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Worklife with Molly Graham

28 May 2026 · 30m · 10 chapters

Episode artwork

Caroline Wanga on the Career Path No One Tells You About | from Hello Monday

In short

Career self-discovery and decision-making using “career maps,” balancing meaningful growth with financial stability, redefining “personal brand” as “personal purpose,” and reframing failure and authenticity in the workplace.

Guest backgrounds

Caroline Wonga is president and CEO of Essence Ventures, a media company dedicated to Black women. She started as an intern at Target, rose to the C-suite over 15 years, left in 2020 to join Essence, and co-founded Wonga Woman. She’s also the author of the memoir “I’m Highly Percent Sure.”

Key claims

You can’t always know your next step; build structured experiences to learn what you like and when to make a “strategic yes” or “thoughtful no.” Money doesn’t negate meaningful experiences—choose paid roles that teach you. Personal brand should become personal purpose. Failure is inevitable; learn to work with it rather than avoid it. Authenticity can start with small, tangible changes.

Notable examples

Her Target “career map” included experiences like leading non-exempt hourly teams, leading leaders, HR exposure, and individual contributor work, each with pre-commitments defining when the experience was “done.” She describes starting authenticity at work by changing her appearance (e.g., cutting braids, wearing blue lipstick) and noticing others didn’t react as feared.

Written by AI. May contain mistakes.

Chapters

3:19

Caroline Wonga's Journey

Caroline shares her unconventional career path and insights.

“Focus on where you are in your professional career.”
5:10

Finding the Right Career Path

Discussion on career mapping and the importance of mentorship.

“Like I had I didn't have a path I was pursuing.”
8:07

Balancing Experience and Financial Stability

Advice on pursuing meaningful experiences while ensuring financial security.

“And the first thing that I would say is give yourself some grace.”
14:10

Navigating Career Mapping

Caroline Wanga discusses the importance of career mapping as a tool for professional development.

“And explain how we can use this as a tool.”
18:03

The Shift from Personal Brand to Purpose

Caroline redefines personal branding, emphasizing the importance of personal purpose instead.

“I worked in a company at Target at the time that had leadership development as a priority, research where you work, right?”
22:22

The Shift from Personal Brand to Purpose

Caroline redefines personal branding, emphasizing the importance of personal purpose instead.

“I don't want to not ask you about failure because you have this conviction that we can turn failure into our competitive advantage.”
25:57

Redefining Failure and Authenticity

Caroline shares her journey of redefining failure and embracing authenticity in her career.

“I became a mom before I became a legal adult.”
28:00

Navigating Authenticity in the Workplace

Learn how Caroline Wanga transformed her approach to authenticity at work.

“In fact, you have a framework for us around it, right?”
31:20

The Importance of Career Maps

Explore the concept of career mapping and its relevance at any age.

“We got one more question for you here from Paul Cotton in Texas, who asks, he wants to return to career mapping.”
33:19

Rewriting Personal and Professional Rules

Understand the significance of intuition versus inner saboteur in career success.

“She says, what rules have you rewritten that were key to your personal and professional success?”
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Transcript

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0:02Caroline Wanga: Hey, worklifers. I'm bringing you something special today that I think you're going to love. My friend Jessi Hempel hosts a podcast called Hello Monday. It's one of my favorites, and if you don't already listen, you should. What I love about her show is how wide she casts the net. Leaders, authors, thinkers, all circling the same question. What does work actually mean to us? This episode featuring Caroline Wonga, president and CEO of Essence Ventures, tells the story of how she figured out what kind of career she actually wanted and how she knew when it was time to make a move. It's the kind of conversation where someone's specific experience ends up feeling really universal.

0:44Caroline Wanga: I hope you enjoy it as much as I did. And if you want more, you can find Hello Monday wherever you get your podcasts.

0:55Jessi Hempel: With no fees or minimums on checking accounts, it's no wonder the Capital One bank guy is so passionate about banking with Capital One. If he were here, he wouldn't just tell you about no fees or minimums. He'd also talk about how most Capital One cafes are open seven days a week to assist with your banking needs. Yep, even on weekends, it's pretty much all he talks about. In a good way. What's in your wallet? Terms apply. See CapitalOne.com slash bank. Capital One N.A. Member FDIC.

1:29Caroline Wanga: This episode is sponsored by Study.com. Life can be messy and complicated, and it can be hard to work towards finishing your college degree when other responsibilities get in the way. Luckily, Study.com is designed to help you earn college credit online and on your schedule. They offer over 220 online college courses that help students make progress towards completing a college degree in a flexible and more affordable way. Knock out your general courses like English, math, and history, and study on your phone or computer for just$95 a month. Study.com courses are fully online and self-paced and designed to transfer to over 2 ,000 colleges and universities.

2:08Caroline Wanga: It's a great way to earn your college degree at an affordable price and on your own schedule, so life doesn't get in the way of your education. Go to study.com slash podcast to browse courses and get 10 % off your first month when you sign up. That's study.com slash podcast. This episode is brought to you by Walmart Business. Here's something I've seen over and over in high growth organizations. The leaders who actually transform how their teams operate aren't the ones with the biggest visions. They're the ones who ruthlessly protect their team's time and attention. And yet so many of us are still losing hours to the basics, like procurement, ordering supplies, chasing down purchases that should just happen.

2:50Caroline Wanga: That's where Walmart Business comes in. It's built to simplify your operations, a huge assortment of business products, everyday low prices, and fast, reliable shipping and fulfillment. You can manage all of it on your schedule, online, in-store, or right from the Walmart Business app. It's Walmart, built for your business. Get your team focused on what actually moves the needle. Sign up for a free Walmart business account today at business.walmart.com.

3:17Jessi Hempel: Forget your age. Focus on where you are in your professional career. Are you in a place where you know what you want to do next or you don't? If you don't, play with the mat. That's how it works. And I will probably have a career map for the rest of my life, but I will probably have 682 of them.

3:36Caroline Wanga: From the news team at LinkedIn, I'm Jessie Hempel, and this is Hello Monday. It's our show about work on our own terms. And if you found yourself here today, my guess is that you are in the middle of the question that so many of us are asking ourselves. What am I supposed to do next? I mean, what's my next right move? Be it here, somewhere else. How do I make the money I need? How do I live according to the purpose that I want? What do I even like to do? Maybe you're not sure anymore. Well, today's episode is for you. Our guest is Caroline Wonga. Caroline is the president and CEO of Essence Ventures, the premier media company dedicated to Black women.

4:17Caroline Wanga: She got her start as an intern at Target. And during the 15 years that she worked there, she rose to the C-suite before she left in 2020 to join Essence. She also has a company, Wonga Woman, that is dedicated to democratizing authenticity. And we'll get into what that means. Her new memoir, it's called I'm Highly Percent Sure. It's an ode to exactly this. Now, if you're watching our episode today, you'll see that we filmed this episode in our Premium Conversation studio. A couple weeks ago, this conversation was released in full, long form for our Premium members. And if you didn't happen to catch it, then you can go back and find the full conversation.

4:58Caroline Wanga: The link will be in the show notes. It's worth upgrading to Premium just to hear it. Now, without further ado, here's Caroline Wonka.

5:09Jessi Hempel: I'm one of those people who really didn't know what they want to be when they grow up. Like I had I didn't have a path I was pursuing. I went to college out of order. And so by the time I got what would end up being a career at Target, because I started as an intern and ended up going to Target, it was literally like I know the brand. They sell cool stuff. What do I want to do here? Like I literally didn't know I'd been offered a job as an operations leader. And I just like I just didn't have anything that was important. I did business so it was flexible.

5:37Caroline Wanga: And you were young, right? I mean, there you go.

5:39Jessi Hempel: Well, I was in my last—they hired me right before my last semester. I was a December grad. I did four years of school and two and a half years. It was a whole different—that's an unhealthy choice. So while we were done, I started as a group leader, but I hadn't decided I wanted to be in supply chain and anywhere else. And so I had a great first boss. And his guidance to me was, well, then why don't you design a map that gets you through a couple of experiences that are core experiences people who work at Target could have to help you decide? So my first map was, what are some core things Target does that I need to try so that I know which ones I like and don't and then can go from there?

6:20Jessi Hempel: And so it was lead non-examined.

6:21Caroline Wanga: I'm just going to stop you because I want to make sure we don't rush past this before people really get the nuances here, right? Right. Because I think that experience that you talk about right there as a young person is so relatable. That moment when you're like, yeah, I'll design the path. But like, what do I want to be anyways? How do I know? Yeah. And so you took that question. How do I know? And you gave it structure. Right.

6:40Jessi Hempel: People gave it structure. And the reason I'm giving you that clarity is because I don't you know, one of my passions is I want you to know the story as it happened, not as you want it remembered. I literally was simply in the question, I have no idea what I want to do here. A mentor-type capacity person is who helped me solve for the fact that I didn't know what I want to do, right? And you will see that my career is riddled with relationships that took ownership of asking the question. Because I wasn't going to say, I don't know what I'm going to do here because I'd have been fired, right? Like, that's what I thought.

7:11Jessi Hempel: So for the person to go, well, what do you want to do? And I'm like, I don't know. Well, how would you feel about not knowing? I don't know how I feel about not knowing. And so it is about somebody that tapped in that I trusted to just stay with me a little bit longer. And instead of giving me what I expected to be the guilt and burden of not knowing, gave me a non-threatening, in my opinion, way to live in that question and not feel pressured, but still at least both optically and strategically see if Target was the place for me. And I think that that was the beginnings of my leadership principles were built in a room where somebody took time to ask just one more question and help me through that ambiguous period.

7:51Jessi Hempel: A lot of us go through when I was scared to say I didn't know, which would have led me to pretend to like stuff that I probably didn't like.

7:58Caroline Wanga: Well, so let me ask you, do you have any advice for folks who may be thinking, well, I want to try to design some experiences to figure this out?

8:06Jessi Hempel: I do have advice for them. And the first thing that I would say is give yourself some grace. I think we've all heard these stories of people who go, I didn't know when I wanted to major in college. Don't let the smooth taste fool you. Right. Like, it's just you are in a season of your life multiple times through your life where you just don't know. And so my first my first piece of guidance would be you will never always know. Like, don't let the inner saboteur and the societal optics of what other people. I used to mimic the highest performing person on my team thinking that's what I was supposed to do.

8:37Jessi Hempel: He was Brad Zelke. He was great, but he was a, you know, 5 '10 white man in Tyler, Texas. And that's not this girl. And so a lot of times when we don't feel comfortable with that vulnerability, we start to try to pretend to be what we think is the best of what we're seeing. And that's the trap you avoid. But it has that I don't know courage then gets paired with who do I feel safe with sharing that that can be my partner. We talk about mentors all the time, but we talk about it for other things. Think about those periods and find somebody you trust enough to ask to be your partner on the journey of I don't know.

9:12Jessi Hempel: Because just having somebody with you, whether they're a supervisor at your level or somebody else, will give you safety for the ambiguity until you're ready to go. The formula goes together. Don't be afraid to look for that person if they don't find you. Because I've been a found girl most of my career.

9:26Caroline Wanga: I love that. And I love the idea of locking it down, of proactively asking for that. Okay. So I want to bring in some pre-submitted questions without leaving, by the way, this idea I want to come back to of the career mapping. But this question comes from Tashay Friedman in Florida, who says, how do you balance chasing meaningful experiences with the need for financial stability, especially early in your career?

9:51Jessi Hempel: Here's what I would offer, and please don't hear this as any sort of condemnation of what you're thinking. Hear this as an offer to adjust it because I've been in that thought. This isn't a preaching moment, right? Stop believing that money doesn't come with experiences. Who told you that, right? And so this idea of choosing experiences versus roles, I might have to do roles because financially I need to get paid. I never said the experiences were volunteer opportunities where you're not getting paid. It's a job. It's a job that you move into to have the experience. And if you don't know what you want to do, having that experience is still important because it helps you know, did I like it?

10:31Jessi Hempel: Did I not? My career map was lead non-exempt hourly people because it's a retailer. It was lead leaders because it's a different kind of leadership. It was going to HR, which I was not going to do, but my mentor went and put it on there and I didn't feel like staying in the meeting. And then the fourth one was individual contributor. And so I want to share that because a lot of times when I talk about roles versus experience and the question comes about pay, people think I am saying that you're taking some sort of financial risk with it. No, it goes back to your first question, which is this is for the people who don't know.

11:05Jessi Hempel: If you don't know, then go after experiences that may not be a role you would have chosen and then see what it does for you. Strategic yes or thoughtful no, but here's the second most important thing that I want the person who asked the question to know. Remember that it is the story you tell about what you want your next experience to do that could unveil experiences you don't know about. And so you still need to make sure, and this is where my map played a role, you still have to have a narrative.

11:33Caroline Wanga: This episode is brought to you by LinkedIn. Running a small business means every hire matters. A bad hire can cost you time, money, and momentum. A good hire, they can change everything. But finding great talent isn't easy, especially when you don't have the time or resources to sift through piles of resumes and find the right fit. That's why LinkedIn built Hiring Pro, your new hiring partner that screens candidates for you. So instead of sorting through applications, you can spend your time talking to candidates and finding your next great hire. With Hiring Pro, you can hire with confidence, knowing you're getting the best talent for your business.

12:13Caroline Wanga: In fact, LinkedIn found that its users are 24 % less likely to need to reopen a role within 12 months compared to the leading competitor. Join the 2.7 million small businesses using LinkedIn to hire. Get started by posting your job for free at linkedin.com slash worklife. Terms and conditions apply. This episode is powered by AT &T Business. If you're running your own business, you know that the Sunday scaries are real. You're thinking about the invoices, the client calls the inventory, the list that never actually ends. And honestly, we usually don't think about our internet or our phone service until it isn't working.

12:56Caroline Wanga: Sometimes a simple glitch can feel like a total catastrophe. That feeling of powerlessness when your tech fails you is the worst. It's a reminder that our connectivity isn't just a bill we pay. It's the backbone of everything we do. AT &T business gets that. They know that for a small business owner, good enough isn't good enough. You need reliability that stays in the background so you can stay in the lead. If you're tired of the friction points and just want a provider that understands the stakes, check out AT &T Business. Powered by AT &T Business. Built to work. Get AT &T Business at business.att.com.

13:36Jessi Hempel: With no fees or minimums on checking accounts, it's no wonder the Capital One Bank guy is so passionate about banking with Capital One. If he were here, he wouldn't just tell you about no fees or minimums. He'd also talk about how most Capital One cafes are open seven days a week to assist with your banking needs. Yep, even on weekends, it's pretty much all he talks about, in a good way. What's in your wallet? Terms apply. See CapitalOne.com slash bank. Capital One N.A. Member FDIC.

14:09Caroline Wanga: I want you to take us back to career mapping. Yes. And explain how we can use this as a tool.

14:15Jessi Hempel: Would love to. So again, the reason, and there's type A's probably in very close vicinity of this conversation that we're having. It me. That's me. Right. And I am the other 25 letters of the alphabet. But here's my point. What I need to be really clear about, use the word map as it matters to you. And this is why I'm starting here. Because everybody's like, well, what book did you get it in? What rhetoric does it sit with philosophy? No, no, no, no. I'm a visual learner, so I drew a map. If you don't like pictures, write words, right? I just want to make that clear because people get stuck in a framework.

14:47Jessi Hempel: So here's what happened. There are three core things that, and I have done other maps afterwards. We'll get to them later that served other purposes, but I'm staying in that first one. The first thing was, where do I currently work? And what are the core things that if you're going to work here could probably be a part of what you do? And again, that's why I gave the example of Target. It's a retailer. I should know if I want to manage hourly teams, whether it be in supply chain or stores, because eventually that's going to be my job if I want to work at a retailer. Like, don't try to make it up to something that the place is not.

15:19Number two, what do you hope to learn?

15:22Jessi Hempel: So if you were to look at my map, I still have it because I doodled it in a conference where I was bored. But the point is, if you looked at my map visually, it would say at the top for one of the experiences, lead hourly team. Underneath it, you would see three statements. Those three statements were my pre-commitment with people who I had relationships with to help me develop it that said, here's what I want to get out of that experience. Not here's how long I want to be in that job. Not here's what I want to do. It was, I am going to have this hourly experience. So one, I figure out if I want to keep being at target two, three.

15:55Jessi Hempel: And what that does for you is that it tells you when the experience is done, whether you like it or not. You can stay after you've hit those marks. But the point of those three points is that at the point that you have found those three things in the experience, you should be at the place where you're ready to say the strategic yes or thoughtful no. The thoughtful no goes, tried it, don't like it, thank you. Strategic yes goes, ooh, curious, let me keep going. That's all it does. And so I did that for every one of the experiences. And then all I did with it, and this is the part that I think a lot of people get stuck.

16:25Jessi Hempel: At the top of this first map was a question mark, remember? Yeah. Right? Yeah. And my commitment was this. These four things are getting me up there. Now, how do those things correlate? Every person I met with, if it wasn't like a business metrics meeting where we're talking about our operational performance and it was a mentorship conversation or just to get to know you or the very special people that come and have big titles at headquarters are coming by and you should show yourself off. Nobody left a conversation with me without seeing that map. And that is difficult for people because it makes you very vulnerable.

16:59Jessi Hempel: Yes. Do I have the political clout to do it? Right. And that's why I said step outside of your operational routine meetings. I'm not talking about where you're talking about the metrics. I'm talking about all of those practices that happen as you network within a company.

17:14Caroline Wanga: With all due respect, Caroline, you're you. You strike me as a person who might be willing to say, here is my mat.

17:20Jessi Hempel: Nope. I'm not that person. But I was in a company where they do that. And again, I am not saying that to dismiss the fact that it's uncomfortable. I'm telling you that it's not because of my personality that it was comfortable. I had done the work to go, what is this place I work? And that's why I said it earlier, like, you've got to know where you are. It's not bad to be somewhere where you don't. But, like, part of what we're talking about here, Jessie, is people are giving away too much agency on what they can impact in their career. I'm not saying everything is within your control, but there are things within your control that are safe and non-threatening to do, but maybe non-traditional that will help you figure out what it looks like.

18:01Jessi Hempel: And that's the story you're hearing. And here's why I say that. I worked in a company at Target at the time that had leadership development as a priority, research where you work, right? And so because it had leadership development as a priority, it was okay conversation to be talking about what you wanted to do next or what your strengths and weaknesses are, what you wanted to eventually be. So there was an environment that didn't make it uncomfortable to talk about your growing. However, the people I was sharing that map with, some of them might have been surprised people who showed up. But again, that's where the people who I had mentoring relationships with were like, hey, Tim's coming down and your butt is going to the meeting.

18:35Jessi Hempel: You just need to be in that room. I'll tell you why later. But the majority of it was meeting with my boss's peers in the building. Every time I did it, what I was saying to them is, I know that because of where I am on the hierarchy of the company entry-level leader, you guys are constantly talking about if I'm a fit. You have these talent meetings over in room 211 where I'm just looking through the glass to see if I'm going to get that next job, right? Like, we know the routines that happen. My only request was when you sit in a room and my name is brought up, whether you're my boss or not, and you start to hear them talk about things I do well, things I need to work on, or you start to hear them talk about, oh, we want to invest in Caroline.

19:14Jessi Hempel: Oh, we don't want to invest in Caroline, right? Whatever that means. When you are in that room, here's what I need you to be for me, person A, B, and C. Beyond my boss. My boss is going to be for me. I need you to be the person that comes back to me and says, okay, here's what you have support for.

19:29Caroline Wanga: What is your view about building a personal brand? And how do you connect this to your concept of a career map?

19:36Jessi Hempel: Two things. First thing is my perspective on personal brand. I'm going to give my answer with a reframe of the question, which is I don't work on personal brand. I work on personal purpose. But I wasn't always that enlightened. So I understand the question. And here's why I share it to you. part of what we have earned permission to do in this season of the general workplace, right, in Times Chronology, I need people to stop trying to be something for work and something for life. Right? And I know why that's been important to survival in the past, right? And so I give that because I only hear the personal brand question when I'm listening to people talk about their professional life, their job, whether you're an entrepreneur or not.

20:26Jessi Hempel: I don't hear anybody talk about personal brand when they're talking about themselves. Like the personal brand of what? You're shopping at the grocery store? Do you worry about the personal brand for that? But I think what's been missed in there, there wasn't adequate communication that we had moved out of this era where you need to build this toolkit about who you are internally for work. And then you have this other toolkit for life. You will lose if you keep those things separate. The modern workplace, the modern world no longer accommodates that, but it forgot to tell you. Because now you're hearing companies say, bring your authentic self to work.

21:04Jessi Hempel: Well, you want 50 %? Because I'm not bringing the, right? And it's not people's fault. It's the workplace shifted in what it started to say it wanted people to show up with without giving them a map about what's different. So my first thing would be, if you are trying to answer the question of your personal brand, I would offer to expand the question to your personal purpose. And then how does that show up when you are working? How does that show up when you are living? How does that show up when you are growing? Right. And I say it that way because it also, and there's an exercise I talk to people about, the question about personal purpose will automatically take you to what your natural giftings are and strengths and will face you with the things you're not good at.

21:48Jessi Hempel: And your job is going to be stop trying to be good at the things you're not good at and spend 90 % of your time doing things in your natural strengths, people, because you will only be a C if you focus your energy on what you're not good at. I fully recognize that the corporate environment teaches you to focus on being better because it's afraid to say I'm not good at that if it's something the company values. But I would say if you choose to go that path, then don't be mad that you're on the hamster wheel. You chose the hamster wheel. The gain will be much more magnified and you will feel a whole lot more grounded in who you are because your personal brand doesn't matter if you know your personal purpose.

22:22Caroline Wanga: I don't want to not ask you about failure because you have this conviction that we can turn failure into our competitive advantage. And it doesn't always feel like that to me. I wonder if you can talk a little bit about that.

22:33Jessi Hempel: Yeah, first of all, I am an Olympic level failure. Let's be really clear about this. And I share that with you because I think we've got to change the narrative that was given to us. That failure is something you try to avoid. If you happen to stumble upon it, please resolve it before anybody finds out. And you better hope nobody saw and doesn't bring it up tomorrow.

22:53Caroline Wanga: This episode is brought to you by LinkedIn. Running a small business means every hire matters. A bad hire can cost you time, money, and momentum. A good hire, they can change everything. But finding great talent isn't easy, especially when you don't have the time or resources to sift through piles of resumes and find the right fit. That's why LinkedIn built HiringPro, your new hiring partner that screens candidates for you. So instead of sorting through applications, you can spend your time talking to candidates and finding your next great hire. With Hiring Pro, you can hire with confidence, knowing you're getting the best talent for your business.

23:32Caroline Wanga: In fact, LinkedIn found that its users are 24 % less likely to need to reopen a role within 12 months compared to the leading competitor. Join the 2.7 million small businesses using LinkedIn to hire. Get started by posting your job for free at linkedin.com slash worklife. Terms and conditions apply. This episode is sponsored by Rula. When you're going through a difficult breakup or a tough time at work or just dealing with the anxiety and stress of everyday life, the last thing you want to do is scour the internet for therapists who take your insurance. A lot of online therapy won't accept insurance at all, which means taking care of your mental health requires paying out of pocket or signing up for a pricey monthly subscription.

24:19Caroline Wanga: But Rula does things differently. They partner with over 120 insurance plans, meaning the average copay is just$15 per session. That's real therapy from licensed professionals at a price point that actually makes sense. With a network of thousands of therapists nationwide, Rula can help you find the right one for you based on your needs, preferences, and state requirements. Thousands of people are already using Rula to get affordable, high-quality therapy that's actually covered by insurance. Visit Rula.com slash worklife to get started. That's R-U-L-A dot com slash worklife. You deserve mental health care that works with you, not against your budget.

25:01Caroline Wanga: This episode is brought to you by National Business Furniture. You can find them at nbf.com. What your workspace looks like says a lot about the way you work and can make a big difference when it comes to productivity. The truth is our surroundings can impact how we think, how we feel, and who we become while we're in them. Your workspace can affect engagement, productivity, and maybe even retention. That's why getting your workspace right matters. It's proof that you value your team. National Business Furniture believes that every business deserves furniture that lasts, service that cares, and a partner that gets it, all on a budget that works.

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25:56Jessi Hempel: But for me, where the rhetoric came from, and I'll tell you that is, I had a child at 17 years old. I became a mom before I became a legal adult. I watched people renegotiate my potential for me without my permission. Go to Harvard four years, you'll do great, get a full scholarship. Maybe you should do community college because you're going to have to take your kid to school. And at 17 years old, I'm not sophisticated enough yet to weave through that and know that it's love.

26:25Caroline Wanga: And so the world looked at you and said, OK, well, now this is the path you're on. And you said, no, no, no, no, this is the path.

26:30Jessi Hempel: No, you're giving it way too much credit for clear thinking. I was a 17-year-old who was now a mother with immigrant parents that came to the U.S. to give me opportunity, and I was a firstborn. Both my parents have their Ph.D. I was supposed to have been going to college. So here's what it created. An 18-year journey of making up for having a kid at 17. And I was sitting at a development conference, and the moderator sees me, and I'm having this emotional moment. And he comes to talk to him like, don't come over here with your like corporate psychology voodoo. I'm fine. Just let me. And so he didn't listen and pull me aside and got me to think about things.

27:10Jessi Hempel: And what came out of that conversation was I was 36 years old at the top of a Fortune 50 company. And I still looked up the girl I went to high school with to see if I had a better job than her. I was sitting in a position that very few people get to do, period. Yeah. And I couldn't see where I was. And so the exercise became, what do I do to resolve this? But the point is, 17 years old became the fail that captured me. When I found out I'd been that way and had to undo it, I had to figure out how to change my relationship with failure because that's how long it had been there. And that's where five fails a day came from.

27:45Caroline Wanga: I love five fails a day, but I am not going to go deep on that. Y 'all will have to find that on your own because we are not closing out today without talking about, I think, my very favorite career advice from you. You know, you speak so eloquently about how you approach your career without negotiating who you are. In fact, you have a framework for us around it, right?

28:05Jessi Hempel: I do. So talk to us about that. I do. I have a framework around it, but here's what I want to be honest with as I say it. That's probably Caroline over the last eight to nine years. So this place I'm going to talk from is not what I've always been. It came as around the time of what I talked earlier. So here's the thing. Because I spent so much time making myself small in order to raise my daughter and prevent anybody from saying I wasn't going to be successful, I had no interests. I had no pursuits. What I knew then is that I needed to do work to redefine who I was and then I needed to spread it into my life, not just work.

28:44Jessi Hempel: And I did it very slow because I was scared. So it really wasn't making progress until I got the DEI job at Target. And my job is to be like, come in on your authentic self. And I'm like, I wear cardigans and I freaking hate cardigans. I don't wear my hair the way I do. I am not the same person at work that I am at home. And I, out of fear, decided that I had to show up as my authentic self, meaning the stuff that I knew intuitively I was afraid to bring to work because I felt it would be that peripheral judgment that would prevent my career. We all know that stuff. And so, but when my job became authenticity, what I couldn't do in that moment was fake it.

29:27Jessi Hempel: I'm like, I'm afraid to change my hair. And how am I going to tell these people to come over here and be their authentic selves here at Target? And so with fear, an immense amount of fear, because I swore I was going to get fired. I said, I have got to start to do some of those things that I have rediscovered that fit in the workplace, but I was afraid to. And the funny thing is I started with my hair. I've always wanted locks. I'd had every hairstyle under the sun. And I cut some braids out the night before on impulse and came the next day and scanned my badge like nobody would, like people cared what I did last night and thought for a week that I was going to get fired.

30:01Jessi Hempel: There were consequences related to questions, but they were bearable. And I was like, ooh, I made it through a week. The next day, it was a blue lipstick. Nobody cared. I'm using aesthetic, but here's why you need to understand what important that was for me. It was one of the core anchors of what I spent every day at work hiding. I want to wear shirts as boots. These are professional. They're just not your professional. And so the aesthetic started the journey of, okay, now that, and I call my clothing armor because it grounds me. Now that I have that, what else is it? But here's what's great.

30:37Jessi Hempel: I started with the thing most obvious, most comfortable, most tangible. I gave less credit for that first move than it deserved. Because the minute I felt comfortable with what I looked like in a meeting at Target, the amount of capacity that I had been taken up, worrying about if I'm wearing the right thing, now was freed up to deliver business results for Target. Go look up an architecture of authenticity. It's literally the map of how I went through my authenticity journey. But I think what's most important to understand is start at the place most obvious to you, not what you think other people care about.

31:12Jessi Hempel: Mine happen to be my aesthetic. Yours might be language. It might be whatever. Start by adjusting the thing you know needs to be different at work.

31:20Caroline Wanga: We got one more question for you here from Paul Cotton in Texas, who asks, he wants to return to career mapping. Does a map apply to older senior execs wishing to transition into new types of roles?

31:33Jessi Hempel: Yes. Here's why I answered that before you finished the question. You did. I've had four career maps. So the first one was, I don't know what I want to be. The second one was, I want to be that. How do I get there? The third one is, what the hell am I supposed to do now? That map that came about, I think I like this work because it touches my nonprofit background. What does doing this work for the rest of my life look like, even if it's not at Target? Because I still got to pay her college bill. And so that third math was, what do people who work in DEI do beyond have DEI roles in companies? I found out people, they write books, they go start consulting, they do all of that.

32:11Jessi Hempel: So I started to play with this idea of if I love DEI, I want to do it at other companies or whatever. What would that look like? That was the third map. The fourth map is active right now at Essence. And I share that because I have never said that the Kermere maps are proprietary to a particular life stage. But because of the type A's that are around me all the time, they always hear this idea of you only do one and you only do it once. What I'm sharing with you and why I could answer the question regardless of what your personal demographics are Every time I was sitting in a curiosity or a moment related to what I wanted to do next The first thing I did was see what kind of map it needs to be And what kind of map it needs to be was defined by what is the box at the top I'm trying to solve for So forget your age Focus on where you are in your professional career Are you in a place where you know what you want to do next or you don't?

33:10Jessi Hempel: If you don't play with the mat, that's how it works. And I will probably have a career map for the rest of my life, but I will probably have 682 of them. But it's become the exercise that has always given the right strategic thought and action to continuing to advance in my career, especially being a girl who's never been qualified for any jobs she's had on paper.

33:29Caroline Wanga: Okay. I love everything about that answer. This question comes from Maxine Gray. She's here with us in the U.S. Thank you, Maxine, for this question. Hi, Maxine. She says, what rules have you rewritten that were key to your personal and professional success? Was she planted? And why did they matter?

33:45Jessi Hempel: Here's the answer to that. It's a simple answer. It's always a long one. Here's the thing. I operate, and that's where the title of this book came from. I'm highly percent sure. There were only a couple things were non-negotiable, and the title was one because I've had it in my head for years. I had to learn two voices. I had to learn what my intuition sounds like, and I had to learn what my inner saboteur sounds like. The reason I had to understand them was because my inner saboteur is a slithery, sophisticated, manipulative sound that capitalizes on everything I've done wrong in life. every speculation I have about what people don't like about me, what I don't like about myself, what might be the judgment I experience, she is well-versed, she is ruthless, she is malicious, and she will attack at any point.

34:43Jessi Hempel: And I had to get to know her voice and how it was different from my intuition because she sounds a lot like my intuition in tone. She doesn't in intent. And the reason I focused on my intuition is because that's the advice I was given when I went to go be a CEO, because I'm a collaborative leader. And I was told you're going to be in a position for the first time where you're going to have to make a lot of decisions by yourself. So you better hone in on that intuition. So doing it for the job then turned and helped me benefit for it overall. And so I would say, acknowledge there's always going to be a negative voice that is you, that is going to use everything that it thinks you did wrong or has been manipulated.

35:29Jessi Hempel: I'm not talking about the people I'm saying, you're talking to yourself. And it is going to debilitate you. It is going to be the one that makes you believe you won't get promoted and all of these things. And it will stay the loudest, most influential voice in your journey until you learn the other one. me learning my intuition did not prevent my inner saboteur from showing up what it did was give me patience for her to run her course gave me permission to study her habits so that i knew how long she stays what's her typical stuff you got you became a mom you don't have a husband like she's got all these stuff she does all the time people don't like you because you're too brash i could endure and study her to be ready for her when i had another voice that was intuition that was giving me all kinds of the right type of insight focused on my strength and my purpose in life to go.

36:19Jessi Hempel: So she may strike, Caroline, you've never been a CEO. What the hell do you get to be, say, you're a CEO for? Nobody wants you to be the CEO of Essence. That's inner saboteur. Intuition was like, you've never talked about roles before. Why are you doing it now? Right? So that is what I would offer. But again, this book is all about that last question. It is about living with your intuition as your weapon that supports you, silencing your inner saboteur through the lens of knowing what you says, letting you run a course, and follow what your intuition says, and let the people around you help you be there.

36:52Jessi Hempel: And I promise you that you will thrive in a way that you didn't know. But most importantly, you will be surprised about how things that are really easy for you become game-changing. And you're worried if they know you did it on the toilet. And that is a sign that you're working in your purpose.

37:09Caroline Wanga: That was Caroline Wonga. She's co-founder of Wonga Woman. She's the president and CEO of Essence Ventures. And she's author of the new memoir, I'm Highly Percent Sure. Such a great title. I love how unyielding Caroline is when it comes to character, right? She's someone who knows who she is. And she also understands that learning this, it didn't come overnight. I hope you heard in our conversation today a few practical ideas for how you can map out your own career, one that is authentic both to yourself and to your goals. We're going to get into all of this and so much more at Office Hours this week.

37:46Caroline Wanga: And I hope you'll consider joining us, especially if you haven't before. We meet every Wednesday afternoon at 3 p.m. Eastern, along with our senior producer, Sarah Storm. I will go live from the LinkedIn news page. There will be a link in the show notes, or you can always find us by following me on LinkedIn. And if this episode gave you something new to think about, well, maybe it'll help someone you know. Text it to them right now. I'd really love you to. That's it for this week, but I will be right back here next Monday, and I hope you will too. I'm Jessi Hempel. Thanks for listening.

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39:06Jessi Hempel: If you've used Babbel, you would. Babbel's conversation-based technique teaches you useful words and phrases to get you speaking quickly about the things you actually talk about in the real world. With lessons handcrafted by over 200 language experts and voiced by real native speakers, Babbel is like having a private tutor in your pocket. Start speaking with Babbel today. Get up to 55 % off your Babbel subscription right now. at babbel.com slash acast. Spelled B-A-B-B-E-O dot com slash acast. Rules and restrictions may apply.

39:42Caroline Wanga: Grainger knows when you're a procurement manager for an office park, you're not managing one building. You're managing all of them. And to stay ahead, you need to see through walls and around corners. Lights about to fail, filters ready to clog, HVAC on its last leg.

39:57Jessi Hempel: If you wait until something breaks, you're already behind. count on Grainger for quality products, easy reordering and 24 seven support. Call 1-800-GRAINGER, click grainger.com or just stop by.

40:08Caroline Wanga: Grainger for the ones who get it done.

From the publisher

Careers rarely move in a straight line, and for many people, the old roadmap no longer works. In this special feed drop from LinkedIn’s Hello Monday, host Jessi Hempel sits down with Caroline Wanga for a conversation about building a career with intention, authenticity, and room to evolve.


As president and CEO of Essence Ventures and co-founder of Wanga Woman, Caroline has spent years helping people rethink success on their own terms. Before leading Essence, she spent 15 years at Target, rising from intern to the C-suite — a journey that taught her the value of continuously revisiting, reshaping, and even reinventing your career map.


Jessi and Caroline discuss:

  • Why your “next right move” may not look like anyone else’s
  • Why playing with your career map, not perfecting it, leads to clarity
  • How, and when, Caroline has created her own career maps
  • The role of authenticity in leadership and life
  • What it really takes to live and work with personal purpose
  • Tools and mindsets for building a meaningful career in today’s world


Caroline also shares insights from her memoir, I’m Highly Percent Sure, and offers a refreshing perspective for anyone questioning what comes next.


Follow Jessi Hempel and Caroline Wanga on LinkedIn, and listen to more Hello Monday wherever you get your podcasts

For the full text transcript, visit https://www.ted.com/podcasts/worklife-transcripts

Hosted on Acast. See acast.com/privacy for more information.

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