Why I’m Glad I Was Single During the Hardest Moments of Entrepreneurship

Single women entrepreneurs don’t exist, according to most business publications. Gaming and digital media hustler Rachel Presser of Sonic Toad Media reflects on single life and how it shaped her entrepreneurial journey.

When you hear the word “entrepreneur”, what comes to mind? What image do you conjure up?

I’d hazard a guess that most people tend to think of a youngish white guy in a snappy suit who buys and sells tech start-ups. What most people imagine doesn’t align with reality, that entrepreneurship and entrepreneurs themselves take on several forms.

Women are overwhelmingly choosing entrepreneurship and free agent life because traditional work has become too inflexible. The digital world has made it more feasible than ever to start your own business without needing partners, employees, or extensive capital. You can happily build a high-five or low-six figure income without all the hassle that comes with this gigantic venture-funded operation where you’ll be told what to do and risk losing control of what you built — and ownership of your labor.

But according to business publications, we don’t exist. Based on editorial direction and what shits up my mentions any given day on Twitter? Women entrepreneurs are either these poor exploited maidens pounding out web content for pennies who need a nice W-2 job to come “save” them, or multi-millionaire girlbosses replicating the same abusive power dynamics we escaped.

Women entrepreneurs face all kinds of challenges that men simply don’t: we start businesses much later in life, for one. Partly out of social engineering to be risk-averse and “get a good job first” like I was brainwashed to do, and we’re programmed not to believe in ourselves. Plus, things like pay inequity contribute to difficulty getting certain sources of capital. Women pursuing the funded venture route tend to get turned down on the mere assumption that they’ll want kids while fathers don’t seem to have to worry about this. Only 2.2% of venture funding goes to women because of this 1950s-style bias that isn’t going away anytime soon.

Then sure, there’s the “mompreneur” niche. Since I don’t have or want kids, I don’t fit in with this group even though I’ve learned useful things and gained powerful insight from them. But this group also tends to skew married and with household dynamics I can’t relate to. Every time I go on Gamasutra to read about the travails of indie developer life, several pieces are by straight married men who may or may not admit near the end that their wives were paying the bills while they built the games and I die a little inside. The industry roundtables where these guys talk about how they couldn’t do it without their wives, yet they nary get a mention in the postmortems? I try not to internally scream when people assume I couldn’t have possibly done what I did without a husband.

Business publications without a specific industry bent also got virtually nothing geared for single women. Not much about the interpersonal aspects of how entrepreneurship affects your life, but I always focused on them in the workshops I taught since it’s more than just “your friends with 9–5 jobs can’t understand your life and career anymore”. It can affect how you date and choose a partner! This Inc article is old, but it bears more questioning: why aren’t there more divorce statistics on entrepreneurial types?

After reading the harrowing anecdotes in that piece, it made me want to cover something that challenges these perspectives: why this single woman is glad I got through the roughest parts of my entrepreneurial journey on my own for the most part.

I never had to fight about personal or business finances with anyone.

Going through a major downturn, or that unpredictably long spell of little to no income against high burn rates when you’re starting out, for the first time can be traumatic on an individual level let alone as a couple.

I’m an experienced stuntwoman in this regard. I’ve fallen out of the moving car and already hit my head a few times. So I know what to do.

I know how to get through chapters of austerity, and I did this without the benefit of a supportive husband — or a controlling one who’d hold a business downturn over my head, or maybe even leave me to contend with the financial mess of a divorce and sudden uptick in living expenses.

Like many people, I initially took a big hit during the pandemic. But then some of it became voluntary after I gained access to government and private funding for my projects, and realized I could take advantage of these slower periods. Unlike prior hard times? I was not only prepared, but also had plenty of personal and business financial cushion. If I have to do a crash landing with a co-pilot, I’m already inured to it. It also prepared me to weather future lean times by myself.

But now for the flipside: what about when you’re making money, got savings and a reserve set up? I think men are not socialized to support ambitious women. There’s no road map for this. Fighting about money can be even more likely if she succeeds than if she’s running on empty for a while.

Having gone through dead zones and months of high earnings alike, I’m glad I weathered the hardest parts and reaping the rewards by myself. It’s prepared me for discussing finances with clarity and setting appropriate boundaries should I find a partner.

I’ve gained control over my time, plus demarcation of work and my personal life, that only years of entrepreneurial experience can bring.

Cisheteronormative socialization with respect to how men are programmed to see women isn’t just about money, and feeling it’s “wrong” for a woman to have the same amount of money as you or even more. It’s about TIME. And I know, I know, NOT ALL MEN, but there’s absolutely this messaging that women don’t deserve control over their time and her time is inherently worth less than yours.

But we choose entrepreneurship to have control over our time with respect to how we work, when we serve customers and clients, and build our websites, games, products, and communities. The same absolutely rules true in our personal lives.

I mean, I roll my eyes every time I see some article handwringing about how freelancers and entrepreneurial types “have work bleed into every corner of the day” because I can tell the author is not used to actually having control over their time. The thing I love most about the particular business I built is that the time away from my clients, fans, and projects is MINE.

It can be too easy to get sucked into something you’re really passionate about, and worse yet, fall into the “business above all” trap. And there’s times you really have to get that bid or project in at the last minute because you were sick that week, it just came up, or time zone differences aren’t on your side. So it helps to communicate about these things!

But at my age, experience level, and ideology, I know when to put the phone down if we got alone time planned. And damn right, I’ll expect the same in return. The whole point of why I fly my own flag is so I don’t have to work 24/7. I’m glad I had years to learn how to fully assert that control and demarcate work from life, I have a feeling some ugly fights could’ve gone down otherwise.

Taxes.

I was an EA for a solid decade, literally wrote the book on game developer taxes, and worked with the IRS on exam materials, so this is an area I take seriously and have strategized to a T.

In times of being a brokeass and a baller, it was actually a good thing I was unmarried because it would’ve taken away my cheap health insurance and shoved me into a much higher tax bracket, unless I had a househusband who took care of my toads full time or some shit.

Hold on…that sounds FANTASTIC at this juncture of my life and career.

I know what I want in both business and life now.

It’s not all financial, even though money is unfortunately an inescapable aspect of all this.

There’s several personal factors I won’t really dive into, namely decades of trauma that took a long time to come to terms with which meant I simply wasn’t ready til my early thirties for a partner anyway. I know what I want in one now; similar lifestyle and values are a must.

But just like how I didn’t really know who I was til my early thirties, the same goes for having a clear plan for business. It took a couple different ventures, funding methods, and exploring business models before I figured out the exact trajectory I wanted to go on and stick with.

Would having the financial and emotional support of a good boyfriend or husband have made that easier and possibly faster?

Maybe. But since the concept of having someone who actually supports and gives a shit about you is basically as foreign to me as my career type is to most normies, I’m hazarding a guess I wound up being better off. I might have been pressured to take a deal I didn’t want just because the income potential was better than the path I ultimately chose, or to not try all of the different things within and outside of gaming and tech that I did.

I mean, I’m glad I’m doing this whole batshit crazy cross-country move in my mid-late thirties and it’s not for a guy. There’s all sorts of power dynamics at play if a woman moves for a man, and they often involve her taking a huge risk on lacking community and family nearby while she can’t get a new job easily. It’s way different when you’re entrepreneurial and make that decision on your own terms. I figure that even if my love life in California will be a nuclear holocaust, at least I’m going to my friends, more support for my industry, and to the happier and better version of myself that resides there.

Because of various events that took place on my west coast tour in 2017 that predicated this desire, let’s just say that they wouldn’t have transpired if I was already spoken for. The immense personal journey that sent me on wouldn’t have happened without my entrepreneurial aspirations and choosing to make travel and events irrevocably interwoven parts of my career and life.

A relationship that doesn’t work out can still show you just one more frisson of the human condition and experience, and help you realize what you actually want out of one. I had spells of purposely and inadvertently closing myself off from men in times of both success and distress: after all, I’ve toughed out the Sonic Toad Recession of 2018, minor and major surgeries, the challenges of traditional and alternative capital sources, and surviving a deadly pandemic all by myself.

So I don’t know what’s ahead. But I do know I’m glad I went through joys and tribulations in the business world on my own, because they taught me how to find a balance between self-reliance and forming a community with other game developers, content creators, and entrepreneurs. Making it through the tough times financially then having more money from my ventures than I ever had in my life— while still being able to have a life — also showed me what I’m capable of, and what kind of communication and boundaries I’d reasonably expect from a partner.