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Start Here About Me Books Courses Geek Blogger’s Guide to Your First $1000 Niche Reviewer Crash Course Niche Journalism Workbook Journalism Web Design Contact No Villains Tech , Writing 3 months ago Sunrise in Potrero H, February 2015. When the Uber driver arrived at the worst Airbnb I’ve ever stayed in, he told me to double-check that I had the right address. On a sunny street in the Potrero Hill neighborhood of San Francisco studded with picturesque townhomes, this building had plywood boarded up over one window and graffiti sprayed on the wall. Inside, I would find out, one of the rooms was inadmissible due to a large hole in the center of the decaying floorboards. Inside I met Roy, not his real name. A man in his ‘60s, he’d lived in this house from his childhood—and seemingly kept it unchanged from then, too. He told me his grandfather built the house in the 19th century. Roy was a Victrola repairman and his living room was filled with ancient record players of varying functionality. When I arrived, he gave me a quick tour: the single bathroom, that we would share. The condemned, off-limits sunroom, its glass walls clearly displaying the dangers within. And the room I was to stay in, a guest room with a vintage teal-green circular bed, allegedly haunted by the ghost of his mother. The haunted room. To his credit, Roy was friendly and had a bizarre sense of humor. He played me music from the ‘20s on a Victrola. He asked me if I was thirsty, and when I said yes, he handed me a mason jar filled to the brim with yellowed toenail clippings. When I went to put down my things, he insisted on going into the guest room before me to yell at the corner of the ceiling his mother’s spirit preferred. LEAVE HER ALONE!” he shouted. His home may not have been able to pass a municipal inspection, but I didn’t feel unsafe. After all, I’d had two choices for where to stay: with Roy or at a motel with too many reviews including the word bedbugs.” My company gave me a budget of about $80 for two nights; they had already paid for me to stay in a hotel earlier the same year. If you followed me online around this time, my dodgy accommodations were not part of my travelog. Instead, I was posting photos of my visits to the headquarters of Crunchyroll, LiveJournal, GitHub, Pinterest, and Twitter. Since I lived in DC and reported on companies on the opposite coast, these business trips were an occasional necessity. My editor was from the same zip code as me and sympathized with my desire to stay where I was. But that meant I sometimes had to travel on a shoestring. At least my new employer was willing to put me up in an Airbnb by myself (plus Roy, I guess). At a previous company, I’d shared a double-bed room with a colleague. I was asleep when she returned to our room drunk, removed her clothes, and stepped into the bathroom. There was some commotion and when I asked if everything was okay, she responded loudly that she was masturbating. Finally, she got into bed. MY bed. I am not a confrontational person. I got up and got into the other bed without a word. In the morning I told my closest friend at work about what happened. He’d been an RA in college and was a good listener. Because a sympathetic ear was all I was going to get in this case. We barely had a travel budget; we had no HR department at all. I simply decided to behave like nothing ever happened. The last time I spoke to this colleague (at least 5 years ago), it went mundanely enough. Perhaps she doesn’t even remember. By comparison, I had it made in the haunted townhouse. I slept in the big circle bed and Roy’s mother didn’t disturb me from the time I closed my eyes to the moment I woke up to photograph the San Francisco sunrise out of the room’s ancient window. I was working a job I believed in while visiting a beautiful city, and as weird as this whole situation was, I was happy. A little while after I got home, my paychecks stopped depositing. The editor-in-chief said not to worry, the situation would be resolved soon. By the time I was owed $10,000 in back pay, I stopped working. I’d sign on in the morning for the all-hands meeting, then go out on a walk. Eventually, we found out the company had been purchased. My memory is a bit sparse on the details, but I had a business trip coming up that I had already been comped, so I went back to San Francisco anyway and ended up meeting the new owner. He was one of those wealthy tech bro visionaries; you know exactly what he looks like without me telling you. He was very big on the Internet Of Things, which was an early precursor to the AI movement. He also planned to spice up the site with more coverage of weed and sex. Minutes after I met him, he said something that will live rent-free in my head until the day I die. We don’t have an HR department, so don’t get mad at me. But would you like to stay on and become our sex toy reporter?” I don’t remember my exact reply, perhaps something about my actual coverage beats at the time (Pinterest, cryptocurrency, the learn-to-code movement, and connected home technology). He didn’t bite, and I was adrift again until I found some steady freelancing gigs a few months later. I’ve resisted sharing these stories in public for a very long time. I love a good travel story, but I don’t want to sound like I’m complaining. It wasn’t always comfortable, but it was always interesting. And believe me when I say there are no villains in this story: shortly after the website purchase went through, I received a check for that missing $10k in the mail. My Year as a Girl Boss Careers 4 months ago 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...