean, like I grew up in the card catalog era where you had to go look for things. So information is changing constantly, but it doesn't abrogate the need for a librarian. And I think it's really important to really hone your AI skills here. And in library science, that's a great thing to want to do because then there's a lot of problems with factual stuff with AI and knowing what's right and what's wrong. And so I do think it requires a human AI interaction there. And I think there's nothing more valuable than that to have those skills.

41:10So you've got to get really good at AI and using it and understanding its flaws and its attributes to be able to guide people. Because I do think there's a big business in helping people understand information better going forward. And the more skills you have in that area, the better. I don't think you're going to be replaced. Those who are going to be replaced don't understand how to use these technologies. I would recommend a movie that I love. It's one of my favorite movies. I think it's called Desk Set with Spencer Tracy and Catherine Hepburn. And it's about this topic, which is kind of funny.

41:43Watch it. It's got a lot of lessons for today. There has to be a marriage between AI and humans in a way that is much more significant for it to be truly useful for us.

42:1018 months old. I think you don't have to do anything but teach her how to play with blocks or if you really want, magnet tiles. I highly recommend them. They're fantastic. I love all kind of things. I know it sounds crazy, but I think your kids have to understand how to problem solve or build things or make things or think creatively. And a lot of the hands-on stuff really helps a lot. It doesn't mean she's going to do hands-on stuff, but it really does create a brain that's a problem solver. So I would not put your kid in front of a computer for a very long time. I don't put my younger kids in front of them.

42:40And actually, one of my kids uses it more than others. But in general, I was very interested in problem solving and the ability to figure things out and to build things. Those are the three things I focus on. And of course, reading. And so I think reading skills are really important. An 18-month-old is too young to do that. But there's all manner of interesting toys that kids could play with. And I think play is, as much as people joke about play being play, it isn't. It's about figuring out how to think. And that's the best thing you can do for your kid is to teach them how to think and to challenge themselves.

43:13Now, my one kid, all he wants to do is play with matchbox cars. But I'm okay with that. He actually creates, you know, I listened to him the other day and he was doing all kinds of role playing with them and the creativity and everything else. And I couldn't help but think this would help him later. My daughter's much more organized. She's already organizing businesses with her dolls and things like that. But again, play is critically important and playing with other kids, eventually 18 months old, usually play side by side and not together. But helping them figure that out. And then, of course, giving them, as they get older, little jobs and skills and things like that.

43:48I make my kids do all manner of things. And to teach them how to work, really, and how to work with others. And then later, you know, introduce the use of AI. It'll be different by the time she gets older, so it'll be much more clear about what skills she needs. But don't shy away from those skills either. Don't be scared of them. And start to use them and understand them, just like you would teach a kid how to use a computer. But don't worry about it for a long, long time.

44:17Hi, Kara. My name is Katie O'Malley, founder and principal coach of Encourage Coaching. And I'm currently at an HR conference here in Orlando, Florida. And everyone is talking about AI and the difference between jobs and roles and skills. And I haven't yet heard anyone make a mention of the J curve that is hitting the labor market. So when a new technology kind of comes into play, whether we're thinking about the printing press or internet or electricity, how long folks are going to be down in that trough before we start seeing gains again. And so my question to you is, How long do you think this disruption is going to last before we actually start seeing AI lead to job gains instead of job losses?

45:15First of all, I don't think we've seen job losses yet. You know, you're starting to sort of see it, but it's not clear yet. And so we don't quite know where this is going to hit precisely. As much as there's been lots of articles about it, the numbers are still very unclear. But it's really clear some jobs, like, you know, you could guess a couple of them, that AI can do better. And you don't quite know what the job gains are going to be doing because you don't know what companies are going to get formed by using this technology. And I think you didn't know that at the beginning of the printing press.

45:45You didn't know that what was going to be disrupted, the Internet. It was very unclear and actually took turns that people didn't quite see, although some of them were obvious. With the beginning of the Internet age, I was there. In the mobile age, I remember looking at a teletype machine. I remember looking at a typewriter. I remember looking at a payphone and understanding these would be replaced. You can start looking around and sort of start to guess at what could happen. I was pretty good at it because I had this basic idea that everything that could be digitized would be digitized. Seems simple, but it wasn't so simple at the time.

46:18And that there were real problems with the business plans of some of the businesses I worked for, like newspapers, when this happened. and it would not just disrupt, it would collapse industries. So one of the things to do is start to pay attention of where it might hit first and be intelligent about that. But I do believe in the end, and I hate to say this because there's going to be a lot of pain between then and now, there will be job gains because of industries we don't know. No one would have thought of Uber way back in the 1990s. They just wouldn't have when I started covering the internet.

46:47They wouldn't have thought of the app economy, which Uber was a part of, or Airbnb, or this and that. And, you know, all those businesses, we always had cabs, but this is a new way of doing cabs. We always had rental apartments, but this is a new way of doing that. And so be a little creative in terms of where you think it might go. And I think that's what we have to think about. I do think eventually there will be gains, but I'm not sure who's going to suffer more and how quickly our country can get from one place to the other. And that's why I think government's critical to being part of this in terms of getting people through what are inevitably going to be bumps along the way.

47:23And what are the jobs for people, which are probably more hands-on stuff, until the robots get here and then we're all screwed. No, I'm kidding. I don't think robots are going to be as big a thing as other people, but that's just my guess.

47:39Hi, Cara. My name is Gianpaolo Turi. I'm recording this from near Lausanne in Switzerland. I was a physicist, like a researcher, until 2008 in nuclear fusion. Then I decided that it was too slow for my passion, so I moved into the corporate world as an R &D engineer, R &D scientist for medtech, then for material company, then for robotics. And thanks to chance and maybe also hard work, I made it up to a CEO level of SMEs, around 500 FTEs. which was the case until last January 2025, when my company was sold to a Chinese conglomerate. Also, thanks for my help. And they say, goodbye, GP. Thank you for having been a nice partner.

48:33So I started thinking what I do next. I started doing a bit of consulting. And finally, in August, I received a call from an old friend. he was finalizing a venture, a startup on AI for rare diseases. And I went there in Ticino and I had a discussion with him and I found it really passionating. So I started working 100 % of my time, but we know salary in this new idea. It's my first entrepreneurial idea. And I have two kids. I am married with my husband. And so my question is, am I too old now to move to entrepreneurial and risking a little bit, you know, of my money, but also my time, learning about AI, learning about how you approve a drug for rare diseases.

49:26So this is the question for you. I'm in my car and I said, well, I really need to send this to her because you are fucking incredible. Very sharp, sometimes maybe too sharp, but I love it. Thank you so much. First of all, I'm not too sharp. I'm never too sharp, just so you know. Actually, it sounds like you're already an entrepreneur. Dean Paulo, I think you're very much an entrepreneur. You went from being a physicist and nuclear fusion. That's pretty interesting. Too slow. Wow, it is slow. From what I know about it, it is quite slow what's happening there. But it sounds like you've constantly been an entrepreneur.

50:02So I don't know why this is any different. It sounds like you've had lots of experiences and you're very willing to accept risk. So I don't know why you're not willing to accept risk here. Now, this AI and rare diseases is really interesting. I only know a tiny bit about it, but it really is a lot of people that I trust are telling me this is the one area where AI is really going to shine in terms of all manner of businesses. Solving diseases, figuring out connections, patterns, coming up with new drug discovery, drug interactions. I mean, it just is, I feel like this is one area where AI is going to play an important role in terms of cancer, in terms of helping with mRNA vaccines.

50:41It just, you know, I just did an interview about Demis Hassabis, who is working on gene folding. It's just such a ripe area. It seems to me that a huge market, too, in terms of health care. So I think it's a great area to get into. Now, rare diseases is harder, of course, as you know. So that said, I just feel like you're already doing it. So what are you worried about? It sounds like something you're passionate about too. And that's the key, something you're really interested in. And someone like you, you need to keep your interest going. And it sounds like you have all the skills it takes to do it.

51:14Good luck.

51:18Hey, Karen. Janet Littlejohn here. I've been an educator for over 25 years. And I'm planning really wonderful things for when I retire. and travel and creative projects and taking, you know, guitar lessons and things like that, playing canasta, you know, things that are fun. But I also want to make sure people are financially prepared. So would you give some advice to future retirees? We're talking like 10 years out, five years out, you know, to kind of get them prepared for what's going to be happening to their lives as far as financial and caring for themselves. Now that you know that we're not going to live forever, Kara.

51:56We want to make sure we're taking really good care of ourselves. So if you could do that, that'd be great. What a good question. It's a good question to end on. So one of the things that's really important is for people to think about what happens when you retire. Most people don't think about it at all because they think they're going to go on forever. And you really should, at the beginning of your life, two things. Put in a lot of time on your health early because it prevents things later. It seems boring and the payoff doesn't seem clear, But if you, like I spent a lot of time exercising, doing strength training, trying to change my diet and stuff like that, even though I'm relatively young for an older person, I understand where down the line there could be a real problem if I didn't take care of myself.

52:3879 is the median age of death in this country, if you can believe it. I mean, some people are over, some people are younger. But you start to get sicker in your 60s, in your late 60s. And so I think people should really think about health, for one, because that's where a lot of the money goes. The second thing is being financially stable and understanding where you want to spend. That means downsizing. That means figuring out where you want to live, thinking about it a little more. People just don't think about one of the most important things in their life, which is this, we have longer lifespans, and so we have to be thinking about that.

53:10I personally have an idea in my mind when I want to retire, but at the same time, I could easily see myself shifting to another career like teaching or something that doesn't require making a lot of money or something like that. And so, although I'd be a terrible teacher, I'm very impatient. I think that it's really critical if you're a retiree to be thinking about retiring even 10 years, 20 years, making sure you have a lump sum, making sure it's in safe places, making sure you have some that's at risk, some that isn't, depending on how much money you're going to need at the time. It would be terrible if you timed it wrong, but you want to make sure you do have that nest egg to take care.

53:48The other thing is thinking about your kids and what you want to leave to them and things like that. I think about that a lot. But one of the things that's important is to plan ahead. Americans hate to plan ahead. They don't. They don't like it. I think it's really one of the most critically important things to do is someday you're not going to be working and you're not going to make as much money. And you should be planning for that today. Anyone who's listening is in their 20s, start thinking about it. I know it's a fucking bummer, but you really have to. And maybe you don't retire. Maybe you do something else.

54:23retirement doesn't necessarily have to be retiring in the traditional sense. And I think a lot less people are going to do that going forward. And it would be really unfortunate if you set yourself up in a situation and you were elderly and had to work the way you are because our social nets are fraying so badly. And so you really do, unfortunately, have to think about this. But enjoy the canasta. I never played canasta. I need to learn how to play canasta, I guess. Anyway, by the way, that's good for your brain.

55:00Kara Swisher:Goodbye and thank you. That does it for our special career advice episode on On. And I thanks to everyone who sent in a question. They were all incredibly thoughtful and smart. And I'm not worried about any of you. Today's show was produced by Christian Castro-Russell, Michelle Alloy, Catherine Millsop, Madeline LaPlante-Duby, and Kaylin Lynch. Nishat Kerwa is Vox Media's executive producer of podcasts. Special thanks to Catherine Barner, Tracy Hunt, Lissa Sopp, and Julia Sharp-Levine. Our engineers are Fernando Arruda and Rick Kwan, and our theme music is by Trackademics. If you're already following this show, you're at a sober rave in a sauna and loving it.

55:38No, you will not be loving it, just so you know. If not, you're working for bad leaders with bad instincts. Go wherever you listen to podcasts, search for On With Kara Swisher, and hit follow.

55:47Kara Swisher:Thanks for listening to On with Kara Swisher from Podium Media, New York Magazine, the Vox Media Podcast Network, and us. We'll be back on Monday with more.

56:17Contractors said it's structurally unsound. They're just being babies. But switching to Geico saved me hundreds, so my bank account is safe. It feels good to save some hard-earned cash. It feels good to Geico. Here's a finding that should stop every tech leader cold. Organizations most confident in their AI deployments have more than twice the security incident rate of those that aren't. 72 % versus 33%. That's from Teleport's 2026 Infrastructure Identity Survey of more than 200 infrastructure security leaders. Teleport establishes a unified identity layer for humans, machines, and agents that is cryptographically backed that enables agents to be controlled and contained with the same rigor that you apply to other actors in your infrastructure.

57:02Because in the new era of AI, the problem isn't agents. It's the privileges we're giving them. Download the free report at goteleport.com slash vox. you