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E34 – Navigating Career Uncertainty: What 4,000 Leaders Told Us About the Future of Work

Season 2 is here, and we’re starting with a simple truth:

No one knows what’s coming next with the AI Economy.

Todd just got back from a 4,000-person leadership conference where top executives, HR leaders, and operators were all saying the same thing: we’re figuring it out in real time.

That’s the backdrop for this episode, and it’s a ‘must listen’ for anyone navigating career transitions. Chris and Todd break down why uncertainty isn’t something to avoid, it’s something to work with.

We talk about what’s actually happening inside companies right now, why the idea of “certainty” was always a bit of a myth, and how to start making decisions even when you don’t have all the answers. You’ll hear:

  • Why uncertainty can unlock opportunity (not just fear)
  • How to stop spinning and start thinking clearly again
  • The shift from transactional networking → real relationships
  • Why slowing down might be your biggest advantage right now

This is the skill: learning how to move forward without knowing exactly how it’s all going to play out. If this conversation resonates with you, visit ReInvention.biz to explore our guided workbook, learn more about us, and start creating what’s next!

https://ReInvention.biz **Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.


 

Episode Transcript

Chris Thide: If we look at what AI can even do right now, do you think you’re gonna outrun it? Do you think that if you keep just moving as fast as possible, you’re somehow gonna like keep pace and be ahead of the game. There’s so much tactical advantage in like taking it slow, being clear, making good choices. 

All right, my man. Todd, season two opener for Reinvention. What are we talking about today, brother?

Todd Jason: We are back, my brother, and I am so excited to be back here with you for season two on Reinvention, and our first season was so amazing and I know what we have in store for season two is gonna be even more impactful and I’m really excited to get to it. And if you’re new to our show, my name is Todd Jason, and I’m sitting here with my biz partner, Chris Thide. We’re a couple of heart centered brothers who love yapping, who love coaching, and who love helping people navigate the murky waters of career transitions. And we started this podcast with the simple premise that careers are up in the air for many people right now. So whether you’re dealing with burnout, disruptions at work. Or you know that disruptions are on the way with AI or other reasons. Our goal here is to help you get clarity about what you can do to prepare for your future. Now the underlying theme of our entire show is the premise that your next career can be your best if you align it with, who you most want to become and not with who you’ve been. So we talk a lot about identity on the show, right? Like your identity and who you believe yourself to be. And we’ll help you open up new mental pathways for what the future can look like for your work. This is a time to be open-minded and proactive. And Chris, we wanted to start season two with a deep dive discussion for how to navigate uncertainty because mastering the art of living and working in the atmosphere of the unknowable future is perhaps the most important skill for people to develop right now. And I know this sounds a little crazy, but I recently spent three days at a 4,000 person conference in Vegas called Transform. Surrounded by all these corporate and business leaders and as we’ll discuss today, this was their core message.

So successful reinvention to me is very closely related to how well an individual turns towards the unknown, faces his or her fears, and learns how to make decisions that may or may not be right.

So this is a big one, my man, and what say you?

Chris Thide: Yeah. Yeah. And this is, you’re right, this is a big one. And I’m really interested because you went to this conference with all these corporate leaders, and as we know, and we talk about a lot here, I had a 20 year corporate career where I maybe never really felt it was right for me, but I did fit in and do the things I needed to do, and I sort of created a persona that maybe wasn’t really well aligned with my core identity.

And part of why I did that was to stay within the in-group of the corporate world because it felt certain and stable and safe, and something that I should not rock the boat to move away from. Even though, at times to the depths of my soul, I was like, oh my God, I have to get outta here. It was like, don’t rock the boat, stay in this certain thing. And the trick of the whole thing is nothing’s certain. It was never certain 

Todd Jason: Right. 

Chris Thide: The idea maybe that was in my head for my parents and grandparents was this sort of 1950s to 1970s notion of the stability of the baby boom generation in this corporate setting, but that was already gone by the time I was hitting the workforce and you know, if it was ever really there, there’s none of it left now. Is at least the way I look at it. and with AI coming and with layoffs that are already happening around the anticipation of that, it’s only accelerating.

That’s my view on it. I’m really interested ’cause you went to this conference with all these, corporate leaders. How were they talking about uncertainty in, in this context?

Todd Jason: Yeah, I love the way that you tee’d that up because when you’re talking about reinvention and reinventing yourself and your career. You have to look at it from two standpoints. Number one, yourself, like who are you? What are the choices that you’re making? What are your interests? What’s the trajectory that you’ve been on? And how can you make decisions that are aligned with the things that you like to do? The things that could make yourself money, where you could find success, but you also have to look at that other part, which is the external. like What environment are we in? What world are we living in? What are the rules of the land?

Right? And so when you talked about the previous generation, they were working under certain rules, that, you know, may or may not exist right now, but I’ll tell you this, in 2026, going to that conference with 4,000 people, like big business leaders were there, like top people from companies, government officials were there and they would get on stage, and it’s all about AI right now. Okay? Like AI was the topic of conversation, and I think it will be for the next couple of years because it is, without a doubt, radically transforming the way that business is being run in our country and around the world. This is the biggest change, maybe we’ve ever seen. Okay. Like I was around in the first internet bubble, Chris, you know, I worked at DoubleClick for four years when the internet came around that changed everything. This is potentially even bigger. 

Chris Thide: Oh yeah. 

Todd Jason: When we talk about uncertainty and you talk about the external environment, what I heard at the conference was no one knows where this is going. Okay. And everyone is getting up there trying to give their 2 cents about what they’re doing as a company, what they’re doing in their roles, how they’re trying to navigate change, like how they’re trying to integrate ai, like all these things. But what I loved about it is everyone was honest, right?

Everyone was like, we have no idea what’s happening. I mean, this is literally what they were saying, we don’t know what’s happening. And the challenge from a corporate standpoint was really interesting because you have leaders, CEOs of companies that are trying to move really fast to capture the lightning rod of AI to streamline their workflows, streamline their processes, streamline their workforce, right?

Like get more profit for less money spent. Like all these things that like CEOs are interested in doing in our world. And you have people that work for companies that are now being trained on AI tools and integrated into what they’re doing to be more productive and effective. And it’s very challenging because people have resistance to that. Just obviously adopting a new technology that is changing every day is really hard. But this is also unique because Chris, AI tools may very well be the thing that replaces their job, in a month, in six months, in a year. So there’s resistance on many levels.

And you know, this conference was all about like HR leaders, that’s what Transform was. It was all the top HR leaders, chief people officers, and so they’re dealing with these challenges of needing to push AI through and massive resistance from people of adopting a technology that is just rapidly changing so fast.

And also understanding that these technologies may replace their jobs. And by the way. I was very popular at this conference, Chris. I was actually asked to go there by one of the organizers and they hosted a dinner for me to talk about career reinvention. And everyone was coming up to me because, you know, when I talked about the idea that everyone has to be really smart about what they want to do in the future and the decisions that they make. these leaders would come up to me in a breakout and be like, Hey, I need to talk to you. Because they’re also not sure about their own own jobs. 

Chris Thide: Of course. Yeah.

Todd Jason: I mean this is just what’s going on. So I wanted to start, and I think we wanted to start season two, just with a very honest assessment that this is a very uncertain atmosphere right now.

Like the external part of reinvention is very uncertain. Okay? And we could talk about it, we’ll bring people on this season to talk about it and we’re gonna dive into AI. We’re gonna do more of that. And I think we also want to take a stance of, the inner personal part of this. What do I need to do? How can I figure out my own future? How can I find my little island of success? How can I figure out, a way to establish myself entrepreneurially or doing fractional work, or even remaining in a corporate environment where I’m still relevant and succeeding. But what do I need to do? And when I say I, Chris, I’m obviously talking from the viewpoint of our listeners.

You know, people that are sitting here be like, what am I getting out of this podcast episode? And right now I think this is, okay, I need to navigate uncertainty. I need to become a master at it. I need to figure out how to make smart decisions as myself because the environment out there is so wonky.

It is changing so fast and spending any time trying to understand that and play with it is almost a moot point. 

Chris Thide: Yeah. Oh man, there’s a lot there and, and then I think, you know, again, like you said, you were in the.com boom, right? And that was an absolute sea change, exponential doesn’t even begin to describe the change that that made. I think the thing about AI, or whatever we call this revolution that’s happening right now is, we really don’t know where the technology is actually gonna go, but everyone’s already acting like it is a 100x event compared to the Dotcom change.

And so the fact that everyone’s already acting like that sort of makes it so. It kind of doesn’t matter whether the technology actually pans out or not, because the CEOs and the people who have all the money and who are making the hiring decisions and changing the directions of these companies are acting like it’s fait accompli.

To me, when we talk about uncertainty, right, I just wanna remind people, this is my orientation and I know that a lot of our listeners probably have this orientation. When you say the word uncertainty, to me, there is an implication of fear I don’t know, monster under the bed, monster behind the closet, whatever it is. And I wanna remind people that uncertainty is also a necessary ingredient in opportunity. And just make sure that we are looking at this through that lens, because I know there are millions and millions and millions of people out there who feel stuck in a corporate job, in whatever role they’re in and in your life, feel stuck.

And the thing that’s keeping them stuck, or part of what’s keeping them stuck is the idea that while I’ve got this certain thing, I don’t want to jump out of the frying pan into the fire. And it’s like, it’s not that certain. So now we’re poking a hole in one of your core arguments as to why you need to stay stuck.

And I think if you take this on in the right way, that can be a very freeing notion and thought to say, actually, if the rug’s gonna get pulled out from me anyway in three years or six months or tomorrow. Maybe this is the time I go for it.

Todd Jason: Yeah, I love this man. And look, I think we wanna dive into some tactics about how to navigate uncertainty. ’cause I think we’ve talked a lot about that. We’re dealing with it ourselves too, right? Like you and I have uncertainty even in our own business, which is fun and beautiful and scary and challenging.

I mean, we’re living reinvention, but I also wanna just take you back to something else that I think is really relevant that I saw at the conference. Okay, and this is really interesting. I think it was a surprise for the people that organized the conference, that tells you how much career reinvention is like the conversation right now.

Okay. So the conference officially started on Tuesday, but on Monday they had sessions. Okay. A lot of people did come Sunday night and Monday to come to these sessions, but at nine o’clock in the morning on Monday, so a day before the conference officially started, they ran a session that was run by a bunch of these HR leaders who had all left their corporate jobs either by being laid off or they just left over the last two years. To start consulting fractional work, social media, influencing one of them is doing that. And they had five of them run a three hour workshop where they literally got on stage and they were talking about what they did how they navigated the sea change, you know, of moving on from their nine to five W2 situation. And the reason why I’m sharing this is that they had a little breakout room scheduled for this at nine o’clock in the morning, okay, the day before the conference started and it to say it was standing room only. You couldn’t get in. I got there really early ’cause I wanted to do a little networking.

No one could get in like everyone wanted to come to this thing. And everyone that I talked to was talking about that session because these five people did a great job. They were talking about everything that we talk about here. They were talking about taking the risk of getting clear about what they wanted to do.

They were talking about navigating the emotional mental turmoil of getting let go or leaving and like, how do you actually do that? How do you build resilience and strength? You know, when you’re feeling bad or disappointed. How do you have conversations with people in your family? You know, how do you start to use your network? Everything that we talk about in our workbook, actually they ran through the workbook, that we

give on our website 

Chris Thide: How dare they Todd, that’s our workbook. 

Todd Jason: Yeah, but I was sitting there like smiling. I’m like, oh, these people reinvented themselves. 

Chris Thide: It’s amazing.

Todd Jason: And there’s five of them that all did it in different ways. Like, maybe two or three of them basically turned their W2 into fractional work and successful coaching businesses or consulting businesses and some of ’em doing coaching, two of them were doing things completely different and they were basically saying, now is the time that you gotta follow these threads.

You gotta explore different things. You gotta open up, and explore, you know, a portfolio career, you know? And you gotta reach out to people and you gotta be humble. Like all the things that we say in this podcast, everyone’s sitting there like, that’s how

I picture our podcast, 

Chris Thide: Yeah. 

Todd Jason: Opening that door, that conversation, because if you’re listening to this, it’s not just listening to two guys yap and talk. It’s like, what do you need to do to get out of your own way? What do you need to do to start exploring these options now? Don’t wait for the SHIT to hit the fan. Be proactive no matter where you’re at, and go for it even harder.

And explore and be creative and even have fun with it, right? Like the idea of having fun with this exploration as opposed to it being really stressful is a

big thing that all five of them said. So I just wanted to to bring that in Chris, because 

Chris Thide: Oh yeah.

Todd Jason: Reinvention was there. Like this conference was reinvention, you know?

And it was amazing to see. 

Chris Thide: That’s beautiful to hear that. I didn’t realize that HR leaders who are like,exemplifying it. They’re living it, they’re living the reinvention. The energy around it is so,woven through the culture right now. And I think, this is such an opportunity for people to examine whether the story they’re telling themselves really resonates with what’s happening factually in the world and in their life and in their career.

and I also think, when we hear about. These leaders that are uncertain, right? the rest of the conference, the people who are sort of like not knowing the direction where things are going. First of all, I think that there’s a lot of courage in admitting that, as leaders in the corporate world. I’m encouraged to hear that and to see that, right? Because that was not always my experience of corporate. But I think that that is also just a call for people who like might wanna stay in their current roles or grow in their current roles or face the fear of AI coming or whatever it is.

Now’s your time, I think, to speak up and to step up and to take things on It’s kind of the lie is being revealed. Like no one knows the answers here. So like it is an opportunity to distinguish yourself even if you wanna stay in your environment. So I think the general theme is like, take it on.

Do not hide from it. Do not pretend that the wave’s not coming. Do not put your head in the sand and hope it doesn’t hit you. Take it on, get into it. If you wanna leave your organization, if you wanna do something new, that’s a great opportunity for that. If you wanna stay in your organization, maybe you can become a thought leader by really diving into this thing and taking on the future, and taking on the opportunity side of uncertainty, not the fear side.

Todd Jason: Chris, I gotta tell you, everyone I talked to said, and this is the line that everyone’s using. AI’s not gonna take your job, but somebody who knows how to use AI will, this is like the line of the culture 

Chris Thide: Yeah. 

Todd Jason: right now, and like everyone’s saying it. And I gotta be honest, man, like I’m gonna be a little bit snarky about it. I don’t know. It might be a line that’s being sold to people so that way they. Get tooled up to help the corporate engine continue to run 

I mean what is AI by the way? It’s an intelligence that’s evolving to do things that we used to do really well, and it’s not replacing humanity, but it’s replacing a lot of things that we have been able to do in terms of corporate roles.

I mean, This is very much what’s happening right now. So I don’t know if that line is still gonna be relevant in, let’s say three or four years from now. AI might replace jobs, you know, and so I think we just have to be realistic around it. Like

we just don’t know. Right. 

Chris Thide: Listen, I don’t want to turn this into the corporate procurement variety show, but in my 

Todd Jason: What does procurement mean? I

forgot. What 

Chris Thide: no one knows what procurement means.

Todd Jason: I just don’t know what Chris Thide did for a living before he met me. Something to do with, procedure procurement, is that the

same? 

Chris Thide: about in a warehouse. I think, I’m not sure he did something in an office. It is this idea of like, when I think about. Outsourcing when really companies were doing a lot of outsourcing, like American companies in particular, were putting a lot of jobs in India or Southeast Asia or wherever they’re putting jobs.

And there are people who here were like very resistant. Like, I’m not gonna share what I do because then they’re gonna replace me. I’m gonna like hoard this work and like not engage with this thing, ’cause then they’re gonna replace me. All those people got let go anyway. All of those people got let go anyway. And in fact, 

Todd Jason: Right. 

Chris Thide: some of those people got let go first because they weren’t playing ball. You gotta play ball. you’re not gonna beat the system here. This is a macro level global event that is going on. You are not gonna be the one who just somehow, yeah, like if you’re 66 and three quarters years old and you retire at 67, then fine run the clock out.

But like, you’re not gonna beat this thing, so if you can’t beat ’em, join em That’s a phrase I just made up. Right? You’ve never heard that one before. Right. So that’s what I’m saying. It’s like lean into this thing and don’t be thinking you’re gonna somehow evade it. Right? Because I’ve just seen that too many times and there’s too many technologies out there where I love the phrase people said, you know, it’s someone who knows AI is gonna be who replaces you.

Looks exactly the same as outsourcing looked. It looks exactly the same as the internet looked, where reports of all jobs being eliminated were largely apocryphal. There were plenty of jobs still that stayed around, but only for the people who really decided to like surf the wave as opposed to fight the ocean.

Todd Jason: I mean, it’s a fair assessment. And again, this may be different. It may be the same. I mean, there’s an argument to be made that AI’s gonna create more jobs. There’s a lot of that, going on right now. I mean, 

Chris Thide: It’s possible.

Todd Jason: Look, we will see you and I can conjecture about it 

Chris Thide: Yeah. 

Todd Jason: I do wanna switch gears a little bit because I want to talk about the personal side of navigating uncertainty.

Because I did have a lot of people at this conference coming up to me. and saying what are you helping people to do? You know, because is there an answer about what I need to do for my career going forward? And there is no one answer. Obviously there isn’t, you know, but it’s the conversation that matters. I was getting inundated with people, still, like emails are coming in, people that want to talk about this because there’s fear and there’s uncertainty. And I think you gotta begin, and this is my own personal viewpoint and I’m gonna share it with you and we’ll see if you resonate with this or not, but it’s not evading or running away from the actual feeling of fear and the feeling of uncertainty.

It’s, you know, you gotta start with sitting with yourself and allowing yourself to recognize the fear and the feelings that you have. it doesn’t mean that you fall down into some endless spiral of depression and, oh, woe is me and the world is ending. That’s not what I’m talking about. But give yourself some space to really understand what it is that you as an individual are scared of. What is it that’s coming up for you? And I told people like big corporate leaders, I’m like, take a day, take a Saturday, and get away from your family and just sit with yourself, go into nature, get out a journal, do some meditation like, really get in touch with what’s coming up for you right now. Because the world is spinning so goddamn fast. Everyone is caught up in the spiral. Like you could just see it at the conference. Everyone’s just spinning spinning,

and that’s the burnout. Like that’s creating 

Chris Thide: Yeah.

Todd Jason: all the burnout. And like the corporate structure itself is not going to change and stop people from getting burned out. It’s gotta happen at the individual level. Like you listener you have to stop and give yourself some space and time. We’ve talked about this a lot in season one, allow and reflect. Like give yourself time to understand what you’re going through.

This is a time to take space. And that is so counterintuitive to what you’re being told by our culture that you gotta move fast, you gotta pivot fast. Like AI thing is spinning people out. Okay. Like crazy right now, and we’re here to say, no, you have one freaking life. It is short. We are all dust in the wind. We are not gonna be here forever.

People listening to our podcast, probably around our age, mid-career, right? So let’s say we’re about halfway through this thing. This life, let’s stop, you know, and reflect and give yourself time to feel what you’re going through, okay? This is a time to slow down as a human, okay?

AI’s gonna run. It’s gonna go faster. The chips are gonna get faster, the information’s gonna get faster, the data’s gonna get faster, everything’s gonna get faster, but, the way for you to find fulfillment and happiness, my brothers and sisters out there, is to take control of your humanity and slow down, you know, and learn to take these moments in time to reflect.

That’s where your answers are. And I would say this to people, Chris and I gotta be honest. Like, people would just look at me like I’m crazy, ’cause no one is saying that, you know, I’m the only one Saying it. But then I could just see this relaxation come over them. Like, yeah, okay, you’re right. Let me just breathe for a minute. Yeah, maybe I should take a day off, you know, and just think about this and journal a little bit. You know, I could just see when I would say it. People, ah, okay. Yeah, that does feel good. And that’s actually, where we begin. 

Chris Thide: Yeah.

Todd Jason: Cause we can’t solve uncertainty. We can’t solve the speed of the world that we’re living in. But what you do have control over is your own orientation in your own way. 

Chris Thide: a hundred percent. the orientation of corporate behavior, in my experience at least, is so antithetical to what you just said, Todd. It’s always like rush, rush, like created urgency. I mean, this was a thing that drove me nuts was like, people are like, no, we need to get this thing done today.

Why do we need to get it done today? We need to get it done today. Okay, great reason. I really feel confident that we’ve gone through a smart process about why this has to get done today. There are benefits to urgency, first, movers, advantage, et cetera, but like there’s a lot of like false urgency built into the system as far as I see it.

Also just in terms of if we look at what AI can even do right now, do you think you’re gonna outrun it? Do you think that if you keep just moving as fast as possible, you’re somehow gonna keep pace and be ahead of the game and like, it’s such a multiplier effect of what can be done, that to me, I think of it as like there’s so much tactical advantage in like taking it slow, being clear, making good choices, and then you can wield your little AI army or whatever you want to do to do the part that goes a gazillion miles an hour. Go a gazillion miles an hour in the right direction because you’ve taken the time to calmly contemplate and made a good decision as to where you’re going with it.

Still in the spirit of experimentation that we talk about, right? But like not running 5,000 experiments, pick the best three.

Todd Jason: I wanna give you an example ’cause I’m at this conference, right? And that conference was obviously really good fodder for you and I and reinvention. This is a good place to be to talk about reinvention. ’cause this is like the conversation, in my opinion about like, what’s going on in the world. And I felt that energy of like, oh, I need to meet everybody. you know, I had that, my own energy of of like, oh, I gotta take advantage, And I caught myself, you know, so I’m going to share with you like, my own way of doing this. Right, you know, in the middle of the day when like, all the breakouts were happening on Tuesday the first day. So a lot of people were there. The conference hall was crazy. You know, there’s a lot of people everywhere. There’s breakout sessions, everyone’s like doing stuff, everyone’s got their tags.

Everyone’s like, you know, busy. And I’m like, I’m gonna allow and reflect. I’m gonna take my own medicine. And I sat there in a chair and I just observed. I watched everybody I just got into a meditative moment by myself, not doing anything, but just calming my nervous system down, you know, just to like be present and like trust that whatever’s gonna happen at this conference is gonna happen at the conference.

Like I can’t really do anything that much about it. You know, I can push and try and all that, but I’m gonna take this other approach, right? I’m gonna actually just allow and reflect and sit there. No joke. I’m just sitting there and these two women come up to me and they’re like, what’s your story? You seem very at peace. That’s what one of them said. She said, you seem very at peace. You know, I’m actually just, sitting here, I’m observing like the craziness of this and AI and we started talking about the conference. They asked me what I do and I said I do coaching.

I’m an executive coach. I have this company called Reinvention about career reinvention. And of course they’re very interested. They’re like, oh my god, what’s that? And so we just got into this whole conversation that was very real. You know, it was like a very real conversation that now, we are talking next week.

You know, they emailed me already, or one of them did, and like, you know, there’s gonna be an opportunity to maybe work together to help some of their situations in their company deal with the workflow and the workforce that they’re dealing with. So my point is that, something really good might have happened by me just sitting there, And being at peace and relaxed and calming my nervous system. And again, I get it, I know what I’m saying here is so against the grain of what everyone else is telling you to do. And there’s fear about being left behind. Like I am not naive to this. Okay? But it’s the way, it’s gotta be the way, because otherwise you’re gonna get spun out. 

Chris Thide: And I say, I think what you did there, which by the way, I just want everyone who’s listening and watching to realize that during that story, the image I had was Todd sitting in a lotus pose, levitating two inches above, a Ea mes chair. 

Todd Jason: I wasn’t, I was in my little button down. I had my little coffee, I was normal

Chris Thide: He was corporate. Okay, good. No, but in all seriousness, what I hear though, it’s like. rather than being transactional, you were being relational. You were enabling a real conversation to happen by just being a human being in the moment.

And like,it’s so cool that you like caught yourself right and said, Hey, I’m like not gonna get caught up in the chatter of this room. I’m gonna observe it and be on a higher plane from it in a sense. I think that’s a thing that, that’s a really good tie into what we’re talking about here, where we talked about uncertainty, but we also talk about like identity, right? We can talk about the fact that it’s not being so frantic about how do I solve this right now is what allows you to have the energy to be open to building the bigger, longer term relationships and connections and unexpected connections.

that are actually what’s gonna help you figure out what’s next for you. 

Todd Jason: Yeah. I love that, Chris. Man. when you said relational and not transactional, this is another way to slice and dice what we’re talking about here, about how to navigate uncertainty, okay. And the conversations that I had at that conference were just very real. I just showed up being very authentic, vulnerable, like I don’t have all the answers.

You know, I, I talked about what I did. I asked questions for people, and I connected with people. I didn’t need to connect with a thousand people. I needed to connect with a handful of humans that maybe I end up working with or I can help in some way, or maybe they can assist us or me, who knows, we’ll see.

The answer right now. Is to go back into the relationships that you have and build them and just reaching out to your network, you know, and having conversations and being vulnerable. Like If you don’t have all the answers or you don’t know what’s going on. I think on LinkedIn, all the dms that, people are trained to send out, they’re very like certain, there’s a lot of certainty like I’m doing this and I would love to do this for you.

That’s not working. 

Chris Thide: Yeah. 

Todd Jason: You know, like this is a reckoning, for human beings in a lot of ways. And it’s agood reckoning if we look at it that way, where we could say, all right, let me, let go of all my ego, let me let go that I’m the one, I,I have all the answers. I don’t know, but let me reach out to some other people and just have those types of conversations. You know, and I think the most successful people do this naturally, like Bill Gurley, who we interviewed in season one, right? This is a billionaire that we interviewed. He has that energy, doesn’t he? He’s just like a beginner mind just like the way that he like talks about AI, he’s like, just curious.

For him, that conversation got so juicy when we talked about building a membership program for what he’s doing. Like tell me more about how you guys do it and what you guys know. ‘Cause he’s curious and he wanted to know, and he shared with us pretty intimately after the conversation ended about what he wanted to do and what his vision was. I don’t think that was his plan, but we connected with him, you know, in a human way and like he felt safe to share. The point is that it’s the relationships that win. You know, reinvention is a time to reach out and be authentic, and just connect with people. And also like developing the ability to listen to others. You know, and it’s not just about you and what you need, it’s also about like really listening to what other people are going through.

Like there’s your magic, there’s your juice. Like AI’s gonna come in and replace a lot of stuff. It’ll never replace the need for human beings to be connected with each other, that will never go away. That is wired into who we are. So start playing that game more, right?

Don’t become AI, become more human. And I think that is eventually what will end up winning. 

Chris Thide: I love that you brought up Bill Gurley. ’cause I was thinking about him and that conversation we had with him recently where it’s just, you know, he’s just happened to be interested in venture capital. It’s not like one of those things where he was like, I must be a venture capitalist because that is a way to make a lot of money.

Like I really authentically believe that that was the thing for him. He was fascinated by it. He just like the way all the mechanics of it work in the markets and helping new businesses come to the market. And that idea of finding your fascination, following your fascination, on some level, I feel if you’re following your fascination, if you’re true to who you are and what you really want to do, and that’s the way you walk through this life and you connect with people genuinely, and you’re open and curious and listening, you can’t go wrong. You know? I don’t know that that turns into a $200,000 revenue business in year one or whatever it is, but like if you like, let go of all that and you just actually are allowing yourself to have that genuine human, curious experience, like that’s life. That’s beautiful, right? And 

Todd Jason: 

Chris Thide: good things are gonna happen and that’s the kind of uncertainty that I wanna operate in and wanna have people think about is that that’s the uncertainty of like faith and belief that, hey, if I follow what I feel.

It’s gonna work out for the best.

Todd Jason: It’s also exploring the different angles of who you are as a person. You know, at the conference, at the dinner that was hosted for me by my friend at Sequoia you know, I was around a bunch of HR leaders and there was this one, HR leader, Kate from Morning Brew who maybe we’re gonna get on the show.

She has a podcast as well. So Morning Brew’s a big deal, right? They’ve been around for a while and she is awesome. Like Kate is a firecracker. She was amazing. We totally hit it off. And, You know, we were talking about reinvention and you know, all the things. These people are all like very successful, they do a bunch of different things. And then at the end of the conversation she told me surreptitiously that she also like does some social media influencing. She has like a TikTok account that has like 75,000 followers and like she posts all these things that has nothing to do with her work. And I’m like, there you go. It’s like funny, but like she loves doing it. And That to me is reinvention. And it was funny how she wasn’t wanting to share that at the big dinner with all these other HR leaders, but then it kinda 

Chris Thide: Yeah.

Todd Jason: came up and everyone was like, wait a minute, you’re an influencer. Get this one of the other, girls at the table, like they didn’t really know each other even though they’re in the same field in New York, but she’s, oh yeah, I follow you. I love your stuff. That to me was a reinvention conversation. Like people exploring different expressions of creativity. I had interviewed Bill Burnett from Stanford a while back and I love that conversation ’cause that’s what he said. He’s like, look. The way that the world is changing is that we’re gonna get back to, being creators in our life.

We’re gonna get back to doing the things that we love, following our fascinations. And eventually, somehow the world will catch up and economies will shift and culture will shift or like that will somehow be a way that people end up thriving, you know, a new way of thriving. And reinvention is a conversation that can help you explore that.So the message to me is open up your pathways. Like network with people in authentic ways. Do the inner work, sit with yourself and feel your own fear. Like allow yourself that beautiful ability to feel what you’re so scared about and what makes you so nervous.

This is the time to do all of it, you know? And then to go out there and be courageous, you know, in the world and experiment with new things. And to me, that’s why I love this conversation, Chris, like I could talk with you. All day about this. Pick your brain about reinvention. Hopefully we’re motivating people to get up off their butt and try new things and, you know, go for it. But I dunno. Just love it man.

Chris Thide: Yeah, it’s a perfect time. I mean, I think the fact that you went to that conference and you validated a lot of the conversations we’ve been having individually of: This is a moment, this is a cultural moment for reinvention, and I’m happy that we are, we’ve already started this conversation and we’ve talked for 30 plus episodes about it, and we’re right in the moment where I hope people who are listening are taking this seriously. Like this could be the opportunity. You know, if you’re midlife and you’re like, Hey, I got 40, 50 years left of this thing, what if that’s gonna be even better than what you’ve gone through so far? And this is a perfect moment to start to take that action to say, let me figure out what that could look like. Let me get that clarity. Let me dive into this. Let me take this on. We’re so excited to be prompting in that thought process and helping people start that journey.

Todd Jason: Boom. I love it. And by the way, if you’re listening to us like, please subscribe to this podcast, follow us along. We do two episodes a week. So we have a lot of conversations. Chris has brought in a couple people that we’ve already interviewed for season two coming up. These are people that have reinvented themselves in very unique and creative ways and it’s awesome hearing their stories.

Like that’s a big part of it. Hearing what other people did. People that left corporate and all of a sudden are opening up like creative shops, retail stores even that you think could never be successful, like massively successful. Like those are the stories that we wanna be bringing on. And other people as well thought leaders, you know, that are thinking about the future of work, right?

And so please subscribe, follow us along like this is an important conversation. the point of it. It’s a conversation that we all need to be having and you know, definitely check out our workbook at our website as well. Chris and I worked really hard, it’s a beautiful piece of work that can help you think about your future a little bit differently than maybe you are now. Breaking down your network and your finances, like even tactical stuff here, getting clarity, making a big vision like the workbook is amazing. It’s a really good place to start your own process. And man, this is it, right? We’re in season two and we’re gonna keep rocking this conversation and keep going. And happy to be on this journey with you, my brother. 

Chris Thide: We got a lot of inspirational yapping to come folks, so stay tuned. 

 

 

 

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