"Fleishman is in Trouble" and the Female Mid-life Crisis

Fleishman is in Trouble is about a lot of things. It’s about marriage, motherhood, aging, career, wealth, work life balance, urban living vs the suburbs, Judaism, Manhattan… but mainly it’s about middle age. It’s about that moment in time when you realize all of your life choices have set you on a particular path and you can never go back. You can blow it all up, but even then, you have to deal with the consequences of your first round of choices. It’s about realizing that your life didn’t quite turn out how you thought it would and giving up on the dreams of your youth. It’s about time running out. It’s why all the characters keep asking themselves, “How did I get here?” It’s why Toby’s divorce seems exciting to Libby, not because she has problems with her husband, but because it represents unknown possibilities. Do you want excitement or stability? Do you need to risk losing everything to realize how good you have it? Do you have ENOUGH?

Although the majority of the series focuses on Toby, we later learn that Libby is actually the main character. She’s been telling Toby’s story from her perspective all along, not just as a plot device but because she figured out how to solve her particular midlife crisis: write a book. Libby realizes she’s not looking to leave her husband or move out of the suburbs she claims to hate so much; the hole in her life started when she gave up her career in journalism. It turns out, the reason she’s so obsessed with Toby’s story is because it reminds her of the excitement she used to feel when researching an article. Libby used to work at popular men’s magazine where she learned that no one is interested in stories from a female perspective. So, the obvious thing to do is trick everyone into thinking you are writing from Toby’s perspective when really, it’s a story about two women. Libby and Rachel.

Both Libby and Rachel are unsatisfied, but for different reasons. Libby, is a former “cool girl” who thought she could find success by playing in a man’s world (literally a men’s magazine), failed and then retreated to the suburbs to raise a family, all the while feeling like she was destined for something better than the moms around her who made the same traditional choices. Rachel is a high powered working mom with abandonment issues (she was orphaned as a child) who believes that monetary success will make her feel worthy to the people around her, only to learn that value to her friends (access, wealth and status) comes at the expense of value to her husband (being a good mother.) To be clear, I don’t think Rachel was necessarily a bad mother, but that’s definitely how Toby views her.

I think a lot of this story is about a woman’s value, or what we, as women, feel our value to be, both to ourselves and others. We know that being a mother and bearing children is valuable, but what happens to women who don’t find fulfillment in motherhood alone? As someone who is roughly the same age as the main characters in the story, I can tell you that we were all taught in grade school about Betty Friedan’s Feminine Mystique, where women were discontent at home and wanted something more. We were also brought up in the age of the 80s working woman where success looked like shoulder pads and commuting in skirts and sneakers. The movies and TV shows we watched as kids were Working Girl, Baby Boom, Who’s The Boss, Murphy Brown, where it didn’t seem like successful working women were the exception as much as they were the rule. We were brought up to believe that we could achieve anything a man could achieve. But nobody ever alerted us to the fact that men who climbed the ladder as far as they could go, often weren’t satisfied either.

Libby and Rachel are both forced to examine where their value lies, what drives their ambition and what defines their success. Is Rachel climbing the ladder because she enjoys work and making money for herself? Or is she trying to seek external validation from her wealthy friends? What does it ultimately cost her? Does Libby want to write a book because she likes writing or because she’s trying to prove something to her old male colleagues who cast her aside? Will she be happy even if her book isn’t a success?

One thing I found interesting is how often Toby tells his wife that he doesn’t care about money. He thinks he’s being humble. But he’s also completely dismissing what Rachel is doing for their family. He’s taking away her value. He doesn’t really ever try to figure out what happened to his wife, because he prefers to think of himself as both the hero and the victim, instead of what he is— unsupportive, ungrateful, self-righteous and a prick. I wonder how much Rachel’s story would have changed just by him acknowledging how hard she was working and how much what she was doing was benefiting their family.

I can see aspects of myself in both Libby and Rachel, and there were a few small details that have made me reflect on the less attractive qualities in myself. I’ll talk specifically about two of them.

Libby as the “Cool Girl”

Libby might not be rich like Rachel, but she’s certainly elitist. She thinks she’s better than the other women around her. We can see this in her choice of an all male friend group, her decision to work at a men’s magazine, her worship of a misogynist writer and her condescension towards all the women who have chosen to live in her suburban town, never recognizing that she is one of them. Libby is the stereotypical “Cool Girl” who thinks that success lies in being accepted by men. It’s only recently that I’ve understood how problematic “cool girls” are and recognized that I used to be one of them, when I was trying to find success as a creative in my first few years in advertising. At the agency where I worked, the men who dominated the creative department loved to say the most offensive things possible to see what they could get away with. As a 22yo, I knew the way to get into their group was to laugh at their jokes and be offensive too. I patted myself on the back for being pretty good at it. I’ve thought about this a lot, because since the “me too” movement, I wondered if this was in fact sexual harassment. I decided that it wasn’t, because I don’t think it harmed me in any way. I think it actually helped me. But more recently, I’ve realized I was part of the problem. Being able to hang out with the boys and go along with all their jokes was probably at the expense of other women. (I will say, I grew out of that phase rather quickly, switched jobs and ended up working for two women who were way more helpful in elevating my career than the men ever were. Maybe Libby left the magazine industry before ever being lucky enough to have a female mentor.)

Rachel Finding her Worth

In the beginning of the episode about Rachel, we learn that she went to a private school where always she felt like an outsider. As an orphan, she longed for the generational wealth, status and sophistication she saw in her classmates, which drove her ambition later in life. Once she started a successful theater agency, she felt like she had something of value to offer, because she could give her wealthy friends easy access to Broadway show tickets and backstage passes. “She bought their friendship.” I have also always thought of myself as somewhat of an outsider. I grew up in a wealthy town, but my parents divorced when I was little and we were hit pretty hard financially. I always had to figure out how to fit in with way less than those around me. I was by no means poor (in fact, I’m certain I was still very privileged by most standards), but it did have a pretty big impact on my feelings of self worth and was a big driver of my need to succeed. For awhile, I really defined myself by my success in advertising, but then I got laid off and telling people I wrote a “mommy blog” was a lot less impressive. But by the time we first started attending preschool in Manhattan, my social media presence was growing online and people began to understand what that meant. I distinctly remember going to a preschool event where someone learned what I did for a living and told the other moms around us. I didn’t have any real friends there yet, and suddenly everyone wanted to talk to me. I honestly didn’t mind. It felt nice not to have to do all the hard work of getting people interested in getting know me. After that, a few of my new friendships became somewhat transactional, and I don’t think I even identified what was happening until years later. I remember a woman (who is still my friend to this day) asking me out for coffee and the whole time I was sitting there, trying to figure out what she wanted from me. Did she have a new business she wanted me to promote? Did she have a friend with a business that she wanted to introduce me to? And then she said, “Hey. I’m just being friendly. I’m not asking for anything.” It was a bit of a wake-up call. Thankfully, that was all more than ten years ago and my friendships now are based on way more.

If you’ve been paying attention to the online discourse about this show, I’m sure you’ve come across “The Fleishman Effect” article in New York Magazine which talks about how the show felt a little too close to home to a certain kind of mom in Manhattan. Moms who are also working their asses off to achieve a level of success, but haven’t achieved enough to give themselves the kind of life they feel they deserve or come close to the level of success they see others have around them. These moms were relentlessly mocked in the comments of that article, but I’m going to go ahead and admit, as a fellow mom in Manhattan, one who has chosen to stay way past the point when many other families move to the ‘burbs, there are some way in which I can relate to them.

I have never really cared about status or the external cues that tell someone you have money— designer brands, Cartier bracelets, a classic six on the Upper East Side. I like to think that is more of an uptown thing than a downtown thing, where wealth is displayed a bit more obviously. But I do sometimes wonder why we are still trying to exist in a world where having a comfortable life is so difficult. Rachel literally has a nervous breakdown over it. Pretty much anywhere else, we could buy a nice house, have money to decorate, send our kids to a good public school, find friends in a similar financial situation and maybe feel like we didn’t have to work so hard to keep up. But instead, we choose to live in a city that we’ve been brought up to believe is the best place in the world (I literally watched my dad choose a life in NYC over living with our family in the burbs when I was 10) and pretend that anything less is “giving up.”

I think what happens in NYC is that a lot of families live here when the kids are babies, and then as their kids get older, they start to move to the burbs for various reasons— some because they prefer the suburbs, some because they think the burbs will be better for their kids and others because they can no longer afford the city. The older your kids get, the smaller the pool of families who have stayed, with a large majority of those families being the ones who can comfortably afford it. I think the reality is that there are a lot of families on the cusp, but TV shows always portray families in Manhattan as ultra wealthy (Fleishman, Succession, Gossip Girl, We Crashed, Sex and the City) so you start to feel like you’re the only ones who don’t have insane amounts of discretionary income.

I think the real question is not why many Manhattan moms feel like we don’t have enough. That to me is pretty obvious. Life here is EXPENSIVE. The question is why we feel like the only path to happiness is within NYC. It’s easy to say that we bought into all the movies and TV shows that portrayed NYC as the center of the universe, but for a lot of us, this is also our hometown with all our family and friends. We have roots here.

When I think about it, I don’t need more to be happy here. And I certainly don’t care about status. I just don’t want to feel like an outsider. I want to know there are other families around me, with kids of similar ages, who also could give a shit about what designer bag someone is carrying, who stay in NYC because they love things like access to lots of shops and restaurants, ease of public transportation, walking everywhere, close proximity to all the cultural stuff, being somewhat anonymous and being able to choose your communities. And when I look around, I have plenty of friends in NYC who fit that description. They are just not the kinds of families currently being depicted on TV. Probably because it would be pretty boring television.

Fleishman is in Trouble ends with Libby deciding to write her book and apologizing to her husband for being so absent. He says, “It’s okay. You always come back.” Then we see a brief glimpse of Rachel returning to her family. I don’t think she gets back together with Toby, but I believe she becomes a present mother again, as she had really been all along. In a perfect world, Toby is forced to reckon with the fact that he deeply fucked up by not doing more to find her.

Will the book fulfill what Libby needs in her life and lead her to happiness? I believe it will for a time. But then five years down the line, there will be another period of discontent that needs fixing. You know the line in Hamilton where Angelica says that she doesn’t want to get together with him because they are both the kind of people who will never be satisfied? That’s who I think Libby is. I think Rachel is probably that too. I think a lot of people who choose to live in NYC are like that, myself included. I take solace in the fact that if I moved to the suburbs, I would probably still be like that. For certain people, there is no solution based on circumstance. Only new goal posts and dreams.

There are a ton of themes that I’m not even touching on here, like post partum depression and what happened to Rachel in the delivery room, but I want to throw it over to you guys to discuss whatever resonated with you the most. What part of Fleishman is in Trouble are you still thinking about? Which characters did you relate to? What do you think the solution is for your own discontent? Or do you think discontent is just a part of life? Or are you Libby’s husband Adam and happy exactly where you are? Please discuss!