#100. The Transitive Property of Freedom

This is my villain origin story

For the 100th issue of this newsletter, I wanted to tell you a bit of a lengthy story that’s been percolating in my mind for a few weeks. This one is long and winding and may be served best with coffee, so I won’t be at all offended if you skip it for now and come back when you have the time to follow me down the rabbit hole. x

Four score and nearly twenty years ago, I was a junior in high school trying to decide what the hell I wanted to do with my life.

My parents had gently put a hermetic seal on my dream of becoming a professional theater kid (true story). They also used a variety of fun scare tactics to discourage me from pursuing either counseling or journalism as my chosen path, too. Both careers wouldn’t make enough money, they reasoned, and it was of the *utmost importance* that I became financially independent without ever having to rely on a man. (Or them.)

After a near-miss with broadcast journalism, I settled on marketing and never looked back. It was the “fun” side of business! A fusion of art and science! It was a completely reasonable suggestion for two very math-and-science oriented parents to bestow upon their emotional basket case of a daughter who had always gravitated towards writing, psychology, and performing/visual arts.

I want to tell stories for a living, I told my parents, with the unbridled enthusiasm of an idealistic teenager. I didn't use those words, exactly, but it’s easy to look back now and see that’s what I was trying to say. I’m fascinated by the human experience. I want to wrap myself in it both personally and professionally, over and over and over again.

That’s great, my mom replied, her trademark candor not leaving much room for debate. You can go to business school and tell stories for brands. That’s where all the money is.

My mom was a second-wave feminist who ended up quitting her career in the late 80s to be a stay-at-home mom, and she instilled in me from a very young age this idea that I would make my own money. She got a bachelor’s, a master’s, and then a PhD, and never really got the chance to do much with any of them. Her life goals were twofold: Get both her daughters into well-paying careers and married to partners who weren’t: A. assholes, or B. smokers.

And thus, I got the distinct sense that she wanted me to, first and foremost, have the long-running career she never had.

After college graduation, she bought me a few sad, ill-fitting corporate pantsuits I never had the opportunity to wear. Unfortunately for the visions she must have had of me rubbing elbows in somber-colored business professional attire, I landed at a boutique website design and branding company at the spry age of twenty-two and wore jean shorts to work pretty much from day one. I think she probably expected (wanted?) me to come home and work for a massive corporate entity like Target or Best Buy, but you can only lead a fish so far outside of water before it starts slapping its fins against the rough gravel.

I didn’t walk the path of becoming a Corporate Girlie, but I did become genuinely obsessed with my career. I moved to Los Angeles for more interesting opportunities – which I definitely found – and became so singularly focused on my career I even managed to convince myself I was an enneagram 3: The Achiever for a while. (How many ambitious millennial women who grew up on a steady diet of achievement and competitiveness mistype themselves as 3s? I’d actually love to know.)

For a moment, travel back in time with me to middle school, where we learned about something called the Transitive Property of Equality.

Don’t worry, it’s easy. If A = B and B = C, then A = C. You remember this, but probably haven’t ever had to use it.

My mother subconsciously performed this equation for me when I was seventeen, which formed the vortex of my existence for the entirety of my late teens and all of my twenties:

A = freedom
B = money
C = career

If freedom = money, and
money = career, then
freedom = career

And so I worked for my freedom. I graduated from college with high honors and a perfect 4.0 in my major. Then I was first in and last out at the office for nearly a decade, working until long after the sun had gone down and catching the train home, nearly collapsing on colorful worn fabric seats in the dark. I drank my own ambition-flavored Kool-Aid when I went back to business school for a second time and drove myself into the fucking ground and straight to the E.R. (only once!) to be the valedictorian of my master’s program. I watched my friends happily pair off as I flitted in and out of ill-fitting relationships, always searching for but never finding the kind of love that felt like freedom instead of control.

In my twenties, one of my exes told me we’d be moving to San Francisco for his job and eventually I wouldn’t have to work, so I promptly dumped him. Another informed me while wandering the cereal aisle on a random Tuesday that he’d be having a baby the following year (my response: with who?), so I dumped him. Another made it perfectly clear he thought his career would always be more important than mine, so what did I do?

Reader, I dumped him. I rose farther and faster in my career than most of my friends while they disappeared into relationships with the partners they’d eventually marry, but I’d been told this was how to do it right, hadn’t I?

My career was the ticket to my freedom. And freedom was more important than anything else, including love. Any kind of love that took away my freedom wasn’t the kind worth having. I still believe that.

Let’s revisit my mother’s equation again.

If freedom = money, and money = career, then freedom = career.

This feels hard to argue with, doesn’t it? There are only three real ways to acquire money in this life, and those are:
1. inheritance
2. work
3. marriage

It was made crystal clear to me from the age of seventeen that inheritance was off the table and marriage wasn’t the “right” way to acquire money, and in turn, my freedom. Work was the only option.

So I worked my career-obsessed ass off and barely ever paused to slow down. Having kids someday never even crossed the stratosphere of my conscious mind in those years. It was only a vague notion of eventually I’ll have to deal with that, but not this year, or next year, either. I’ll push parenthood off as long as I possibly can. It was only love and work, work and love. These were my mother’s goals for me.

But at twenty-seven, I started to get restless. I went to grad school to inject some new energy and opportunity into my career. I found a guy who embodied the very definition of “good on paper.” We got engaged.

Then my Saturn return came for me like a bat out of hell and tumbled my life around in a hot dryer for about a year.

Somewhere around my thirtieth birthday, I performed the equation again. But this time, I was older, maybe a little wiser, and I wanted to come up with my own version. I wasn’t happy, but I felt distinctly like I was about to embark into the next major phase of my life, much like I’d done at seventeen. How could I find happiness through the equation? I couldn’t quite come up with the answer. Some of the things I thought would bring me happiness hadn’t.

I thought again about what my mom said. Freedom. Freedom is the thing you need. Freedom is the key to everything else. I knew in my bones that much was true.

Around this same time, my sister had her second child, and a new question began its quiet invasion into my mind. I was about to get married, and my soon-to-be-betrothed had made it very clear he wanted kids. Soon. I couldn’t exactly answer the happiness question, but the equation seemed to be telling me something else. In its simplest possible version, here’s what me and my inner truth came up with:

A = kids
B = less freedom
C = undesirable

If kids = less freedom, and
less freedom = undesirable, then
kids = undesirable

There was that word again; that obsession with freedom. I didn’t want less of it, I wanted more of it. The equation had detected a clear flaw in my life’s plan.

I called it the Transitive Property of Freedom™️. I called off the wedding, moved out of my ex’s house, and started over on my own. I spent a year recovering and contemplating my life choices, and then six months in therapy proved my equation was correct. Freedom was the key. And then I met my husband, who had applied the equation to his life the same way I did.

I’m not saying this calculus I performed is correct for everyone – I’m saying it was correct for me, in this particular decade, in the country I live in. I know plenty of people who wrote a completely different equation, with totally different inputs that led them down the path of having kids. But once I finally understood the equation how I’d written it, I felt like I had solved the proof of my own life.

I think the Transitive Property of Freedom helps examine the situation America finds itself in right now, with more women than ever choosing not to have children. Right now the focus is mostly on millennials because of our age – eventually, that honor will transfer fully over to Gen Z. As the current custodians of the Trump administration’s ire, I think it’s freedom that we need to pay closer attention to.

Relying on a marriage partner for financial security is abhorrent to many millennials, on both sides of a partnership equation. Maybe this is because of a dynamic we saw with our parents and/or our friends’ parents; maybe not. One partner relying on the other financially used to be the norm, but times have changed.

It’s a lot of pressure to provide financially for a non-working partner, and it can create an unwanted and potentially damaging power dynamic. Historically, it’s often been money keeping women in bad marriages, because they literally can’t afford to leave. (Remember, freedom = money, and money = freedom).

So where does that leave most of our generation? Both people in a partnership choosing to work. Both because we want to, and because it’s an insurance policy against an unknown future. And this setup would be great if American society was designed to actually support that lifestyle once a couple decides to have kids. But it isn’t, and working mothers are the ones who get fucked by the system.

I think a lot of millennial women were raised by boomer mothers who encouraged us to buy our freedom through our careers. And there are so many women out there who have careers and children (74% of mothers with kids under the age of eighteen were working as of 2023), always performing a difficult balancing act of both. If that’s you reading this, please know I think you’re incredible. I don’t know how you do it.

Then there are those of us who choose either a career or children to make life a little easier. (I acknowledge both of these choices come with privilege, but that’s a different essay). Obviously you know where the dice landed for me.

My mom is sad for me – she thinks I’m going to miss out on the best thing she ever did. She never got to have a long career, though, so how does she know it wouldn’t have been the best thing she ever did instead?

But here’s where I tie all of this together into something resembling a thesis statement: I think it’s ironic that my mother pushed me so hard academically to ensure I’d have a career and my freedom, but never did anything to help me develop an affinity for motherhood.

Maybe she assumed that a biological drive would take care of it, but if that impulse is buried somewhere deep in our genetics, I don’t have it, and neither did she. My mom had children because that’s “just what you did” in the 80s, not because she felt driven by a desire to do it.

I didn’t hold a baby for the first time until I was the absolutely bonkers age of twenty-four. As a kid, I was ripping the heads off of barbies, faking an allergy to the color pink, and hammering nails into trees in the woods behind my house instead of playing with baby dolls. I picked a chemistry set over an Easy-Bake Oven, happily. I was never offered a babysitting job, not once, even when all my friends were somehow doing it constantly. (I never asked for one, either, to be fair.) I reffed soccer and sold ice cream to drunk college kids instead. I was the only one of my friends in college to have a job (I worked part-time at The Gap, thank you very much) and I was the only student in my entire year to get an internship during my Study Abroad semester.

I’ve spent literally none of my life preparing for motherhood, and all of it to have a career. And to my own mom, I just want to say – are you really that surprised?

I look at my life now, and it seems I’ve come all the way back around to my seventeen year-old self who just wanted to tell stories for a living. She’s still me, even all these years later. I have four different jobs/creative outlets I’m currently trying to balance that have something to do with storytelling, and none of them are parenting. I spend a majority of my free time working on one of my many creative pursuits, including this one.

At thirty-five, I spent a year writing a book instead of having a kid, and it was the most satisfying thing I’ve ever done in my life. I can’t wait to do it again.

Stories are freedom, which is why I’m telling you this one. Deciding I didn’t want kids was freedom. Focusing on myself and my career is, and I think might always be, freedom. Finally finding love – the right kind of love – has been freedom, too.

Giving myself permission to finally pursue something my parents steered me away from when I was younger is freedom.

I still don’t know exactly where happiness fits into the spectrum of my life experience (is happiness even the end goal, or is the pursuit of it enough?), but I do know where freedom fits in. Thanks in part to my mother, it’s the thing I’ve built my entire life around.

Freedom on its own isn’t happiness, but friendship is, and I have that in spades. Love is happiness, pursuing my passions is happiness, and so is having time to myself. Raucous laughter is happiness, and so is the golden calm of a quiet night in. Good conversation with people I love is happiness, and so is getting lost in the pages of a book. I’ve found happiness in so many little things I can experience and observe in the magic of the everyday, whereas freedom has always felt like something I need to actively pursue.

These days, freedom feels like it’s something that can also be readily given and even more easily taken away.

It’s ironic that this endless pursuit of freedom may be something that wasn’t even my idea in the first place, but rather a concept instilled in me by my own mother. I wonder how much of it was intentional, and whether she ever imagined that it would eventually lead me away from a life with kids. After she reads this essay, I’m sure I’ll ask her.

On a personal level, I don’t think women deciding not to have children – for any reason – is a problem that needs to be solved. Every person can choose for themselves what they want their lives to look like, and every choice is equally valid.

On a societal level, though, I do think there’s a lot more to unpack here. Not just about deciding whether or not to have children, but everything that comes after. How all women should be afforded more paths to freedom, no matter what they choose to do with their lives.

I think maybe I’ve always been guided by my version of the Transitive Property of Freedom, and probably always will be. If things in America were a little different, a little easier, maybe I would have chosen differently. I guess we’ll never know.

It’s funny looking back on things that happened when I was half the age I am now with a new perspective and twice the life experience. Some things feel so clear now that weren’t at all back then.

I imagine myself at age seventy, sipping a cocktail and thinking back on all of this – remembering the decisions I made and the world I lived in once. I can only hope I’ll feel I made mostly the right choices, and that the world has only changed for the better.

And when the time comes, I hope all my friend’s daughters will feel they have better options than I did. And I hope they’ll know my door is always open to talk about their own equations.

I wonder where mine will take me next.

x

Whelp, that’s all I’ve got for this week. Come tell me your life story in the comments?