#18: This may be the best time to make a career pivot

May 1, 2024


About The Episode

Contrary to popular belief, many new mothers don’t fundamentally change their career goals after having children.

Often, instead, they are inspired to act on something they’ve always known and felt about their career trajectory. 

They don’t want to settle for “fine” anymore. If they’re going to be away from their families, the work needs to be meaningful and worth it. 

Take Allison’s story as an example: After her son was born, she embarked on her own career pivot. Her experience with parental leave motivated her to bring an idea to life – which meant she pivoted from a sales leader to entrepreneurship.

In this episode, we welcomed Jess Galica, who wrote a book after interviewing working women like Allison to learn more about why and how women pivot their careers.

We cover  the impact motherhood specifically has on career pivots. We also dig into the five emotions that lead up to a big career pivot and what Jess found most surprising while doing research for this book.

Links & Resources


Disclaimer: This podcast transcript is autogenerated and may contain minor errors or discrepancies


Allison: Hi Jess, I'm so excited to have you here to talk about your book Leap. Not only what's in the book, but also your personal experience writing the book. So thank you so much for joining us today.

Jess: Hi Allison, yeah, I'm so happy to be here and happy to chat.

Allison: I want to start by talking about how you opened the book. So first of all, I love this book. I read it cover to cover. I have a million notes in it. I think it took me like two days to get through it, which says a lot because I have three young kids. So I was carving out late nights reading it. So I wanted to start by telling you that. I absolutely loved it. 

And I've spent a lot of time really taking notes and thinking about the intro portion, which is basically the five emotions that women tend to go through as they are contemplating, evaluating, and sort of, I think as you call it, preparing to pivot or lead up to the pivot. So I wanna start by asking you to share a little bit more about those five, which are dissatisfaction, isolation, guilt, reluctance, and fear. 

Let's start with dissatisfaction, which is the first one you cover in the book. Obviously it's not stages, I found this one particularly interesting because of those five emotions…I clearly remember when you interviewed me for this book, afterwards you said, wow, you're one of the only women that I interviewed that didn't have that dissatisfaction emotion before you pivoted. And I thought about that a lot since you told me that because I thought, oh, really, that's so fascinating. So tell me more about what you found around women feeling really dissatisfied and how that was one of the major emotions that sort of led them up to a major career pivot.

Jess: Yeah, well, the first section, as you mentioned, is about emotions. And I think that's so important because I hope the book helps to normalize that these types of emotions that we navigate throughout our careers are so typical and so common, right? So there's nothing wrong with you if you're feeling a particular emotion as it relates to your work. This is a really common thing. 

But dissatisfaction is a common emotion that I think many women experience at work, and particularly a lot of women who are reaching a certain point in their career, like a midpoint of their career. And that dissatisfaction can come from a lot of things. But I think one overarching theme that I noticed is for a lot of women, they feel like there's this tax that they're paying simply to kind of exist at work, right? 

So we know that even when women are performing at the same levels or at higher levels than their male peers, they're not promoted at the same rates, right? We know for women who might be in more entrepreneurial ventures when they're seeking funding, even if they're presenting the same exact pitch with the same exact company data and success rates, they're not getting as much funding or as positive feedback. And then there's also this feeling of women who are just operating in male dominated environments where they feel like they can't show up as themselves. There's this sense of, gosh, it's so hard to show up every day, and I'm also not reaping some of the benefits. 

And I think that leads to this sense of dissatisfaction of, you know, kind of throwing their hands up and feeling like I've had enough. And so now maybe it's time to think about doing things differently if this path that I'm on isn't rewarding me in the way that I want it to be. Or even if I'm going to stay on a more traditional path.

Well, maybe it's time for me to at least align what I'm doing with work that feels really purposeful or meaningful or will give back and create value for me in some new way. So I think it's that moment where women are finally kind of listening to themselves and that voice inside their head saying, hmm, maybe I want something a little bit different and maybe I'm admitting that this isn't it.

Allison: Yeah, I think what struck me with what you just said is you kind of combine dissatisfaction and isolation. And I think we do oftentimes go hand in hand, it's exhausting. And you question, why am I doing this? And this was a common theme throughout the book, right? Of like, am I doing this because I'm expected to do this because this is how I was raised? It's like society's expectation of what success looks like.

Jess: Yes.

Allison: And oftentimes what that looks like for high achieving women is you're going into a place where women have not been before. And so it's kind of like that, I guess as I read it, I thought it's hard to untangle dissatisfaction and isolation for many women. And even in your answer, you kind of grouped them together, which I find really fascinating. And I think it's probably quite common from what you found interviewing all of these women in the book.

Jess: I think so. I think actually all of the emotions in the first section of the book are intertwined or can be intertwined in some way. You mentioned stages and we talked a little bit about this. I don't see the emotions as stages, as it's one gate that you get through and then you feel the next. They're often, they're all jumbled up in your head, in your heart. These are things that you're feeling all at the same time. Just like you called out that dissatisfaction and isolation can be intertwined, I also see a relationship, for example, to guilt.

I'm feeling dissatisfied, I'm the only one, and yet I feel guilty about the fact that I'm complaining about this or wanting something different even if I might have what's deemed to be an excellent job. I think you're getting to a point that's so important, which is that you can't always cherry pick one emotion. Sometimes these are just so intertwined and you're experiencing them all at the same time.

Allison: And even with the other three – guilt, reluctance and fear – I mean, I resonated very strongly. I didn't resonate as much with, in my personal situation, dissatisfaction and isolation. I was actually very happy in my current job, but I had this other idea, Parentaly, which was really motivating to me. And I kept thinking about it, and I could not stop thinking, I have to do this, I have to do this, which I'm very fortunate. I had two great options, but I definitely understood the guilt, reluctance and fear.

And you spent quite a bit of time talking about socioeconomic guilt. And I think that's, and I was going to ask you this question and now I'm sort of leading in with my opinions, but I think that's so interesting from a woman's perspective because you talk in the book about how women are more conservative when it comes to financial decisions. I found that personally as well. The biggest reason why I did not start Parentaly was because of money.

That was it. Like, what am I possibly doing to my family if I leave this thing that's really great for me financially to take on something that's risky? When you interviewed all of these women, how frequently was the socioeconomic piece raised of reluctance and guilt?

Jess: So yeah, it's big. I think the financial element is a part of almost everyone's story in some way. And listen, it should be, right? We should be thinking about financial considerations when you are contemplating a big change to your career that might have different outcomes on the financial income. So, I never, ever want the takeaway to be, oh, we shouldn't think about money, we shouldn't think about the socioeconomic. 

But I think there's two things that are important for women. And one, we talked about these intertwined emotions. Oftentimes the socioeconomic guilt is intertwined just with that, right? That guilt, right? Of feeling like, oh, wow, well, not only am I worried about the money, but there's also a little bit of shame about putting your career first, right?

So it's not just that, oh, well, I'm worried about how am I going to pay my bills? But it's also this feeling of discomfort with, well, I'm choosing to invest in myself and my career and what I want. And that's what I'd really love women to get away from. 

I don't want women to feel any shame about prioritizing their interests, their careers, or what they want really out of their work and life. Certainly we all have to do that within the backdrop of financial realities and what we can do.

Part of the takeaway I hope is that women start to feel really empowered to say, well, let, let me not create a narrative that saying I can't do this financially when it's really just about a discomfort or a shame around putting yourself first when so many women and in particular, I think mothers, if you're in that role, um, have really been conditioned to be in the service of others.

Allison: That's such an interesting point because I think you're right. If I were single and contemplating starting my own business, I don't think I would have had any guilt because I can make that decision for myself and I can decide to live the downstream impact of if I make a poor financial decision or whatnot. I'm very comfortable with that. 

But you're right that when I was making this decision, it was, Oh my gosh, what is this going to do to my husband? Because now he can't take a risk. Only one of us can take a risk. He works at a really large company, and now we depend on him for our health insurance. We depend on him for money. You know, we depend on him for so many things because I am taking this risk. And he was great because we made this decision together. 

Obviously he's going to reap the benefits of this hopefully, but it's a long-term decision. You know, I mean, now I'm four years in, and still I'm the one with the riskier role. And I think a lot about what this means in terms of what, you know, honestly, this sounds a little bit ludicrous, but I was thinking about if I start this business, do I need to change childcare for my children? And that was like the thing that I really struggled with was if is that selfish? But I didn't want to ever have to make a choice that negatively impacted my kids because I had chosen to do this big career with it.

I'm curious, as you were interviewing for this book you interviewed so many women from different walks of life. Did you see any specific themes with mothers?

Jess: Hmm. I think motherhood is such a personal experience for everyone. Parenthood is such a personal experience for everyone. But here's the theme that I can say, is that motherhood often was a point in time when women were choosing to reinvent or pivot or change their career. And I think this is more common, and the data shows this, this is more common than fathers or  men stepping into fatherhood roles. 

And so I think what we can say kind of across the board is that stepping into parenthood, specifically motherhood, is such a dramatic change to anyone's life. I talk about it like a pie chart, right? And it's like, okay, if career was taking up half of that chart or even more, all of a sudden parenthood gets jammed in, the pie is going to change, right? The size of the slices is going to change.

And so I think what I saw for so many women is that the time when they were reevaluating their career coincided often with these moments in motherhood, whether it was stepping in becoming a mom for the first time or navigating those early, very intensive years of parenthood. So I think mothers are making decisions around their careers and either choosing or feeling like the burden that they need to kind of reshape and remove their career in order to fit with motherhood more. 

So the consistent theme, I would say, is that there is absolutely an overlap in women re-evaluating their career as they navigate these very intensive periods of motherhood. But there's—

Allison: And why do you think it is? I'm going to interrupt you because I think people are really surprised. We see this with our Parentaly programming. People, HR managers…they're all shocked at how often people go into parental leave. I think the societal assumption is, oh, they want to just hang on, right? Like their priority is now their child. So they just want to hang on in a steady state. And what we find is no, they are reevaluating everything and oftentimes making a major career pivot within the first year that they return to work.

Jess: Yeah.

Allison: Why do you think that is based on what you just said? Basically, it's the same thing, but I'm curious if you found, I don't know, like I wanna dig a little bit more into like, why? Why is that happening?

Jess: Yeah, totally. So I think part of it might fall more in line with that traditional narrative that maybe you do hear from HR or whatnot, which is that we know that women in particular, a disproportionate amount of childcare and housekeeping work is falling on their shoulders relative to men. That's true no matter what, no matter what the makeup is. Most of the research is on male-female partnerships, right? But even if you're in a dual earning, equal ambition household, women are doing four and a half more hours of household and childcare work per week. They're still doing more even if they are the primary earner or the sole breadwinner in their household. 

And so there is some reality of, wow, women are just feeling more of this burden on their shoulders and they're kind of forced to think, like, I've got to find a different way to do this and maybe, you know, break out of this box that I've seen my career fitting in. So there's some element of that.

I think the lesser talked about part is that I think most women, I mean, motherhood is not joyful in every moment. Let's be real, right? But there is such a joy typically that women are experiencing in this motherhood role, right? And such a fulfillment and this real feeling of kind of resonance in the work that they're doing. And I think that resonance and that fulfillment that many women feel in parenthood kind of raises the bar in a way for work. Where it's like, well, wait a second.

I'm having this experience where this very difficult job is still feeling great and purposeful and meaningful to me. Should I also be raising the bar to expect that out of my work, where maybe the just plugging along like HR suggests and sticking in my role, suddenly it feels like, huh, I'm kind of not willing to just accept that. I want bigger. I want more. I want different. And I wish we would hear more about that narrative. And I know, Allison, you celebrate a lot that...

Shifting into motherhood isn't just about stepping back. There are plenty of moms who feel really ambitious and really powered up to go after something bigger and different. I think there's two sides to the story that I just described that can help to shape and make it the reality that a lot of women are thinking about, shaking things up after becoming a parent.

Allison: Yeah, I think it's definitely a narrative out there of like, and even and it's not from HR. I actually think this is more from middle management, for lack of a better term, that thinks, well, they should be thankful that they have paid leave, they should be thankful to come back. And this is sort of what I see from society, right? It's not like any specific person or whatever. 

And what I'm actually seeing from the women that go through our program is exactly what you've described, which is, and it's funny, it's not I'm not thankful, it's this could be better at work. Like I'm wasting time. I'm doing things that are meaningless. And by the way, if the company would lean into this, it's bad for the company to have employees doing meaningless work and inefficient work. 

Jess: Mm-hmm.

Allison: And so, it's so interesting the way you talked about having this joyful, really hard thing and how that makes people feel like, well, can't I have that as well at work? We see that all the time. And then I think there's also a segment of people who think I'm very unhappy at work, but I'm going to hang on for a year. This is like the most common thing that we see if they're not motivated to make a big change throughout that parental leave experience. I'm going to hang on for a year until things at home feel more stable. And then I'm out.

Jess: Yes. Yep, yep. Yeah, and that can be a really successful play for many women, right? I talk a lot with women about there are different modes that you can have throughout your career. Sometimes that cruise control mode is the most strategic thing. I think we see throughout that women are kind of shifting up or shifting down gears.

There's always these very binary narratives that are kind of clickbaity, right? Like lean in or opt out. But what I see so much more often is like it's all in the gray area. And I love Neha Rush, Mother Untitled, her work around this that we like to think that motherhood and career fits into these binary boxes of like, I'm going all the way in, I'm highly ambitious, or I'm pulling all the way out, I'm a stay at home mom. But for most women, the decisions and choices and ambitions and goals that they have sit somewhere in between those two.

Allison: I also think that managers and companies would be shocked at, I hate to say the small things, but the very small things that are very personal and totally different across each woman, that if only they were solved, would be game changing for that woman's career. I just think that it's like, it's so different per person. And I love what you said about, it's not that they're choosing to lean out or not, or lean in and or whatever, I forget how it's going.

Lean in, lean out, I don't know. It's not really that. It's that they've found a few things that they know are wrong. And you talk a lot about there's this disconnect between value and career, and that's sort of like what leads to a pivot. I am constantly shocked at how frequently, if you address those, and of course this is like my whole business, I believe in career coaching in this moment, being incredibly powerful. Oftentimes, there is so much opportunity to pivot within your organization.

Jess: Yes

Allison: And I think that that's really important too, is your book obviously talks a lot about people making major pivots. But I think that there are a lot of lessons in the book as well for being able to pivot within your own role, within your own company. Because usually, I shouldn't say usually, it's often not a massive disconnect. But if your manager is doing something that is difficult for you or if it's a scheduling thing or if it's, you know, there's usually things that you can point to that are solvable that can allow you to pivot your role in a much smaller way.

Jess: Yeah, absolutely. And to your point about, yes, when we think about a career pivot, right, the easy story, the Hollywood version is like someone goes in on a Friday and quits their job, you know, and is free the next day and they launch some, you know, wild next career. And it just doesn't work that way, right? And it's in two respects. One is that I think when we think about a career pivot, we envision that it's this very spontaneous, quick, immediate, you know, it happens on one point and then the change happens.

It's not true, right? What my interviews showed is that most of these pivots are executed over a long time, right? These are kind of multi-year strategies. And then the second thing to your point is it's not always this dramatic, I'm quitting corporate and I'm launching my own company. There are pivots within organizations, there are pivots within industries, right? I think we absolutely have to find a continued path for women to stay in corporate. I am never promoting that women should leave corporate in droves. We absolutely need women to stay there and be successful there.

But I think what's good about those two things, like the fact that it takes a long time and the fact that it doesn't need to be this wildly dramatic pivot, is that it actually makes it way more accessible for women. Because you might have a woman who says, well, oh, I'm risk averse. I'm just not going to do something wild and crazy, right? And oh, I could never start my own company for XYZ. Wonderful, right? 

Still having a strategy and knowing how to pivot is incredibly important to navigate your career and also have the power to make choices and decisions and very importantly, feel that you can walk away from situations that are no longer serving you.

Allison: Yeah, it drives me nuts when people say, well, she became a mother and realized this and that's why she quit. No, this has been happening for a very long time and becoming a mother was the final straw that broke the camel's back and made her or gave her or empowered her to make that choice. I want to make sure that we talk a little bit about your pivot, how you would describe your pivot because I think you're, I don't know if you would call it a pivot necessarily, but

Jess: Exactly.

Allison: You've navigated your career in, I think, a really fascinating way that actually highlights a lot of what you've just described, not this throwing my life up in the air and doing a complete 180. Talk more about back, I guess, bring us back a couple years ago when you started this book. What did that look like and what has, how would you describe how you've pivoted your career over the past few years?

Jess: Yeah, I think you're right that I'm a great example of someone who has taken time and not fully thrown in the towel on corporate world, right? So I spent the first decade of my career in pretty traditional corporate roles, navigating tech and management consulting. And in early 2020, after more than a decade of this, I kind of just pulled up and felt like, huh, this still doesn't feel right. I don't feel like I'm on the right path.

And even though everyone else was telling me that this path that I was on was a wonderful one, I myself felt really lost. And at the same time, I was stepping into motherhood for the first time pregnant with my now three-year-old. And I just had this strong desire to listen to that voice saying, this isn't it, and consider doing things differently. And so long story short, that's where the book was really born, right? Was a curiosity out of, well, I think I want to do something different in my career.

How do I start and learn from other women? And when I started having those conversations, it became really obvious that, okay, this isn't just about me. There are so many other women who are reaching this point mid-career and kind of pulling up to reevaluate. And so I decided that I wanted to do something and turn it from this very personal inquiry about my career into a much bigger research project, and of course landed with the book format to help more women. So that started in January, 2020.

And since then, I have flexed my corporate career in a few different ways to make it work. So I've been in full-time roles, I've been in 50% roles, I've been in an individual contributor role, also managing a team of 12 people globally. And so I've been able to navigate and kind of flex up and down my corporate career to fit kind of the goals and the vision that I have for that next phase.

And part of that was that along the way I had two kids. And so I was also thinking strategically about, well, do I wanna change things up so dramatically at a time or do I wanna kinda play into that, wouldn't necessarily call it cruise control, but hold onto some of that stability and structure while I also navigate these very intensive years of parenting. And so for me, that slow and steady approach has worked.

I do think that upcoming I'll probably have a bigger leap, so to speak, that moves away from that model that I've been using. But for now, it's been the right approach for me to achieve the many objectives that I have, not just in career, but also as a mom and in life.

Allison: You talk in the book about the test and learn approach, which I also did. So I actually started Parentally with a co-founder. She and I were both working full time at our 60 hour per week jobs. And we took nights after the kids went to bed to get Parentally off the ground, at least the first MVP version. And that took us probably like nine months to get. It took a very long time.

What did your first stage look like? Because you did a similar thing with the book. You didn't start with the book. What was the first thing that you did to start testing to move you in this direction?

Jess: Yeah, the first thing that I did was starting conversations with other women. So it really genuinely started with just a selfish goal. I was like, what do I want out of my career? Maybe I want to change. Let me go talk to other women who have done this. So it really did start with me. And then in those early conversations.

Allison: didn't even know about that at that point. This was just like, I want to learn more to decide what do I do with this interest?

Jess: Yes, yes, yeah. I mean, I wouldn't even say the interest was formed, right? I just kind of knew, hey, I'm on this career path. It's not feeling right to me. I have this voice, you know, this curiosity about maybe switching things up in a bigger way, right? I had made small changes, and yet I never felt fully like it was the right thing. And so I wanted to learn from other women. And then what really was the light bulb moment for me is I thought this was a me problem. I was thinking, what is wrong with me? Why am I never satisfied in my career?

Why does it never feel like the right fit? Like really, I was like, what is so defective about me? And then when I started having conversations with other women, I realized that, wow, I mean, my gosh, it felt like every woman who I spoke to at a similar point in life, you know, mid-career, thinking about caregiving, whether that's motherhood or caring for aging parents, I mean, everyone, it seemed like, was having this kind of career crisis or evaluation.

And that's where the light bulb moment went off that I felt like, okay, this isn't just about me. This is a really interesting problem to solve. And there's so many ways that you can solve problems. But I think for me, I was just drawn to researching it and writing about it and kind of approaching that problem from a thought leadership perspective. So I didn't have a vision of writing the book and doing this thought leadership work from day one. It kind of found me in a way just from my own curiosity and my own journey.

Allison: And you started, and correct me if I'm misremembering this, you basically had a website, you were publishing almost like blog posts, you started a podcast. At what point, and I think you've started, or back then I think you started to experiment with career coaching. Like how did that all then come into more of like a crystallized package? Or is that still in flux and you're still trying to figure out all those different ways of sort of packaging up this knowledge and this expertise?

Jess: Yeah, I feel like on any good journey, there's some things that I know and still some things that I'm figuring out. So you're right that I started with more blog interviews written, you know, full form type things. And then I thought, wow, I'm gathering all these incredible interviews. I think there's really something here that could be turned into an actual book that would be kind of this, you know, memorialized kind of point of view on this topic.

I was doing these interviews written and realized how much time that took. And I thought, huh, it might actually be even quicker to do a podcast, which initially for me, a podcast felt so intimidating. And so well, oh, that's so much work to do. But then I realized, you know, I tested and learned. I realized actually it's more work to write these things out after I've been recording them. And so I was always sort of testing the format along the way. I had an interest in coaching and started training along the same timeline in 2020.

Allison: Yeah.

Jess: And then my work, you know, publishing content on LinkedIn and the website and the newsletter started to garner just some interest in coaching. So I had some very, you know, kind of fall into my lap coaching opportunities with women. So you're right. Yep. I've been doing coaching since 2020. So, you know, that's what I've learned and that's what I've known along the way. Now moving forward, I think I'm at a crossroads where I'm figuring out, okay, I have this focus, right, on women navigating careers and in particular changes.

What's the next format that I want to play in? Is it focusing on the coaching? Is it focusing on paid speaking? Is it doing more of the thought leadership and content production? Those are three of the big areas that I've tested and played with. I think now I have to decide where I want to place my bets and invest my time.

Allison: That was going to be my next question: what's next. So you already answered it. I love your story because I think whenever people ask me for advice I hate to say, oh, do what I did but I really do think especially given all the research that you've done, everything in your book about the guilt, the fear, the hesitancy from women. The number one piece of advice I have is to test because I think there

Again, I love how you talk about this Hollywood version of pivoting and taking a big leap, which is not the right way to do it. It's not the right way, unless you have millions of dollars just sitting around and you have none of these fears and you have a major safety net. I think we think that when people make a big pivot, it's immediate when in fact, there is so much that we can all do to test. And it doesn't need to take a lot of time. You don't need to quit your job.

Jess: Yes!

Allison: I even tell women who are going into parental leave, oftentimes they'll say, oh, maybe I'll try something on parental leave. Oh my gosh, no. Focus on the child. Like you can actually do a lot when you're working an hour a week to just explore an interest. And so I think what I love about your story is you didn't know where you were headed. You just knew that there was this curiosity. You started doing, like you had a bias to action and you started doing it and you see where it goes. And it grew into something that still, who knows where it will go. But I just think you have such a cool story that I think is very relatable that a lot of people can and are doing today as opposed to, you know, even my story of starting my own business. Most people fail at that. And so it's like, that's not really the right path for most people. So I love it.

So I will end with this final question. What was your biggest surprise in writing this book? What is the biggest, I don't know, like thing that took you aback when you were interviewing all of these women.

Jess: Oh, that's a good question. The biggest thing that took me aback. Yeah, I think the biggest theme, one of the biggest takeaways that has really, really stuck with me is that I think when we think about change and a pivot, there is so much focus on what you're giving up or what you're letting go, right? And as you'll see in the subtitle of the book, right, I think what really has stuck with me is that I think I'm not giving up is this very core belief that a career change, a career pivot, a reinvention, it doesn't have to be about what you're saying no to or what you're letting go. It's also about what you're saying yes to. And in so many cases, what I saw is that women actually were using these pivots and these changes to really get ahead. So there's this feeling of risk, of what if this fails, what if this goes the wrong way.

And we tend to perseverate on that story and that narrative. But what I love to see was the many stories of women who were able to also ask themselves, well, what if this wildly succeeds? And what would that look like? And so I think this idea that was the biggest surprise of the book, but has stuck with me the most, is this notion that we think of it as letting go, but actually it's this opportunity to get ahead.

Allison: I love that. Well, thank you so much for speaking with me today. We will link out to all of the different places that people can find you. And I assume you're still doing career coaching, so if folks are interested in working with you, they can also reach out via your website. Is that the best way or LinkedIn?

Jess: You can find me on LinkedIn, Jess Galica or the website is ReclaimYourCareer.com.

Allison: Great, well thank you so much for being here today.

Jess: Thanks, Allison. This was so fun.