2024 Podcast recap: what I’ve learned so far from career flippers from around the world
In this episode, host Jenny Dempsey reflects on the journey of her podcast, 'The Career Flipper,' sharing insights gained from interviewing various guests who have successfully navigated career changes. She discusses the importance of finding one's calling, transferring skills from past experiences, taking calculated risks, and the necessity of continuous learning and adaptation. Jenny emphasizes the significance of overcoming fear and self-doubt while balancing practical needs with the pursuit of dreams. The episode concludes with a message of encouragement for listeners to stay curious and brave as they embark on their own career journeys.
Takeaways
Jenny Dempsey (00:00.238)
When I started this podcast, I had zero grand plans. The idea came to me one night in a dream early in 2024, and I remembered that dream and the dream wouldn't leave my mind. It was very persistent. And I remember thinking, why is this popping up in my head at random times throughout the day? Who am I to start a podcast? I'm a nobody. But that little spark of an idea
didn't fade, and I kept telling myself, well, okay, maybe, just maybe, if talking to other people about their career flips makes me feel less alone, maybe if I put it out there and share it, it'll help someone else feel less alone too, maybe like even one person. And that's exactly what happened. And hearing from every one of my listeners,
And every single guest that came on to share their stories, the struggles, the leaps of faith, the doubts, the breakthroughs, has been such an incredible gift. It's really powerful to realize that we're not alone in the messy, brave process of flipping careers. There's something comforting in hearing that others too have felt scared and unsure and overwhelmed, yet
still managed to make it through. And each interview made me feel like I had some permission now to explore my own path, to really see rejection as not the end, but as a redirection. And just to feel less alone while making a big change. And the podcast really has become a way to normalize the messy journey of flipping careers and whether it's turning a layoff into an opportunity.
finally pursuing a passion that you'd tucked away, or taken the leap to try something completely different. I have learned so much from each guest who's shared their story with me. And in the past six months, I've interviewed 30 career flippers from around the world. Some are old friends I reconnected with after learning about their pivots. Others came through referrals, Google searches, or even me awkwardly sliding into their DMs.
Jenny Dempsey (02:24.62)
And however we've crossed paths, these guests have all become a mentor to me. Not just to me, though. I really hope to you, And so as we wrap up this first season, I've put together the three biggest lessons that I've learned from each career flipper. And I found some reoccurring themes. And I just really hope they spark some thoughts for you as we head into the new year.
But before I get into those, I want to make sure you know that the 2025 season of The Career Flipper kicks off on January 16th. So if you haven't already, be sure to subscribe on your favorite podcast platform to stay updated. Or you can visit the Career Flipper website to sign up for the newsletter. hey, if you have your own Career Flip story you want to share, or maybe you know someone who does, please reach out and connect with me. I would...
Love to have you on an episode and share your story with our community. So here's to new beginnings and next chapters. Okay, now I'm going to share what I've learned.
Jenny Dempsey (03:38.296)
So the first thing that really showed up in a lot of episodes was about your calling and how do you find your calling? And when I first got laid off, I wasn't necessarily looking to find my calling. But what I've learned after talking with guests is that your calling isn't set in stone. It evolves. And sometimes when you go looking for it, you're not going to find it because it might already be right under your nose.
And when I asked myself, you know, really reflecting after a layoff of like, well, what is it that I'm meant to do? I've just gotten, you know, hundreds of rejections. And I always thought that I was just a customer service manager, a corporate, you know, worker bee. And that was really the only career path I'd known. And there's nothing wrong with that. But the callings, they do shift. And they're often these hidden, like,
golden threads or, like Taylor Swift says, invisible strings that connect us from one thing to another. And we may not know it until a later point. And all we need to do is just pay attention. And I mean, for me, it started with picking up a junkie table and imagining its potential and then learning how to do it. That one moment really sparked a creative outlet that I never knew existed. However, when I look back,
I had done similar things in the past and going even all the way back to when I was a child. had family members in my life who did woodworking, who did paint furniture and art. Lots of art all around me and I just never connected the dots until I did. So if you're in that role, in that place where you're trying to out what's your calling, how do you even find it?
Slow down, pause, get curious. You might just find something unexpected. for example, Jeremy Smith from episode six took an opportunity that he didn't know he was gonna love and found a new passion working with sea turtles. And through that experience, he learned that while he loves that, it wasn't the right path for him anymore. And it then reignited his love.
Jenny Dempsey (06:01.806)
for vintage furniture, something that he grew up with that was always around him when he was younger. And now that's his business. So sometimes your calling can appear in the smallest or most unexpected moments simply when you take an opportunity that just shows up on your path. You never know where it's gonna lead and you just wanna sit back and pay attention to it because the other doors that could open might really surprise you.
Okay, the next one is about skills and what skills you bring with you when you flip your career. And what I have learned talking with other folks who flip their careers is that you're not actually starting from scratch. You're building on your experiences. I used to really think that when I was pivoting to furniture flipping that I was losing everything that I ever knew.
when I worked in tech and customer service and experience. But I've since realized that all the skills I developed in my former jobs can apply on this new path. Things like communication, problem solving, leadership, community engagement, social media, just simply customer service and how to write to a client. These things that we've learned along the way are valuable.
and transferable. So I really encourage you, if you're kind of nervous about changing careers and losing everything that you may have thought that you've worked so hard to build, look at that experience. Look at those past jobs and think about which of those skills you really can carry with you to your next opportunity or starting your own business or whatever that looks like for you. Like for example,
Leslie O'Flahaven took her teaching skills as a high school English teacher and then transformed them into a thriving business to help corporate companies and startups and small businesses write better to their customers. And even Julie Morris, who also she spent a decade getting her PhD and to teach at a university level. And then
Jenny Dempsey (08:27.094)
she left to work in tech and she uses so many of the skills that she learned during that time in academia to apply towards training programs and internal education and different types of technology and learning styles. So the lessons that you've learned and the experiences that you've had can lead you to the next chapter. Don't discount.
your past experiences, they will still apply with anything that you do moving forward. So this next one came as a bit of a surprise to me. And it's gonna sound silly when I share it because it sounds very logical, but I never really thought about career flips this way until talking with others and finding a common pattern that career flippers, typically most of them, take calculated risks.
And these small, smart steps are, you know, they're not jumping blindly. They're not just leaping off the cliff. You know, it's so easy to get overwhelmed by the what-ifs, like, how will I pay my bills? Or what if I fail? But the truth is, most career flippers take these calculated risks, and they plan a bit, they research a bit, they test the waters before diving in, they start small.
They're not just leaping off the cliff. And while there's nothing wrong with taking that deep dive and jumping blindly and going all in when you fully believe in an idea, that is absolutely encouraged. I think when it comes to the day-to-day reality of changing careers, there is also power in calculated risk taking and doing a bit of planning and researching before diving in.
And I kind of equate it to how I like to take a trip. Like for example, I love to know where I'm gonna stay, how I'm gonna get from place to place, maybe one or two sightseeing points, and then I want the rest of it to be all up to chance to wander and explore and find random places and adventures. And I feel like when your foundations are covered, you might...
Jenny Dempsey (10:48.502)
Some of us, maybe not all of us, some of us really thrive on the unknown, but some of us want to kind of know how things are going to get paid and then we can use some of that extra money to fund our dreams before going all in. Like for example, Natalie Schuman and her husband spent many years researching and saving for their dream of owning a dive shop and their patience paid off when they took the leap after getting stuck.
touring different islands and looking at different dive shops and they got stuck there during COVID. And then they're like, well, we actually love this. So was like a chance encounter, but there was a little bit more planning that went in beforehand. But then there's the example of Roy Atkinson, who's an incredibly talented musician and took the leap to become a touring musician and was absolutely successful at it. And he knew that he
If he sacrificed a lot of things like money and time and just put it all into his dream, that it would happen. And I think that belief also helps us because calculated risks can only stay calculated risks. And then if we're not believing in ourselves or we're not pushing it, we could get stuck in like, that's a fun idea. That's a fun idea. I'm just going to keep researching until I'm ready. we're never, we may never actually be ready.
There are still leaps that come with it, even with a calculated risk. So I think all this is to say is that a little bit of planning might help you feel a little more confident as you dip your toes into the next chapter, but don't let it stop you from actually taking that leap. There's logic and then there is still the dream.
that needs to happen. And so it's kind of this balance between the two. And I know sometimes when circumstance happens, like for example, I got laid off and I couldn't find a new job and I had to think fast on my feet to figure something out. And my career flip became something that just happened because I had to find something, but I really leaned into things that I enjoyed, creativity, and to get really resourceful about how to do it.
Jenny Dempsey (13:10.892)
in a unique way. So I think when we look at it in a new lens and know that calculated risks are okay, it's okay to start slow and research and plan, but don't let it hold you back from taking that leap. And kind of building on that, the next one is really about learning and adapting and growth. And hearing other career flippers talk about, you know, what the time in between, you know, from when they're at their
old role and then they're wanting to move to something else and what they learn in between. That growth, that personal growth really comes from being open to learning. When I first got started in this furniture flipping podcasting journey, I didn't know what I was doing, but I was curious.
I am curious. I'm very curious by nature. I love to ask questions. I will ask all the questions, which might be annoying for some people, but I'm just curious and I want to learn from people. And I really learned along the way how to flip furniture by asking questions, doing my research, trying and failing, trying and succeeding. And the same with podcasting. If you listen back on some episodes, some of the sound is not good.
I was learning, getting different mics. Some of the edits might be a little choppy. You know, there's so many things that I learned over time and just did better each and every day. And being open to learning new things for any industry, for any career flip, whether you're sliding, gliding, dancing into a new role or a different industry or starting your own business, it's, I really think...
This is such a crucial part because you don't know it all. And there are people that know a lot and they probably don't know it all either. And they're trying their best. But if we all talk to one another, we really can learn a lot from each other's experiences and embrace this unknown and be willing to learn new skills. In addition to the ones that you've already had from your past experiences, like for example, Galina Marcus.
Jenny Dempsey (15:29.582)
She went from working a marketing tech job to complete burnout and then starting to promote her own art that's now in galleries. And she launched a nonprofit, the San Diego Art Directory, and then even started her own podcast to feature artists from around the world. And she didn't know how to do these things, but she used her past experience and her ability to learn new skills.
to stay curious and really keep learning along the way. You know, these next steps that we're all thinking of taking might require some new skills. And how do we allow ourselves to be willing to learn and adapt and grow into something new? This next and last lesson is probably the most important one to me because it's been the
hardest for me to navigate. And I feel silly even saying it because I have not figured this out. But hearing from other career flippers who also navigate it and then seeing them be wildly successful in their endeavors is like, it's really motivating to know that even when you feel the fear or the self-doubt or
the lack of worth, if you push through it and don't let it control you, it might still be there. In fact, it probably is still gonna be there, but you just keep going. You acknowledge that fear. You don't let it stop you. There's gonna be really hard moments, sometimes more than others, and every small step forward counts. Even if it's teeny tiny and you're crying along the way, it counts.
And I think, I mean, I could go into many examples throughout the podcast, but ultimately you don't have to have everything figured out. You you could just keep moving forward. And as cliche as this sounds, trusting the process, because sometimes, and I guess this is no secret, like other people talk about this, I'm no expert on it, but
Jenny Dempsey (17:57.346)
You know, our minds are just trying to keep us safe. We put ourselves in a situation that is new and uncomfortable and, you know, might not have the security that we have known for many years. Our minds are going to freak out. And I think when we lean into that, which is perfectly natural and normal,
we can learn to talk ourselves kind of out of it. And that's honestly what's really helping me, think, you know, talking with career flippers and learning that, yeah, it doesn't have to control you. You can keep going even when you feel it. And it's going to be worth it, even on the hard days. And as I reflect on the entire season of the career flipper, I'm really
This is gonna sound so silly, but I'm really struck by how often I called myself delusional for dreaming big.
But now, at this point, six months later, I realized that believing in your potential isn't delusional. It's brave. And these stories from everyday people making career flips possible is inspiring. And if they can do it, you can too.
And I guess I want to be totally upfront with you that when we're doing these things, know, we sometimes, well, most of the time, we need money to fund our dreams. And it's just part of the journey. And I think hearing from others on social media, it can feel a little frustrating or discouraging at times to think like, I want to lean into my dreams and make this happen, but I also need to pay my bills. How do I balance both? it?
Jenny Dempsey (20:03.122)
shameful to get a part-time or full-time job while I'm trying to build this up on the outside. And I would never want money to be the thing that stops me from going after what I love. And I wouldn't want that for you either. I know for myself, I am 100 % committed to making my dreams happen. Whether it's hosting career flipper meetups in real life or
speaking at events about career changes, writing a book or whatever else comes up along the way. You know, I'm committed to making the dreams happen, but that said, I'm also keeping it real with you. I might need to take on a full-time job for a bit to help fund the dreams and cover the bills and give a little bit of that security to keep afloat. And that's okay.
That's okay if you have to do that too. There's no shame in that, you know? The practical stuff needs to come first, but that doesn't mean that you have to give up the bigger goals. It just means we might be juggling both. And I know that I'll keep working hard to make the dream happen on the side, and I really hope that you do too. But it also might feel like awkward and silly to some people.
You know, like admitting that I need to step back and do a more traditional role to kind of make things work, but there's nothing wrong with that. I don't know. In fact, I'm learning after talking with so many other career flippers, it's really part of the process. And I think we often get so caught up in thinking that we have to be all in right away. But sometimes taking these smaller practical steps really allows us to get where we want to go without sacrificing
the things that we care about. So if you're interested in being a part of my journey or whether you want to host a career flipper event or you want me to speak at your event or you want to be on an episode or I don't know if there's some other way to collaborate where what I'm doing can help lift you up and achieve whatever it is that you're flipping to, just know that I'm here.
Jenny Dempsey (22:23.774)
and I'm ready. We're in this together. So reach out to me. My email is hello at thecareerflipper.com, but you can also find me on Instagram, TikTok, LinkedIn, wherever. Just please, let's keep our dreams going one step at a time. And so as we wrap up this first season, I also want to take a moment to thank you.
Your support and feedback have been, my gosh, such a huge motivator for me to keep going with this podcast, especially knowing it's helping you think about your own journey. Because we're doing this together. Like I'm not someone who's an expert on this. I'm literally doing it right alongside you. You know, this year has been full of surprises and growth and really cool connections of career flippers. I mean, I'm honestly so grateful to each
of you tuning in. Like you listen to this. You learn with me and you're flipping right alongside me. So here's to more adventures ahead. Thank you for all the reviews and streams and likes and comments and letters and I'm just keep it coming. I'm so grateful. And as I mentioned before, season two is coming your way on January 16th, 2025.
I really plan to have it packed with some really great stories, a lot more expert insights from folks that know the career flipping world in and out that can help you really navigate your own path. And honestly, I'm wanting all of to pick their brains too. You know, my dream is really to grow this podcast into a global community where we get to meet in person, we get to share our stories and we get to learn from one another and
Maybe even one day I'll kick back and read a career flipper book together. So if I, you know, someone who didn't always feel that I was worth it or believe in myself and the self doubt was there, and it's slowly not controlling me as much anymore, if I can do this, so can you. So stay curious and stay brave. Stay on your path.
Jenny Dempsey (24:52.61)
my friend, what's the best that could happen?