From corporate chief financial officer (CFO) to executive and leadership coach, meet Ricky Padgett
Ok, quick question for you: Ever feel like your work and identity are all tangled up?
Today, we’re chatting with Ricky Padgett from Burlington, Vermont. He’s a certified executive and leadership coach, and he’s been there. In this episode, Ricky shares his career flip story—from being a CFO to still doing CPA work, while coaching others to navigate their own big career changes. He talks about how staying true to your values is key when making those big decisions. Plus, he highlights the power of asking for help when you're going through change. Spoiler alert: you don’t have to figure it all out alone! Ricky also opens up about the challenge of separating who you are from what you do—and why it’s so important to give yourself permission to redefine what success looks like for *you.*
And for listeners of The Career Flipper podcast, Ricky’s offering a 20% discount on his coaching program!
Episode Takeaways
Connect with Ricky
https://www.padgettcoaching.com/
Mention The Career Flipper Podcast for 20% off a 3-month coaching package!
Jenny Dempsey (00:00.148)
Asking for help is a true superpower. And so many people are afraid to ask for help. Welcome to the Career Flipper, a weekly podcast featuring career change stories from people all around the world in all kinds of industries. We talk about how they get from point A to point B and all the twists and turns and surprises along the way. If you've been thinking about switching careers, consider this your permission slip.
I'm your host, Jennie Dempsey, a career flipper myself. After years working in customer service and experience leadership in the tech startup world, I got laid off and I unexpectedly found myself flipping furniture in my garage, rescuing pieces that were headed for the trash and giving them a new life and then selling them. You can check out my makeovers over on San Diego Furniture Flipper on Instagram and TikTok, if you're into that sort of thing. So I started this podcast because
Honestly, I felt really alone and a little weird, well, okay, a lot a bit weird about my career flip. But I posted on LinkedIn about it and suddenly I started talking to others who've also made career changes and I learned that I'm not alone. There's a lot of people out there pivoting their careers and hearing their stories has been really inspiring. It made me realize that it's never too late to switch lanes and every conversation I've had teaches me something new.
So I figured if these stories are helping me feel a little more confident and a little less alone on my path, maybe they could help you too. That's why I started the Career Flood Project, to share these amazing journeys and offer support to anyone thinking about in the middle of or maybe have already made their own career flood. Okay, question for you. Have you ever felt like your work and your identity are all tangled up?
Today, we're chatting with Ricky Padgett from Burlington, Vermont. He's a certified executive and leadership coach, and he's been there. In this episode, Ricky shares his career flip story, from being a CFO in corporate to still doing CPA work while coaching others to navigate their own big career changes. He talks about how staying true to your values is key when making those big decisions. Plus, he highlights the power of asking for help when you're going through change.
Jenny Dempsey (02:23.95)
Spoiler alert, you don't have to figure it out all alone. Ricky also opens up about the challenge of separating who you are from what you do and why it's so important to give yourself permission to redefine what success looks like for you. Let's get into the episode now. It's a pleasure to be here with you. It's great to see you. It's great to see you too. You know, I just for everyone listening, I want them to know that we met
because at my former company, offered a career coaching of bundle where you could take advantage of this. And I remember not many people at the company took advantage of it. And I was like, yes, I'm in. And I got matched with you. And you really came into my life at a time of lots of change. And we worked together for almost a year. And I think it was maybe every other week.
You know, hearing your story and having you guide me in a lot of the challenges I was facing at kind of this up and down time was so incredibly supportive and helpful. And I haven't forgotten it and hence, you know, still keeping in touch today. You have left an impact on me throughout my career, whether I was at that company and they offered such a generous bundle or even now as, you know, moving on into different career paths, like you've really.
just continue to leave an impact. And I'm so grateful for you. So I'm, I'm excited to have you on to chat more about it. So tell, tell everyone about you, Ricky, who are you? What do you do? You tell, you tell that. And one, so thank you for that. That means a lot, a lot to me. My name is Ricky Padgett. My company is Padgett coaching and I'm based in Burlington, Vermont. grew up in the Florida panhandle.
And I have gradually moved further and further north as I don't like heat. So my formal training and most of my career was in finance. I was a CPA. I still am a CPA, but I'm also a certified executive and leadership coach through the ICF. Did my career flip back in 2019? And so I have been doing
Jenny Dempsey (04:48.108)
I've been doing some, as you mentioned, sort of some career coaching. I've also done some leadership coaching and executive coaching. And I work primarily in healthcare spaces in my private practice. Although I certainly, as I meet people through different avenues, I continue to see that to expand. my finance career was pretty much exclusively in healthcare finance. And one of the things that
that I noticed as I was after about 30 years in a variety of different roles, I just started feeling like I wasn't really where I was supposed to be. I wasn't doing exactly what was going to fill my cup the most. And in the last place that I was at internally, there was a lot of need for coaching in that organization. as a finance person, I think they were surprised when I volunteered to throw my name in the hat.
But I started to take advantage of all the different programs that they were offering to just learn more about coaching. So I did everything they offered internally. Then I went externally and it was during that external program we did a values exercise. Maybe that's one that you and I did together. I don't remember, but, it was powerful for me. Very powerful because
Well, I know I've had values my entire life. I don't think I ever slowed down enough to really name what they were and understand how they guided me when I needed them the most. And it was just such a, it was a scary time because I realized then like I can't keep doing what I've been doing. the values that really had been guiding me and had helped me make decisions when things were difficult or overbearing or overwhelming in the past.
I could see they were starting to come into play again. And that's sort of what led me to flip my career. know, speaking of those values, actually, our listeners can't see this, but I have a Post-It note that has been on my computer monitor, rewritten multiple times just because things fade and all that stuff, but of the values that we worked on together. So yes, we definitely did that exercise.
Jenny Dempsey (07:08.946)
And throughout this kind of change in my career path, focusing on those values as they become anchors. And they've kind of kept me on this different path, feeling more secure in a way. And so yeah, I hear what you're saying and it's cool to hear your experience with them and how that impacted you. Cause I'm like, yeah, like that was such a big part. And I think we did that pretty early on when we started working together and they have literally become anchors in.
how I make decisions. And also if I feel a certain way or I'm triggered by something, I'm like, why is that? that's because, you know, my authenticity value is being triggered right now. You know, it kind of goes both ways. So it does. It absolutely does. And so, you know, I guess I would also say at the same time, it was really hard to give up a guaranteed paycheck and health insurance, right? Like anytime you think about changing careers, and particularly if you're going to do something
out on your own where there's not a super big safety net, it can be scary. Yeah. It's terrifying. It's absolutely terrifying when you make that choice. then you kind of mentioned, you had that feeling of there was something else. There was something else. And so can you speak a little bit to that? Where do you think that...
comes from? Like, how do we suddenly think like, this isn't what I'm supposed to be doing. Like, I'd love to hear from you, like, when you've worked with other people, you know, whether it's executives, leaders, or, you know, just, you know, regular career coaching, like with me, like, how does that show up for other people? Where does that feeling really come from? Gosh, that's such a great question. And you know, deep, I truly believe it comes from deep within within us, right?
And that's why I love coaching is because I have this very firm belief that the answer is always inside of the person that I'm talking to. And my only role is to just help them to pull it out of themselves. And so, you know, think it was something that was, I think from a very young age, I think I've always been someone who wanted to other people, like be the best they could be. However they define.
Jenny Dempsey (09:30.866)
that, not by how society defines it, not how I might want to define it for myself, but how they define it. And that really got awoken for me when I went through my own coaching program. Tell a little more about that. Like when that started to awaken, like what showed up for you in your life? How are you starting to make decisions? How did that? I'm so curious. How did that happen?
So I'm to tell you, I'll be very vulnerable with you. I immediately went into therapy because I thought I had lost my mind. Yes, get that. I did the same for you. Right. And it was so interesting. I went to someone that I'd worked with previously when my dad was diagnosed with an illness and we knew he was going to not be with us very long. So I had some rapport with her. She knew me right. But one of the things that she
started to pull out of me was, you these stories, stories from my past that where I'd made pivotal decisions about my career. And she started to sort of help me put together a story about what, why, you know, why was I really doing what, what I was doing? It wasn't, I was really good with numbers. Like I've always been amazing with numbers. Not to say I'm perfect, but because I do my mistakes.
But as we all do, but it was always about growing the staff or growing the team that I was working with, like leaving them better off than perhaps when I first came into like partnership with them. And so it, it slowly helped me to sort of understand that we did this exercise called the noble purpose and it was just the most amazing exercise. And that's right. Really like,
what helped me to come up with the, you know, my purpose is to help people become their best self by their definition, on their timeline, and just sort of be the person who's holding space for that work to happen. And it sounds like by you doing that amazing work, it has also given you permission to hold space for what you want to do and how you...
Jenny Dempsey (11:54.072)
Like you were able to be, you were able to do better and to become what you wanted in order to like let others do it. Is that, that's kind of what I was hearing. Absolutely. Yes, absolutely. And I would tie that back to my values. So it's allowed me to work in a way that my values are now very much aligned. And when I noticed that maybe I'm either being offered a piece of work or I'm in the middle of some work and I noticed that there's some value misalignment coming into play.
I feel like I'm much more prepared to deal with that. Sometimes it may be saying no to a piece of work because it doesn't align with my values. Other times it's learning to hold my value but continue the work in partnership with the organization or the team or the leader to make sure they get the value they're looking for from the services. Can you talk a little bit more to the values?
to do that assignment, remember you sent me a list. There was a list of words. I mean, I'm sure anyone can Google and I'm actually sure you have a really great resource. can't remember it off the top of my head, but there's a list. So the types of values are very descriptive. For example, mind connection, creativity, authenticity, purpose, consistency, things like that. And so for anyone listening who's trying to figure out their values,
I think we also have separate values of like family, relationship, like there's those as well, but these are just about, like, I guess, can you describe a little bit more about what these values, like what these values are? Sure, sure. I would say like they are guiding, like to me, they are the guiding principles that we hold inside of ourselves that help us make decisions day to day without sometimes even being cognizant that we're holding.
Yeah. Right. And so when I think about mine, integrity is like one of the most important ones for me, followed by actually professional development. So learning and growing is really, really important to me. And anytime I feel stagnant in that area, I am not my best self. Yeah. Yeah. So there, I think of them as core values. So they're not just professional values, right? Because if you take
Jenny Dempsey (14:19.926)
If you just look at yourself through a professional lens and you don't include your personal self, then you're not being your whole authentic self. And so sometimes I will supplement if someone's really struggling with something just from a work perspective, I may supplement them with some just like professional type values, but most of the values that I provide to people are more holistic in nature. So they cover the whole person.
all aspects, it's up to them to decide which ones they think carry the most weight for them. That's such an important reminder too, because even when we show up at work, we're still ourselves. We're still our whole selves. I used to think, and honestly, I think we worked on this a lot together, that work was my worth. Work was the only thing that I was good at, and then everything else was just kind of like, yeah.
And I saw how that impacted my relationships, my health, you know, all of these things. And it wasn't until like I kind of started to, I got laid off and then started to really think about these things. I was like, no, like the, am more than just when I'm good at. So when we talk about these values, does, you know, encompass the whole person. It's everything because we are still ourselves when we show up at work and, there's so much more. Absolutely. Yeah.
So you were in finance, you're good with numbers and you felt that you weren't doing what you wanted to do and you had these opportunities to learn and grow and develop your own skills while also helping others. And then you took this leap. Can you talk a little bit about that point when you're like, I'm going to do this? Because we were just talking about the money thing and how scary that can be.
But when it's tied to our values and tied to these things that you've kind of already been working on or working toward, you know, it's almost like a calculated risk at some point. Like, can you talk a little bit about more when you like leaped into the deep end? Like, what was that like? Yeah, it was, it was super scary. It was also, I think it took a lot of courage. I think that's probably the word that people shared with me the most that I started to like hold onto.
Jenny Dempsey (16:43.82)
particularly now that I'm at the five year mark. So, and I'm feeling like I've accomplished what I've wanted to do, but definitely scary. From the coaching program, we had something that we called like an accountability partner. I maintained my relationship with her well after the program. And I remember she would...
She would push me so hard and she would challenge me and she would say like, Ricky, repeat after me. I can leave my job and I will be okay. It took some support from a lot of different areas, both family, friends, and eventually even coworkers as I started to sort of share what my dream was. There was a lot of support. So, and I would say like, one of the things I learned that I've really held on to is like, and I use this a lot now in my coaching work is like,
Asking for help is a true superpower. And so many people are afraid to ask for help. Right. And I'm not, not great at marketing. I knew that was going to be something I just wasn't good at, but I asked for help and said, know, where, where do you think I could, where do you think, you know, what would make the biggest, get the biggest bang for my buck? You know, I I'm not, that's not my specialty. So I had to ask for help.
Yeah. my gosh. Why is asking for help so hard? I feel that same way too. Especially, I worked in customer service for 18 years and all I did was help other people who were asking, you know, obviously questions about a product. But even then sometimes people are still like, there's an ego attached and there's, you know, fear like, I'm not going to get help anyways. I'm going have to wait in a queue. Like even just for things like that. But when it comes to our own selves and things we need help with.
even just asking, you open this jar? Sometimes we don't do that. Like, I mean, the scope of it. it's so, it's so interesting what happens when you do start to ask and how people are like, one, willing to help two, they feel better about themselves when they can help. And three, you're more likely to help others because you got some help and it's kind of like this full cycle. I, I know that I've had to work on that a lot over my life and
Jenny Dempsey (19:03.402)
It's amazing. I love asking for help. I'm like, I'm going to just always ask. and, and I, but it gets to that point when you can't. hearing you say that really resonates and hearing how that helped you, you know, cause we don't know everything and that's totally okay. There are people that do and how can we like leverage their skills? Absolutely. Absolutely. I definitely think there's a vulnerability to asking for help and I acknowledge that, but I also
know, one of the things I remind people is sometimes when they don't ask for help, they are robbing another person of that opportunity. Yeah. Right. Right. Because and think about when you think about trust building and relationship building, I mean, asking for help is a way to start to form a bond that is extremely powerful. Yeah, it's very true. It's very true.
you do reach a level of vulnerability when asking for help, especially about these personal decisions that we're making, whether it's career or other things in our lives, you know, asking for that help for hard things does require that level of vulnerability. And, yeah, it just, yeah, I like how you say robbing them. Gosh, that just like kind of stabs you in the heart. Like, well, I don't want to do that. Like, yeah. So asking for help,
being something on your journey that has helped you. Are there other things that you have support network, you're asking for help and you're doing the work, you're learning what you need to learn in order to do this great work? Are there any other things, because that's a lot, but are there any other things that also helped you when you made this decision to leap and take this different path? Did you hear, there naysayers?
Was there imposter syndrome? Were there any other challenges that came up? then how did you navigate those? There definitely were other challenges. I would say there definitely were naysayers. I would say you mentioned the support network. That support network, I think of it as my own personal board of directors. I lean on those a lot. And I think that's something I wish I would have had that piece of advice.
Jenny Dempsey (21:26.282)
when I was 22 years old going into the workforce, right? Right, right. Because that's a really, that's such an important tool to have in your toolkit. The imposters, there was definitely, there's time, there's even still times today when I have to, you know, I find my internal self going, you're a CPA, right? Like it would be something really hard or it's going to take a lot of like interpersonal dynamics and interventions in a conversation.
And I'll hear that little voice go, but you just do the numbers. And I've learned just, you know, I let it literally let it go in one ear and out the other. And I remember like the person in front of me is human and I am human and we can connect. And that allows me to, to move forward. One of the other things that really, I would say helped me and I, you know, I think you and I might've touched on this at one point. And one of our conversations is I had a
I held a loose vision for what I saw for myself, right? Like my creation. You hear people talk about vision boards. Like I have a vision board, but it's not like one you would read about in the magazines. It's literally like, think of me, right? As a, as a finance person, I've got some bullet points on there. I've got a couple of strong words, not a lot of pictures, but it was my vision of like what I wanted for myself. How.
you know, a vision of how people would find me. What would be the outcomes of the work that I did with people? What would be the words of recognition that I would receive from the work I was doing? Right? So I had this very loose vision that I continue to refer back to, and keeps me grounded. And I say loose because, you know, it, it, needs to change from time to time. And I'm not going to get everything I'm looking for from every engagement.
I get enough that it keeps me motivated, happy, engaged, and always trying to do better for the next time. Yeah, I do remember us talking about that. And I think what really got me excited about that was because the vision boards, when I'm putting a picture there, then that's all I'm thinking of. And sometimes I get stuck like, well, that didn't look exactly how I expected it. And to have a little bit of flexibility with these things because they do evolve. also,
Jenny Dempsey (23:47.864)
there's unexpected surprises that will show up and suddenly you're like, ooh, this is cool. I'm gonna do this, but I never imagined this happening. But the only way to get there was to stay on this path and it led you in this direction. So being open to opportunities and having that loose vision, I agree. I I think it is such an important part. It's helped me a lot over the past several months, even creating the podcast.
I didn't really know what it was gonna do, but I knew that this is what I wanted to do and I'm open to opportunities and have kind of like the vision with it. But yeah, it's very flexible. It is that loose vision. And I'm glad you brought that up because I feel like a lot of people can get very stuck and like it's gotta look a certain way and it's not very black and white. In fact, it never is. It's always gonna look, I don't know, totally different depending on the day. I always say to myself, it's gonna look how it's gonna look.
Yeah, right. And I have to be, I just have to be okay with that. Right. Cause when you work for yourself, as, you know, work, work will come in waves. Yeah. Yeah. Very much. sometimes it's like, my gosh, I have too much. And sometimes I'm like, where's the next piece of work going to come from? And I've learned that was probably one great piece of advice. Someone gave me was learn to ride the wave of the work.
and be okay with that. And that, you know, it can be scary at times, but you trust the process and you do good work and you're rewarded for it. Yeah, right. And just to keep going, knowing that there will be an up to the down all the time. Yeah. I actually have a little tattoo on my wrist. The, is the quote of, can't stop the waves, but you can learn to surf. so even though there's
might not be any ways out there. You still know how to surf. You still got your board and then you'll be out back in the sea again very soon. little things like that. But, know, with, with career flipping, I think a lot of us sometimes, you know, are doing these out of, know, we sometimes have the choice and there are some people that it's circumstance that finds them, whether they're laid off or they get hurt and they have to make a pivot or.
Jenny Dempsey (26:11.212)
You know, sometimes things happen like that and it can be challenging with the ups and downs because we may not be have been prepared for it. And I'm curious if, you know, for people listening that might be in situations like that, you know, is from your kind of like, you know, executive leadership perspective, are there any things that you have seen help people and kind of guide them?
when the unexpected happens on their career path and they may not be sure how to do this because they just weren't prepared. Sure. Yeah. No, that's a great question. And I do see that. One of the things that I often think about when a situation like what you described happens is there's a period of time where there's going to be grief, right? And you're going to experience all the stages of grief.
You know, one of the things that I often, I do every single time I have a new client or a potential client pitch is I remind them, I like, am, I do not have any type of mental health background or training, but I do know that when people find themselves sort of at a crossroads, you have to be prepared for the, for the grief and this different stages of it. And so finding a support person, whether that's a counselor, whether it's a career coach, whether it's a best friend.
Right. They can help you navigate that. But just talking through that with someone can be really helpful. Yeah. So true. Talking through it, accepting that there is that grieving process and it's not going to take a couple days. It's not going to, you're not going to wake up and feel better in a week. Like it could take a really long time. it's non and it's very nonlinear. It's not going to be, you go down and then you go back up. You're going to loop around a couple of times. Right. And that's okay. Right.
I would say one of the biggest challenges though that I've coached around is when the identity, and you sort of alluded to this earlier, when a person's identity is tied to their role at work, right? And they've poured themselves into the organization or the role or this definition of who they are is so closely tied to what they produce.
Jenny Dempsey (28:29.888)
And that's hard to untangle. When you're grieving that it's like losing a part of yourself. And then suddenly you have to keep going, but you just feel so conflicted and, and it's sometimes empty and having to find who you are again. That's hard. Exactly. Exactly. When I, you know, I mentioned earlier in the conversation that I
finished the coaching program and knew like I needed to do something different and sought out, you know, like some professional counseling. One of the things that I had struggled with initially was the whole identity, right? Of this is who I am. This is what I've worked for all my life, right? I've been a CFO. I've been a chief operating officer. How do I let let go of that? Right? And it was, it was through some work. I think she gave me the Myers-Briggs if I remember correctly.
She asked me if I'd ever taken and I was like, you know, I think I did like back in my twenties, but I don't remember much about it. And she gave it to me and then gave me a bunch of literature. And, and all of a sudden I started to see my preference is right in a new light. And I would be, started to say not to put myself in a box, which, you know, sometimes with assessments that can happen, but to say, like these are the qualities that make good coaches.
that make good counselors, that make good development people, right? It allowed me to give myself some permission to redefine my version of me. Right there. Permission, the permission to do it and that others are doing this as well and that it's completely okay. Yeah. Yeah. You know, as we're talking, like I think that was probably the theme of some of the things I've
we've talked about today, but also as I think back, I think all of the support pieces that I and people that I had around me, each of them were serving a role to help me give myself permission. I think that's something really important to pay attention to when we're thinking about changing careers, doing something brand new. It's going to take a lot of permission on a lot of different levels. And we don't always have to have everyone signing off.
Jenny Dempsey (30:49.08)
think that's the thing. It's also like, like you mentioned the NACEIT, like there's going to be people who are like, yeah, no, I, I'm not buying that you're doing this or whatever it is. but still being able to be like, no, these other things give me that permission. And that's how, that's what I'm going to follow. Yeah. It's our own permission. That's most important. Yeah, that's true. That's true. Yeah. Right. Right. Right. Yeah. I take back what I said. It is, it is all about.
semi-retired people please or I get caught up in that. But yeah, no, you're absolutely completely agree. I understand that. I definitely understand that. We've covered a lot today, Ricky. feel like there's just the themes of the things that you've brought up, like from your journey, from the journeys that you have supported others in. Me is included. I want
First of all, thank you so much for getting vulnerable, for sharing all of this. And I know that someone listening will take this away and it will impact their life as well. I would love to have people be able to connect with you and learn from you. And if they have questions or work with you, whatever that might look like. Ricky, how can people find you? Sure, sure. Well, so my website is Padgett.
coaching, that's padgettcoaching.com. There is a place to connect with me on there. My email is that same website address and it's just ricky at padgettcoaching.com. So that's a great place to reach out to me. And if someone's looking for a coaching package, I'm happy to offer 20 % off my three month program if they mentioned the career flipper podcast.
And thank you for having me, on this podcast. I really appreciate it. thank you so much, Ricky. Thanks for that generous offer. Take advantage of it. I hope someone does it. You're incredible. I've loved working with you. I've loved having you on today. Thank you so much, Ricky. Well, thank you. It's always a pleasure. Thanks for tuning in to this episode of The Career Flipper. Be sure to connect with Ricky using the links in the show notes.
Jenny Dempsey (33:10.7)
If you enjoyed this episode, share it with a friend who might need little nudge on their career path. And if you can, please subscribe and leave a quick review. It might seem small, but it helps the show reach more people who could really use all the stories of career changes and personal growth. Plus, when you subscribe, you'll have more flippin' stories like Ricky's queued up and ready to listen to. And if you're thinking about switching into customer service or maybe leveling up your skills while working with customers in your own dream business,
I've got online courses packed with tips for my years in customer experience leadership. Over 14,000 students have already taken them. So head over to thecareerflipper.com slash courses to check them out. What I love most about doing this podcast is knowing that these stories might inspire someone who's feeling stuck to finally make a move toward their dreams. That first step is always the hardest, always is, but it can lead to something pretty cool.
So thanks again for listening and I can't wait to share more with you next week. Keep on your path, my friend. What's the best that could happen?