If you’re feeling stuck in your career, this episode might be the wake-up call you’ve been waiting for.
Sara O’Connor is the definition of a modern Reinventor – former attorney turned full-time artist, poker industry leader, writer, and entrepreneur. In this conversation, she shares how she walked away from a prestigious legal career, navigated burnout and identity shifts, and built multiple creative income streams on her own terms.
This isn’t a “burn it all down” story. It’s a masterclass in Strategic ReInvention – making a plan, running experiments, and betting on yourself before you feel fully ready.
We dive into:
- Why most people stay stuck (and how to break out)
- The financial reality of reinventing yourself
- How to test a new path without blowing up your life
- Navigating identity, fear, and starting over
- Why ReInvention isn’t one move – it’s a lifelong mindset
Sara also opens up about neurodivergence, entrepreneurship, and how embracing who you actually are can unlock entirely new paths.
If you’ve ever thought: “How did I get here… and what do I do next?” – this episode is for you. If this conversation resonates with you, visit ReInvention.biz to explore our guided workbook, learn more about us, and start creating what’s next!
**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
Sara O’Connor: What was kind of the aha moment for me, my very first show was at a church garage sale. Okay, it’s not prestigious. I was just like, let’s just go and make some connections. And I think I sold a $75 piece and booked a $100 commission, and that was a huge success.
Todd Jason: Chris, my brother, big day on reinvention. Who do we got? What are we doing?
Chris Thide: Todd, my man, we have got a real life Reinventor I’m super excited to talk to today because she is a serial reinventor. I mean, she defines reinvention. She was a lawyer, she’s an artist, she’s a poker player, educator, writer, advocate. And you know, yeah, people are well-rounded, but like, no, she’s doing these things for a living and she’s gone through it like sequentially, multiple reinventions.
She’s got a really great story and we’re gonna let her tell it. But first, let’s introduce our guest, Sara O’Connor. Welcome to the Reinvention Podcast. Thank you so much for being here with us, Sara.
Sara O’Connor: Hello gentlemen. Hello community. Let’s prepare to change our minds for the better.
Todd Jason: Yes
Chris Thide: I love it already Sara thank you. And Sara, just so you know, I heard your story on another podcast and it was about people getting unstuck in their careers and the beginning of your career story felt a lot like mine, right? Except you got out a lot sooner. Like I stuck around for 20 years and just kind of, you know, grinned and bore it. Right, but you got out pretty early. I will talk about, I think you liked what you did, maybe more than I liked what I did. You excelled at it, but it was maybe just the structure and rigidity and top down and maybe some oppression from the top down in the corporate structure is what got to you.
Sara O’Connor: And that’s kind of the nature of the beast, unfortunately. But when you have an entrepreneurial individual who’s very creative and you kind of don’t let them spread their wings, they’re eventually gonna fly somewhere else if they’re smart enough, in my opinion.
Chris Thide: For sure, and that’s exactly what I sensed and heard from you is that I think it was a matter of time in a sense that you were gonna have to come outta your shell, but I wanna start back in the shell, right? Like, let’s start at the beginning.
Sara O’Connor: Yes.
Chris Thide: And by the way, I, I feel like I emulate you a little bit and maybe I can be inspired by you because I felt a lot of pressure to like go do the quote unquote right thing. Was that kind of the place you started your, initial career from like the right thing to do? Or how was that?
Sara O’Connor: It was really interesting for me, so like, let’s go all the way back to college. Where I, like many people, had some favored things, but not necessarily sure how to turn it into a career. I in fact, even considered going to art school. I was always artistically inclined. I thought about being a ceramicist. If you go to art shows and you see potters, please thank them because that lifestyle is absolutely brutal on the body and the mind.
So I decided that lifestyle wasn’t for me, but I didn’t know what to do with myself. I did a lot of different clubs and extracurriculars, but nothing felt right for the forever future. And so my roommate just happened to be studying for the LSATs. I had just happened to do mock trial back in high school. I just happened to realize that the job market was absolute shit. More so for my stepbrother who was a few years ahead of me. ’cause we’re dealing with the early two thousands and it was just atrocious. And so I thought, well, I love school. Let’s try law school. I did not do too well on my LSATs, I think I did something like 154. And if you’re in the culture, that’s good enough to get into some schools. But not good at all. But I ended up doing extremely well in law school.
I was second my first and second year of law school, so I got my second and third year paid for through scholarship that I earned. I did not expect that at all. You always hope that you’re a smart cookie, but to kind of do better at each level of education was such a blessing, because by the time my husband and I thought it was time for me to get out of law and to do a move for his job and potentially my new artist’s job. It was an incredibly invigorating ability to be able to say, I’ve actually paid off all my law school debts because I didn’t have as many as the average student.
And I think, being shackled by college debt, being shackled by graduate school debt, that really puts us in a hole early on to just become wedded to golden handcuffs that don’t serve us well as people.
Todd Jason: Mm-hmm. Yeah. Well said I gotta say that, I almost went to law school, you know, and for some reason I just didn’t. That’s where everyone thought I was gonna go. So such a great story that you started and you could kind of almost see, it just kind of happened, right? That this is where my life went, and this is the situation for so many midlife reinventors right now.
Sara O’Connor: Yes
Todd Jason: people are like, how did I get here? Okay, things happen and here I am, and now I have this house and this family, or these situations and this money and this 401k or whatever it might be. Now I’m not really happy and the world is changing and now I’m sitting here like, what do I do? Right? So, l et’s talk about your reinvention a little bit. So now that we got you into law, you
did well and then it sounds like you started to think about making some shifts, you know, a little bit earlier on. Walk us through kind of what happened, and how you started thinking about, and this idea of maybe changing or exploring other options dawned upon you.
Sara O’Connor: Sure. So the law firm that I worked at was one of those big time international law firms. It was huge, and while I enjoyed a lot of it, one thing they don’t teach you in law school is how to be a good manager. And while I had a few good managers that I loved working for, genuinely loved working for, they didn’t have enough projects for me, and I was so low on the totem pole, I wasn’t yet able to bring in new clients to an international law firm because I was still a baby attorney.
Right. I only worked in the legal firm for about four years. And that’still quite green in the belt, and so while I did have some excellent mentors, and excellent managers. I did have a few managers who were not good matches for me, including one who pursued me in a way that was unprofessional and really affected my mental state of mind to the point where it got so intense, I actually went on medical leave. You know, I, I don’t know if this resonates with you two gentlemen, but I’m sure it resonates with a few people in your audience. My eye would twitch from stress. And it wasn’t necessarily from the bad manager. It might’ve been my billable hours X, Y, Z, whatever it was.
My body was genuinely having a physical reaction to the constraints that I was under, and it just wasn’t good for me. And so when I was on medical leave. I decided to play with my husband’s paint set. He’s not an artist by any stretch of the imagination, but we just had some paint laying around and I remembered back when I was a child, I used to love playing with Perler beads, which is those tiny little multicolored plastic beads that you put on a little design and then you iron and you lift the paper, yada yada.
Well, I’m neurodivergent through and through and have been since a very early age because what I would do is I would take thousands of these beads, mix them, sort them, mix them, sort them. And I thought, well, that’s kind of silly to do that as an adult now. How can I make that permanent? So I started doing pointillism, which is painting by tiny dot.
And now if you look behind me, I do big, big landscapes, very abstract, very colorful, very, very heavily textured pieces. And it’s developed over years of practicing with my art. And so, to make a long story short, my managing partner at the time. Pulled me into his office and he said, well, Sara, I know you’re starting to sell your paintings, and that’s all well and good, but we want you to be a lawyer 24 7.
Now, were there male colleagues who had side hustles and were allowed to have side hustles?
Chris Thide: Yeah. Right.
Sara O’Connor: Was I allowed to have a side hustle? No. So my husband and I basically said, this is an untenable situation. He’s been courted by a big time business in another state. What if a year from now we get our finances in order.
I reinvent myself as an artist. Try it out because it had always been something that was in the back of my, buffer just constantly part of my identity. And then we could focus on his career leveling up. So it was kind of a win-win for both of us, but it took about a year. And so for people who are listening, you may feel panic and constrained and frankly kind of fight, flight, or flee in your situation.
That’s normal. That’s okay. Accept yourself where you are and make a plan to figure out your life moving forward. Do not act rashly, do not act emotionally. Act with foresight as to who you are as a person. That would be my advice from lived experience.
Chris Thide: I love that Yeah And the way you tell your story there Sara you know, it’s, you had a conversation with your husband and you guys thought about, okay, how can we play this out? And what I hear is you say. Oh, I’m gonna take this as like an experiment. Sounded like you were already selling pieces at that point right? And so you had some proof, but then you’re like, all right, let’s, see what a year looks like on this thing. Like, let’s lean into this thing.
And that’s something that we talk about that all the time with Reinventors and the people who are listening is. Let’s run an experiment. Let’s run an experiment and gather some data and see what we find. And now I think what you found was that you had a market for this stuff, right? So that’s a really good thing.
And by the way, a terrible situation that you describe in, in the corporate law setting where they’re like, discrimination and the way that they approached that and kind of didn’t give you the same opportunities as the men might’ve gotten, that’s just bullshit.
Sara O’Connor: Yeah.
Chris Thide: But have you ever run the counterfactual of, in a way the ironic good thing is that they kind of pushed you to the brink to say, oh, you kinda like forced me to make this decision in a way that was the right decision for me.
Sara O’Connor: Yes.
Chris Thide: If you had been caught in the middle. Have you ever thought about that where like, what if they were like, cool with it and just let you roll? Like, would you have stayed in law five more years or.
Sara O’Connor: I mean, that’s the fascinating thing. We can play fantasy land, I have no idea. Because I think what also resonates with your audience is the money is hard to walk away from. The title is hard to walk away from. It’s so ingrained in us that I could have seen myself putzing around, certainly.
But the thing was, I reached a point where I realized, you know, I’m a lower tier associate right now, which is exactly where I’m supposed to be at my age. Do I want to be a senior associate? No, not really. I like managing people, but it doesn’t have to be in law. Well, do I want to be a first year partner? No. Do I wanna be a managing partner? No. Do I want to be on the board of this law firm making decisions on behalf of everyone? No. So what am I doing on this ladder? Get off. It doesn’t make sense.
I think it was inevitable. And I will say, I try not to be smug, but I did have a little smug moment when I was saying goodbye to all of my colleagues and there were several managing partners who said, I wish I had your moxie.
I wish I had your drive. I wish I had your talent. There were several people that I talked to that you could almost see them processing the woulda shoulda coulda in my own life for them.
Todd Jason: I love that. I mean, I think what Chris and I always talk about on reinvention and this concept of reinvention is that these conversations offer our listeners the ability. To dream and even just to get some internal permission to think differently their trajectory. And someone like you does it.
Like you actually literally cross the chasm and you do it. And you do it successfully. And we want to hear about the success of this. Chris, I think we want to get to what your business looks like now and all these other things that you did. Poker and all that, but let’s not get there quite yet because I’m just curious about the process. And you said a couple of things that. Really hit home for me that are very relevant to the reinvention philosophy that Chris and I have. Like we have a workbook that we tell people to take, you know, and a lot of the things that we do in the workbook, you said, right, like you talked about making a game plan, you had conversations with your husband. The money that’s hard to walk away from is much harder to walk away from when you don’t make a financial game plan that allows you to see some level of window or security by which you can explore these new options. So you did a lot of these things naturally, right? Like you had that conversation, your husband had a job, he was moving, you had a passion, you had art that was always interesting to you. You had an idea, like you had a bunch of these pieces. And then you kind of made the decision to walk away, right.
I think that a lot of what you’re saying also was your talent and also the circumstances that You set yourself up to be a successful reinventor, right? It
Sara O’Connor: Thank you.
Todd Jason: Wasn’t just random. You actually like did a lot of these things naturally, which is why Chris, I love that you met Sara and brought her on the show. ’cause it just corroborates a lot of the things that we talk about. Right? So here’s my next question. I want to hear your feedback on that, but I wanna lead you into a question of, when you started to explore art, you know, as a business, I want to hear about that as well. Like was what was it like? You have to sell and you have to market and this is a totally different thing than law. How did you go about figuring figuring out that new business? ’cause this is a big thing for Reinventors right now. It’s like they have the idea, but it’s also like, well how do I do it? Like, what do I do? Did you get a model? Did you like take a course? What did you do to figure out how to be successful in this new world?
Sara O’Connor: I tried a lot of different things. Some of them worked, some of them didn’t. I am very cautious about, artists in particular, buying classes from other artists who haven’t been in the game for a long time or who are just coaching to coach because that becomes their real bread source instead of actually creating the art and being in the trenches and doing it.
Your workbook, however, seems right in line with what you should be thinking about when you’re thinking about making the change. What was kind of the aha moment for me is. My very first show was at a church garage sale. Okay, it’s not prestigious. I was just like, let’s just go and make some connections.
And I think I sold a $75 piece and booked a $100 commission, and that was a huge success. The biggest differentiator for me was do people outside of my friends and family want my work? If yes, there’s something viable. I didn’t wanna interrupt you, but one of the most important things when you are going out on your own, and I’m doing this at another talk for another organization, is as much as we want to be entrepreneurs as Americans in particular, and there’s this very, like me, me, me, solo journey process.
It takes a bloody village. So like to the extent this podcast has a community, lean into that community. Lean into fellow entrepreneurs. Lean into fellow explorers and be not obnoxious, but open and loud about who you are. Because then like case study right here, you get invited to podcasts to talk about your dreams.
And talking about your dreams, whether you believe in manifestation or not, actually makes them more likely to happen.
Chris Thide: T hat’s so spot on I mean she’s basically reading the workbook out loud for us and I don’t even think she’s seen it. Todd you know why I wanted to have Sara on? cause I heard her and I was like, Oh my God. Like this is spot on. This is what we need everybody to hear.
And you said something that, I think is so important, Sara, that I want everybody to really lean in and listen when you’re launching your new thing. One, no putting on airs. Oh, they got a folding table at that church. I’m there. Two, once you make the first sale, like outside your circle of people who are doing a pity sale or whatever it is, once you make your first sale, it’s all scale from there. You have proven the case n equals one. Now just turn it into a thousand, 10,000, a million, or whatever it is.
And you got there because you are running it from an experimental standpoint, Right, So it’s like 175 revenue and the first church sale was not like a proof of anything besides I can do something here, right?
Sara O’Connor: I mean, that was less than my billable hour, you know what I mean?
For a whole day of work that was less than a billable hour. But that was my fricking billable hour. That was my effort, my revenue, my proof of point. It feels different when you have ownership over your own life. It just does.
But remember any entrepreneur who says it’s easier working for yourself than anyone else, that’s bs. Entrepreneurship is hard work.
Todd Jason: It’s a lot of work.
Chris Thide: Sorry Todd I just wanted to go down the road for a second ’cause I think this is the right moment to do it. And Sara, you can stop us if it’s not the right place to go. But mentioned neurodivergence
Sara O’Connor: Yeah.
Chris Thide: and in fact Todd and I were just recording an episode where we talked about this, where, you know, I have ADHD. There’s a spectrum we can talk about, but like, I think that. Todd does not, maybe he does, but like, not to the level that I struggle with it.
And so we’ve had challenges as partners and collaborators sometimes. ‘Cause I’m like not processing things in the same way I wonder both in the law world and in the entrepreneurial world, if you’re open to talk about it. Have you had to sort of assess or, or have you had to manage that or think about like, how does work work for me within the way I process things.
Sara O’Connor: You have to. Anyone who doesn’t is setting themselves up for failure. You have to have such a candid, and honest conversation with yourself. Consider frankly working with a therapist with it, right? Because some of these societal expectations are so ingrained in us, it takes extra, individuals who are outside of your circumstance to help you kind of see, how to reinvent yourself in a healthy way. Taxes is something I don’t do. My husband helps me with taxes. My mind just doesn’t process that way. To jump the gun, one of my best friends, James Cloutier and I have started a 501(c)(6) called Rail Bird Creations to publish news and to advocate in the gambling community with a focus on poker.
He’s our president. I’m the CEO. CEO creatively and like, how do we move forward? A president makes sure the ship can keep functioning.
Chris Thide: Yeah.
Sara O’Connor: Our lawyers had said to us, Sara, since this is kind of your baby from the jump and you’re inventing this, you’re putting forth most of the seed money.
Do you wanna be CEO and president? And you have to take a step back and go, am I capable of being president? No. Do I want this to be viable? Yes. That’s James’s strength. So we give James that responsibility and we give myself other responsibilities. you have to think about yourself very, very critically.
And I think one of the things I struggled with, is being honest about myself, about what I want for myself and what I want people to see when they look at me and think of me. And you have to be humble and you have to be willing to say, I’ll take the blow in order to have my dream come to fruition.
Because there is nothing worse in my opinion than keeping up with the Joneses in your own mind. There’s no one in there but you.
Todd Jason: I love that. I just have to say that, one of the things that a lot of Reinventors struggle with is identity. We talked about that I think even before we got on. This is a reinvention of your identity, Right. And a lot of people in corporate that are in jobs that either they’re burned out or they’re being challenged by potential disruption in AI or looking themselves in the mirror and are realizing that their current role is changing so fast, or they may have grown out of it.
And there’s a lot of stress and that causes, well, do I stay, do I go, do I stay in my industry? Do I fully reinvent and become an artist like you? I mean, this is what is up in the air right now. And I think this conversation
Sara O’Connor: For sure.
Todd Jason: Is just so relevant because you’re obviously somebody that’s crossed the chasm. But I do wanna ask you a couple of questions about your reinvention, right? Because you left a law career, you know, you’re a, an associate and you’re working your way up and there’s certain money and salary and status associated with that. And then you went to be an artist. Okay. And it looks like from what we’ve intuited here, that it’s not just art you’re doing, you’re also working in poker. You have an organization, so other things have grown out of your reinvention that I want to hear
Sara O’Connor: Yes.
Todd Jason: But I am curious about like the financial part because I think a lot of people are talking about, oh, with AI coming, there’s a big movement of people, leaders that are saying that there’s gonna be a resurgence in the humanities and arts and people making money doing stuff like what you’re doing. And a lot of people are like scoff at that. Like, yeah, right. Like, how is that gonna work? How is everyone gonna be an artist? I mean, this is just what
Sara O’Connor: Right.
Todd Jason: Thinking and I get it. It makes sense, but you’re somebody that’s done it. So talk to us a little bit about that. Like as an artist, somebody that’s working in the creative field now, coming from a very non-creative field in a sense in law, have you been able to make good money? Like how have you navigated the financial piece to this?
And with that, Sara, I would also, you know, maybe this is a second question, but how did other things grow out of your reinvention as well that are, related to or not related to?
Sara O’Connor: Yeah, it would certainly be a struggle, and I do not have any qualms about this. My life would be very different if I didn’t have my spouse along with me, because he is the main breadwinner. He gets the cake, I get the icing. So it’s what works for us as a team when you don’t have a team, that year long plan of escape that I had would’ve been a three year long plan of escape for me.
You just make it work. For me that last year of working in law was so much easier because I had a new goal that I was working towards. So even if that length of time becomes three years or five years, think about it like going to college again. College or your trade set or your skillset just becomes what you do on the side, and it might take you longer than it takes someone else. That’s okay. Like what you are building is different from what someone else is building. If I was born a multimillionaire, we might not be having this conversation at all. You know what I mean? It’s just, it’s different. Everyone starts on different starting points and we all end at different starting points.
So it works well for me because I have a partner that combined our finances make it possible. My business is thriving, but frankly, I’m done with outdoor art festivals. My husband was my unpaid volunteer who would help me set up and tear down and travel across the United States to sell my wares, and now I’m pivoting with my art business to make room for the poker and the writing and the authoring that I do.
Because that’s now my new passion. I know what it takes to be an artist. I did that for 10 years. That’s like my longest stint I’ve ever done with anything as a professional. Um, you know, I, as you guys had said, I taught for a while and loved that I tutored law students for several years. I loved that.
And so I’ve been missing the teaching and the writing that I got to do. Before, and I’m returning to that now. But now my lens focuses on poker and making the game fun again for people. So I’m kind of reinventing at the same time we’re having this conversation because literally the legal work is being filed for our 501(c)(6) now.
You know what I mean? So this is a very exciting time. I am trying to think. I had been a writer for a poker organization and when they had decided to sell their business, they cut my pay down because it was higher than anyone else’s. And they said to me, well, we’re now going to have more editorial control over what you write.
No you’re not. I will then do my own thing because I at least believe, rightly or wrongly about what topics should and shouldn’t be covered. So once again, I have set my sails, but again, it’s not alone. It’s with a community because no one can go it alone in my opinion.
Chris Thide: Absolutely. There is a through line and I guess, can we call Sara a re reinventor? Or a re re reinventior, or how many res can we get on the front of that?
Sara O’Connor: Yeah, it’s a few.
Chris Thide: But there is a through line and I’m gonna make a nerdy poker analogy, and you’re gonna check me if I’m right here. No, no pun intended.
Sara O’Connor: Oh, check is a good one, that was a good pun.
Chris Thide: No pun intended on check sorry we’re getting real, but what I think of sometimes with people who are contemplating reinvention. Like if I think about you’re in your law career and you’re like, Hey, I’m starting to sell some art. But like certainly at that point, your art was not replacing your salary. Right?
Sara O’Connor: No, and it, full candor, it has never reached what I earned as an attorney.
Chris Thide: But, what is the price we’ll pay to do the thing that’s in our heart and soul that we actually care and love? That’s a whole, you know, you could put a huge dollar amount on that, frankly, if you wanted to compare apples to apples.
But I think a lot of times people get hung up. In fact, I know, we know, Todd and I, we’ve spoken to people get hung up on this idea of, I make $150,000, I just gotta build my side, hustle up to $150,000 and then I’ll quit. And it’s
Sara O’Connor: Nope.
Chris Thide: And it’s like where are those hours gonna come from you human being? I’m foaming at the mouth to get to my poker analogy, which is, I think of the idea of the semi bluff. You don’t have the winning hand, but you have a hand that could improve to be the winning hand, and you act at the table as if you have the winning hand, you’re believing cards will come ’cause you’ve gotta draw in poker. But in life, what you’re betting on, and this is what I heard from you, Sara, you’re betting on yourself ’cause you’re like, I don’t know right now that I have the numbers to make it work, but I know that I will make it work and I believe in myself, and so I’ve got enough evidence here that I’m gonna push and go for it.
Sara O’Connor: Yeah, absolutely, and I think, the one thing we can be absolutely sure about is we don’t know if reincarnation is real. We don’t know if heaven is real. We don’t know certain things except that, I’ve got one life to live and I’m going to cram as much as I possibly can in my time while I’m here. You know, it is wonderful to me that I have created a legacy where some of what I’ve created will be passed down to family members. How long? I don’t know. My work could end up at Goodwill for some families, but at the end of the day, I have created a lasting impact for my collectors.
And in the poker world it’s hard to tout your own, successes because I’ve only been in the industry for about three and a half years. So again, I’m still a young scrappy buck in the game. But people have told me that I am making positive waves in ways other people haven’t. And so you have to believe in yourself, and I don’t know if your listeners know this player, but Phil Hellmuth, who is a world well-known poker player
Chris Thide: He’s a little bit of a cry baby when he catches a bad beat, yeah, yeah, all good.
Sara O’Connor: He shouted out one of my books on No Gamble, No Future, which is a very, very big deal, at least in the poker industry. And so that was again, a proof point for me that like, I’m not even in the bleeping room and I’m being talked about by people as big as him. I am on the right path.
Todd Jason: Yeah, you’re giving so much gold here, right? You know It’s really just a beautiful story and Chris, going back to what you said about she’s a re re reinventor, there’s a reframe here because reinvention doesn’t connote one move. Okay. It connotes a philosophy in terms of how you approach your life and your work and your money making, because a lot of people have been stuck on one conveyor belt for a long time, and it’s hard to get off that conveyor belt.
Sara O’Connor: Were conditioned to being cogs ever since grade school.
Todd Jason: We’re programmed to be on this conveyor belt. And now it’s like a lot of people are being forced to, whether by their own internal mental state or by society or AI or whatever to like, think about it. But the big shift is more away from I need to get on another conveyor belt. that’s my reinvention, more to, I’m an explorer of my own life, you know, and I’m going to try a bunch of different things and I know that I need to make a game plan and I need to create some semblance of security like you did with your husband.
And like, you do have to use your cognitive mind to make a game plan. But the shift isn’t to, I’m gonna find my next thing and that’s it for the next 20 years, per se. It could be that, but it’s more like I’m constantly looking at opportunities and exploring them. And there seems to be for people like you that I’ve been around. This emergence of life force that
Sara O’Connor: Yeah,
Todd Jason: when you’re living this way, you’re excited about your day, you’re creating, you’re free. There’s a
Sara O’Connor: I don’t get the Sunday blues. Monday at 7:00 AM yeah, I’m fucking ready to go. You know what I mean?
Todd Jason: This is such an important p oint, you know, because this is why we’re doing this we need to open up the doorways for people to think about themselves as artists, as creators, as explorers. And you need to have a workbook like what we have or have a natural ability to game plan and look at your money and look at your relationships and do all of those things, right? And I also just gotta say that I don’t know what you’re authoring, but I’ve interviewed a lot of people and I’ve been coaching for 20 years. You also have a real keen ability to motivate people on particular career reinvention, like I think you’re speaking very succinctly to like what we’ve been talking about and what I’ve been living for years, which is the actual art of opening yourself up from getting off the old identity and path to something new. You do it naturally and like I think there’s
Sara O’Connor: Thank you.
Todd Jason: another potential avenue for you there, like maybe working more with us or we do another interview, but I just think there’s something more there because. need that, and I think you.
have
Sara O’Connor: Yep.
Todd Jason: natural, powerful, and exuberant way to express it.
Chris Thide: I think that this is what resonated when I, when I heard you, it resonated so well for me is like, Todd and I are looking at reinvention as a mission from a sense of, yeah, we want to help individual people.
We want the people that are listening to be helped by this, but, for me on a deeper level, it’s like there are artists, there are creatives, there are people who have things inside them that they’re not bringing out into the world, I don’t wanna aggrandize it too much, but I guess I’ll go there. Like, to me it really is like changing the world. If we can help people to bring out what they’re suppressing and what their essence is, that they are holding down and waiting for the family to go to sleep so they can go fuck around on piano for 10 minutes at night. Like I want that shit out in the world from everybody. And I think that’s where your energy goes.
Sara O’Connor: I’m not beating around the bush. It is pure magic, when you help someone unleash themselves, when you help someone give permission to be themselves, it’s one of the most beautiful things you can do as a person, in my opinion.
Todd Jason: Yeah. And, and you’re doing it right now, like you really are doing it right now. So, I’m curious, like, so as, as a reinventor, as an entrepreneur, like how are you playing with AI? Like how do you hold what’s happening in that space?
Sara O’Connor: I really love using AI. Do I use it in my art business, like my painting business? No. Do I use it in my poker business, all the time? And I will say poker, Twitter had a lot to say about it. A lot of people were very, very, very upset with me, but it makes it stronger, it makes it more analytical. It makes me allow to do more with less time. And separate from article writing where I put now, you know, AI assisted, I use it when I’m starting to think, is this a good business strategy? What would be a PR backlash reaction? How do I deal with conflicting viewpoints on who I am as a creator?
I personally think AI is here to stay. AI allows you to reinvent yourself. Have a freaking chat with it, like literally have a conversation with it about, these are my skill sets, these are my desires. What do you think I could do next? What should I do next? It is phenomenal at helping you potentially map out that game plan that we were talking about.
What is your financial structure for the next three years? Here it is. What skill sets do I need to do to have a side hustle? What is that structure of the side hustle? Use it to structure your life. And create that game plan. You don’t have to create content with AI if you have a moral or an ethical conundrum with it.
You can use it as a kind of sounding board for what you’re hoping to create. AI is not the enemy. It is a new creative tool. Are you afraid to take a train or a car? Then you shouldn’t be afraid to use AI.
Chris Thide: The distinction that I like to make is that I think it’s such an incredible tool and I love how you, you said I use it as a, you know, sparring partner or a brainstormer. For me, when people fully outsource something to AI, that they sort of haven’t actually set anything up there.
That’s where it goes wrong, I mean that’s were you just get garbage in garbage out, or nothing in garbage out. But when you’re using it in the right realm I mean, even from a writing perspective, you bring in your idea and you load it all up, and then you use it to structure. For the way my particular version of neurodivergence works, that’s incredibly helpful because getting from, vomit draft one to final draft is where the whole thing falls apart for me. So if I can supplement that with the tool, but I love the fact that you are embracing it as any other tool, and we are 100% there on this podcast where anyone who’s listening, like if you’re not using it. What are you doing?
You gotta get in there and play with it, and you’re gonna find your way to use it. It might not be like what you see everybody else telling you that they use it this way or that way, but you really can’t ignore it. You have to get into that. You have to figure out what works for you there.
Sara O’Connor: And one of the most fascinating things is, is I told chat GPT, that I have bipolar disorder, and that means I can experience high mania, which is a glorious but dangerous feeling, and I can feel low, low, feelings of depression once when I was dealing with extreme backlash for using AI, and I was trying to kind of go back and forth with AI on how to kind of navigate this system and what my response would be.
AI even said, woo, that sounds a little, too manic, a little too spicy. Do you wanna cool that down? It can help you with tone. Think about this, paint a picture. You are finally ready to make that leap, and you feel like, I wanna kind of stick it to the man for a second when I draft that final email, AI will help you say like, ah ah ah do you, really mean to burn that bridge? And it’s incredible in that regard.
Todd Jason: I mean we’re totally pro AI here. I mean, not only is it not going anywhere, it’s probably the biggest technological shift we’ll ever see. The level of integration that this is gonna spur over the next 10. I have an 8-year-old kid. I mean, I can’t even imagine what her life at 20 is going to be like just like the way that we’re interacting with data and information in the world is gonna be radically changed. So, I mean, look, my dad is 82 and he never stayed on technology. He just like rejected technology and like, it’s not a great way to be.
And I think there’s a fine dance ’cause we want to remain human and we wanna like do our art and all that. like getting off of the technology train because we don’t believe in it, you know, or we’re frustrated or whatever is like also not a great strategy. So we all have to find our own way. But I think what we really wanna be doing here, especially for Reinventors, is use the tool. Like this is a tool that can help you get to your success faster in a bunch of different ways, so I love that you brought that in. By the way, I just wanna cap us off by saying, and I know you guys, we will give you guys the last word, but I’m grateful that Chris, you brought Sara on and I love hearing your story. I think we could yap for like another two hours and
Sara O’Connor: Oh yeah.
Todd Jason: get more energy like just hear more stuff about how you hold this stuff and what you’re doing. But it’s really impressive,
Sara O’Connor: I appreciate that.
Todd Jason: And like the way that you did it, it really is exactly embodying what we talk about on the show. And I think these stories are just so important, ’cause I got motivated a bunch of times on this call being like, oh, I need to do this. I need to think more creatively. I need to get more fearless in the way that, I’m doing X, Y, Z,
And I think that is the important thing. ’cause we all have the ability to reinvent ourselves. Every single person has the ability to make a change that’s positive for their lives and their family’s lives. Every one of you can make a game plan. Every one of you can get up and do something slightly differently. You did it. We’re doing it. Other people are doing it, there’s no time to waste. Like the world is changing very fast. Stop being stuck. Okay.
Make the choice to reinvent, and Thank you for being such a model for it. I really appreciate it, and it’s really amazing to meet you.
Sara O’Connor: Thank you so much. Ditto, ditto, Ditto,
Todd Jason: Yeah.
Chris Thide: That’s why we wanted to have you on here Sara, because I just know there’s people listening that are gonna hear that we heard it, right? We got the wake up call. We got that feeling, and just really, really important for people to be able to envision that possibility for themselves. And you do such a great job. I mean, your story. Again, I want to run through a brick wall right now, so I appreciate you, Sara. Thanks for being with us.
Sara O’Connor: Yeah.
Todd Jason: Amazing. We’re gonna have you back on I think. I think we gotta do another one.
Sara O’Connor: Yeah, I would love that. You know, if I can end on a cliche artist analogy, you are your own clay. You are your own canvas, paint and paint brushes. Everyone is their own artist. What are you going to create today?
Todd Jason: Boom. Let’s do it. Get out there, guys. This is your day. Let’s go. Thank you.
