For Unconventional Women Living in the 21st Century with No Roadmaps

Whitney Dunlap-Fowler
8 min readOct 24, 2021

When living outside the box is the only existence you’ve ever known.

It’s amazing to me sometimes how crushing some of life’s milestones can be for those of us still navigating our way forward through adulthood.

Even more amazing when you realize that these milestones or, socially constructed points of achievement used to determine if your life is a failure or success, follow you from birth to death and are seemingly unescapable. This is true even for those of us who, like me, try to push against the high probability of getting sucked into the predictable, expected & pre-determined cadence of life.

I’m not quite sure when it happened for me exactly.

In college, a professor told us to always question the content in the books we were reading, a fact that had never occurred to me because until that moment, books had always been presented as absolutes. Critically analyzing philosophies from dead theologians had not yet become a natural part of my daily activities. While that interaction may have served as a catalyst for me to begin questioning why we do the things we do, the journey to a “contrarian lifestyle” was a key part of my identity long before that moment.

In middle school I refused to wear sneakers despite the fact that the Air Jordan Brand had my entire school wrapped around its finger. “Why would I want to show up looking like everyone else?” I thought as white shoes with light blue Nike swooshes invaded hallways between classes. Instead, I found a pair of my mother’s old knee-high boots and wore them everyday because the sound of the heel clicking made me feel closer to the adulthood that I was aspiring towards (if I only knew then what I know now- ha!). I wore those things until the heels ran raw and they were no longer reparable.

In high school, to coincide with my desire to feel unique and different, I made it a mission to stretch my wardrobe so that it didn’t look like I wore the same outfits everyday. I discovered how good I was at this goal when an upperclassman I had a crush on told me he could never keep up with me because I “never wore the same outfit twice” and I was “too high maintenance” for him. Who knew knowing how to mix and match JCPenney juniors department clothing could deliver such a crushing blow to my nascent love life? Regardless, that comment never stopped me.

When I turned 16, I didn’t rush to get my driver’s license- for me a car was not a priority. When I finally realized I had no choice, I got the first thing I could find and cared nothing about what it said about me. My sun-blasted, 87 Toyota Camry, whose color had faded closer to the silver metal it was made of, was a great find, despite the number of minimum wage paychecks I sunk into a vehicle that had lost the will to live. (I would eventually move to a city that wouldn’t require me to own a car).

My freshman year in college, I was highly astute and never drank or even considered drugs (yes, I was a rule-following nerd… sorry?). It was not until a week before finals, spring semester that it donned on me that I may have been missing the full “college experience” and found some alcohol to “devirginize” my first year. I wasn’t a fan and I’m still not to this day.

So yes, it is clear that the seeds of an “unconventional lifestyle” had been planted in me for quite some time. When opportunities emerged, I would choose to diverge from the pathways of “expectancy” when I could. However, there were still many things I pursued that were very much a part of life’s predictable cadences. Money for instance, was the key to ensuring that I could live a life outside of the breadcrumbs that had been left for me to follow so I prioritized a traditional education and career pathway to do so.

Besides, I was a child- not a miracle worker. Free-thinking comes with time, maturity and confidence.

The milestones we experience up to age 25 are, arguably, the easiest ones to navigate. No one tells you how your 30s will mentally rock you from your core and make you question your own existence as the shadows of your 40s silently loom in the background, stalking your fading youth & crucial life decisions like an unrelenting death sentence of expired time (while this is how it feels, I’m pretty sure the 40s are fine…aging just brings out the most dramatic reactions in us).

It should be no shock to anyone then, that at age 36, I still have not warmed up to the prospect of having to achieve the main “big three” milestones of my 30s (children, marriage & home ownership). At this age, the pressure of pursuing these particular milestones feels much heavier, foreboding and unescapable than those in the past and have served as a sustained place of tension and anxiety for me.

All of this forced me confront the myriad of ways I’ve chosen to swim against the current, and WHY. Once I was able to reflect on my past decisions and the reasons behind them (a story for another day), my reluctance began to feel more manageable. But I still wasn’t quite sure why I continued to feel such a high degree of animosity towards a social system I had (let me tell it) chosen to ignore.

The truth is, sequestering yourself from the rules and expectations of your community/society requires an incredible amount of fortitude, diligence and dedicated energy. It is a taxing endeavor to not give in to peer pressure and choose a life lived on your own terms- especially when everyone but you seems to be going in the same direction.

What makes it worse is that society rarely celebrates or sees women living unconventionally. They are rarely, if ever, portrayed in movies or popular media and if they are, they are often not the main characters of the story.

On the rare occasion we do see unconventional women, it’s often executed in the most dramatic ways. They are featured as rebels often with short or loose, “untamed” hair. They have an “uncontainable wildness”, bi-curious natures, insatiable sexual appetites, and are almost always emotionally detached. More than anything they are portrayed as gun-wielding hot heads who either physically kill or emotionally hurt people the people they come in contact with.

But contrarians are diverse and unconventional lifestyles exist along a spectrum that has yet to be fully defined. We also don’t necessarily wear our lifestyle on our faces (or in our hair as Hollywood likes to assume). Not only are these characterizations one note, but they leave us without clear examples for what a realistic life, differently-lived could be and how it could flourish without children, marriage or the ownership of things we never cared for.

Because the writers, producers and directors who get elevated to the limelight are mostly men, and because screenplays of original storylines are less often greenlit, it’s probably safe to assume that no one knows how to write for women who live life outside of the box without making them highly problematic antagonists. I find this unfortunate because there are very real women today and throughout history who have existed in unconventional ways but whose stories were not always celebrated.

When it comes to celebrities, women like Diane Keaton, Tracee Ellis Ross, Mindy Kaling, Charlize Theron and Oprah Winfrey are just a handful of women who have chosen to live unconventionally- and all in different ways. But even they have had to endure public scrutiny and prodding around the the most intimate parts of their lives. Not only are their stories not as elevated, celebrated, or known, but because they are celebrities, it can be difficult for their lifestyles to feel accessible or relatable to the common woman.

Where are the big Hollywood stories of childless, unmarried women who chose not to settle and who whose lives are filled with love and joy without the societal titles they are expected to aspire towards? Where are the portrayals of women whose stories of motherhood are not rippled with trauma around conception, and who have chosen to be childless from the beginning, or who chose motherhood later in life through adoption of fostering? Perhaps more than anything, where are the depictions of women who, like me, are struggling to navigate these pressures and who have ongoing conversations in their heads about the types of humans they ultimately want to be?

The irony is, there are a litany of films and ad campaigns playing on the theme that we are more than our titles: wife, mother, caregiver etc. with the goal of making women feel heard and seen. But there are less films and examples demonstrating what life looks like without those titles in positive, reassuring ways. Hollywood & popular media are not only failing to keep up with lifestyles that are already existing , but they are also failing to speak to a generation of women desiring to see themselves and their choices in media without judgement, pressure or critique, and without being boiled down to an obscene, unrealistic trope.

In a world where unconventional women exist, where are our pathways and our reflections of self?

A successful life can also be an unconventional life well-lived as long as it is fully based on who you are- not who your parents, your community or society says you should be. More than anything, the power of living unconventionally means having the ability to change your mind, or reconsider anything you thought you may have wanted in the past because you answer to no one but yourself. Who doesn’t want to be as free that?

Based on the countless conversations I’ve had with friends and random acquaintances on this topic, I’ve discovered that the anxieties I’ve had on living “out-side-the-lines” are shared by many women, rather than just a few. Because of this, the future I see for myself is clear. It is filled with travel, love, great food, girlfriends and new adventures — but it doesn’t look like anything that I, or the women I’ve spoken with, have ever had the ability to see or witness with our own eyes.

Despite this, it is clear that the women of my generation will likely be the ones foraging our way through, making mistakes and creating the necessary road maps of unconventional lifestyles while leaving the necessary markers for others to consider or even follow. I just hope that the road maps will be enough to expand the menu of lifestyle options for my pre-teen nieces so that going against the grain in their near future can feel more familiar, more navigable and less paralyzing than it has for me.

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Whitney Dunlap-Fowler

A Cultural Strategist & Semiotician. I write about brand strategy, market research and life from my perspective. www.touchofwhit.com, www.insightsincolor.com