From C-Suite to Clarity: Jennifer Carter on Career Reinvention

In this episode of Career Coaching Secrets, host Pedro sits down with Jennifer Carter, leadership and career coach and founder of Flashlight Thinking. Jennifer shares her journey from C-suite executive to full-time coach, sparked by a moment of clarity that forced her to reexamine boundaries, identity, and what she truly wanted from her career.

They dive deep into imposter syndrome, pricing your expertise, designing a three-month transformational coaching engagement, and helping high-level women stop settling for “crumbs” in their careers. Jennifer explains how she helps clients clear old stories, reconnect with parts of themselves they’ve buried, and confidently pursue work that aligns with who they are now, not who they thought they had to be.

This conversation is honest, energizing, and packed with real lessons for coaches and professionals ready to design a career (and life) that actually fits.



Connect with

LinkedIn: https://www.linkedin.com/in/jennifercartersocialimpact/
Website: https://www.flashlightthinking.com/
Instagram: https://www.instagram.com/jencartercareercoach/

Transcript

Jennifer Carter: 0:00

Three months minimum engagement. And, you know, we really start off taking a deep dive into clearing out all of the old stories and baloney that's getting in your way. I see people like, I want to make more money, I want to grow in my career. If I I had one of my clients message me today, like they're thinking about walking out of their job because they just can't take it anymore. And it's figuring out like why you don't see yourself in another role or why you think that you're stuck with what you have, like, oh, thank you, sir, for the crumbs. I'll just keep going here and I'm gonna apply for a job that's keeping me right at the same level, even though I want a higher level, but I don't think I can. So it's digging deep right into what those things are. It's designing a life that you actually want. Do you want flexibility? Do you want to work on this one niche topic? Do you want to bring your whole self into the work? There's a woman that I'm working with who's been doing the same thing in the tech arena for the past 10 years.

Davis Nguyen : 0:59

Welcome to Career Coaching Secrets, the podcast where we talk with successful career coaches on how they built their success and the hard lessons they learned along the way. My name is David Swain, and I'm the founder of Purple Circle, where we help career coaches scout our business to $100,000 years, $100,000 months, and even $100,000 weeks. Before Purple Circle, I've grown several seven and eight-figure career coaching businesses myself and have been a consultant at two career coaching businesses that are doing over $100 million each. Whether you're an established coach or building your practice for the first time, go discover the secrets to elevating your coaching business.

Pedro: 1:30

Welcome to Career Coaching Secrets Podcast. I'm Pedro, and today's guest is Jennifer Carter, a leadership coach who helps burn down women in high-level roles get clear on what they actually want and design a next chapter that fits their real life. After building a successful career that looked great on the outside but felt drainy on the inside, she made a pivotal shift that reshaped how she works and lives. Through her company, Flashlight Thinking, Jennifer helps leaders identify what's draining their energy, set stronger boundaries, and move forward with clarity and confidence. Her work is direct, practical, and focused on helping women get unstuck without blowing up their lives. Welcome to the show, Jennifer. Thank you so much. Nice to meet you. Nice to meet you too, and great to have you. And you know, I like to rewind a bit. I'm a sucker for the origin stories, and we were talking a little bit about that pre-podcast, but you know, every coach has that moment where they look at their life and say, I guess this is what I'm doing now. Right. So when was that for you?

Jennifer Carter: 2:43

Gosh, it was really, I would say, just this past January. I was at my grandmother's funeral, and I had been coaching and teaching leadership and whatnot on the side, and I was a C-suite level executive. And I'm at my grandmother's funeral. I'm about to go give her eulogy, and I get a text from my boss that asked for an explanation for some numbers that I wasn't even in charge of. And I'm like, what am I doing that I'm worried about work right now? But I'm about, I want to be present before my grandmother and celebrate her life. Um, and it was at that time I'm like, why am I doing this? I need to set some really hard boundaries. And then everything just kind of happened from there, right? The stronger I became and the more that I knew exactly what I wanted and how I wanted my life to go, everything else just fell away. And I've been doing this full time now since June of 2025. And it's been such a blessing, you know. I get to help people every single day and get to know them and see their greatness.

Pedro: 3:47

Okay, that's interesting. I mean, obviously, your boss helped with that transitioning, right? To getting it full time is like you got that that that spark, reignited spark, you know. So when did it shift, you know, from I'm helping people to I'm building a real business around this? Because at the start, we're always, you know, testing water, trial and error. But when I did, hey, this is a real business now.

Jennifer Carter: 4:11

Oh my gosh. So in 2020, I was like, I'm gonna make this a real business. I'm gonna do this. And then it's one foot in, one foot out. I'm not smart enough. I don't have connections, I'm not experienced enough. And I've been doing this work for I don't know, 15 years at that point. I'm like, but I still didn't believe in myself enough. And so I was just kind of, you know, half-assing it. And then June 1st, I was without a job and I said, this is what I'm doing, period, and nothing can stop me. I'm just gonna go forward full blast. And I think it's it's conscious decision. It's not waiting for the perfect moment. It's not when you think you're smart enough, good at it enough, have it all figured out because what I've learned is you're never gonna have it all figured out. I change things every single day. You know, it's it's it's perfect, but it's an evolution of learning and trusting yourself and asking for help. But it really didn't happen until June 1st when I made that decision.

Pedro: 5:07

Yeah, I mean, it's good that you've been through it, right? Because that's a testament for your clients that you you actually believe in yourself for a while and then you what I suppose you're trying to help them with, right? In a way, right? So to get past that. I don't I don't know if that's imposter syndrome or what we're talking here.

Jennifer Carter: 5:27

It's for me, I think it is imposter syndrome, especially when it comes to the business. I never saw myself as an entrepreneurial person until I realized my whole career of building programs and partnerships, even though it was tied to a very large organization, it was entrepreneurial in nature. And at the same time, I had been building a career for so long, and I was so tied to I'm climbing the ladder, I'm gonna make a certain amount of money, I'm gonna be a C-suite executive, and then I'm gonna be a CEO one day. I was so tied to that one narrative that I built for myself since I was, I don't know, 21 years old, starting off as a case manager in my very first job. I knew I was gonna be CEO one day. And so a lot of that was just letting that go and seeing what else was out there. So there was a, it's almost, I think, grieving that former vision of yourself and knowing that you are more than the plan that was in your head.

Pedro: 6:24

Okay. And after you got rolling, who are the people that kept showing up? You know, I I understand that C sweet level women, you know, the ones you realize, because at the start, as we talked, we tasked a lot. Sometimes we see coaches trying to, you know, embrace the entire world, but when did it you realize, okay, these are my people, you know?

Jennifer Carter: 6:45

I still haven't realized at all. Honestly, it's been, you know, that at first, and I I love that, you know, at first, um, I I was doing everything. I was doing a group and one-on-one and teaching and strategic planning and fractional work. And then the people that kept coming to me were people that needed help with their career. And I told um one of my best friends one day, I'm like, girl, I think I'm a career coach. And she said, duh, you're a career career coach. And so then um I repositioned um to really focus on career coaching and executive coaching for women, period. And it's so funny because now that I've done that, like more men are starting to come to me too. And I'm like, what is happening? And organizations that are coming to me for things that I don't even market anymore, like, can you do our strategic planning? Can you do a training for this? And so now I'm still toying with the idea, do I reposition again? Do I just keep going for a while and see what happens? So it's absolutely a journey, and I'm not tied to it. I think the more I show up just being myself, the world reflects back to me what it needs and what I'm here for. So I I've stopped trying to force it, especially this past 30, 60 days, and just seeing what happens, and it's been very, very bringing.

Pedro: 8:10

I will talk about the part that nobody escapes, marketing. So how do people usually find you?

Jennifer Carter: 8:16

You know, that's a great question. I have a um a big I love making friends with people. I've never met a stranger, so I do a lot of reach outs. I'm on LinkedIn a lot, and I'm on Instagram too, is um at Jen CarterCareer Coach, and I've just started making these reels for the past um 30-ish days, and I have to tell you, it's been the most fun. I started doing a podcast called called Unmute Yourself, where I'm interviewing women who do extraordinary things, but I just want people to know that they're extraordinary too, even though they don't see themselves that way. So I'm out there a lot, I get a lot of referrals.

Pedro: 8:53

Okay. All right, so let's talk business for a second. Let's say that uh people find you right on Instagram with your upcoming reels and the ones you're having fun doing so much. On LinkedIn, they resonate with your work, and eventually they want to know what working with you actually looks like. So everyone builds their coaching business a bit differently. So when someone actually becomes a client, Jennifer, what does that experience look like right now?

Jennifer Carter: 9:18

It's a hoot and a half. Three months, three months minimum engagement. And, you know, we really start off taking a deep dive into clearing out all of the old stories and baloney that's getting in your way. I see people like, I want to make more money, I want to grow in my career. If I I had one of my clients message me today, like they're thinking about walking out of their job because they just can't take it anymore. And it's figuring out like why you don't see yourself in another role or why you think that you're stuck with what you have, like, oh, thank you, sir, for the crumbs. I'll just keep going here and I'm gonna apply for a job that's keeping me right at the same level, even though I want a higher level, but I don't think I can't. So it's digging deep right into what those things are. It's designing a life that you actually want. Do you want flexibility? Do you want to work on this one niche topic? Do you want to bring your whole self into the work? There's a woman that I'm working with who's been doing the same thing in the tech arena for the past 10 years, and come to find out this woman like worked for one of the biggest radio stations in the United States early in her career, or helped um with Lollapalooza. She's like, Oh, I really loved that time. I'm like, like, bring your whole self just because it was long ago. Don't forget what you love, you know, and then it's and then it's positioning, working on your resume and your interview prep, figuring out a custom outreach strategy and getting confident in saying, yes, this is what I want. I'm not settling for less. This is the kind of culture I want, and going for it full steam ahead. It's so fun.

Pedro: 10:56

Oh, right. So the structure, just so our audience can understand and I can understand, we're talking about basically one-on-one interactions. That's what we're talking about. Or do we have a group component or an online course? Or how does that play out?

Jennifer Carter: 11:10

One-on-one. One-on-one. Everything is custom. I want to make sure that you get the attention that you need. It's uh, I just I did relationships with people and they text me. They have an interview that comes up. Oh my gosh, I have an interview. I'll do whatever I can to make sure that they have a little prep beforehand. I try not to take too many clients because I want to give that attention. Um, I don't want people to feel like just a number. I hired a career coach at one point and I felt like just a number. And I want to make sure that my people know that they're very, very, very important in the world. And so are their gifts.

Pedro: 11:44

I mean, your work seems pretty hands-on, right? You have the one-on-one component. And so my my question is, how do you think about capacity so you don't stretch yourself too thin?

Jennifer Carter: 11:53

Oh my gosh, absolutely. I have a wonderful production assistant for my podcasts. I've built in timing and systems in my work of when I do my books and whatnot and reach outs. Um, I'm soon to the point where I'll be looking at hiring somebody to help with more of the calendar management and scheduling and really just looking at the things that only I can do, can't do, and help us break through the day. When I first started, now this is I mean, I really did just first start, but even up until last month, I was working 12 hour days just because I loved it so much. And any break that I had, I'm like, what can I work on now? Can I work on this content? Can I reach out to this person? Wouldn't it be cool if? And just this path past month, I stopped trying to control it all and just let it flow. And guess what? Nothing's falling apart and it seems to be easier. It's really, it's really, really in this point.

Pedro: 12:50

It's great that you were able to set up a team, right? An assistant, um, production for the podcast person. So one thing that every coach wrestles with at some point is pricing, right? And we're not talking about hard numbers, okay? And it's about basically how to package their their work. I mean, some do hourly, some do packages. How do you think about it today? Because that's really a path of sometimes self-force that you compare of how much my time is worth, especially with the service industry. So and if there were lessons along the way that shaped how you landed where you are, where you are.

Jennifer Carter: 13:24

Yeah. When I first started, I was doing a lot of sessions for free to build my business, credibility, network. And then it was like, okay, I guess I'll do it by session. And it was so scary to start to ask for more money. And I just a couple months ago, I actually doubled my prices. And the first couple sales calls, it was like, oh my gosh, oh my gosh, right? It can be it can be scary, but it's it's I've gotten comfortable with knowing that I'm providing a transformation for people and not a transactional service. And that when people see a value in the work and that they're willing to invest in themselves, money is just money. It's not a nickel and dime thing, right? Like when I thought back back to my more corporate life, the amount of money that I threw away on facials and gyms and clothes and shoes and dinners and and it just goes on and on and on, right? And like we don't want just invest that money in ourselves to actually be happy instead of trying to mask it all. So that is and it's still work that I'm doing, right? With knowing value. And as my books get more and more full, it's easier for me to be comfortable with charging that premium price. I have 22 years of experience. I was a C-suite executive. I teach for University of Texas Extended Campus and Center for Professional Education, right? I've worked for one of the largest nonprofits in the nation, probably the world. And so why wouldn't I charge for my expertise and my energy? I also um I belong to um a mindset mastery mastermind, a tribe, mindset mastery tribe, and it's been so helpful. Like even when I'm feeling down, like no, I'm gonna live in a box on the street. Um, they're like, Jennifer, that is not true. Just keep going, just sit with going, right? So it's right, it's been fun. Yeah. I'm learning a lot about myself.

Pedro: 15:30

Right. I I like how open you are about this, right? I love that. And that's a solid look into how you approach pricing structure. Now, I'm curious about where you're taking all this. Looking ahead, where do you see the business going? Are you thinking about scaling, hiring, or is there a next step you're excited about?

Jennifer Carter: 15:47

Pedro, let me tell you, I have a vision. Okay.

Pedro: 15:50

Let's go.

Jennifer Carter: 15:51

I see I see a seven-figure brand, period. Okay. I see national speaking stages, I see a book, um, I see eventual lighter touch coursework for folks that might not be ready to pay that premium price. I want to help as many people as possible in ways that feel good to them. Um and I don't know exactly how I'm going to get there, but I know that I have the faith in myself to simply be myself and continue to leverage opportunities and grow and share and be me. And I know that that's gonna that's gonna happen.

Pedro: 16:29

I see why not by the energy we're we're exchanging here. I can and you can feel it, right? I can feel it. I mean, Pedro, let's do it. I like I like that the energy. No, because money also money is all about right commitment. So I get it. Okay, cool. I mean, of course, whenever we're aiming toward the next chapter, there's always something we're refining in the present. So, what are you currently trying to improve or tighten up in your business right now?

Jennifer Carter: 16:54

Oh my gosh. Um, what am I trying to improve or tighten up? Managing lead. Oh my gosh. Messages, messages, messages, messages, messages. Who, what, when, where, how. Um, so I've got to figure out how to do that a little bit easier. It's really, it's really easy, y'all. I'm sure you know, to get stuck on this all day long and so many different platforms and ways to reach you. Um, so I really need to work on streamlining that, I think, for scale 1000%.

Pedro: 17:22

Yeah, I mean, you didn't get into coaching to manage a CRM and build automations, I guess.

Jennifer Carter: 17:29

Yeah, I don't my um friend Lauren, she's like, okay, Jennifer. Okay, Jennifer, this is what we can do. Oh, have you thought about? Have you thought about? I'm like, oh, okay. But my brain doesn't work that way. It's not, I don't have a process-oriented brain. I have a creative brain, you know? And so I just want to talk to people all day. And I when I know something's not working, I know it's not working, but I can't tell you how to fix it, fix business process stuff.

Pedro: 17:56

Okay, okay, Jennifer. I want to switch gears for a second into something a bit more fun. Not that this is not fun. I'm having fun. But if you're down for it, I got a quick game for you. Let's go. Okay, let's do it. Okay. We'll look at this through the lens of business investments, okay? Things like coaching, masterminds, training, marketing, team, you name it. Okay. It's simple. I'll give you four prompts and you tell me the first thing that comes to mind. If there's a story behind it, even better. Okay. So, what's the first business investment you remember making in your coaching business?

Jennifer Carter: 18:35

My coach, when I was how old was I? 30 years old. I still work with her this day. I know you said in my coaching business, but when I think about it, I invested in my own coach. Her name is Lisa Lee. She's amazing. I hired her right after I had my first child. And I was trying to figure out how to manage being a new mom, and a growing career, and how that all looked. That was the first time I really paid or invested in myself. And it was the best decision I ever made, hands down, because she still is an outside influence and uh neutral third party that can call me on my bullshit. And she'd been encouraging me to go out on my own probably since the second time that I met her. And I just and she finally got me there. Yeah.

Pedro: 19:27

Yeah. Okay. So next one. What's the most recent one you made? Most recent business investment you made.

Jennifer Carter: 19:34

The most recent business investment I made was um in a company called Smart Coach. And so they've been really helpful in teaching me how to sell. I'm much more comfortable now. And how to make content. I do like being in front of a camera and I'm like, I I just got so released to LinkedIn. I like LinkedIn, but it just seems so sad. There's so many angry people. So LinkedIn folks like you know, like the world is dying, corporate sucks. You know what? Corporate does suck, but can't there be something more fun about work? Um, and so then they to really taught me Instagram, which was really fun. Them and I still invest in my master mind group with Paulina Tillman. Life changing, mind changing. Best financial business decision. I think it's mindset mastery tribe because I would have given up the first month if it weren't for them. When you have a down day, it's easy to say, why am I doing this? I'm not meant for this, see, I'm proving it right. But you when you know there's a group of people going through the same thing, they're like, Jennifer, you just, you know, got a new client last week and you like why are you down on yourself? Just keep going. And in different ways to think about things and heal a relationship with money. Um, so so that's been really, really helpful.

Pedro: 20:53

Okay. What one investment you wish you could get your money back on?

Jennifer Carter: 20:59

The very first career coach I hired. Which is maybe why I ended up here in career coaching. When you think about it, right? Like my whole my whole corporate career was around workforce development and helping people get jobs. And then when I hired that career coach, I thought they were gonna like help me and they just outsourced a resume and said, Okay, I'm here if you need me, but I'm like, but what do what are you gonna with? And then it's cricket. Like I wanna yeah. So I think I think that would be it.

Pedro: 21:24

Okay. Looking at those, how has your approach to investing in the business changed over the years? If it has, you know.

Jennifer Carter: 21:31

Um, I know I look at what I need okay, so at first I paid for everything. I got everything, I got all of the different schedulers and premium subscriptions and this and this and this to the point where they all overlapped. I'm like, why am I paying for this? How do I make them all together? What do I get rid of? What do I keep? Um, and so now I've really scaled that back and looked at just one thing at a time, what problem I'm trying to solve, and then look for the solution instead of I don't know what I need, so I'm gonna take everything.

Pedro: 22:03

Stop piling up, you know, tools and try to organize in one big thing.

Jennifer Carter: 22:08

Yes, because like you know, I built my website five, six years ago, and then when I'm like learning new things, adding new systems, technology changes, I had you know, a calendaring system here, a calendar system here, and a calendar system here, and then it was just it was just do you use Stripe, do you use PayPal, you know, or you Venmo? So to think through all of your systems first and just decide. And it's okay to switch, but I was paying for like everything. So really figuring out what problem you're trying to solve first before you're just panic, subscribe, buy, premium plan, whatever.

Pedro: 22:44

I love that. Yeah, I we I recently talked to him and and he told me, I mean, in a way it's similar because he told me he was like, I I was such a perfectionist equipment, right? Oh, I need a perfect camera, I need the perfect laptop, and blah blah blah blah blah. And he's like so many hours with that mindset. When I started, you know, creating my content, that really just didn't matter that much, you know.

Jennifer Carter: 23:09

Right. It doesn't, it really doesn't. And you better think this you go along, but you don't you don't need it right now.

Pedro: 23:16

That's so true. Jennifer, and if someone listening wants to connect with you or follow your work, where can people find you and connect with you?

Jennifer Carter: 23:23

Sure, on Instagram at Jen CarterCareer Coach. My email is Jennifer at flashlightthinking.com, or you can find me on LinkedIn at Jennifer Carter.

Pedro: 23:34

Okay. Flashlight thinking. Can I expand a little bit on the name? Because I like the name.

Jennifer Carter: 23:39

It makes me so happy when I think about it because I shine a light on things that people can't see for themselves. Whoa, right?

Pedro: 23:46

I love the name. Oh yeah. Don't tell me your logo is like a flashlight.

Jennifer Carter: 23:50

Don't tell me it's a little a little light bulb with little people inside of it.

Pedro: 23:54

Oh my god, that's so cool. Okay, there were, you know, a few things you shared today that really stuck with me. The fact that you said it you still didn't believe in yourself, you know, at the start. That's so authentic. I love that. You know, you're not trying to play an act. You're just you're just you. I thought that I love that. Oh, you're such an open book about pricing and the struggles with that comes along with it, you know, like you started doing for free, and then you got your testimonials, and then you start charging, and then you're like, oh, and I it that happened, and I then you're you dialed then forward, you know, that didn't stop you. I love that. Also, your first investment, you know, being a coach. So at the end of the day, we need to practice what we preach, right? So we see a lot of coaches that they don't have coaches for themselves. And I mean, come on, right? If you're trying to to improve people, you know, with transformational change, it would only make sense that you also need that, right? Constantly. Right. So yeah, I do what you do, Jennifer. And you know, I appreciate you being here today and sharing so openly. It was great having you.

Jennifer Carter: 25:01

You're joy. Thank you so much. It's been wonderful, and um, I hope to stay connected.

Davis Nguyen : 25:06

That's it for this episode of Career Coaching Secrets. If you enjoyed this conversation, you can subscribe on YouTube, Spotify, Apple Podcasts, or wherever you're listening to this episode to catch future episodes. This podcast was brought to you by Purple Circle, where we help career coaches scale their business to $100,000 years, $100,000 months, or even $100,000 weeks, all without burning out and making sure that you're making an impact and having the life that you want. To learn more about our community and how we can help you, visit join purplecircle.com.