Am I Too Old For My Job? with Debbie Millman | Crooked Media
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October 11, 2023
Work Appropriate
Am I Too Old For My Job? with Debbie Millman

In This Episode

If all my coworkers are younger than me, am I still relevant? How can I stay motivated and engaged until retirement, when I’ve been working so long and it still feels so far away? Should I tell my boss I’m struggling at work because of menopause? Debbie Millman, educator, artist, and host of the podcast Design Matters, joins host Anne Helen Petersen to answer all these questions from listeners in the later phases of their careers.





Anne Helen Petersen: Hi, everyone. I’m Anne Helen Petersen, and this is Work Appropriate. [music plays] So there’s a conversation I had with one of my best friends about her job that stuck with me for, I don’t know, the past decade. She works at the intersection of comms and PR, and at the time we were in, I think, our earlyish thirties, she was thinking about what her next career move should be and how she needed to position herself smartly because she knew from watching the rest of her industry that workers and women in particular reached their forties and suddenly they were no longer relevant. Comms and PR was a young person’s game and as the clock ticked, you either had to find yourself in a leadership role or start figuring out your exit strategy. Now, whether or not you agree with that wisdom, it was one of the first times I really thought of a career as something with expiration dates. And before you start muttering things and shaking your head, remember that I spent most of my twenties and early thirties in academia, a place where, yes, you have deadlines to reach tenure, but then you just like keep maturing like a fine wine. Supposedly, all I’m saying is I hadn’t really thought about timing out of a career, and I’m still thinking about whether or not it’s a real thing or a story we tell ourselves as we try and grapple with shifts in our ambition and what we want out of a job. And I know I’m not alone. We’ve received dozens of questions from people in their later career, which we are going to very broadly defined as more than 15 years in your field. To answer these questions, I wanted someone who was first and foremost in their later career and pretty publicly in that later career, but also someone who’s in a field that like PR seems to at least outwardly privilege some mix of youth and cool. I found that person and was thrilled when she agreed to come on the show. She’s sort of a celebrity. If you are in a a certain world on the Internet. And I really appreciated her bold, unvarnished perspective, not just on her own later career, but on what others can and should ask for and expect in their careers. Maybe this is just the advice you need to hear right now. Or maybe this will be the conversation that gets you thinking for the first time about what your later career will look like and how you want to resist or remodel those expectations. I think you’re going to love it. 


Debbie Millman: My name is Debbie Millman and I’m a designer, an artist and educator, author and host of the podcast Design Matters. 


Anne Helen Petersen: So something we’ve talked about in the past on the show is the idea that careers happen in phases and seasons. And I would love to know how you describe this season of your career that you’re in right now. 


Debbie Millman: Oh, it’s a good question. What is the season of my career? [sighs] The eye of the hurricane. [laughter] School started two days ago. I haven’t started my podcast again for the new season, so everything is very still. And nice, relaxing. But I know what’s on the horizon. [laughs]


Anne Helen Petersen: Do you feel like with your career? You know, I’ve gone through these periods where, like there are times where I feel like I’m, like, resting and holding energy. And then times where I’m like, I’m really busy, but I’m really into being really busy like it is. It’s giving me more creative energy. And then places where you’re in the more like the burnout phase where you’re like, nope, need to pull back now. Like, this is too much. Have you felt those cycles in your own life? 


Debbie Millman: Well, I am always wondering if my busyness is not about productivity, but more about creating a false sense of value or worthiness. So I’m constantly, constantly. 


Anne Helen Petersen: Yeah. 


Debbie Millman: Thinking about that and how much what I’m doing is what I really want to be doing. And that’s a question that I’ve been grappling with and thinking about more and more and more the older I get. 


Anne Helen Petersen: I think a lot too, about like I’ve finally reached this place where I have some financial security, but I don’t know how to leave behind the feeling that at any moment it could all go away. 


Debbie Millman: 100% every single day of my life. [laughs] If you figure out how to get past that, please have me on speed dial. Speed dial, please. 


Anne Helen Petersen: I mean, is it just like having a pension? Is that like what makes— [laughs]


Debbie Millman: No. No. 


Anne Helen Petersen: Yeah. 


Debbie Millman: You know, I remember when I was in my twenties and I was really broke. I mean, I. 


Anne Helen Petersen: Yeah. 


Debbie Millman: There were months where I didn’t know if I could pay my rent or my student loans, and I’d have to choose or food or, you know, And I was constantly scrambling. And at one point I had three jobs just to make ends meet. And I remember thinking, oh, if I could just save $1,000, I would feel safe forever. Now, this was 1983, and $1,000 was a lot more than it is now. 


Anne Helen Petersen: Mm hmm. 


Debbie Millman: But I scrimped and I saved and I finally had $1,000. And I was like, well, maybe if I had 2000, you know, it was. 


Anne Helen Petersen: Uh huh. 


Debbie Millman: And so it’s never enough. It’s never about that type of security, making you feel safe. It’s about your own inner self feeling safe and then enacting on that foundation to be able to make sound decisions about what you want to do and how you want to do it. I think. 


Anne Helen Petersen: Yeah, I think so. [laughs] Okay, going back. I’m glad you mentioned being in your twenties because back then, what did you think your career was going to look like? 


Debbie Millman: Honestly, I don’t know. 


Anne Helen Petersen: Mm hmm. 


Debbie Millman: I, at the time was really compelled to be self-sufficient. I had only myself to rely on. And the lead gene in what I was doing was being in Manhattan, having my apartment. I had roommates, but I was really working towards a goal of living on my own, and I was sort of willing to do anything I could to make that happen. And so while I was absolutely thinking about my career, I didn’t have any I mean, I had a couple of connections and they did help me a great deal, but I didn’t have any connections in the design business or the magazine business. And I was really flying by the seat of my pants. And just as, you know to quote the great Talking Heads song, I was just making it up as I was going along, and I knew that I wanted to do something creative and I knew that I wanted to do something that had some sense of purpose, but I had no idea how to envision a future at that point. 


Anne Helen Petersen: Yeah. Sometimes it’s a type of person. Sometimes I think it’s like what industry you’re in the future doesn’t. It’s not visible. Like if you, you know, I wanted to be a professor in part because to me that future was visible. Like I knew, oh, you get a job and then you stay in that job for like 20 to 30 years or like I had read, Wallace Stegner’s Crossing to Safety, which is a portrait of two couples. Both of them are professors like at University of Wisconsin in Madison. And I was like, this is this is what I see in my future on my horizon. But then, you know, in journalism, I’m like, I have no idea what’s on the horizon, the horizon changes every single day. 


Debbie Millman: Oh absolutely. I mean, I wanted to my dream in my senior year of college was to get a job in Vanity Fair. 


Anne Helen Petersen: Yeah. 


Debbie Millman: Vanity Fair had just relaunched. It wasn’t the celebrity magazine we know today. It was more of a literary arts magazine. 


Anne Helen Petersen: Yeah. 


Debbie Millman: And I did submit my portfolio to Condé Nast, and I did get an interview, which was miraculous in and of itself, but I didn’t get the job. [laughs] And so after that, that was kind of the only thing I had envisioned. That’s what I wanted. And my heart was broken and then I moved on. So I did get a job working at a magazine, but it was a cable television magazine. But at the time, cable television was, you know, a big deal. 


Anne Helen Petersen: Yeah. 


Debbie Millman: So while it wasn’t the creative behemoth that I thought Vanity Fair was under the leadership of Charles Churchward, who was the design director, at least what it was in the magazine business. 


Anne Helen Petersen: Well, and to get that much success, like if you would have gotten that job at Vanity Fair right out of college. 


Debbie Millman: Oh I would have been killed. I would have died. [laughter] Seriously, I my interview was everything you see in The Devil Wears Prada. 


Anne Helen Petersen: Yeah. 


Debbie Millman: And I was wearing a blouse with a big bow [laughter]  and pantyhose and yeah, I would have I mean, I made Anne Hathaway in that movie look like Miranda Priestly just in comparison. So, yeah, I wouldn’t, I would have I don’t know. I would have been like, run out of New York. I really would have been. 


Anne Helen Petersen: So we’re going to get into our questions. But I think it’s worth noting that the people who submitted questions about later stages in their career, they’re all women who are really, I think, grappling with these questions. Why do you think that is? 


Debbie Millman: Because we’re sensitive to our environment, because we are always striving, because we always seem to want to make more of ourselves, because we never think we’re good enough. You know, everything that America Ferrara said in Barbie. [laughs]


Anne Helen Petersen: Do you think, too, that ageism plays differently for women in those later stages of their career? 


Debbie Millman: I don’t think so. Having been at the helm of a brand consultancy for as long as I was. 


Anne Helen Petersen: Mm hmm. 


Debbie Millman: And now running a graduate program for as long as I have, I actually see people of all genders struggling to find their footing if they change direction or if they change direction willingly or unwillingly in their fifties. The struggles are more difficult for LGBTQ, more than gender, specifically in terms of binary gender. 


Anne Helen Petersen: Yeah. 


Debbie Millman: But I do think that historically women have had a much more difficult time, and I’m really talking about right now the branding discipline. 


Anne Helen Petersen: Okay, So let’s get into our questions. We’re going to hear the first two questions back to back, and they both are about relating to younger colleagues. Our first question is from Jennifer. 


Jennifer: I work as a tech in a large pharmacy. I’m in my fifties and most of my colleagues are in their twenties or early thirties. There are some big advantages. My supervisor sees me as reliable and a voice of maturity and our older clients relate well with me. There are also some disadvantages. Everyone, including the boss, avoids the lame jobs and I end up doing most of them. I’m a noticer. I notice everything and the others are able to work with blinders on. They do their tasks and leave, and after I do mine, I take the time to organize and set up for the next day. It’s a different work ethic. So how do I avoid being everyone’s work Mom? I feel like I’m picking up after my own kids. I don’t want to be a nag. 


Anne Helen Petersen: And then the second question here is from Janet, and Melody is going to read it. 


Janet: I’m an anti aged female IC in tech I have no interest in going into management, but I like being a solid contributor on my team. I get good performance reviews twice a year, but I’m the old person on my team. I don’t mind mentoring up and coming professionals. I’m also very aware that I look old, maybe even more so because I’m on Zoom, staring at my wrinkles and wattles every day. Am I relevant anymore? 


Anne Helen Petersen: So both of these people are trying to figure out what their places in the workplace when they’re not managers and their peers are a couple decades younger and one person is kind of tired of being what she sees as the work mom. And then the other says she doesn’t mind mentoring, but she, I think, is a little like, do people even want me as a mentor? So I’m wondering if we can kind of reframe how these people are seeing their role at work. What what do you think when you hear these stories? 


Debbie Millman: Well, the first person that has shared their question, my my response is, why are you enabling everybody? Nobody is forcing you to clean up after your kids. [laughs] The fact of the matter is they’re not your kids and you don’t have a responsibility to clean up after them. If you are staying after they leave and cleaning up, you are enabling their bad behavior. Because when they come in the next morning, it’s all clean. 


Anne Helen Petersen: Right. 


Debbie Millman: Why are you taking the responsibility to clean up other people’s messes? And so I would question, is that how you’re feeling valuable? Is that how you’re feeling like you’re making a difference? If if that is if the answer to that is yes, that’s not the answer, you are going to need to really make a difference. You’re going to be making a difference by contributing what you do, not cleaning up after everybody else’s contributions. So the first thing that I would do is say, stop, stop cleaning up after everybody. Stop. Let them take their blinders off. And then you’re all on the same playing field. I wish the caller was, was here because I would say, Why do you feel so compelled to clean up after everybody? 


Anne Helen Petersen: Yeah. 


Debbie Millman: They are not your children and you are not their mom. If they are seeing you as their mom, you are allowing that and enabling that. 


Anne Helen Petersen: Right. Right. And I love that you point out that that might be the place where she sees her value. And maybe that’s because she’s not understanding all the other ways that she has value. Right. Like, she even she enumerates some of those ways. Right. She says like other the you know, the older customers really relate to me. And like, I’ve been there for a long time. My supervisor sees me as reliable. I wish she could say I am reliable. I am a voice of maturity, not just my supervisor sees me as reliable and a voice of maturity.


Debbie Millman: Right. Well, that’s interesting because the second person that had their question, you know, if you’re on Zoom all day, fix your video preferences and touch up your appearance. [laughter] I mean, girl, I am nearly 62. 


Anne Helen Petersen: 100%. 


Debbie Millman: I don’t want to look at my saggy ass wrinkles. Uh uh. I have my filters on all the way, touch up my appearance and make up for low light. And I look like Sharon Stone. No, not really. 


Anne Helen Petersen: Yeah. 


Debbie Millman: But you know what I mean. 


Anne Helen Petersen: Yes, 100%. That is such a simple thing. And I don’t think that means that you hate your face. I think it means that no one should look at their face this much. Right. So not only put your filters on, but also turn off the view that allows you to see yourself. On Zoom.


Debbie Millman: Mm. You can do that, too. I mean, I put always pin the person I’m talking to so that I don’t have to look at myself as big and as much. 


Anne Helen Petersen: Yep. 


Debbie Millman: And that definitely helps. But I also don’t think people look as deeply at our faces as we do. Most of the time when we’re talking on Zoom, we’re looking at ourselves, not other people. And so. 


Anne Helen Petersen: Yeah. 


Debbie Millman: I think that people are looking at us far less than I think we think they are. I think what both of these women have in common is that they’re assuming that other people. 


Anne Helen Petersen: Yes. 


Debbie Millman: Think about them in a specific way. And the first the first question stop, stop, full out enabling others and work on your own contribution. As for the second. There are times and I you know, I don’t know the circumstances here, but I do find that young people tend not to ask as much of others that are older for whatever reason. So she might need to offer she might need to say, you know what, I’m looking to mentor someone. This is what I can provide. And if anybody’s interested, let me know. 


Anne Helen Petersen: Yeah. 


Debbie Millman: And then see if somebody takes the bait. If they don’t, then go volunteer somewhere else. You don’t need to necessarily be mentoring people in the workplace. 


Anne Helen Petersen: That is such a good point. Oh, my gosh. Like, first of all, I’ll say that we have so many questions from people who are saying, I just wish that I could find a mentor in the workplace. Right. Like, I wish we could matchmake almost. 


Debbie Millman: Yeah. 


Anne Helen Petersen: And then the other thing I’ll say is that if you’re not finding that source of value within your team, maybe finding it externally through doing mentorship programs with high school kids. Right. And like, I’m do not mean this like an infantilizing way whatsoever. I’m saying, what if you do mentoring outside of your workplace that then gives you more confidence within your work? 


Debbie Millman: Absolutely. There’s the Big Brother program, Big Sister program. I know that AIGA, the Professional Association for Design, has a mentorship program and they’re always looking for people to volunteer to help the next generation find their way. So I think if you want it badly enough, make it happen for yourselves. Don’t wait for somebody else to ask you. But that, I would say, is true in everything. Everything. [laughs] There are very few things in my life where somebody was just like, Well, here, Debbie, you can have this. You have to make yourself available, but also seek out opportunities and ask. [music plays] 


Anne Helen Petersen: So our next question is about finding your place not just in the workplace, but in the whole industry. Let’s hear from Tracy. 


Tracy: I’m in my mid-forties and experiencing later career in the creative industry. I have a bunch of experience and I had worked my way up to a pretty high level but burned out at the agency I was with and had been making decent money but just didn’t know where to go or what to do because everything that was quote “up” unquote the ladder or even lateral wasn’t really what I wanted to be doing. I felt stuck for ages and I ended up taking a different job with a pay cut in the hopes that it would also be less intensity hours and well work, which it has been. But I’m concerned that the backwards movement and title will look bad for the next time I might interview. And I’m also concerned about aging out of this industry. How do I balance having gained enough experience to be valuable with getting older and aging out of a creative industry that is super competitive and filled with so many fresh young creatives who aren’t burned out and who are cranking out super creative work for cheap. 


Debbie Millman: That’s a yeah, that’s a really intense question. 


Anne Helen Petersen: Right? [laughs] And there’s a lot going on. 


Debbie Millman: This is a really, really intense question. I’m trying to decipher what she’s really asking, which I think is. 


Anne Helen Petersen: Yeah. 


Debbie Millman: I think. Tell me if you disagree. I’m conflicted between being super ambitious and having a lifestyle that I want. 


Anne Helen Petersen: Yeah. 


Debbie Millman: And can I have my cake and eat it too? [laughs] Can I take a step back but still be able to take a step to, two steps forward when I’m ready or if I want to? And the answer is I have no idea. I have no idea. [laughs] It really depends on who’s looking and how you present yourself and how you position yourself in the marketplace. Plenty of people come back after having children. Plenty of people come back after taking a medical leave or family leave. I think that the real question is how can I tell myself I’m still ambitious if I take a step backwards? And why is she thinking about taking a step forwards or two steps forward when she’s just made this lifestyle change she seems to like? So I think she has to come to terms with what she’s done for herself, which is really brave, which shows a lot of self-awareness, which shows a lot of self care. And I think that rather than think about the next step, maybe embody the step that she’s in, and if she did take a step back to be able to do other things or to be able to have a better lifestyle, concentrate on that. If she has extra time, start a self-generated project, the self generated project might catapult her into new arenas that she might not have even been available for if she was working 24/7 at a different job. 


Anne Helen Petersen: You know, I’ve seen a similar narrative with a lot of people who’ve burnt out and who’ve figured out this. I can’t do this anymore. I don’t want to do this anymore. I’m really unhappy. I want to fall back in love with my work in some way again. And they take that step back and they they find if they’re lucky, they find a job that allows them to still do the work that they like. But less of it, right? Like less intensity of it. But then, you know, we still live in the same work environment. And I think the way that she points out, like there are all these younger people who haven’t burned out yet, who are who are doing this other work, like she feels she feels some ambivalence about it. 


Debbie Millman: Yeah. 


Anne Helen Petersen: And that is totally normal. It makes absolute sense. There are a lot of other people who are going through something really similar, and I think as you really smartly point out, she needs to spend some time, whether it’s talking with a therapist, talking with a good friend, talking with herself, journaling, figuring out exactly, you know, how she feels about this. Am I going to be profoundly unhappy if I stay here? Right, If I’m not ambitious or am I? Can I find other places to put my ambition that aren’t just my work that I do for pay? 


Debbie Millman: Yeah, I mean, I think also she needs to evaluate maybe what the more deep seated foundation of why she took this step back and recognize that. There were reasons she did that. Are they still relevant? 


Anne Helen Petersen: Yeah. 


Debbie Millman: Has she looked at those reasons enough? It sounds like she feels guilty for doing this. And that might be something to to look at and grapple with. 


Anne Helen Petersen: Or that like she’s going to regret it later in her life. 


Debbie Millman: And she might, but then she can change again. 


Anne Helen Petersen: Yeah. Yeah. I think she sees some like horizon ending and maybe has some anxiety about that. 


Debbie Millman: Well, you know, that is a. Very real possibility if she gives up. 


Anne Helen Petersen: Yeah. Yeah. 


Debbie Millman: And it might be harder, but it’s not impossible. 


Anne Helen Petersen: And I think, like, you know, less stress, less work. What does it feel like? What does it feel like? What does your sleep feel like? What are your weekends feel like? Like. Spend some time thinking about that balance to like really seeing it instead of only seeing the. What about my future potential for growth and all that? Sort of thing.


Debbie Millman: Absolutely. 


Anne Helen Petersen: So our next question is about figuring out the later part of your career when the middle part didn’t go how you expected. This is from Dana. 


Dana: I’m a mom in her forties with several advanced degrees in the visual arts. After getting married in my late twenties, my spouse and I made the decision that I would step back from schooling and work so that we could have kids. Life throws you surprises and my break was longer than I anticipated. Now we are a good 15 years later with three kids and a surprise set of twins with two kids that have some special needs. I’ve tried to get back into my area of study, but being gone so long is making that tough. Even if I get an initial interview, part time jobs do not pay very well and are unforgiving on availability that works around school hours. Needless to say, these types of jobs are unrelated to my educational background. I don’t like being so entirely dependent on my partner financially. I’m concerned if something were to happen to him or if we were to decide one day to separate. I’m in a very precarious position. I noticed many of my female friends never entirely left the workforce, partly out of fear of being in my position, despite being well-educated, continuously employed and vested in their careers. They all make less than their spouses or more financially independent them in my current situation. They would also struggle to support a family on just their income. Going back to school seems indulgent when I still have unpaid student loans from the first time around. What do you do if you can’t return to the industry you trained to work in? Can all that education be a waste? How might you leverage the unconventional experiences you’ve gained working in a grocery store or as a PTA board member? Or simply how you can proficiently manage a household on a single family income, which often calls for creative ways to cover expenses? 


Anne Helen Petersen: I really like this question because I think she does see her value, and sometimes that’s something that’s missing in in women talking about this scenario, they’re like, I haven’t been in the workforce. I have no skills. Right. But she is she sees that she has a lot of skills. And I also she has multiple degrees in visual arts. She’s really like she loves that work. And she she is good at it, I’m assuming. But the financial anxiety [laughs] which is just I mean, I think especially for me, so I’m in my early forties. I think a lot of my peers saw our parents, our moms go through scenarios that left them kind of stranded in some ways. Right. And and had internalized that fear of what happens if everything that you thought was going to work out didn’t work out. And as the question asker points out, like they have kind of they’ve insured their lives against that in various ways. What do you see with this question? 


Debbie Millman: Well, she hasn’t ensured that in a lot of ways. And my question to her would be, why have you waited this long to have the conversation with your husband about equity? 


Anne Helen Petersen: Hmm. 


Debbie Millman: If she’s worried that if someday they separate. What does that mean. 


Anne Helen Petersen: Yeah. 


Debbie Millman: If someday we separate, what’s going to happen? Well, this is not the time to ask that question. The time to ask that question was 20 years ago when you made these decisions. And I know many women that have had conversations with the men in their lives, or vice versa, men that are having the conversation with the women in their lives, that if I’m the primary caretaker, what guarantees do I have? If you happen to up and leave the coop. This is not a power position for her to be in. 


Anne Helen Petersen: Mm hmm. 


Debbie Millman: Now, in terms of having to reenter the workplace, she’s not going to be able to land a job solely on having good PTA skills. She must. I don’t know what part of the visual arts she’s in, but if she is in the graphic design business, she needs to make sure that her skills in all of the creative tools that are used are up to date. So I would work on making sure that all of her digital skills are current. Now, she’s not the only woman in this situation, and there are many women that run businesses that have grappled with these ideas, even if not themselves, and other women that work with them or for them, or they might have started their own business very much because of this type of occurrence. 


Anne Helen Petersen: Yep. 


Debbie Millman: I would seek out women in the visual arts that are in the same age range and reach out to them for A, advice or B, opportunities. And there are lots and lots and lots and lots of different ways to do that again. My familiarity is in the graphic arts. Make sure you go to the conferences. Make sure you are aggressive about introducing yourself. Start making some of your own self-generated work. So there are many, many, many people that do work entirely on their own and have created careers from self-generated projects that went viral or was highly popular. Look at the work of Jessica Hirsch, Lisa Congdon, Timothy Goodman, Jessica Walsh, and create your own self-generated project that you can promote. And the more you can do that, the more visible you’ll become for doing your own work, which will then, I think, become more seductive to others that are hiring. Make sure you can update if, again, in the visual arts, update your Behance portfolio, work on your website. There are a lot of things that you could do without necessarily having an au courant current job. 


Anne Helen Petersen: Right. I hear her anxiety about not wanting to go get another degree since she has student debt, but brushing up on her skills. That doesn’t have to mean going to get another full degree. 


Debbie Millman: Absolutely. 


Anne Helen Petersen: It can mean taking classes at the community college, which are incredibly affordable in most cases. It can be seeking out online courses. 


Debbie Millman: Absolutely. There’s so many Creative Live, General Assembly [?] has a great whole series of programs about reinventing yourself, Dorie Clark does as well. There’s so many people whose work is just about helping other people find their calling or refine their calling. 


Anne Helen Petersen: Yeah, so I think what we’re asking her is, first of all, let’s start doing this work. Like let’s do it for whatever reason. Maybe your marriage is secure. Maybe it feels slightly not as secure, but let’s do it. It’s not too late, but it’s time. And start with those training aspects. But then also get out there. And if that means that you have to pay for childcare to get out there. That’s job training. 


Debbie Millman: Absolutely. 


Anne Helen Petersen: Because I think that’s what gets in the way sometimes is people are like, well, I can’t do that stuff. Basically career development because I don’t have childcare. But you’re never going to do it. 


Debbie Millman: And maybe let’s look at the husband. Step up a little bit. [laughter] Right. You know, she’s been supporting him for all these decades. Let’s turn the tables. 


Anne Helen Petersen: Even if you can rely on that one income, we just don’t know what life is gonna do.


Debbie Millman: But for anybody listening that has decided made the decision that I want to be the primary caretaker. I want to be able to create a life for my children that is centered around my children. Then you must have a conversation with your partner before so that you outline the expectations. So you outline the guardrails, so you do feel safe and secure about the choices that you’re making. You don’t want to be in a position where 20 years later you’re in a, Oh my God, what have I done moment? 


Anne Helen Petersen: Right. Because the other thing that happens in situations like this is that women don’t leave marriages that have become toxic for whatever reason because they do not have a life raft. 


Debbie Millman: Exactly. 


Anne Helen Petersen: Right. And men. They will leave without thinking because they will always have that primary income. So it’s easier for men to leave and harder for women to live and not as inequitable, just foundationally. 


Debbie Millman: Absolutely. 


Anne Helen Petersen: So these conversations are so important to have. 




Anne Helen Petersen: Our next question is from someone who like me, is named Anne and it’s very, very relatable. 


Anne: How do folks navigate later career when you’re around 50 and still have what feels like a very long time left to work, but you’re emotionally ready to retire? It feels like there are very few options for moving to a different job at this stage. When you’re not interested in taking on more responsibility or working harder. I’m already working as hard or harder than I want to, and relocating is not on the table. 


Debbie Millman: I don’t understand the question here. What’s the question?


Anne Helen Petersen: They don’t want to work anymore. They want to retire. 


Debbie Millman: You know, I want world peace. [laughter] You know, I mean, we all want we want a lot of things. I mean either work two jobs now, bank the money and retire sooner, or just suck it up. 


Anne Helen Petersen: Right. 


Debbie Millman: I mean, there’s no. Believe me, if I had an answer to this question, I wouldn’t be working. [laughs] I’m 62. I wouldn’t be working if I knew what that answer to that question was. 


Anne Helen Petersen: You know, my granddad worked for [?] and was like, you know, the classic like started with [?] and then worked there his entire life and then retired with a pension at age 55. And then he just like sat in his backyard in the suburbs of Minneapolis and like smoked cigarettes and listened to baseball on the radio. Right. Can you imagine retiring at 55? And I used to hold a lot of resentment towards that whole ideal. And then now I’m kind of like, well, wouldn’t it be cool if we could all just work as much as we wanted to? That would be cool.


Debbie Millman: Well, I have a I have a couple of responses to that. First is, did he want a retired 55? 


Anne Helen Petersen: Yes. 


Debbie Millman: If he wanted to retire 55 maybe what he wanted to do was sit in the backyard and daydream and smoke cigarettes. And maybe that was his idea of living the dream. 


Anne Helen Petersen: Totally. 


Debbie Millman: You know, one of the things that I thought was so interesting, it was it happened when Sex and the City came back on the air and the TV show now known as And Just Like That. And there was a meme that went around that showed the four Golden Girls and the four women from Sex and the City, and they were the same age in the new, the new, the revamped. So these women were in their fifties. 


Anne Helen Petersen: Yeah. 


Debbie Millman: And the Golden Girls, I think all but Estelle Getty were supposed to be in their fifties as well. And it’s a very different. 


Anne Helen Petersen: Wow. 


Debbie Millman: World that we’re living in now. If she wants to retire early, she needs to work doubly hard now to make that retirement possible or to be on a much more stringent savings plan. But there’s no easy answer for wanting to work less and still earn money. There’s just, I don’t know, that answer. 


Anne Helen Petersen: Yeah, I think my advice to this person would be, you know, sometimes you’ve got to do the work and just think you just got to do it, but then see if she can find some joy in these other parts of her life. Right. That aren’t her work because it seems like right now her job feels like it just feels exhausting for whatever reason. But maybe just don’t they just coast on through and find other things that make you feel like you like living right now? 


Debbie Millman: Well, if it’s really about the job not being satisfactory. 


Anne Helen Petersen: Hmm. 


Debbie Millman: And the response to that is retirement. There are other options. I mean, if she’s in a position where she does want to retire, maybe it’s a matter of finding another job. You know, going back to some of the that earlier question from the woman that took this step back, maybe it’s a matter of having a hybrid position where she’s not quite as intensely busy, but not making as much money, but can begin to see the rainbow at the end of the tunnel. 


Anne Helen Petersen: Yeah, you know, she says there aren’t that many options at this age. But you know what? Poke around. 


Debbie Millman: Well, unless she’s 90, I think we know what we’re talking about. [laughs] There are lots of options is always options. There’s always options. There’s always options. 


Anne Helen Petersen: I think sometimes we tell ourselves stories that there aren’t options. 


Debbie Millman: Well, I think it becomes a scenario where we’re afraid of rejection. We’re afraid of judgment. We’re afraid of shame or embarrassment or humiliation or what other people will think. And ultimately, I think we have to really analyze what’s the lead gene here is the lead gene. I want to change my life? Is the lead gene. I want a different better job is the lead gene. I want to feel more engaged? You know, branding, which is my area of expertise in many ways, is the art of sacrifice. You have to decide what you stand for, and in doing that, you then make choices about what you don’t stand for. And I think a lot of the questions that we’re hearing today are how can I feel safe and secure right now but do something that is going to require some risk and uncertainty. And I don’t know Anne, I don’t know if you can do both at the same time. And I would love it if we could. I’m struggling with that myself. I want to do some new things, but I’m afraid to do them. It requires some sacrifice now in order to attain this thing in the future. But there’s very little that we could do in life that doesn’t. Very little we can change in our lives. That doesn’t require some risk and some sacrifice. And I don’t know that there’s any way to make it any easier. 


Anne Helen Petersen: Yeah, it’s hard. And I hope that this person thinks about that. Right? Like we are not at the endpoint. There are not zero options here, but you might have to weigh, you know, what do you want. 


Debbie Millman: And take risk and take a risk. You can’t change anything without taking a risk. And risk is difficult. Risk then creates uncertainty and uncertainty creates vulnerability, and then we become paralyzed. 


Anne Helen Petersen: So our last question, I’m so happy we have this question. It is about trying to work when your brain and your hormones have other ideas. This is from Andrea. 


Andrea: I’ve heard that there is more awareness these days about menopause and that some companies are making accommodations. I work in tech where my boss is male, and so are most of the people who would make the decision as to whether I would get a raise or a promotion. And recently I’ve been having a lot of brain fog where I could forget the word I was about to say in the middle of a presentation, or if I’m trying to be persuasive. I also recently broke down crying in front of my boss, which was a first for me. And I know that this is all related to perimenopause, but I’m wondering in an industry where I’m already perceived as being less than just because I’m a woman, if I would be doing myself any favors by letting them know that this is all about perimenopause, I feel like it would make them want to hand me less responsibility and at the same time, what must they think if I can’t finish the sentence? 


Anne Helen Petersen: So again, I’m so glad we have this question, because I think the more we talk about menopause publicly, the more like this won’t necessarily be something that seems stigmatizing, as this woman, I think feels. In. 


Debbie Millman: Yeah. 


Anne Helen Petersen: In her situation. What is your reaction to this question? 


Debbie Millman: My reaction to the question is that she needs to go to an endocrinologist and a gynecologist or any other type of doctor that’s going to help her because she shouldn’t have to be suffering with brain fog. And it’s not something that’s going to be solved by sharing the information with coworkers because they can’t help. All they can do is accommodate. And it sounds like she doesn’t want accommodation. 


Anne Helen Petersen: Yeah. 


Debbie Millman: It sounds like what she really needs is some good medical advice and to be able to work on what will help her feel better across the board in and out of the workplace. Having gone through menopause, I can tell you that brain fog is not necessarily a given. And so I would say, first and foremost, she needs to work on her own physical and emotional health with a professional before she starts to reveal what’s happening with her coworkers. 


Anne Helen Petersen: Yeah, and, you know, we don’t know for sure. Like what? You know, what she has maybe sought out, but she doesn’t really talk about whether she has. 


Debbie Millman: Right. Well, I think there are ways to accommodate brain fog unless she has long-covid, which I know a lot of people with long-covid are suffering from brain fog. And I know that right now there’s not any type of remedy for that. But for menopause, there absolutely is. And there’s a lot of alternatives. And I know a lot of you know, because of my age, so many of the women an my partner’s also going through menopause right now. So there’s a lot of different things that can be done to help alleviate some of those symptoms. 


Anne Helen Petersen: What were your your resources when you were going through menopause? What what seemed to help? Like was it talking with other women who would give you recommendations for doctors or what to bring up with doctors who might not need seem to know what you feel like they should know, because I think sometimes that’s a problem, too, right? 


Debbie Millman: Yeah. I mean, I talk to my therapist a lot. 


Anne Helen Petersen: Yeah. 


Debbie Millman: I went through an early menopause. I went through menopause at 46 and was done like one year. And then it was over. Everything was was finished. [laughs] And so most of my friends were like, Oh my God, that’s early. And there was like, the shame of that and the judgment of that. Not that I feel like they were judging me. It was really more self judging. And so. I really had to rely on medical professionals to help me. 


Anne Helen Petersen: Did you become a resource for your friends then because you had it earlier? I find that this is happening to me because I’m having colonoscopies early because of family history, and I’m the one who’s like, okay, this is like, this is my recommendation for when you should schedule it. And like. 


Debbie Millman: Yeah. Absolutely. Absolutely. Absolutely. Yeah. 


Anne Helen Petersen: So if she can seek some help that actually does try to address some of these symptoms instead of like I should just suffer through it if she doesn’t want accommodation. Is there a conversation to be had with her manager at some point that says, just I just want to let you know I’m dealing with some symptoms of menopause? I’ll tell you if maybe I need some more time for something or something like that. Like, does that seem like a good conversation to have? 


Debbie Millman: You know what? Anne. I. I don’t know. I don’t know. When I was in my late thirties, early forties, I was doing fertility treatments. I didn’t tell anyone. I got divorced. I didn’t tell anyone for six weeks. I didn’t want anybody to think, oh, she’s being emotional because she’s getting divorced or, oh, she’s being emotional because she’s taking fertility shots. I don’t know that that’s the right decision. I don’t know. Now, looking back on it, I remember having a miscarriage and lying about it and telling people I had a death in my family, which technically I did. But, you know, I wasn’t forthcoming. Nobody knew. And I didn’t want anybody to know because I was afraid that people would judge me. I think I was weak. Think I was emotional. So I don’t know that I’m the best person to ask about this because I don’t know that my own way of living through some of those transitions was healthy. 


Anne Helen Petersen: Yeah. You know, one thing I might suggest to this person, even though they feel like their particular office and their industry is very male dominated, there’s someone else going through this and it might not be in your company, it might be in another company. There’s someone else in tech that is going through this. So. 


Anne Helen Petersen: Yeah. 


Debbie Millman: How do you find those people and how do you start those conversations? 


Debbie Millman: Yeah, I mean, I think you have to just look around, look around, see who else is. I mean, I don’t know. The last person I would want to talk to about menopause would be a tech bro. I mean, the very last person on earth [laughs] would be a tech bro. 


Anne Helen Petersen: 100%. 


Debbie Millman: Like, how would they what are they going to do with this? Most men don’t even like to think about things like that, let alone talk about it. 


Anne Helen Petersen: I know. 


Debbie Millman: So, I mean, I have to think about, you know, what’s your end goal here? What is your result? What is the I mean, in a perfect in a perfect world, on a perfect day, you tell somebody and be like, oh, I’m so sorry. And please let us know and do the best you can. I mean, women have to fight for a place to just, you know, nurse their children in the workplace just to pump milk. I mean, come on what world are we living in? You know?


Anne Helen Petersen: If you had this conversation with a tech bro, and they’d be like, what? You can get brain fog from menopause. Like, you know, like, I think there’s just—


Debbie Millman: What’s menopause? Like, wow. 


Anne Helen Petersen: I thought that was like your period, you know? [laughs]


Debbie Millman: I know, I know. I’m generalizing and I’m being really somewhat discriminatory in this regard about tech bros. [laughter] But yeah, you know, I’ll just leave it at that. 


Anne Helen Petersen: Okay. So our advice for this question asker is find a really good doctor—


Debbie Millman: Find a really good doctor, and talk to you. Talk to a therapist, talk to a therapist, talk to a medical professional. And if you’re in a position in the workplace where you’re getting real pushback about some of the physical limitations or the intellectual limitations that you’re feeling, then I would go to H.R. 


Anne Helen Petersen: Yeah. That is fantastic advice. And I appreciate also your willingness to say I don’t know exactly what advice I would give because I don’t know if I would give myself that same advice. 


Debbie Millman: Yeah, absolutely. One thing I do share now is, is those types of conundrums and certainly with my students, you know, with they have mental health issues, I’m incredibly empathetic because I had so many of my own, but I didn’t feel comfortable at that time sharing with anybody other than my therapist or other medical professionals. I never wanted to tell anybody, which makes you feel very lonely and disconnected. So I don’t recommend that either. I think you have to do whatever you feel comfortable doing, but it’s hard to ask advice when the person you’re asking the advice of didn’t always behave in ways that were noble. 


Anne Helen Petersen: I think that sometimes the sign of wisdom is is being able to recognize that in your own life. And that’s why, you know, it makes your advice even more valuable because you’re able to look and reflect on that and on that. And we are so grateful that you made the time to come and talk today and share all of that wisdom. If people want to find you on the Internet. Find more of your work. Where can they go? 


Debbie Millman: or @DebbieMillman on Instagram and X. Is that what it’s called now? [laughter] The social media site formerly known as Twitter and all the others they’re all the same. Debbie Millman. 


Anne Helen Petersen: Thank you again. This has been a real pleasure. 


Debbie Millman: Thank you. And thank you very, very much. 


Anne Helen Petersen: Two announcements before we go first. 




Anne Helen Petersen: Thanks for listening to Work Appropriate. If you like this episode, you should check out a couple of similar in vibe episodes from our archives. I would personally suggest big working parent questions with Lydia Kiesling. And is it too late to start over with Ailsa Chang? You can find all those in our back catalog at, or just try putting the name of that title into your Spotify or wherever you get your podcasts. Submit your questions at or you can send a voice memo with your question to Work Appropriate at Don’t forget to follow us @CrookedMedia on Instagram and Twitter for more original content hosts takeovers and other community events. You can also follow me on Instagram @AnneHelenPetersen and you can sign up for my newsletter Culture Study If you like the show, it’s so helpful for us if you go rate and review us on your podcast app of choice. Or you can send this episode to a friend, it really helps. Work Appropriate is a Crooked Media production. I’m Anne Helen Petersen, your host. Our executive producer is Kendra James. Melody Rowell is our producer and editor. Alison Falzetta is our development producer. Music is composed by Chanell Crichlow. Additional production support from Ari Schwartz and a special thanks to Katie Long and Sarah Geismer. [music plays]