Jeff Wozer shares his career flip journey from aspiring hockey play-by-play announcer to comedian to writer to speaker.
Ever wondered what it takes to leap from one career to another, chasing dreams and overcoming doubts along the way? Meet Jeff Wozer!
Jeff's career flip story starts with a dream of being a hockey play-by-play announcer, pivots into stand-up comedy, and then transitions into a fulfilling career as a speaker. In this episode, Jeff opens up about the challenges he faced and the doubts that tried to hold him back, all while emphasizing the power of believing in yourself and following your true passion.
Jeff’s insights will inspire you to embrace discomfort, take that leap, and move confidently towards your dreams. Don’t miss this inspiring conversation!
Episode Takeaways
Connect with Jeff Wozer
Jenny Dempsey (00:00.078)
It's awkward, you feel very vulnerable. There's gonna be a lot of moments like, what am I doing? But you just gotta have that belief. You gotta chase it.
Hello, Flippers! It's your host, Jennie Dempsey. You know, one thing I'm discovering with our career flipper community is that life isn't about just one big career flip. There are usually many flips along the way, and each flip helps us connect the dots, even if they don't seem related at first. In this episode, you'll meet Jeff Wozor, my friend and former colleague who's had multiple flips and some flops.
from comedy to writing to speaking. And through it all, he shares the importance of learning from each experience and believing in yourself. I'm super excited for you to hear his journey. Let's dive into the episode. Hi, Josh. Jenny, how are you?
Oh, I am. I'm doing fantastic. How are you doing? Thanks for being here on the Career Flipper. Thank you. I'm just honored to be a part of this, Jenny. I'm so excited for you with this podcast. Thank you so much. You know, we've known each other going on almost 10 almost 10 years at this point, working together back in the day at a content company. And, you we've actually never met in person. We've always worked, you know, remotely.
And I think that's so cool. Crazy, isn't it? When you pointed out that it's been 10 years and yeah, we never cross paths in person and here we've always kept contact and the magic of technology. I know it is. It is pretty wild what we're able to do with all of that stuff. I've just always been so inspired by you. When we work together and we chat about
Jenny Dempsey (01:51.82)
you know, the work stuff, but then we also would talk about the other things you were doing in your life outside of that work stuff, because that work stuff was just part time for you. you know, actually, can you just tell people a little bit about what you do right now and where you are in the world? I'm a speaker. I go around the planet keynoting on digital balance. Most people think, my gosh, you know, here comes some dinosaur going and tell us to throw our phones.
in the water and you know some kind of Luddite or it's none of that. Heck is amazing. It's kick -ass amazing but that's the problem. It's too amazing. So amazing we can't take our eyes off our screens. And I had my brain kind of hijacked by the internet where I now have difficulty focusing especially when it comes to writing and it pisses me off. And so that's why I began speaking about this because this could happen to me and all I'm trying to do is just raise some awareness. You know not
Again, not about throwing our devices away, but raising awareness, what we're losing in the process, our ability to be focused, our ability to be present, be more intentional. when we're in the moment, that's life's magic time. That's when we're kicking ass. That's when cool things are happening. So that's all I'm trying to do. So that's what I'm doing now. Yeah. I love that. I love that. And from just talking about how technology brought us together and how there is a balance with it and how you got to this point.
I'm excited for you to share your career flip story with everybody. know you're in Buffalo, New York. You just had some tornadoes, right? You're up there and - Yeah, it was crazy. We had a tornado rip through the area, one about three miles away from me. That doesn't normally happen for this part of the country, but I guess it was remnants of the hurricane barrel that came through here. Yeah, crazy.
Yeah, definitely crazy. I'm glad you're safe. I'm glad we're able to record this today and I'm just going to get right to it. Jeff, tell your career flip story. OK, I've got two to talk about. First one, the early part of my life. All my growing up all my life I knew I wanted to be, believe it or not, a hockey play by play now. So say believe it or not, because it's very specific. Now I didn't want to be football. They want to be baseball. Just hockey play by play radio.
Jenny Dempsey (04:09.262)
I love the sport, play the sport, and the idea of getting paid just to watch hockey every night appealed to me. So after I went to Syracuse University and after I graduated, oddly enough, the first job I applied for was as a writer for the David Letterman show. It had nothing to do with hockey play by play, obviously. And that was kind of like that little seed in my brain.
telling me, it's like, I'm not sure if hockey play by play is the career I really want to chase. Because as a kid, I was always the class clown in high school and college, all that type stuff. So I naively sent a resume. was like a movie poster. My resume was made in a movie poster. And I think I called it the unemployed graduate, a takeoff from the movie, The Graduate. And I had all these little funny quotes of people saying, he's unemployed, blah, blah.
And I'm just thinking, my God, Letterman's got to hire me just from this resume alone. And I had no credentials whatsoever outside of making classmates laugh. And it was just very naive of me. Of course, I never heard back from them. So I went into doing hockey play -by -play up in Vermont. And I was up there doing division one, division two, hockey play -by -play. And it actually went kind of well. I won an Associated Press Award and like, okay, my career path is going well.
And along the way, the radio station also hired me as a news director. And I unabashedly could say I was probably the world's, the planet's worst news director of all time. I was constantly getting in trouble for making jokes on the air. And there was just something inside of me. It's like, man, if I'm doing all these jokes, just something inside of me that's just telling me, come on, go for comedy, just pursue it, give it a shot. And I didn't know what to do. You know, I, not growing up in the Los Angeles area, the New York city area.
I had no idea how to break into show business. So I, after four years in Vermont, I quit and decided to move to LA to be a writer. That's all I wanted to do. I wanted to write. I had no acting background. That didn't appeal to me at all. And on my way out to Los Angeles, I stopped in Vail, Colorado, where my best friend was living. And he and I, best friends since we were kids, we were on the same ski team, went to college together.
Jenny Dempsey (06:27.822)
And I thought, well, okay, I'll spend three months in Vail, Colorado, and then continue on to Los Angeles. But if you've ever been to Colorado, it's a trap. Three months turned into 24, 25 years. I just got stuck in Colorado. So beautiful. So there I was after being in journalism and everything. Next thing I know, I think my first job in Vail is delivering pizzas. And it's like, how the hell did I go?
this happened. But while I was there, I noticed there was a TV show in Vail, Colorado. It was a locally produced show called Vail Valley Sunday. And they had a person who was doing a takeoff on the news, kind of like Saturday Night Live, trying to be, you know, and I was like watching this person, was like, man, I think I'm funnier than that. So one day I went to the producer of the show and I said, man, could I give this a shot? So she gave me a chance
it took off. You know, I was getting a lot of local press was doing stories on me. I had the owner of Vail Associates, George Gillette threatened me because I was making jokes all the time about Vail Associates. So I was like, OK, it's getting noticed. So it's like, maybe I could do this comedy thing. So that was also I was doing the career flip in a comedy. A lot of false hope when you're doing that. And so I saw that things were going well for TV shows. So I was like, man, I don't have to go to L .A. You know, I could.
kind of honed my act out here in Colorado. And then I spent a summer in Chicago, taking classes at the Players Workshop of Second City. And I kind of, you know, that kind of gave me some validation that could hold my own with other funny people. Moved back to Vail, Colorado, and I did a, it's like, well, they were doing a local talent show. And I was like, well, I'll try stand -up comedy. And it kicked ass. yeah, I didn't know what I was doing.
But it just got a lot of laughs and it's like, my gosh, maybe I should be a standup comedian. I'd never considered being a standup comedian. I always just saw myself as a writer. And then a few weeks later, there was a local club in Vail that was doing a professional comedy show. I knew the owner and I said, hey, do you mind if I do some jokes at the beginning? And the other comedian said, no problem. And that kicked ass.
Jenny Dempsey (08:50.134)
And then one of the comics who saw me, who was based down in Denver, this kid named Dave Booblets, he goes, man, you got to come to Denver and do some shows. I'll get you in a local club. was called Wits End outside of Denver and Westminster. So I go down there. I've never been in a comedy club in my life. I've never seen a live comedy show in my life until a weeks earlier. And so there he went on stage and just bombed. I just bombed.
But there was something about that where it wasn't like, I got to quit. But it was just like, I got to figure this out. And I did. I eventually figured it out, moved down to Denver, and it began touring full time as a standup comic. So that was my first career flip, going from journalism into standup comedy, something I never, never, ever considered in my life. And the fact that that first one that you did and you said you bombed and you kept going, like you took from that instead of saying, no, this is it. This is the end of the rope. You're like,
I'm actually going to learn something from this and do better. Like it didn't stop you. I think for a lot of people listening, sometimes we go into these new paths and if we don't do good immediately, then we're like, okay, cool. I'm going to do something else. give up. But you didn't. You kept going. I think that's so vital for anyone trying this out. I just read something recently by one of the guys who does the cooking shows. can't think of the guy. Anyhow, but he just said, you know, he had so many.
He had, don't know how many successful restaurants, but the only time he ever learned of this business was the restaurant that failed. And so it's just, and I thought the same thing with comedy. It's like, man, when you have a good set, you're really not learning anything. But when you bomb on that stage, that's when you're learning how to deal with the awkwardness, the uncomfortableness. And when you get, I remember when I got up stage that when I was driving home, I was just like, man, I was thinking of jokes that failed. And it's like, how could I change it? How can, and right there was a science like, man, if I did not,
Instead of like rejecting this or telling myself I can't do this. Instead, I was like, Oh, how could I fix this? I was like, okay, there's something here. And that's exactly, think there's always going to be failures along the way, especially when you're starting out, but you've got to take that not, not as a negative, but as a positive. It's a learning experience. think one of the first ads that came out for, I remember Michael Jordan back in the eighties, you know, the greatest basketball player ever. He comes out and does this narration about he's he missed 26, uh, game winning shots.
Jenny Dempsey (11:13.806)
He missed 9 ,000 shots and he was just going about all his failures and he was just talking about he learned from those. And I think anyone who's starting something new, it's don't, you know, don't automatically assume if you have a setback that, oh, I made a mistake, learn from it. Use as a positive experience. Yeah, absolutely. Learn from it. Don't let it stop you and keep going. And then you kept going. And then what happened next? Because you said flips plural. So let's hear what happened next, Jeff.
Well, they draw my build. I began doing stand -up comedy full -time touring all over the country and it was awesome. And it was fun, but it's a tough go. It's a fun career, but it's a very tough business. The only thing is a stand -up comic, I quickly realized is anyone in the arts, I guess, for that matter, you have no benefits. Unlike a real job, you don't have insurance, you don't have retirement accounts.
You don't have anything. All you have is time. And I remember working with Dave Chappelle after the shows, people always come up to the comics like, I want to be a comic. What would you recommend? Every comic always has good stage time. Dave Chappelle said, get a business degree. And when I heard that telling the telling to this person was the audience, it just struck me. It's like, my God, he's so true. I mean, that's so right where it's like, I've got to take advantage of this time. That's the only thing I have is time.
So I began freelance writing. And again, I never thought of myself as a writer, but I applied to a, contacted the editor for a magazine. It's now defunct, not because of me. Well, maybe it is because of me, Rocky Mountain Sports, where they, the editor, if she'd be interested in the humor article, and she said, well, send me something. And I sent her that and it was well received. So I was like, gosh, I could do writing now.
So I began doing a lot of freelance writing while I was on the road. It was awesome. was the perfect marriage between the two jobs. could, you know, perform anywhere in the country. Never had a check in an office and I could write and it was great. It was a perfect marriage with comedy. I began doing that. And then once you get published in a magazine, you get picked up by other magazines. So I had this nice little career path going with comedy and writing, but then I got greedy and I was like, man, I should start writing for online companies.
Jenny Dempsey (13:38.016)
And suddenly, kaboom, everything exploded where suddenly I have clients all over the planet. You know, I'm writing ghost writing for a celebrity doctor in Australia. I was writing humor scripts for a production company in India. was writing kind of humorous bike tour descriptions for a bike touring company in France. And it was great. I was getting all this money from just freelance writing and kind of like, you know, again, because of tech, I was able to, you know, write for all these companies, all these people over the planet. It was awesome.
And, the problem is I began spending a lot more time online, you know, 40, 50, 60 hours a week. And I didn't think anything of it. I remember my girl for the time, she's like, man, watch it. It's going to get you. You're going to get addicted. I'm like, there's no way I don't play video games. You know, it's like, and my whole jam in life has also been the outdoors. I mean, the fact that I live in Colorado at the time I was living at 8 ,524 feet, uh, at the end of a dirt road in the Colorado Rockies.
I had more wildlife and humans around me. It was just phenomenal. And the last thing I want to do is spend more time on my screen than I had to. I wanted to be outdoors, skiing, backpacking, mountain biking, all that type stuff. So I was like, man, there's no way it's going to get me. And then one day, I missed a writing deadline. And then I missed another one, and then another, and then another. And I couldn't figure out what was going on because I never had this problem before. And I was always very
punctual. I always made it a point to get my articles in on time. And now I was missing all of them. And I sat down and then all of sudden it dawned on me that it wasn't because I did not want to write, it was because I could no longer write. I lacked the mental stamina to focus. Before I could go five, six, seven hours at a time and no problem. Now I was lucky if I could go 15 minutes with all of getting that urge to, oh, I should check email. I should check the news. I should check sports. And that's when all of hit me. It's like, oh my gosh.
The tech is hijacked my brain and it really pissed me off. So yeah, and then I read an article and there's a cover story in the Atlantic Monthly called Is Google Making Us Stupid? It was written by Nicholas Carr. And when I read that, he was sharing stories about professors and authors that he knew that were experiencing the same problem. They can no longer write. They can no longer focus on reading.
Jenny Dempsey (15:59.756)
And I think Nicholas Carr, he had this great quote, something I used to be a diver of words. He goes, now it's like, you know, instead of diving into it, it's like I'm at a jet ski, just skimming along on the surface of the words. And I was like, man, that's exactly what it is. When you try to, when I try to read now, you know, I cannot focus. It's just kind of skimming along because again, being on tech where tech wants us to click and wants us to skip, it does not want us to have a deep thought. And so that's when it hit me and it really pissed me
And that was my motivation for my next career flip, where I was like, man, I should speak on this. I didn't know how to get into speaking, knew nothing about it. I was on a subscription service. It's called now it's called the bash. I used it for comedy bookings. And then one day, like they'll send you like job openings, like, hey, there's a someone wants a comedian for here, some, blah, blah, blah. And then one day I saw a thing where they needed a speaker was in Syracuse, New York. And I was like, well, I should do speaking, maybe talk about.
digital distraction. So I said, you submit a bid, I submit a bid, talk about it all, talk about how tech is affecting us. And they booked me. I was like, oh man, it's like someone's calling my bluff. It's like, oh, now what do I do? And I like five months to write this thing. And of course I waited till the last minute and the week of my dad passed away. I did not have a speech. I drive to Syracuse, the eve of the speech, 10 o 'clock at night, I just decided I'm going to call the
I'm supposed to be doing the closing keynote. That's what's crazy. I didn't just get hired as a speaker. I got hired as a closing keynote. I'm like, but at that, the eve of the, uh, of the speech, I just felt I had nothing. I didn't know what I was doing and I was going to call the booker and just say, look, I apologize. I can't do this. But then something kicked in where I was like, look, you've got 11 hours. You've got 11 hours to you go on stage at night in the morning. You've got to get your ass together. You know, just finish the speech. And then I had to memorize
That just clicked in with me. It's like, don't know if I'm ever going to get another chance at this, you know, to speak. And I don't want to blow my one chance because at the time, you know, comedy was kind of wanting down. It's a young man's game. And it's like, man, I don't know how much longer I can do in comedy. So I've got to make this work. I've got to make this happen. And that's where it's like, man, you got to have belief in yourself. And so I went in that speech pissed off because I only had one hour sleep going into the speech. It resonated with the crowd. I completely surprised by
Jenny Dempsey (18:24.514)
But after that, I was like, man, maybe speaking is it. And then since then, speaking has taken off for me. And it's just, you know, I've kept it improved in my speech and now I'm keynoting all over the country. So it's kind of cool. So cool. It's so cool. And it's so cool that it came from this place of like, you had something you were struggling with and you noticed it, you identified it, you kind of gave it a name, you know, this distraction. You were able to like see it for what it was. I mean, like, yeah, I don't like this.
But then the thought came in your mind of like, well, I could speak on it. Not only because, well, and maybe this resonates, but like, I'm guessing the speaking maybe also helped you kind of heal and work through it. But also you knew that other people, know, after the article that you read, other people are also experiencing it. And if you could go out and talk about it, you could help others work through it because you've been there and you're in it. You're still struggling with it. You know, it's kind of just this thing that you can relate.
with other people on. So the fact that you showed up at this event and you didn't have anything and then, you know, you're angry. I'm picturing you're angry. You're tired and you're sitting in front of this crowd and you fricking rock it because it's this authentic story and people like, I mean, I resonate. I hear that. Like this is so relatable to me. I'm sure people listening are like, yep. Hi. Hi. It's me. I hear that because we're all in it. And
the fact that it's your true story, but it came from this place of like, could, I'm going through it and I could help others. just, I think there's like a switch that kind of goes in our minds sometimes, at least when I'm learning, when I'm talking to other people who are career flipping and doing certain things, they're creating these things from a place of struggle, from a place of this really was hard for me. Maybe I can help someone else who's also going through it. I mean, even this fricking podcast,
I started this as a way because I wanted to create a resource that I wish I had the day that I got laid off. So I wouldn't have felt so alone. And so I'm kind of like, I don't know, could you speak to that a little bit more and talk about what does it mean to you to speak on this topic when you're keynoting around the world and every time you leave that stage, what do you leave with? How do you feel sharing this story and these struggles with others?
Jenny Dempsey (20:45.42)
You know, how does that impact your life too, Jeff? That's something I did not expect in terms of how satisfying that is to have like someone come up to you after and just say, wow, you know, that really impacted me. I remember after the Syracuse speech, I was walking out to my car and a gentleman who was he was having health issues. He was struggling with his weight and he came up to me and he just said that had a massive impact on my life.
He says, just that speech. goes to write, he goes tomorrow, I'm going to call in sick and I'm going to go fishing. He goes, and I'm just, you know, get some outdoor and it just, and that really hit me. It's like, wow, to have that kind of impact. I'm again, something I did not know what I was getting myself into, but that really resonated with me where it's like, wow, if I could help other people with sharing my story, what a great thing to do. And fortunately for me, I had the stage background, so I was comfortable with being on the stage. Thanks to comedy.
And that really helped. it's been so powerful to be able to adjust to the this past winter slash spring. I did a five week college tour and just the emails and messages I was getting from the students about my message, how it impacted them was just incredibly rewarding. And it's such a great motivating thing. And that's, you know, that's basically turned in my why now. And I think of anyone, if you're going to do that, you if you're going to flip a career.
Don't focus on the how or the what am I going to do? Focus on the why, the purpose of it, because that's what really drives and you'll figure it out as you go along. That's such great advice. We can get so caught up with the plan, with the strategy, with, you know, all of the things like how do we make this happen? But if we just kind of like let it go and just just do it and it will all it will all work out and lead us into different things. I think what's so important and what really stands out about your story to me is that like you didn't know these things.
You're like, I'm gonna be, I'm gonna talk about hockey. And now you're talking about digital balance. And so it's kind of like all the things that happen in between all of the steps, all of the struggles, all those moments where you're like, I don't know what I'm doing, but I'm just gonna do this. And you just keep doing it. And it's so fascinating to me how it all does work out. I think these episodes that I'm chatting with people around the world like you, Jeff, and I hear these stories of like, it just works
Jenny Dempsey (23:10.136)
And there's proof, there's factual proof that it works out and it's okay to be on a path where you don't necessarily know where you're going. You just gotta keep going. It's not gonna be easy when you make that change, especially when people are career flippers, especially because you're not gonna get a lot of people in your corner where they're gonna be, what a great idea. Most people are gonna cast some doubt on it. And that just makes it difficult for you. But you gotta focus
know, your internal what makes you click. You've just got to have that faith. You got to make that leap without that net and have faith it's going to work out. I was just reading a book called The Mindful Athlete by George Mumford. And he had an interesting story where this guy, he ended up being a mentor for the Chicago Bulls, Michael Jordan. Then he went to Los Angeles, the Kobe Bryant. And he became, he talks about, you know, being present, mindfulness, being in the moment.
But his story was, you know, he got racked by, he had a big, he was arrested and for drugs and everything. And while he was in prison, he began practicing mindfulness and then he got out of prison. Then he began working in the finance world and he just hated it so much, but he was also practicing mindfulness on the side. And then one day he, he decided that he's going to try to make like a teaching Zen, teaching Buddhist Buddhism, treating mindfulness.
as his full -time profession. And he walked into his finance office and he just said, that's it. I quit. And all the people he worked with said, how can you do this? How can you just quit a job and just totally switch careers? And he said, the sad thing is everyone that he was telling him this all hated their job as well. And yet no one had the guts to make that change. And here he made the change. And like he said, he would never, never.
And his wildest dreams, do you ever expect that he'd be a coach for Michael Jordan, the coach for Kobe Bryant, perhaps one of the greatest basketball players, but that's the path he took. But he just said, the sad thing is he just doesn't, he always remember that how many people, when he worked in finance, just said, what are you nuts? Yet they all hated their job. They did not make that leap. So you've got to have that, take that courage. It's uncomfortable. It's awkward. You feel very vulnerable. There's going to be a lot of moments like, what am I doing? But you just got to have that belief.
Jenny Dempsey (25:28.354)
gotta chase it. mean, there was a quote I was reading, came out by Brent Underwood called Ghost Town Living. He bought this Cerro Gordo. It's just on the California border, right in Nevada. He bought this ghost town and he's gone through, he's famous on social media now because he details that he's gone through fires, he's gone through floods. He's lost so much money trying to revitalize this town, but he just said it's given him a purpose. And he just said, you don't want to go to your grave with a song still in you.
You don't want to go to your grave with that, I wish, I wish I would have done this. Instead, you want to go to your grave with, I'm so glad I did. And that's how he feels about it. I think that's something you got to think of when you're making that switch. You got to believe in yourself. You got to be true to yourself. And what are some things that people were telling you throughout, you know, your path, those naysayers, are there things that stand out to you? It's kind of like things that maybe were a little bit harsher
than others that you may have received over the years when you were kind of following your path? I never told anyone I wanted to be in comedy. I just did it. Because I was even embarrassed to tell anyone that. It almost seems audacious. It almost seems like, it makes you think you could be a comedian. And so I never really told anyone that. never, to my parents' credit, they kind of supported me.
Although I recently came across my mom's journals and it's like, well, maybe they weren't, you know. no. Yeah. So it was like, I don't think she was too happy about that. You know, and then I remember my switching into speaking. I did have that from some people. It's like, what makes you think you could be a speaker? You know, especially you have to have a story.
and you've got to own that store. You know, so I had doubts about that. But again, you just got to believe you got to be true to yourself. You got to listen to yourself. I've never been a linear nine to five type person. So I'm kind of used to, you know, taking chances. And I kind of feed off that. But the bottom line is you just always got to believe in yourself when you do it. You got to give yourself a shot, because if you don't believe in yourself.
Jenny Dempsey (27:30.19)
who no one else is gonna believe in yourself. So you gotta commit to yourself at first. Those are powerful, powerful words right there. When you're sitting in a room and you're in a job and you're just like, I'm not, this is not lighting me up. I don't get to be lit up. Don't even believe that you get a choice. It's hard to shift your mindset around like, I believe in me, I'll choose me, I'll do that. But I think so many people always say that. know, some people are like, I'd like to do this. Just do it.
They don't have the guts to do it or, I can't be, it's just, you know, they think it's a dream rather than it's a reality or, but I, again, I think of Steve jobs when he talked to the graduating classroom, Stanford, you could find this online. It's just a fantastic graduation speech, but he was talking about connecting the dots. Always go back, connect the dots in your life. And it all seems to connect. And he was talking about, you know, when he went to read college.
He took calligraphy class. Everyone's like, why are you taking calligraphy class? But that actually helped him with when he was designing the Apple computer, when he put such an emphasis on aesthetics, when everyone else he was working with, all the designers, computer designers, like, man, why are you wasting your time on the aesthetics? But that gave Apple its identity. And so it's just, again, you connect the dots and you just feed it.
But you got again, you just have to follow your truth. think of Bronny where she was an in -home caregiver in Australia. So she worked with a lot of people in their final days. She wrote a book about this and the biggest regret out of anyone was always they weren't true to themselves. So I think if you're, if anyone's on that verge, thinking, I should quit jobs. And regardless of how, if it's just a job that didn't exist, look what you're doing now. I mean, how many people do you know with you just going around grabbing furniture and
refinishing that. mean, it's, it's weird. It's definitely not something I ever saw myself doing. And I now cannot not do it. Like exactly. But that's just it. You just, you know, you got to be true to yourself. And that's, know, cause I remember talking to you, that was kind of like a hobby of yours. And so there's obviously, there was a passion of that. That's, know, now you're turning into a career, which is just phenomenal. But I just think that's so true. But when Bronnie Ware just said, it's like so many people said they wish they'd been
Jenny Dempsey (29:48.45)
intruder yourself. Yeah, it's not easy. It's not easy. No, it's not. And sometimes we need a smack in the face to really wake us up to I mean, I'll be very transparent with you, Jeff. Like I it's very unlikely that I would have shifted my path away from the traditional nine to five had I not gotten laid off and gotten, you know, hundreds of free job rejections. If I
Because I just thought that's all I was good at. That's all that I was destined for. didn't necessarily. Sometimes I did really not like it, but there were times where I liked it enough to the point where I was like, yeah, this is this is all I'm good at. But it wasn't until I got laid off and had that smack in the face from the universe and then started to have these weird dreams about flipping furniture more or like look in this street corner. there's something there today. That's so weird. I just had a dream about I guess I'll take that and fix that up. Starting a podcast
literally dreaming about it, waking up in the morning like the career, what am I dreaming about? Am I going, am I delusional? You know, these weird things. But I'm in that boat of people that would not have made the change. And I sometimes like think back and I'm like, wow, I would have been one of those people at the end of my life thinking I wish I would have been more true to myself. I'm so great, you know, it sounds nuts to say I'm so grateful that I got laid off and didn't have a stable paycheck anymore.
you know, to keep me looped into this place where I might not have been able to show my true self. So it's just such an honor to be able to talk with you and people from around the world about these things. And, you know, if it encourages one person out there, one other person, you know, your story, Jeff, someone hears you say that and, you know, they're listening and they're like, okay, I'm just gonna do it. And their life changes and they're more true to themselves than
This is 100 % worth every single second, every penny from my savings, every splinter in the garage, flipping furniture, it's worth it. And I'm guessing you can say something similar for your path as well. yeah, making the choice to believe in yourself, even when it might be crazy, even when others may think you're crazy, but knowing that it's worth it. You got to lean into discomfort, embrace discomfort.
Jenny Dempsey (32:09.888)
embrace that vulnerability because it's not going to be easy at first. know, again, you're going to have naysayers and where's that money going to come from? You've got to lean into it because that's when the magic happens. You know, accept that as part of the learning process. So we're all there when everyone makes that change. We're all going through that, but you always feel better. What else? You make that leap and it's like, wow, you feel really good about yourself. You know, after doing it, it's like, you know, it gives you confidence and it's like, damn, what was I in most people?
I bet if you talk to make those changes, always like, what took me so long? Why was I waiting to do this? Right, right. What took me so long? Yeah. And knowing that it's not the end all be all, that where you are and you might flip to one thing, but knowing like, you know, with you, there's multiple flips. There's other things that may show up for you. And in order to get to that point, this is one flip on your many flip journey. Like we're constantly just gymnasts.
flipping around. And it's just one thing that always leads us to another. Just going back to what you said, like connecting the dots. Yes. Yeah. Jeff, I have like goosebumps. I'm just talking with you and hearing your story. And thank you so much for being so vulnerable and sharing so much. I appreciate you. And I want other people listening to be able to connect with you. Where can people find you? How can they reach out to you, Jeff?
Online, I'm best found on LinkedIn, or else you could find me at my website, jeffwoser .com. I've got a lot of videos on there about digital distraction. There's a way to contact me via there. And if anyone's looking for a speaker to talk about digital balance, just digital awareness, please contact me. I'd love to help. Thank you, Jeff. I hope people will reach out. We have a lot to learn from you. I know I'm constantly learning from you. So thank you so much. I'll have all the links in the show notes. Jeff, thank
for being here today. Awesome, Jenny. It was an honor. Thanks so much. Thanks for tuning in to this episode of the Career Flipper. If you liked it, please share it with a friend who could use some inspiration. Don't forget to leave a review and hit that subscribe button for more amazing episodes every Thursday. Your support helps me reach more career flippers and career flippers to be. Make sure to connect with Jeff Wozor using the links in the show notes. If you'd like to connect with
Jenny Dempsey (34:32.888)
just head over to thecareerflipper .com. Whether you're thinking of flipping in the middle of the flip or have flipped before, remember, you're not alone and the support is out there. Keep on your path, my friend. What's the best that could happen? I'll talk to you next Thursday.