Career Advice: Kara Answers Listeners’ Questions

Summary

Podcast Summary: On with Kara Swisher – “Career Advice: Kara Answers Listeners’ Questions”
Vox Media | June 25, 2026 | Host: Kara Swisher

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Overview

In this special listener-driven episode, Kara Swisher, renowned journalist and no-nonsense career pragmatist, answers listener-submitted questions about navigating careers amidst turbulent times. Topics range from leveraging AI and coping with bad bosses, to balancing passion with practicality and transitioning between industries. The episode offers candid, practical, and sometimes blunt guidance, with Kara’s trademark wit and directness. It’s a compelling resource for anyone thinking about their next career step in an AI-disrupted, uncertain job market.

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Key Discussion Points & Insights

1. Adapting and Growing in Your Current Career

• The Realities of Self-Promotion for Artists
  Caller: Sue Frieda (03:49–05:02)

  • Sue, a seasoned sculptor and introvert, struggles with social media’s demands for attention.
  • Kara’s Advice (05:02):
    • “You have to be promiscuous on social media... Unfortunately, it has to be genuine to you.”
    • Suggests starting with a social media manager and platforms that feel less intrusive, like Instagram or LinkedIn.
    • “It is a modern version of advertising, and by the way, it's free.”

• Dealing with Terrible Bosses
  Caller: Shelley Wilson (07:06–07:30)

  • Should you revolt, advise, or leave?
  • Kara’s Advice (07:30):
    • “I have always left. I just leave. I don't think leading a revolt is a very good idea... But you're not going to change things.”
    • “Start your own thing if you can, or go find a place that sort of is more in your wheelhouse.”

• Juggling Multiple Careers
  Caller: Ben Crowder (09:43–10:38)

  • Ben balances a tech role at Microsoft with his passion as a fantasy writer and narrator.
  • Kara’s Advice (10:38):
    • “Cut anything that you don't find interesting… make hay while the sun shines.”
    • Recognizes that demands can be temporary; prioritize what’s important or lucrative when the moment is right.

• Frustrations in HR and Doing Good Work
  Caller: Tommy Howard (11:36–12:26)

  • Is HR doomed to suck, or can it be transformative?
  • Kara’s Advice (12:26):
    • HR is “often far too much for the employer than the employee.”
    • There are companies that care, but systemic issues persist. Employee involvement and ownership would improve things.
    • “The more you care about your employees, the better the business tends to be.”

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2. Making a Career Change

• Pursuing Passion vs. Financial Security in AI-proof Fields
  Caller: Alex Nickel (17:50–18:40)

  • Balancing community-oriented, “AI-proof” work with earning a living.
  • Kara’s Advice (18:40):
    • “There is sort of an AI proofness to all community gatherings… you're just sort of starting to see a real push by young people towards community.”
    • “No matter how you slice it, these are professions that earn less than AI.”
    • Be prepared for financial trade-offs, but notes a trend toward in-person and communal activities.

• Positioning Yourself in a Growth Field: Climate Entrepreneurship
  Caller: Robin Bennett (20:29–21:29)

  • A mid-career leader wants to move into climate-focused entrepreneurship.
  • Kara’s Advice (21:29):
    • “Do your research... try to get in on a startup of some kind.”
    • Don’t be afraid to change careers at any age; networking, training, and researching dynamic fields are key.

• Turning Side Projects into Professional Work Caller: Victoria Zunich (23:11–23:43)

  • Aspiring investigative journalist, seeking a way in.
  • Kara’s Advice (23:43):
    • Start with small stories, build expertise over time.
    • “Investigative reporting is really hard to do on your own… it's a team sport.”
    • “Let's not try to boil the ocean today. Let's start with a tiny little thing...”

• Shifting from Public to Private Sector Caller: Kara Stevens (25:21–26:47)

  • Counselor and nonprofit leader now targeting edtech or advocacy consulting.
  • Kara’s Advice (26:47):
    • Leverage existing networks and experience.
    • “You have enormous experience... someone with all these kind of skills are very valuable to the private sector.”
    • Consulting/contract work can be a good entry point; expect some rejection but keep persisting.

• Overcoming Ageism with a Nonlinear Resume Caller: Bruce Hackney (28:50–30:32)

  • 62-year-old with a creative career history.
  • Kara’s Advice (30:32):
    • “The way you reframe it is you’re a can-do person… to fix the problem, create a system.”
    • Focus messaging on being a reliable problem solver, not age.

• Navigating a Contracting Media Industry Caller: Dorothy Novak (32:03–32:44)

  • Public media TV producer concerned about industry contraction.
  • Kara’s Advice (32:44):
    • “It’s not a sinking ship, it’s an underfunded ship.”
    • “Try to hold onto your job as long as you can… assess what part of your job you like doing the best.”
    • Flexibility and exploring growing adjacent fields, such as podcasting, are important.

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3. Adapting to AI in the Workplace

• Building on Technical and Public Service Experience
  Caller: Carolyn Champa (39:08–40:03)

  • Librarian with cybersecurity background, wondering how to bridge these skills with AI.
  • Kara’s Advice (40:03):
    • “It doesn’t abrogate the need for a librarian.”
    • Hone AI and information science skills; human judgment in managing information will be crucial.
    • “There has to be a marriage between AI and humans.”

• Preparing Kids for the AI Era Caller: Clayton Winters Machad (41:56–42:10)

  • What skills should an 18-month-old develop for the Age of AI?
  • Kara’s Advice (42:10):
    • Focus on play, problem-solving, creativity, collaboration and reading. Avoid early computer use.
    • “Teach them how to think and to challenge themselves.”

• AI Disruption and the Labor Market’s “J Curve” Caller: Katie O’Malley, HR Professional (44:17–45:15)

  • How long will the disruption last before job gains arrive?
  • Kara’s Advice (45:15–47:39):
    • We haven’t seen clear job losses yet, but gains will come from unforeseeable industries.
    • “There will be job gains because of industries we don’t know… be a little creative in terms of where you think it might go.”
    • Government should play a role in cushioning transitional impacts.

• Is It Ever Too Late to Try Something New? Caller: Gianpaolo Turi (47:39–49:56)

  • Late-career physicist turned CEO now working on AI for rare diseases, worrying about jumping into startups at his age.
  • Kara’s Advice (49:56):
    • “You’re already an entrepreneur… it sounds like you have all the skills it takes to do it.”
    • “AI and rare diseases is really interesting… this is the one area where AI is really going to shine.”

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4. Later-Career Planning and Retirement

• How to Prepare for Retirement Caller: Janet Littlejohn (51:18–52:01)
  • Teacher planning for financial security, health, and fulfillment in retirement.
  • Kara’s Advice (52:01):
    • “Put in a lot of time on your health early because it prevents things later… being financially stable and understanding where you want to spend [your money].”
    • “Start thinking about it. I know it’s a fucking bummer, but you really have to.”
    • Consider alternative ‘retirement’ paths (e.g., teaching, creative work), plan for longevity, care, and legacy.

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Notable Quotes & Memorable Moments

• “I have always left. I just leave. I don’t think leading a revolt is a very good idea. It's not your business.” – Kara Swisher, on dealing with bad bosses (07:30)
• “You have to be promiscuous on social media… unfortunately, it also has to be genuine to you.” – Kara Swisher, on self-promotion (05:02)
• “HR is often far too much for the employer than the employee.” (12:26)
• “There is sort of an AI proofness to all community gatherings… You're just sort of starting to see a real push by young people towards community.” (18:40)
• “It’s not a sinking ship, it’s an underfunded ship.” – On the state of public television (32:44)
• “Hone your AI skills… [There’s] nothing more valuable than that to have those skills.” (40:03)
• “The way you reframe [a scattered resume] is you’re a can-do person... someone who can fix the problem, create a system.” (30:32)
• “Teach them how to think and to challenge themselves… Play is critically important.” – Advice to a parent re: preparing kids for AI (42:10)

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Timestamps for Major Segments

• 03:47 – Social media advice for artists
• 07:06 – Escaping bad bosses
• 09:43 – Balancing IT work and creative writing
• 11:36 – Good vs. bad HR
• 17:39 – Mid-life career changes
• 28:50 – Reframing a nonlinear career, overcoming ageism
• 32:03 – Surviving public media and industry contraction
• 39:08 – Adapting library skills for the AI era
• 41:56 – Teaching kids for the AI future
• 44:17 – AI and future of the labor market
• 47:39 – Is it ever too late for entrepreneurship?
• 51:18 – Preparing for retirement

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Takeaways

• Directness Pays Off: Kara continually advocates for self-awareness, action, and honesty in assessing career directions.
• Don’t Fear Change—Or AI: Skills in learning, networking, problem-solving, and adapting to tech will remain vital.
• Value Connection and Community: Even in a data-driven era, the human touch is irreplaceable in information, community, and creativity.
• Plan—Financially and Otherwise: Start early, think ahead, and reconsider what “retirement” means for the modern worker.

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For anyone navigating their next move, this episode is packed with real-world advice, Kara’s signature candor, and enough optimism to reassure even the most anxious professional.

Transcript

[Kara Swisher]

I don't like to dance and I don't like to dance naked in a sauna. So there you have it. They weren't naked. They were semi naked. Anyway, neither here nor there.

[Podcast Host/Producer]

Hi everyone From New York magazine and the Vox Media Podcast network.

[Kara Swisher]

This is on with Kara Swisher. And I'm Kara Swisher. We're doing something a little different on this show today.

[Podcast Host/Producer]

For this episode of On, I'll be the one answering questions.

[Kara Swisher]

Your questions. For the last few weeks, you've all been sending us your career advice. Questions you've asked about everything from how to think about using AI at work to dealing with bad managers to preparing for retirement. And I've got at least some answers for you. It's a really good time to do an episode like this too, because there's a lot of anxiety about the job market right now. I think everyone is feeling it. People are worried about AI, the war in Iran, the Trump administration's policies, and what it all means for them. I want to do this episode because I get asked for career advice all the time. I get open my own business, I should charge for it. Actually, maybe I will charge for it and it'll be my career, my next career. But actually, I think people ask me about career advice frequently because I change my careers a lot and I take a lot of risks with them and it usually ends up pretty well. And so when people are, especially in media, transitioning, I'm the go to person usually because I don't sugarcoat it. I've had so much fun answering the questions you sent to me. So don't go anywhere.

[Podcast Host/Producer]

Thanks again to Odoo for supporting this show. Odoo wants to be your ultimate all in one, fully integrated platform to handle everything. Seriously, everything. Inventory, CRM, accounting, HR and much more. No more shopping around or settling for expensive services that can only handle a

[Kara Swisher]

fraction of your business.

[Podcast Host/Producer]

Thousands of businesses have made the switch, so why not you try Odoo for [e-mail] that's o d o o.com. Support for this show comes from Cohere. As AI advances, one thing matters more than ever.

[Kara Swisher]

Staying in control.

[Podcast Host/Producer]

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[GEICO Commercial Voice]

When I got a new

[Kara Swisher]

car, I thought my insurance premium would increase and empty my bank account. Like if fatween won the lottery.

[GEICO Commercial Character]

I've invested most of my winnings in chicken tenders because they're bomb. But bro, I bought a house and it's sick, bro. I'm thinking the floor is gonna be all trampoline, bro. With the helipad on the roof. The contractor said it's structurally unsound, but they're just being babies.

[Kara Swisher]

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

[Podcast Segment Announcer]

it is on.

[Kara Swisher]

We're back with a special episode of on where I'm answering the questions you all sent in asking for career advice. So let's just jump right into it. A lot of you had questions about the ways to adapt or grow in your current line of work. Sue Frieda sent us this question about the role social media plays in her

[Podcast Host/Producer]

line of work as an artist.

[Sue Frieda (Caller)]

Hi, Kara. I'm a huge fan. I love your work. Okay, so I'm a sculptor. I've been an artist for 30 years. I went to RISD. I've had a pretty good career, which means I've shown internationally. I've ran my own gallery, I've sold to celebrities, I've had Runway shows. I make wearable sculpture and other kind of sculpture for the wall. But I am not making a strong living. Like I can support myself barely. But I don't really know what else you do except do become like a hype machine. Like if I could get recognition, I'm sure I would sell a lot more things and I would make a lot more money. But I'm not a hype person. I'm kind of an introvert. I just don't really love the spotlight. So how do I get around that with making myself known in the world if I'm not really that kind of a person? Do you have any advice for me? Like, should I hire somebody who's just really good at marketing? Should I, like make a fake social media Persona? I don't know. It just feels like another whole body of work to become famous. And is that really what you have to do to sell art?

[Kara Swisher]

Thank you, Sue. That's a great question. I agree, it's really frustrating. It used to be you did your work and you were recognized for good work and same thing for writing as with sculpture, I guess, or anything you do, the quality of your talent should matter the most, and it still does to an extent. But the fact of the matter is there's so much noise in the world that a lot of lesser people are getting more attention and they do better. I think it's really hard if you want to get more people to understand you. Not to be on social media, I hate to say it, and you have to be on all kinds of social media. You may want to find the one that's most comfortable to you, whether it's YouTube or Reddit or LinkedIn. I know that sounds crazy, but actually there's a lot of interesting people on LinkedIn. What you really do, and I hate to use this expression, but I use it. You have to be promiscuous on social media. You've got to get your stuff out there. And unfortunately, it also has to be genuine to you. You can hire social media people, but it really, a lot of times does have to come from you and the quality of work you're doing. Being successful on social media is a genuine thing, whether you're Kim Kardashian, you may not like her, but she's certainly genuine and has done a really good job. So I think maybe start with a social media manager that helps you figure things out and helps you figure your mess. You know, again, it has to be true to you. And what I would do is go online on whether it's Instagram or TikTok or whichever platform. Instagram's probably the easiest one to work with for now, or YouTube and start seeing things that you like. It may not be in your area. There's a lot of really amazing food influencers who I think actually are doing great work and, you know, maybe show someone how you do your work or how you make things or people are really interested in process. And it doesn't have to be a stunt. It should be the real you. So I know it's terrible, and I know you may be an introvert, but I don't see how you can't. It is a modern version of advertising, and by the way, it's free. And so I. I spend a lot of time on social media more than I want to, but it's really important.

[Listener/Caller]

Hi, I'm Shelley Wilson. I am from Providence, Rhode island, and my question is, what advice do you have when you're working for a jerk? Is it to leave that company? Is it to complain and give advice on how to improve things? Is it lead a revolt? I encountered it a number of Times in my career. And I'm just curious what advice you have, Kara, for other people. Thank you.

[Kara Swisher]

I have always left. I just leave. I don't think leading a revolt is a very good idea. It's not your business. If they want to operate that way, that's the way they're going to operate. But you're not going to change things by, you know, if you remember the Tom Cruise movie where he plays an agent who essentially says, who's with me? And nobody is. I just think that's a waste of time. It's not something you really can't do it. So revolt doesn't really work. And I used to sort of wallow in gripery and I don't think that works very much in life. I think it makes you unhappy and they don't care and it actually your work suffers for it. And so I always leave. I always leave. That's my thing. I did it many times in my career. And in fact, one of my first and early jobs, well, I got fired from one of them and I deserved it. Another time I was working in a place for the McLaughlin Group. I'd written about this and he was sexually harassing a woman. I witnessed it. We complained, and the people in charge didn't want to do anything about it. This was in the before times, although the current times feel like the before times. And I left and a year later I was asked to testify because he did it again. This guy did it again. And I testified against him. And I feel great about it. It was really hard. I was a very young person, but it didn't matter. I was working for a terrible person. And I left essentially because they weren't going to change. I did leave the Wall Street Journal because of issues. We had a number of economic issues with the Murdoch folks. And of course we weren't. Walt Mossberg and I were very thrilled to be working for him. At one point. They did some terrible things at some of their other publications. And we left and started our own thing. And again, my one line is, go and start your own thing if you can, or go find a place that sort of is more in your wheelhouse of people that you're like, I'm having this issue right now with a contract I have, which I've talked about publicly with cnn. I just don't want to work for the Ellison family. And I think their choices are incompetent around the media stuff that would affect me. And so I'm hoping they'll out of the contract. If not, I'll just wait there and leave at the end of that. But yeah, I leave. I'm really old and I'm still leaving when I don't agree with people. So that's what I say, start your own thing. It's always best in the end and there's lots of opportunities.

[Ben Crowder (Caller)]

Hello Kara, My name is Ben Crowder and I'm a 45 year old senior manager in Microsoft's GovCloud division, working with our public sovereign customers in their AI journey. If you looked at my LinkedIn profile though, that wouldn't be immediately obvious because there most of my posts are concerning my other life as a fantasy writer and narrator on Audible. Lately, with the AI craze hitting every industry, I've found it very hard to balance my IT life with my writing life. And I've had to delay the release of my third book because I've been assisting all levels of government, state, local and federal with their AI journey. I know that you too have a lot of different lives as a podcast host, a journalist, a writer, a media personality, and I'm wondering if you have any advice on how best to approach a situation involving two wildly different careers with distinct demands and schedules. Looking forward to hearing your answer. Thank you very much.

[Kara Swisher]

I try to keep things that keep me interested and if I'm not interested, I might cut them. And so what I would do is cut anything that you don't find interesting. It sounds like you have a lot of choices here and I know, you know, sort of you, you make hay while the sun sh and right now AI helping people figure out how to deal with the AI craze, whether it's government, whatever, is a big business right now and a lot of people need your help and so you kind of want to take advantage of it, especially if you can make some money and solidify yourself there and maybe hire more people. But it sounds like being a fantasy writer and narrator is cooler and fun and I bet you have more fun doing that. So, you know, you may have to put that to the side for a little while and take advantage of this timeframe because it's not going to last forever. So that's what I would say. Although I'd love to know what your fantasy I'm going to go look it for you LinkedIn. But you know, again, helping governments get through this AI stuff is really important, especially state and local governments. So you're doing God's work in that regard.

[Tommy Howard (Caller)]

Hey Kara, this is Tommy Howard from Seattle, Washington. So I've been HR professional for almost 20 years I've had the rank of the guy answering the phones at the front desk all the way up to VP of the organization. I got into the work because I wanted to do great things for decent people. But unfortunately, I found myself doing terrible things for even worse leaders. One of my superpowers has been helping organizations modernize their business practices if they might have fallen behind the times a bit. Unfortunately, what I found is when leaders say they want to do these things, what they really want is for people to stop complaining and to carry on with their shitty business practices. So is HR or talent or people and culture or whatever lipstick we're putting on this pig these days doomed to suck, and you're just basically doing terrible things for terrible leaders and that's what the work is? Or are there companies out there that are actually trying to do good for their people?

[Kara Swisher]

I mean, that's a great question. You know, mostly it's usually the first that there's bad leaders who just don't like hearing employees gripe. I mean, I think that's the case. I think HR is often far too much for the employer than the employee. And there's really not a lot of care for the employees themselves. To be fair, it's sometimes a mixed bag. Sometimes they actually do genuinely care about people. But it's a hard thing because, you know, you want to run an efficient company. I see that. And then at the same time, people have all different kinds of needs. And I think HR is. Is put in the most uncomfortable of positions in that regard, because ultimately you are kind of working for the CEO, no matter how you slice it. I wish that people would care more because the more you care about your employees, the better the business tends to be. And at the same time, there's been a real backlash against all kinds of practices, whether it's DEI and things like that, which are designed to have a healthier workplace. I've always felt that employees should own parts of the company. I've always just felt like that sort of puts everyone's interests and it aligns them and that there should be more employee involvement in hr, in everything else, not just as it's always pitted against each other. And instead of trying to figure out the best way to have a company, I don't think at all you have to be doomed to doing this. I've seen lots of companies, and they haven't been perfect. Any of them, who do spend a lot of time caring about their employees. And I'd like to see that a lot more. We'll be back in a minute.

[Podcast Host/Producer]

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[Kara Swisher]

Some of you had questions about making a career change, so let's get into some of those. The first one comes from Alex Nickel. He has a question about balancing passion and the need to make a living. Oh, the age old question.

[Alex Nickel (Caller)]

Hi Kara, Alex here from Victoria, Canada. You and your guests have mentioned a few times on your various shows that with the rise in AI and social isolation, now is a good time to go into the performing arts. As someone who had a professional career in musical theater but transitioned into the tech and business space, I'm wondering what your thoughts are on pursuing career paths that are AI proof and beneficial to society but have a significant financial disincentive. I want my work to promote gathering and socializing in a time where streaming and social media platforms want you to stay home alone on your screens.

[Interjecting Voice]

But.

[Alex Nickel (Caller)]

But I'd also like to be able to buy groceries and raise a family. What are your thoughts on balancing a safe career path versus a socially valuable career path?

[Kara Swisher]

I was talking more about creativity, Alex, versus performing arts, which I love by the way. And I do think there is sort of an AI proofness to all community gatherings. And I don't just mean performing arts though. I love it. No matter how you slice it, these are professions that earn less than AI and so you're gonna have to take a salary cut when you're in these areas and you're more vulnerable at the same time, you know, you're just sort of starting to see a real push by young people towards community, towards in person things. And it cannot be disrupted by AI. It just can't. The only thing it can do is keep people in that social isolation and then not attending these things, but you see a real push for it, whether it's people going to church, whether it's people joining mahjong games. For my show, I was at this incredible games night that organized by this young man who brought together all these mostly young people actually, but there were older people there too, playing games, putting their phones down. I'm like, that would be a really good business, wouldn't it? Another one was a sober rave. This woman's built this amazing company of people just dancing in all manner places. Was in a sauna and it was incredibly awkward for me. By the way, I don't like to dance and I don't like to dance naked in a sauna. So there you have it. They weren't naked, they were semi naked anyway, neither here nor there. There's all manner of things you can do that are sort of community based and I do think people are going to be rushing back towards them. Again, it might not make as much money as doing tech and AI, I'm sorry to tell you that, but I always love when people go into performing arts and again, I think it's ripe for some real innovation in terms of how people consume it. Next we got a question from Robin Bennett. She asked how she can best position herself in a field where she sees a lot of potential growth.

[Ben Crowder (Caller)]

Growth.

[Librarian Caller]

Hi Kara, thank you so much for considering my question. I'm a 52 year old CFO currently of a small business and I'm also in an MBA program. I have a background in science and ecological research so I have a master's in ecology and then went back to school to get my MBA because I didn't know really much about business at all outside of some accounting. And I'm really looking to kind of be in the room where it happens. Kara, like you always talk about how the next great frontier is going to be somebody that can pursue climate entrepreneurship and the next company set of companies that are really able to look at that as an opportunity is going to really be able to take climate science to the next level where it emerges with entrepreneurship. And I'm specifically interested in that intersection. So if you have any advice on that, how to get in that room and how to find out where those opportunities are, that's what I'm looking for. Thanks a lot. My dog Aiko says hi.

[Kara Swisher]

Hi Aiko. I love that you're going back to school. Like you're a cfo, so you're probably good at accounting and sort of running businesses, but it's really important to get even More skills. I love when people go back to school. I took a 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 I really 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. There's all kinds of areas. 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 at advanced manufacturing to try to, it's, 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. That'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.

[Victoria Zunich (Caller)]

Hi Kara, thanks for doing this. My name is Vicki and I consider myself a re emerging journalist. I 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 we're

[Kara Swisher]

going to pitch them.

[Victoria Zunich (Caller)]

What else do you think I should be thinking about at this stage? Thank you.

[Kara Swisher]

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. I'm so in awe for investigative reporters. 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, you know, 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, it's a real slog. What I do is I try to start smaller, I guess, maybe a smaller investigative process and let it. I 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 found. And so I would start small 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. And 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.

[Kara Stevens (Caller)]

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. I've chaired non profit boards. I've worked with our family court system. I've even founded a grassroots advocacy organization

[Kara Swisher]

in my own community.

[Kara Stevens (Caller)]

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 change.

[Listener/Caller]

Wow.

[Kara Swisher]

It sounds like you have enormous experience and I would think private sectors would find that valuable. It 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 coming that are working on that stuff. Someone with all these kind of skills are very valuable to the private sector. And 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 I would. One of the things that's really important, and it sounds like you have the skill, is incredible ability to network and understand and maybe start thinking of people you've worked with that might. Might give you an idea. One of the things I do when I was thinking about leaving places, I talk to everybody. I talk to everyone. And often it comes from a strange place, a tip or an idea or something that occurs to me, but you gotta 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. Although 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.

[Bruce Hackney (Caller)]

Hello, Keri Swisher. This is Bruce. I live in New York city and I'm 62 years old and I've been unemployed for 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. So 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 Cara 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 and tech and media. You 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?

[Kara Swisher]

First of all, stop asking AI questions they don't know. All they did was just vomit up me at me. I 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. I 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.

[Dorothy Novak (Caller)]

By the way.

[Kara Swisher]

I think it's. That's another thing you can tell yourself you don't. You're 62, you don't want to run the company, you don't want to do this. You just want to, you know, 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. So I would say I wouldn't worry about your age as much as putting the message out that you can get things to done and you can use tech skills and stuff like that. You have those skills and I hope you get a job. Next, we have a question from Dorothy Novak. She worries about pigeonholing herself in a changing industry.

[Dorothy Novak (Caller)]

Hi, Kara. I'm seeking career advice. So I work in public media and as you know, things are really, really rough, 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 feels, kind of feels right now like we're on a sinking ship. And I hate that feeling because I

[Kara Swisher]

love what I do.

[Dorothy Novak (Caller)]

I love our mission, I love our supporters, I love, I love it. But I'm in my mid-50s, I'm a single mom. Where do I go from here? Thanks. Thanks a lot. Bye.

[Kara Swisher]

I don't think public television is a sinking ship. You gotta 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 that 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. And so doing what you're doing, there's gonna be fewer people and there's just no two ways around it. I talk to a lot of these people who run these stat. As much as they'd like to keep people employed, they're not gonna 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 gonna be around. It's just gonna 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. And 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 onto your job as long as you can. There's gonna. 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 area because that's video now, by the way. All podcasts, like, look at me, I have a face for radio. Public radio, 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.

[Podcast Host/Producer]

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[Kara Swisher]

I usually find protein shakes gross. These are amazing.

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[Kara Swisher]

So are dogs.

[Listener/Caller]

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[Kara Swisher]

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[Kara Swisher]

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[Kara Swisher]

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[Kara Swisher]

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[Kara Swisher]

A 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.

[Carolyn Champa (Caller)]

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, a six and a four year old. We also love K Pop Demon Hunters. So here's the thing I Career career advice. Thanks for doing this. I am a librarian, but I've done cyber security work and I. I honestly hated it.

[Kara Swisher]

Hated it.

[Carolyn Champa (Caller)]

What I love is the human side of information. I 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 Bridget responsibly. 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.

[Kara Swisher]

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 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 it 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. Information 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 fact, actual 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. So 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. You're just 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 called, I think it's called Desk Set with Spencer Tracy and Katharine Hepburn. And it's about this topic which is kind of funny.

[Librarian Caller]

Watch it.

[Kara Swisher]

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.

[Listener/Caller]

Hi Kara, I'm Clayton Winters Machad. I have an 18 month old daughter and I'm worried about how AI is going to reshape the job market. What skills should I be teaching her that will be the most successful in the age of AI?

[Kara Swisher]

18 months old? I think you don't have to do anything but teach her how to play with blocks. Or if you really want Magna tiles, I highly recommend them. They're fantastic. I love all those things, Legos, things like that. So I would start with those 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 and actually my older kids. One of my kids uses it more than others. But in general I was very interested in problem solving, in 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 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. Now 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. I 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 introduce the use of AI. It'll be different by the time she gets old, 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.

[GEICO Commercial Voice]

Hi, Kara, My name is Katie o', Malley, founder and principal coach of Encourage Coaching, and I'm currently at an HR conference here in Organization, 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?

[Kara Swisher]

First of all, I don't think we've seen job losses yet. You're starting to sort of see it, but it's not clear yet. And so we don't quite know 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 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, you didn't know that was going to be disrupted. The Internet, it was very unclear and actually took turns that people didn't quite

[Podcast Host/Producer]

see, although some of them were obvious.

[Kara Swisher]

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 pay phone 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. And 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 gonna be a lot of pain between then and now. There will be job gains because of industries we don't know. No one would've thought of Uber way back in the 1990s. They just wouldn't have. When I started covering the Internet, they 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 was a new way of doing cabs. We always 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. And 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.

[Interjecting Voice]

Hi, Kara, My name is Gianpa Touri. 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 and D engineer, R and 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 Micah Co. Was sold to a Chinese conglomerate. Also thanks to my help. And they say goodbye, gp, thank you for having been a nice partner. So 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 Ventura 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 with no 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 risky? Talking 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. So this is the question for you. I mean, my car. And I said, well, I really need to, to send this to her because you are incredible. Very, very sharp. Sometimes maybe too sharp, but I love it. Thank you so much.

[Kara Swisher]

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, Gianpolo. I think you're very much an entrepreneur. You went from being a physicist and nuclear fusion. That's pretty interesting. Too slow.

[Dorothy Novak (Caller)]

Wow.

[Kara Swisher]

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, so 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. 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 huge market too in terms of healthcare.

[Podcast Host/Producer]

So I think it's a great area

[Kara Swisher]

to get into now. Rare diseases, harder of course, as you. 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 sounds like you have all the skills it takes to do it. Good luck.

[Janet Littlejohn (Caller)]

Hey, Karen. Janet Littlejohn here. I've been an educator for over 25 years and I'm planning really wonderful things. So 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, and caring for themselves. Now that you know that we're not gonna live forever, Kara, we wanna make sure we're taking really good care of ourselves. So if you could do that, that'd be great.

[Kara Swisher]

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 gonna 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. 79 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. I 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. 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 gonna need at the time. It would be terrible if you timed it wrong, but you wanna make sure you do have that nest egg to take care. The other thing is think. Thinking about, like, 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. As a. 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. Retirement doesn't necessarily have to be retiring in the traditional sense. And I think a lot less people are gonna 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 connection. Canasta. I never played canasta. I need to learn how to play canasta, I guess. Anyway, that, by the way, that's good for your brain. 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 Roselle, Michelle Aloy, Kathryn Millsop, Madeline laplante Duby and Caitlin Lynch.

[Podcast Host/Producer]

Nishat Kirwa is Vox Media's executive producer of podcasts.

[Kara Swisher]

Special thanks to Katherine Barner, Tracy Hunt,

[Podcast Host/Producer]

Lissa Sop and Julia Sharpe Levine.

[Kara Swisher]

Our engineers are Fernando Arruda and Rick Kwan and our theme music is by Trackademics.

[Podcast Host/Producer]

If you're already following the show, you're

[Kara Swisher]

at a sober rave in a sauna and and loving it. No, 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.

[Podcast Host/Producer]

Thanks for listening to on with Kara

[Kara Swisher]

Swisher from Podium Media, New York Magazine,

[Podcast Host/Producer]

the Vox Media Podcast Network, and us. We'll be back on Monday with more.

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