Mailbag: “I did everything right in my career, so why am I miserable?”

Summary

HerMoney with Jean Chatzky: Mailbag Episode Summary Episode: Mailbag: “I did everything right in my career, so why am I miserable?” Release Date: March 7, 2025

In this insightful mailbag episode of HerMoney with Jean Chatzky, host Jean Chatzky teams up with executive coach and author Karen L. Dodd to address listeners' pressing questions about career fulfillment, success, and overcoming professional dissatisfaction. Drawing from Karen's expertise and personal experiences, the episode delves deep into understanding why achieving traditional career milestones doesn't always equate to personal happiness and offers actionable advice for redefining success on one's own terms.

---

Introduction and Guest Overview

[01:24] Jean Chatzky: Jean introduces Karen L. Dodd, highlighting their prior conversation about Karen's book, Gilded: Escaping the Trap of Empty Ambition, which focuses on finding genuine fulfillment in one's career. Jean emphasizes that many listeners are grappling with balancing pressures from work and home lives, setting the stage for a meaningful discussion on achieving success without sacrificing personal well-being.

---

1. Feeling Accomplished vs. Feeling Tired

Listener Question (Britt): Britt, in her early 30s, feels that despite checking all the right career boxes—earning degrees, landing a high-paying job—she remains unfulfilled and exhausted. She wonders whether she's experiencing typical career burnout that might resolve with a promotion or job change, or if she needs a more drastic lifestyle change.

Karen L. Dodd’s Response: [02:48] Karen L. Dodd: Karen empathizes with Britt's experience, sharing that she faced similar feelings in her early 30s. She suggests that Britt might have "put your ladder up the wrong wall," meaning she may have pursued goals misaligned with her true passions. Karen advises Britt to embark on an inner journey to discover her genuine purpose and what truly excites her, rather than merely striving for traditional success markers. She emphasizes that fulfillment comes from aligning one's career with their soul's direction rather than external expectations.

Notable Quote: "If the top of the mountain doesn’t feel very good, nothing has gone wrong. It's okay. You just tried something that was in opposition to the direction of your soul." — Karen L. Dodd [02:48]

---

2. Distinguishing Between Wrong Job and Wrong Field

Jean’s Follow-Up Question: Jean seeks clarity on differentiating between being in the wrong job within the right field versus being in the wrong field altogether, especially when considering factors like toxic work environments or lack of autonomy.

Karen L. Dodd’s Response: [04:35] Karen L. Dodd: Karen explains that the crux of fulfillment lies in engaging in work that "lights you up inside." She shares her personal transformation story, where changing her internal relationship with her work allowed her to find joy in the same organization she previously found stifling. This shift in mindset and self-awareness enabled her to create meaningful connections and thrive professionally without necessarily changing industries.

Notable Quote: "If you're not lit up from inside, everything around you is going to mirror that to you, and you're going to have to find a way to get out of it." — Karen L. Dodd [04:35]

---

3. Re-entering the Workforce After Raising Children

Listener Question (Grace): Grace, in her 40s, took time off to raise her children and is now re-entering the workforce. She feels immense pressure to prove herself and catch up with younger colleagues, resulting in stress and doubts about her path.

Karen L. Dodd’s Response: [06:50] Karen L. Dodd: Karen reassures Grace that her feelings are entirely normal. She encourages Grace to reframe her time spent raising children as valuable years of personal development and skill acquisition, such as multitasking and managing complex schedules. Karen suggests focusing on solutions rather than dwelling on feelings of being left behind. She also dismisses outdated financial advice that emphasizes starting investments early, emphasizing that it's never too late to build financial security.

Notable Quote: "Those years that people spend mothering children are not wasted years. They're extremely hard work. They're enormous personal development." — Karen L. Dodd [06:50]

Jean’s Addendum: [09:57] Jean Chatzky: Jean reinforces Karen's advice by sharing her own experience of starting to save later in life and succeeding, highlighting that it's never too late to improve one's financial situation. She also points out the efficiency and multitasking skills developed through motherhood as significant assets in the workplace.

---

4. Transitioning to an Exciting Post-Retirement Chapter

Listener Question (Pam): Pam, a 55-year-old professional, feels bored despite a successful career and substantial retirement savings. She seeks guidance on transitioning into a more exciting phase of life that balances fun with financial stability.

Karen L. Dodd’s Response: [14:21] Karen L. Dodd: Karen advises Pam to view retirement not as a complete stop but as a transition to meaningful work. She recommends assessing one's "zone of genius" versus the "zone of excellence" using tools like The Big Leap by Gay Hendricks and the Gallup Strengths assessment. These tools can help identify passions and strengths that can lead to both personal fulfillment and financial success. Karen strongly advocates for continuing to work in a capacity that brings joy and leverages one's talents.

Notable Quote: "The things that we love to do are the things that we can excel at and achieve mastery at. Mastery is something that can never be taken away from you and will usually be far more conducive to wealth." — Karen L. Dodd [14:21]

Jean’s Contribution: [16:16] Jean Chatzky: Jean complements Karen’s advice by suggesting a reflective exercise: recalling enjoyable activities from childhood to tap into innate passions. She encourages embracing playful interests as a pathway to rediscovering what genuinely brings joy.

---

5. Avoiding the Trap of External Definitions of Success

Listener Question (Reagan): Reagan, a young woman at the start of her career, is determined to achieve success without falling into the same traps as her siblings, who are financially successful but personally miserable. She seeks advice on avoiding a career that prioritizes money over fulfillment.

Karen L. Dodd’s Response: [18:36] Karen L. Dodd: Karen advises Reagan to prioritize her gut instincts and passions over societal expectations or financial incentives. She warns against pursuing lucrative careers solely for monetary gain, sharing her own story of regretting a high-paying but unfulfilling job choice. Karen emphasizes the importance of aligning career choices with personal interests to ensure long-term happiness and success.

Notable Quote: "Don’t sell yourself into a career that you don’t want just because the paycheck is higher." — Jean Chatzky [19:17]

Jean’s Addition: Jean shares her personal anecdote about choosing a high-paying job that led to immediate regret, which she later rectified by returning to her passion. She underscores the relief and happiness that come from following one's true interests over financial incentives.

---

Conclusion

Throughout the episode, both Jean Chatzky and Karen L. Dodd emphasize the importance of self-awareness, aligning career choices with personal passions, and redefining success beyond traditional metrics. They advocate for embracing one's unique journey, leveraging personal experiences as strengths, and continuously seeking fulfillment in both professional and personal spheres.

Final Takeaway: Success is not solely defined by external achievements or financial gains but by living authentically and pursuing what genuinely ignites one's passion and joy.

---

Join the Conversation: If you found this episode enlightening, consider engaging with HerMoney programs like Finance Fix and Investing Fix, designed to empower women in their financial journeys. Visit HerMoney.com to subscribe to the newsletter and stay updated on the latest financial insights tailored for women.

Transcript

[Jean Chatzky]

Investing right now feels scary. The markets are swinging wildly, headlines are nerve wracking and making smart money moves can feel overwhelming. But here's the good news. Our investing fixed portfolio, the portfolio that was built by my all women investing club investments chosen by our members. It's holding strong. Why? Because we invest with strategy, with confidence and with a community that helps us navigate the ups and downs together. In our last session, two new stocks were pitched for the group to vote on and to add to our portfolio. And if you join us for our next meeting, you can see which stock made the cut. You can even cast your own vote the next time around. And the best part, your first month is completely free. Investing Fix is where women come to build wealth together without the Wall street jargon. Join us [e-mail] that's fix with two X's and let's grow your portfolio one smart decision at a time.

[Karen L. Dodd]

The answer always lies within discovering who you are and what you want to do and then your audacity to do that on purpose. And if that means changing industry, maybe it does. But otherwise it's just different places, different faces. But the only thing that really needs to change.

[Jean Chatzky]

Hey everybody, I'm Jean Chatky. Thanks so much for joining us on hermoney for a special mailbag chat with executive coach and author Karen L. Dodd. I hope that you all caught our earlier episode with Karen where we talked about her new book, Gilded all about escaping the trap of empty ambition, particularly as it relates to our careers. We've heard from so many of you who are facing pressures, various pressures in your working lives, your home lives. Today, Karen is going to tackle your biggest questions about success, fulfillment and finding a way to want more in your careers without it taking more from you. Karen, thank you so much for being with us, for giving us your time.

[Karen L. Dodd]

Thank you so much for having me. It's a joy to be here.

[Jean Chatzky]

All right, you ready to dive on in?

[Karen L. Dodd]

Let's do it.

[Jean Chatzky]

Our first question comes from Britt. She says, I'm in my early 30s and I feel like I've done everything, quote unquote right. I got the degrees, landed the high paying job and basically checked all the boxes. But instead of feeling accomplished, I am literally just tired. How do I know if this is normal career burnout that will dissipate once I get a promotion or change jobs or if I just need to go live in the woods?

[Karen L. Dodd]

That's hilarious. That's exactly what happened to me in my early 30s. Brit, I think what's happening is very Likely not going to go away, won't dissipate. The voice is going to get louder and louder and louder. And if it does, Brit, then really what's happened is you've just put your ladder up the wrong wall. Many of us do this. Many of us climb that ladder, checking every single box like I did, and doing everything, quote, unquote, right, only to realize at the almost top of the ladder that you have made a mistake here and you've actually climbed the wrong ladder. Here's how I know. It's because the ladder is supposed to feel very good to you. The top of the mountain supposed to feel very good. If it doesn't feel very good, nothing has gone wrong. It's okay. You just tried something that was in opposition to the direction of your soul. I recommend getting down from the ladder, which is going to cost you. It'll be very painful to semi start over, but really take the time to go on an inner journey and discover your purpose. To really discover what lights you up, what you would do if nobody would pay you, what you are becoming when you do this thing that you genuinely want to do. And by the way, same in love and in other departments of your life. And usually that inner journey, while it takes a while, pays off with dividends because you never put your letter up against the wrong wall again.

[Jean Chatzky]

How do you distinguish, Karen, between the wrong job in the right field field and the wrong field? Because I think that's kind of at the heart of this question, right? I mean, you could have a job with a toxic work environment or a bad boss or lack of autonomy, and yet maybe the underlying work in some way feeds you or could feed you if you were in a better space.

[Karen L. Dodd]

Yeah. So that. That's sort of the answer. The answer is there is no real wrong job, wrong company, or even wrong bo. What's really happening is you're not doing that which lights you up inside. If you're not lit up from inside, everything around you is going to mirror that to you, and you're going to have to find a way to get out of it. And by the way, you may find your way to the same industry, but you will find a new configuration within yourself that actually works for it. Let me give you a great example. I was working for a big luxury company. I thought that the problem was the job and the bosses and the organization and the fluorescent lights. Now, the fluorescent lights were grotesque in my defense, however, I was not being the fullness of who I am in that job. I was so stunted, I was so fear based. I was so trying to fit myself into this little box that I couldn't relate to anything around me. And as a result, all I really manufactured was a lot of political strife. Instead, years later, when I trained as an executive coach and a trainer and a speaker and then revisited that company, they were the first people who hired me. Isn't that amazing? I found a completely new relationship to my work within that organization, to the people around me in that organization, and to the exaltation of what we were able to create together. Just a totally different relationship to the very, very same circumstances. So really, the answer always lies within discovering who you are and what you want to do and then your audacity to do that on purpose. And if that means changing industry, maybe it does. But otherwise, it's just different places, different faces. But the only thing that really needs to change is you.

[Jean Chatzky]

This question is from Grace. Grace says, I took time off to raise my kids, and now I'm re entering the workforce in my 40s. I feel a lot of pressure to prove myself and to catch up on everything. It feels like I quote, unquote, missed. I'm constantly worried I'm behind and need to do more just to get on par with other colleagues who are younger than myself. But working longer hours and feeling this constant level of stress bubbling just beneath the surface is not what I signed up for. So I'm wondering a few things. How long will I feel this way? Should I look for an easier job? Is this normal? I would love your advice.

[Karen L. Dodd]

Oh, it's totally normal, Grace. Who hasn't felt that, by the way? You can feel that in a couple of dimensions. First, the return to the workforce. And second, you can feel left behind in other dimensions of life. For example, some people feel left behind when they haven't saved until they're 40 and they think that they're very, very behind. And it's almost impossible to catch up and I'm really exhausted and maybe I should do something else, like, I don't know, marry rich or something. Okay. This is a natural impulse. It'll last for as long as you're willing to stare at the problem and not at the solution. I would start to stare at the solution and own it. Grace, those years that people spend mothering children are not wasted years. They're extremely hard work. They're enormous personal development. They're finding faculties within yourself that you never knew were there. Managing a house, managing schedules, probably years of deep enrichment that you've totally neglected. Like, for example, the many hours that I spent watching Marvelous Mrs. Maisel. Not a waste of time. Enormously enlightening. And so the question is, how are you willing to spin this? Are you willing to spend this as this was completely dead, wasted time, or are you willing to reframe this as this was a glorious investment in self that I'm now going to use for my glory in a completely new environment? The second thing I would reframe is the assumption that you needed to acquire some kind of a skill to catch up with everybody else at work. I don't know about you, but almost everything that existed in my work universe 10 years ago, Gene, doesn't exist anymore.

[Jean Chatzky]

Absolutely.

[Karen L. Dodd]

I mean, if you dropped me an understanding of Instagram 10 years ago, I wouldn't be well equipped to handle that either. So the world is evolving at a very rapid pace. You're literally just entering it at the same point that other people are entering it. Your job is to combine that with your prodigious life experience and spin that in the direction of moving forward. Now, here's how this ties back into just generally the understanding of your psychology to work with you rather than against you and anything, especially as pertains to money. This idea that you've been left behind and you cannot make up for lost time is an extremely, tremendously painful feeling. And it keeps you not only fixated on the problem, but fixated on regret. You. You cannot do anything with that energy. I remember Gene rejecting with all my heart 10 years ago when I was broke, the work of Susie Orman, a very mean lady who kept accusing me of spending all of my money on lattes, and Tony Robbins, who also very meanly said in a book called Money that if I didn't start saving in my 20s and didn't start investing in my 20s, I would never, he literally said, never, be able to make up for that time. Well, guess who's laughing now, Tony, hold my drink. I remember thinking, you know what? This is not good enough for me. And I'm not going to think in this direction because it's going to make me immobile. It's going to paralyze me from actually claiming that everything I've done terribly has actually been a very good experience, because it's clearly shown me what not to do, which is already going to save me tremendous amounts of time ahead. And now my job is to get with the program, to learn the levers that are available today as best I can, and to do my best to aim at a better future. And all I can say is it works out definitely worked out better than if I had continued to stare at the problem.

[Jean Chatzky]

Yeah, no, I completely agree on the finances. Absolutely. The best day to start saving was 20 years ago. The next best day is today. Right? You start today, you up your game, you set some goals and you figure out how to get there. And I've seen people do it. I did it starting at 40. I've seen people do it starting at even later years. So Karen's absolutely right about that. The other thing that I would just add to your amazing answer, Karen, is that I found that being a mother and managing kids and work made me so much more efficient and able to. I know multitasking has a negative connotation in some circles, but it really made me able to tackle a lot of different things. Well, yeah. And use that. You Grace, you now have that skill of knowing how to maneuver in these different universes. That's going to be of huge, huge help at work. And so I think if you can get past these feelings which are truly inner, you're going to find that the whole world just opens up. We are going to take a very quick break before we do that and come back for our last two questions. A quick word from our sponsor. You know that feeling when you slip into something so soft, so luxurious, your whole day just feels a little extra special.

[Karen L. Dodd]

Special.

[Jean Chatzky]

That's how I feel every time I wear one of my Quince cashmere sweaters. They are my secret weapon for adding everyday luxury to my life without blowing my budget. Whether I'm recording an episode or heading out for lunch, I throw on something from Quince and instantly I feel polished. I feel put together. But Quince is so much more than affordable cashmere. I recently swapped out my old bedding for their hotel quality sheets and game changer. Silky, soft, breathable and way more affordable than the other premium brands. Give yourself the luxury you deserve with quince. Go to quince.comhermoney for free shipping on your order and 365 day returns. That's Q-U-I-N-C-E.com hermoney to get free shipping and 365 day returns. Quince.com hermoney Eczema isn't always obvious, but it's real.

[Pam]

And so is the relief from Evglis. After an initial dosing phase of 16 weeks, about 4 in 10 people taking EVGLIS achieved itch relief and clear or almost clear skin. And most of those people maintain skin that's still more clear. At one year with monthly dosing EVGLIS Lebricizumab LBKZ a 250mg per 2ml injection is a prescription medicine used to treat adults and children 12 years of age and older who weigh at least 88 pounds or 40 kilograms with moderate to severe eczema, also called atopic dermatitis, that is not well controlled with prescription therapies used on the skin or topicals, or who cannot use topical therapies. EBGLIS can be used with or without topical corticosteroids. Don't use if you're allergic to ebglis. Allergic reactions can occur that can be Severe Eye problems can occur. Tell your doctor if you have new or worsening eye problems. You should not receive a live vaccine when treated with Epglis. Before starting Epglis, tell your doctor if you have a parasitic infection searching for real relief? Ask your doctor about eglis and visit ebglis.lilly.com or call 1-800-LilyRx or 1-800-545-5979 and.

[Jean Chatzky]

We are back with Karen L. Dodd. We're answering your questions about ambition and success and how messy it can sometimes be. And we've got one from Pam, who writes, I'm 55 and have had a successful career, but to be honest, I've been bored for most of the last decade. Thankfully, I've saved enough for a good retirement in a few years, but I know a traditional retirement isn't for me. I want to do something else else. My question is what? Is there some kind of an assessment I can take, or someone who can help me figure out where my skill set may plug into a more exciting field? My only requirement for this next chapter is fun with a little bit of money.

[Karen L. Dodd]

Yeah, great question. I think it should be fun with a lot of money. I love that question, Pam. First of all, you're 55. You're most likely to live at least 30 more years. So I don't know about the retirement as an idea. I think we need to work and we need meaningful work. So it's not a particularly bad thing to consider an unorthodox retirement, if you will, or a life transition. Life transition or career pivot is the most common case scenario for coaching, so I recommend it with all my heart. But yes, there are some tools that will already take you much, much closer to discovering what your zone of genius is. In other words, what lights you up, what will produce fun, and if you are willing to embrace it, I, unlike Scott Galloway, believe it will make you very wealthy. It's really usually the things that we love to do that we can excel at and achieve mastery at. Mastery is something that can never be taken away from you and will usually, as a result of that, be far more conducive to wealth than any other, if you will, exploration. So the first tool is a book called the Big Leap by Gay Hendricks, who I'm so proud. Blurb my book because I admire him beyond words. Not just because he has two cats gene, which I think is the apotheosis of happiness, but also because he's an exceptional writer. An exceptional writer. And the Big Leap is wonderful and includes wonderful exercises for you to go through to really discover your zone of genius versus your zone of excellence, which is probably where you've been operating, which has produced boredom or stagnation for a while. The second thing is Gallup Strengths. Gallup Strengths is an assessment that you can get online. You only need the top five. I think that assessment costs $25, and it's really, really useful to you to at least start to consider, perhaps things you didn't consider that were areas in which you truly have talent and you may want to develop a little bit further. And again, if you're ready to do a real deep dive on who you are and what you really want to do and how you want to build that, I couldn't recommend executive coaching more.

[Jean Chatzky]

I think that's a great recommendation if you're looking for just a cursory hack to maybe bring you a little bit closer to the thing that you loved. Somebody once recommended to me that when you're feeling stuck about what it is you truly like to do, think back to what you liked to do when you were 11. That 11 was that magical age before you hit puberty, before you hit that really messy junior high school stage where nothing was good. It's sort of the last age at which everything was good. So think about what you liked doing then, and maybe you can tap into a little bit of that right now.

[Karen L. Dodd]

I love that. And I want to just add a tiny hack if we have a second.

[Jean Chatzky]

Sure.

[Karen L. Dodd]

And it is. Don't judge whatever you come up with. When I was under the age of 11, when I really started to remember who I was, I remembered that I was basically Manny from Modern Family. I was a chubby theater geek who loved reading and liked talking. And I never considered those marketable skills right until I started to think, that's truly what I love to do. What can I do with it? It doesn't matter what you come up with. It's truly what you love to do.

[Jean Chatzky]

High school and college theater, by the way, because I was a theater geek, too. Everybody should have to do high school and college theater. Those skills are. They've helped me, they've helped my children. Getting comfortable being out in the world, whether you're an introvert or an extrovert, is, I think, so crucial to how we live our lives today. So I'm a sign up all your kids for the fall play, 100%. Our last question is from Reagan. Reagan says, I'm a young woman just starting out. I want to be successful. I have big dreams. I also have big brothers and sisters who are. Are honestly now miserable in their careers. They're working long hours in jobs that don't engage them. And the only redeeming thing they have to share is that they make a lot of money. They have the same goals that I do. But I don't want to wake up in 20 years and feel like I lived my life for someone else's definition of success. What advice would you give to someone at the beginning of their career to help avoid this trap?

[Karen L. Dodd]

Relax and don't do that. I wish I had heard that when I was a kid. I didn't. I only heard the opposite, which is that you see that that's what you should be doing. And I followed that advice, which was terrible. Thank God I didn't get into McKinsey. It would have been even worse than the career I ended up having. Follow that gut instinct, Reagan, and ask yourself to cultivate something in the direction, at least in the direction of something that you're truly interested in or truly passionate about. You will end up exactly where you're supposed to be without the fear. You'll end up where you're supposed to be faster with the fear. You're going to waste an enormous amount of time in the wrong direction. That's my honest advice.

[Jean Chatzky]

And Reagan, don't take a job for the money. I did it. I did it. Coming out of college, I was offered two jobs, one in a magazine. And I had spent years building a resume that was perfect for a job at a magazine. It was what I wanted to do. But I went to college at the University of Pennsylvania, which was incredibly pre professional. And I felt like there was something wrong with me because unlike a lot of my classmates, I wasn't going through on campus interviewing for Wall street jobs, retail jobs, other corporate jobs. So I threw my resume in and I went through that process and I got a job in a training program for a major retailer. A job that paid twice as much as the job that I was offered at a magazine paid and I took it. I took it. I moved to Hartford, Connecticut. I bought a car. I started working in this department store. It took me about two weeks to say, you are an idiot. It took me about eight weeks to convince my parents to take this car off my hands and move to New York and get another magazine job for $500 less a year than the first magazine job was gonna pay. And I just breathed this huge sigh of relief and was never happier eating Chinese soup for every meal cause it cost a dollar and came with rice. If you're doing what you love, I'm with Karen. I think will follow. But don't sell yourself into a career that you don't want just because the paycheck is higher. Karen, thank you so much for doing this with us today.

[Karen L. Dodd]

Thank you. Huge pleasure. Thank you.

[Jean Chatzky]

If you love this episode, please give us a five star review on Apple Podcasts. We always value your feedback and if you want to keep the financial conversations going, join me for a deeper dive. Hermoney has two incredible, incredible programs. Finance Fix, which is designed to give you the ultimate money makeover, and Investing Fix, which is our investing club for women that meets bi weekly on Zoom. With both programs, we are leveling the playing fields for women's financial confidence and power. I would love to see you there. Her Money is produced by Hayley Pascalides. Our music is provided by Video Helper and our show comes to you through Megaphone. Thanks for joining us and we'll talk soon.