My Year as a Girl Boss

Me in 2013

It was 2013 and I’d just arrived at the largest suburban house I’d ever been inside. I was at a stranger’s place for a two-day writing workshop, and I paid $500 for the privilege.

The house belonged to one of the workshop participants, who reached out to the instructor and offered to host her in order to tempt her into offering a workshop locally to her. It was billed as in DC, but it was actually in a fancy part of Maryland where the homes looked like estates. The host had made her money as a lawyer; one of her neighbors was a Supreme Court justice. I joined about a dozen other students in the chef’s kitchen, milling about while eating fancy (and entirely vegan) treats. I was 26; other attendees ranged from around my age to in their 50s. However, we were all women, and we were mostly white. 

I decided to invest in this program right after I decided to become self-employed. It’s no coincidence that 2013 was also the year John and I got married, meaning I could join his healthcare, the same year that I aged out of my parents’ plan. After I left the Daily Dot, I was certain the only thing that stood between me and success was a killer mission statement for my website. And this workshop was going to help me create it.

Presently, the instructor arrived. For all her success, she was only two years older than me. Like the other students in attendance, I’d closely followed the details of her life on her blog, from quitting her 9-5 in 2010 to her whirlwind rise to seven-figure success as a ghostwriter and writing coach. For the purposes of this story, it doesn’t matter who she is; just know that I thought about her more often than about people I actually knew. Perhaps it wasn’t healthy, but a major reason I signed up for this workshop was that I wanted to meet her. A second reason I had a hard time admitting to myself: I wanted to be her. 

The workshop was about writing foolproof copy for your website designed to clarify your brand, attract a larger audience, and develop products and services. Sounds straightforward enough. But weirdly, it began with a tarot drawing. According to the ten pages of feverish notes I took over the workshop’s two days, it was The Seven of Fire, which still means nothing to me. Then, we went around the room introducing ourselves and the businesses we wanted to create. When one woman announced her goal to educate on the dangers of vaccinating children, there was an uncomfortable silence. She did not show up for the second day of the workshop.

Awkward moments aside, it was intoxicating to be surrounded by wealth and mingling with the women who were certain to be my new best friends as we all grew our businesses together. One detail that eluded me at the time: many of these women were independently wealthy. Like the ex-lawyer who hosted the event, they treated writing workshops as a hobby. 

Perhaps I was a bit distracted, since my car had broken down the day before. (And here I was, spending $500 on something other than the repairs!) I’d gotten a ride from a neighbor to the workshop but I would need to find my own way home. Luckily, I met another participant who lived close by and offered to drive me home and back again the next day. She invited me into her messy sedan, pushing aside a huge stack of books on the passenger seat with titles like Love Worth Making and, I’m 100% serious, Sex For Dummies. Completely unabashed, she explained that she was a Mormon, recently engaged, and had received the books as gifts from a family member. I suppose things worked out, since last time I checked her Instagram, she had three children. And if you’re raising an eyebrow at my obvious judgment here, please know that she got the last laugh: she now runs a seven-figure business. I later paid her for business coaching and ended up attending an energy healing session, but that’s another story

When I got home and John asked me about the workshop, I was almost embarrassed to talk about it with him. I’d invested what was for us a huge amount of money, and I got vegan food and quasi-spiritual circle time. I didn’t want my newlywed husband to think I was making bad decisions. I think I realized already that this workshop wasn’t going to deliver the results I was hoping for, but I wasn’t going to miss the second day because I chose to be a journalist and that means I’m nosy. One of the participants was an urban shaman, whatever that is! Just ask my friends: I STILL talk about the unusual career choices I heard about at this workshop. 

The next day began with a second tarot card (The Eight of Air) and a poetry reading. But before long, we got to the meat of the workshop: generating dozens of blog post topics, drafting emails to potential mentors, and bio-writing. The writing exercises were open-ended and general enough for any business plan; good or bad. That was also the problem: at the time, I could have used some tough love about my unrealistic plan to make a living writing Kindle books about geek journalism that I’d priced at $5.99 each. At the bottom of the Google Doc where I wrote my notes is a 90-word website bio that I never used. It looks like I opened the document once, a month later, and then never again until now. 

So what did I really get from that $500? I got to meet the writer I admired and to realize I didn’t want to be like her after all. But more usefully: I got the opportunity to build connections with the type of women who can afford to pay $500 for a two-day workshop. I didn’t write any of the blog posts whose titles I dreamed up at the workshop, but I received multiple leads for copywriting employment from other attendees. I failed to generate much useful writing from the workshop, but if the workshop had been a job interview, I would have passed. My niche as a self-professed geek and my history of tech writing made me memorable to other students, who recommended me for different freelancing contracts. Likewise, I recommended opportunities that didn’t work for me to students I met there, and later hired the woman who gave me a ride home for a more practical business coaching session.

I can no longer afford the workshops that this writer offers. Forget DC; she is now offering far more elaborate week-long retreats now in places like Maui and Tulum. She recently advertised a book publishing retreat at $10,000 a pop. As usual, the real benefit isn’t anything that’s being taught, but alleged access to the kind of people who can help you fast-track success. There’s even a VIP ticket for $20K that includes a private dinner with non-fiction agents at the Big Five. Later on, the sex-book haver told me about attending a conference for $25k in the Bahamas. It was about spirituality, but she ended up meeting wealthy clients there who patronized her business, making her wealthy in turn. In retrospect, this makes perfect sense: the hefty price tag is about buying access to those more privileged than yourself. 

Over 2013 and 2014, I attended multiple conferences targeted specifically at female entrepreneurs. Even the most practical ones had that kitschy “girl boss” vibe. It was the era of the blog, the height of the influencer. Each conference I attended was one I found out about online and centered around a successful woman and her cult of personality. Time and again, nothing I learned at the conference was as valuable as the connections I made there.

Sometimes when I am feeling pretty low, I look up acquaintances that I met in my year of workshops, envious of the way their careers have grown and scaled. I think a big part of my failure to thrive has been my skepticism, my closed-mindedness to the zeitgeist. I have always resisted the way that women’s entrepreneurship seemed so tied to spiritual practices like tarot and pink girl boss font, the same way that specifically men’s entrepreneurship workshops of the era seemed tied to landlord scams and chad alpha mindsets. Another part: my resistance to change and my refusal to delegate or scale. My income varied dramatically over the years, but I certainly never hit six figures. The year I was pregnant with Eva, exhausted and less productive than normal, but before lockdown torpedoed my income, I only made about $30k, or roughly one ticket to a spiritual writing workshop in Capri. 

A decade into the future, my year as a girl boss is on my mind while I’m emerging from a fog of full-time parenting, trying to remember who I am, what I’m capable of, and what I want to do next. I started digging into my conference notes to see what I could salvage and I found a much younger version of myself, optimistic to the point of naivete, blind to my own privilege, confident that the right advice from the right writer would make me a success. I didn’t realize that what I was really paying for was the chance to be seen there at all.