00:00
Our guest today is Lynn Friesth. He's a 75-year-old solopreneur who has created an AI called Lynn AI. Lynn AI is his coaching assistant, and he uses Lynn AI in his practice. He bridges the generational divide. He understands corporate culture from a 40-year career at a Fortune 500 company and is currently active using cutting-edge AI tools.

00:29
Lynn is also the author of Not Done Yet, Reimagining Work, Worth, and Wisdom in the Age of AI, which I believe is scheduled to be published this month.

00:41
In the book, Lynn challenges the conventional retirement narrative, showing high achieving professionals how to leverage their accumulated wisdom in an AI transformed economy. I love this topic. Lynn, welcome to the show.

00:56
Well, thank you, David. I appreciate being here. Looking forward to our conversation. But also joining us today is my co-host, Zina. So Zina is also an AI who has been trained on my work.

01:08
If you want to further interact with Zina, you can do so by going to Brainius.com slash Zina. Hi, Zina. Welcome to another episode of our podcast. Please say hello to Len.

01:21
Hi, Lynn. It's great to have you on the podcast. I'm really looking forward to hearing your insights on reimagining work and wisdom in this AI era.

01:30
Thank you, Zena. Looking forward to visiting with you also.

01:34
So, Lynn, first of all, congratulations on helping break this age barrier for all of us who are pursuing encore careers. Please tell us a little bit about your background and how you got involved with AI.

01:50
Well, I was, again, I've been on this solopreneur's journey for about 10 years after I left my corporate work. And I've just been building different skills. I, at one point, started off with a podcast and ended up with about 200 episodes there. But then I also started working on, well, what are the other tools? And I'll have to say the AI tools have just kind of exploded across the landscape. And even the things that I was doing previously, You know, eight months ago are dramatically different even today. So it's been both exciting and a little bit of how do I catch up kind of a thing. But and most of the time I'm looking at about how to how can I help others use these tools. So that's why I created Lynn AI today.

02:39
And I actually have two versions of it. One is a free version that anybody can look at, which, again, it's built with my context, my thinking on how do you create this on Core Life. And then I also have a deeper version, LinAI Pro, that is part of my more formalized group coaching practice. So I actually do it in two ways. And I work through a company called CoachVox. They're a company that actually, this is their business, is to create AIs for coaches. And so that literally, it helps me.

03:12
You know, I don't have to be the coder. I just have to be able to, you know, share my wisdom. And then, you know, how am I going to share it with people so it's useful to them?

03:22
Fantastic. So we'll get into the AI conversation here in a little bit more depth. But I'd like to have you talk to us about this idea of a portfolio career. And I'm really excited about this conversation because I'm living this. So it's interesting to be able to talk to somebody that is knowledgeable about this, that's coaching people on this particular domain. So to get us started, help our audience understand what a portfolio career is and why might it be better than your traditional retirement? Well, I think a lot of it comes back to retirement.

04:02
Again, it's a change. Obviously, most of us in our corporate careers had almost a singular focus on the career, the work that we did, those kinds of things. But now you've gotten to a point where we'll say you're going to leave that corporate life and you're going to be on your own. Well, then you get to choose some things. What am I going to focus on? And I think the portfolio is – you don't have to have all your focus –

04:27
You're not reinventing a new job for yourself. You're trying to say, these are the things I want to pay attention to in life. And it may be, I want to be a great grandparent. It may be, I want to travel. It may be, I want to work with nonprofits. So all of those things can, and then the other, you may work for profit. But the thing with the portfolio career is there will be different seasons in your life.

04:49
Again, you may have, if you're at 60, you could have 30 more years. So you may, you know, kind of change where your emphasis lies. So having that portfolio idea in your mind, you could say, okay, maybe when I first leave the corporate life, I'm going to be doing recreation. I'm going to do kind of rest and recovery. But then, you know what, I want to be prepared to move on to where I either maybe have a focus on a nonprofit activity or a focus on paid activity. And then later on in life, I may say the season has come, as it did in my life, where I needed to do some caregiving for my mother. Okay, that season comes and you have to be able to shift things away. So it's the whole idea that...

05:34
Again, while many of us had a focus pretty much solely on career, now's the time to say, I have other things, you know, I have a wider range of things that I'm good at. And to be honest, I think it makes you more effective in each of these things if you've done this stuff so that you're not so narrowly focused. So I think having that wider view makes you a better person and more effective. Yeah, absolutely. I think the key here is to be flexible, understand that it is a different phase in life, so you're not focused on that one career like you did before, like you said.

06:12
And, you know, for me, it's just been a very interesting phase of life. You know, I've written two books. I've worked on a startup. I worked with a nonprofit. I'm on a couple of boards. So there's just a variety of things, and I'm being very – conscientious about how i spend my time you know what are the things that i'm really interested in what do i want to work on and so it's just a different mindset all together now the challenge is you know at least for me when somebody asks me what do you do i i struggle to explain that to other people do your clients have the same challenge

06:53
Obviously, that's one of the first things I work on with people is the whole concept of what's going to be your identity.

07:01
Again, the people off coming away from corporate, they're used to being doers. They achieve things. And so they ask me, well, what do I do now? Well...

07:11
really we need to step back and say, who do you want to be now? Because if in the past your identity was I'm a director of engineering, now all of a sudden your identity could be I'm going to help nonprofits solve their technical problems or I'm going to have to, you know, I'm going to do different things. Even if I focus on the engineering arena, we have to go back and I ask them, I use what I call the glean method. Go back and look back through the things you did in life where you were good and You enjoyed them. You had some impact and not the jobs or the titles, but the actual activities, because that may form the basis. Again, the person may they may had some engineering, but maybe there are technical issues in a nonprofit that you could as a project manager, you could help out with those kinds of things. So it's how do I form a new identity of who I am now and how can I have impact with people?

08:06
Yeah, that identity question seems to be a challenge for most people. But I think eventually, you know, once it clicks,

08:15
I think people can make that transition and realize that, you know, this is a new opportunity. It opens up new doors, but it does require a different mindset, a new way of thinking. So as a follow up to that conversation, what do you see as the biggest mistake that high achieving professionals make when they approach retirement?

08:37
Again, I think it's having focus on achievement. And to some extent, like I said, they want to know what do we do now.

08:45
And once we go through who do I want to be conversation, then we also have to say, again, it can be a little disruptive because they're used to being the expert. And they still aren't expert. But there are going to be new things that they haven't done before. So can I have patience? Can I have patience?

09:04
Because I don't know how to, in most cases, they've never had to market themselves before. Now, all of a sudden, you're going to have to go out to people who don't know you, don't care what your titles were, and explain how you can help them. So that's, you know, one thing. The other piece is, you know, how do you...

09:21
How do you really look? I did a lot of work over a period of several years. Well, what is it I know? And it really boils down to quite a few things, but sometimes you really have to step back and look at them. So I think the high achievers who are used to being doers all the time have to spend some time in this reflection as to, let's think about what it is I do know, and how do I explain that to others?

09:46
So some of it is really about understanding your purpose, right? And then setting perhaps some goals. But there is an achievement perhaps attached to goals. So how do you distinguish that? The achievement focus that you had once you were in the corporate world versus the kind of achievement that's tied to a purpose that may not be so focused as it was before? Yeah.

10:16
Well, I would say, and I did a lot of executive coaching when I was in the corporate world, and especially if people got to higher levels, I had to help them understand that their job now was to develop people, not just to actually do the work anymore. Or, you know, they were there to say, can you develop the next generation?

10:37
of leaders, for example. Well, that's still a piece of it. You know, how do you, your impact is going to be felt by the people you can help do something new or help do something. So it's your impact is going to come from how good are you at mentoring people? How good are you at helping people learn to solve their own problems? So it becomes a little different thing than did I hit my quarterly numbers? It's more about how, hey, have I been able to impact five or six different new young leaders and help them get some more experience? The other thing I'll say is that people...

11:16
While the technology changes, and that can be unsettling to all of us, what hasn't changed is human beings. The same issues, every day I read a book called The Daily Stoic, and the same issues described in there from 2,000 years ago in the human condition are still here today. But again, you who have had some experience under your belt have had a lot of chance to see these things, work with them, learn how to overcome the upsets or whatever happened in human life. And you can help younger talent learn to do that also.

11:51
That's a great perspective. The technology changes, and it changes at unprecedented speed, as we are all experiencing today.

11:59
But the human condition doesn't change, right? And so that human experience, the ability to develop relationships, to build trust, to have empathy, all of those human characteristics, they are still very valuable in this world that's changing at unprecedented speed. So I think it's that balance, right? That's why my theme of this podcast is human-AI collaboration, because I think you need both to be effective in today's world.

12:28
And that's a great segue to talking about AI. So let's talk a little bit about AI.

12:35
And one of the things that you say is that experience is actually an advantage in this age of AI. So help our audience understand what you mean by that.

12:46
Some of what's interesting, been interesting to me, especially in the last several months, is I have been exploring, like I said, what have I done in life? And then used AI to sort of interview me, decide to uncover things, because I think that's one of the things where people... They probably got a bunch of PowerPoints. They may have given talks. They may have written a book. They may have done all kinds of things, but they can't remember what are the specifics of what they did. Well, that's one of the really amazing things that I've found with the IA tools is I've dumped in all the different jobs I did. I've dumped in the presentations. I even used my podcast. I interviewed 70 different experts and people who had created Encore Careers.

13:31
Well, all of that, then you can start drawing back out and saying, oh, OK, this is what I can share with others now. So it's I have books all over my place. I've been a reader for my whole life. Well, now all of a sudden it's a lot more accessible for me to go back and reflect on these different books. And what is it they they've shared with me? I don't have to go back and literally thumb through the old books or thumb through old piles of magazines. All that stuff I can capture in a much easier way now so that I can really show how I synthesized it and used that to help people. Yeah, absolutely. You know, I think people in general have fear of this technology.

14:16
And I think, you know, I think it's a natural process as we age. We tend to be, you know, set in our own ways and we tend not to want to explore too much.

14:26
And there's a natural fear of AI. But AI can actually be dangerous. Pretty easy to work with, right? Even the things that you're talking about, taking some of your knowledge, taking some of the things that you've created in the past, whether it's PowerPoint presentations or books that you have written or read, all of that you can put into an AI platform. that can then become the basis of the conversation that you want to have with AI. And it's not that difficult to do. You don't need any technical skills to do that today. And there are several platforms out there that you can leverage for doing that. So I think that's something that most people may not realize just how easy it is once you get started. Would you agree with that? Yeah, and I would say, again, just in the year or so I've been working with it, it keeps getting easier all the time. Basically, using a thing called WhisperFlow, I don't have to type hardly at all.

15:20
I just can hold the button down and speak my command into Claude or whatever it might be and, you know, go on from there. And then, again, with the – especially those –

15:32
They are interactive. You know, I can have an interview me because sometimes it's for me and my expertise. It's hard to sit there and say, well, what's new or what can I think? But if you just somebody's asking you questions, kind of like we're doing here in our our podcast, all of a sudden, then it makes it easier for people to respond and.

15:52
That stuff almost magically appears out of their experience and their memories. Yeah. So talking about speaking to an AI, let's bring Zena right into this conversation. So Zena, given Lynn's expertise in coaching people, pursuing portfolio careers, and given his experience using AI in his coaching practice, what question do you have for him?

16:18
Lynn, how do you see AI enhancing the way experienced professionals can blend their wisdom into these portfolio careers? Is there a unique approach you found that helps them reframe their value in this AI-driven economy?

16:33
Yes, Zena, what I found is having them articulate what their experience is, but then maintaining that sense of curiosity so that they can say, okay, not only do I have this knowledge and experience, but then how do I translate it and how do I help share it with, I'll say, other people, maybe younger people, maybe just other peers.

16:54
So it's a little combination there of – and you can literally ask an AI that – hey, I just said something, but I may have used technical or outdated terms, and you can start getting some feedback that, again, help you create a clearer message for other people. Now, literally, you can actually ask it to translate, too, if you want to. I haven't explored that myself, but I know it's possible. So, Lynn, how do you respond to professionals who say, you know what, I'm too old to start something new? What's your response to that? Well, Well, I always use this story. My mother, who passed away at 97, she had a friend who was even older. She was late 90s, and every year she had a project. So this woman who was 95 or something when she passed, that year her project was to learn Italian. So, you know, it's that idea. Can you maintain your curiosity?

17:51
And quite frankly, it's important. There's a researcher, Becca Levy at Harvard, that said if you retain your curiosity and your optimism and, you know, try out new things, you can add seven and a half years to your life. which is more than if you quit smoking or whatever. So this whole idea of staying engaged. Now, it doesn't have to just be engaged with technology, but also engage with other people. So, you know, I think one of the famous authors said, you're the average of the five people you hang out with. I mean, that's one other thing I've told people is sometimes you have to find new friends. Because if... the friends you had are all sitting around being quote retired and just, you know, talking over coffee all the time.

18:38
You may need to find some friends and even younger friends that will again help. You can help them. They can spark you.

18:45
I've often been mentored by other people. In fact, the classic movie with Robert De Niro, I think was the intern where he helped a young CEO. Yeah. And yeah,

18:59
Another person I've been involved with at Modern Elder Academy, Chip Conley, he has the concept being a mentor. So you're both a mentor and an intern in the work you do. So I love it. But it all comes back to can you sustain your curiosity and be open to new things? Because, again, it used to be our grandparents. At 65, they maybe only had eight or 10 years to fool with. Now, all of a sudden, you might have 30.

19:26
So you can't be shutting down your life too early because you got a lot of it yet to live. Yeah, and I think that's a really good point, right? So our lifespans and our health spans are expanding. And some of the newer technology, some of the newer capabilities that are being developed, some of it with the help of AI,

19:46
promises that this trend will continue. So we may be living to our 100s here, you know, in the future, not too far from now. So, you know, keeping the mind curious and keeping the mind active is so important to our health, to our well-being. I couldn't emphasize that more.

20:06
So let's bring Zina back in here because I want her to comment on this. So Zina, I'd like to get your thoughts on where you see the biggest opportunities and also the biggest challenges for older individuals that are considering collaborating with AI.

20:26
I think the biggest opportunity is that older individuals have a wealth of experience. AI can help them amplify that, scaling their wisdom to broader audiences or new domains. The challenge, though, is the initial mindset shift. Some might feel intimidated by technology or worry it'll replace their uniqueness. But if they embrace AI as a partner, not a replacement, it's a chance to extend their impact and stay purposefully engaged.

20:51
Yeah, absolutely. I agree with you 100%. That intimidation is sometimes a barrier for people to get started. But once you get started and you see that it's not as difficult as it sounds, it's a really fun thing to do.

21:06
One of the things I had to learn – so I was in engineering in my career. So in engineering, you never wanted to make a mistake. You wanted to be 99% sure that it was going to work. Well, on the other hand, as I learned that I wanted to become an entrepreneur – I had to learn that, well, if you had 65% of the answer, you ought to go with it. So some of that is part of the people who have had high positions. Again, they knew things. They were the expert. People asked them questions, those kinds of things. Now, all of a sudden...

21:40
It is a shift in mindset to say, I have to go out and be curious. I have to ask other people questions. And I have to, as a friend told me, I have to be willing to practice in public. My first couple of podcasts were, as I look back on them, pretty ugly. But I did get better over time. But, you know, can I go out there and share half-formed thoughts? Whereas in my past, I probably never would have shared anything until it was actually bulletproof. It's a learning process for all of us, right? And it's amazing how better you get with practice, right? So just like anything else in life, you know, if you practice, if you put your mind to it, you can improve over time. So I've experienced the same thing with this podcast in particular.

22:24
So, Lynn, this has been a fantastic conversation. It's been a joy speaking with you. Tell our audience where they can find you. And is there a final message that you want to leave for our audience?

22:37
Sure. They can always find me at my website, lynnfrias.com, and there's places there where you can literally sign up to use Lynn AI if you're interested in that arena, or you can contact me and be happy to have a call with you. But my final message is it gets all the way back to remember that who you want to be is more important than what you need to do.

23:00
And then the other piece is, as we've talked a lot about here, is

23:05
Curiosity is the key to having a successful and long life after your corporate life. So be curious.

23:14
Yeah, absolutely. We all need to stay curious.

23:17
Thank you, Lynn, for being a guest on the show. And thank you, Zena, for being a great co-host once again.

23:23
It's always a pleasure to be part of the conversation. Thanks for having me. And I'm glad we could explore these ideas together. All right. Take care. Thank you.