Six months at Medium
A Seattleite’s rambling retrospective on reentering the workforce after almost 15 years of self-employment
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This weekend, I was out doing what I spend much of my time doing on weekends, which is walking around my neighborhood in Seattle. For better and for worse, Capitol Hill is not the bohemian geighborhood it was when I first moved here in 1997 (better: the gays can comfortably live anywhere in Seattle now; worse: the artists and bohemians got priced out)… but for me, those shifting cultural sands make city living interesting.
The dog and I were walking home after dropping a return off at a local Amazon Fresh, the oddly automated grocery store experiment. We wandered past a boutique on Pike Street that I’d recently read was closing soon, and I decided to pop in.
Ritual is an upscale boutique known for its gender-neutral gothic apparel, high-end leather harnesses, gorgeous tarot decks, and other esoterica. It’ll always be famous for me because once, while on a date with a demisexual federal investigator, he glanced at the gothic attire in the window and said, “That’s what I feel like under my work clothes.”
Walking into Ritual this weekend, I found the proprietress behind the counter, sorting black candles.
“I heard you’re closing,” I said. “I’m sorry… slash congratulations?”
“Both,” she said. “I just need to shift gears and get a job with health insurance.”
“Girl,” I said conspiratorially, leaning on the counter, “I got a job this winter for the first time in 15 years, so when I say I get it, I GET IT.”
“…and?” she asked.
“And,” I said. “All those years of therapy? It turns out I wasn’t as broken as I thought. It turns out that feeling anxious and insecure are actually natural emotional responses to being a single parent running a small business for a over a decade.”
We talked for half an hour about the realities of small business ownership, parenting humans, and which local tech companies have the best gender-affirming care benefits for dependents. It was one of my favorite kind of neighborhood chats.
In part because it made me take a moment to be super grateful.
…I love those moments.
Six months into my first day job in almost 15 years, there’s much to be grateful for.
I don’t want to misrepresent myself as a Suzy Sunshine who doesn’t have challenges at work, because that’s inaccurate. Those who know me (I mean, actually know me) know that I have a deeply cynical, snarky side.
It’s just that after toiling in the trenches of self-employment for so many years, I am really, deeply loving having a job. More specifically, I am genuinely enjoying having THIS job. (Also, I’m so relieved not to be working my old job.)
Let’s taco ‘bout it.
I enjoy what I do
I had the extreme privilege of not having to get a job. My publishing company still exists, and I still work my old job a few hours a week. (More about that later.)
Not needing a job meant that I had the ultimate luxury of taking a job with Medium because I thought it sounded interesting.
Talking to publishers all day? Interesting!
Helping to develop products to support folks writing and publishing their work? Interesting!
Structuring programs that incentivize quality storytelling instead of content farm garbage? Interesting!
Simply put, the biggest reason I work for Medium is because it’s interesting to me. The money is nice. The benefits are great (more about that later).
But I already had a job. I already had a salary.
I chose to take this job because, well, it’s interesting! I’m a curious and enthusiastic person, so I genuinely enjoy this job.
My boss is way nicer than my old boss
My old boss was cruel and worked me relentlessly. My new boss talks about “psychological safety” and slows me down when I try to talk around my concerns with something.
My old boss asked me to think about work 7 days a week. My new boss reminds me to get my two-week paid vacations on the team calendar.
My old boss threatened me constantly with gloom and doom. My new boss makes sure that I know I’m appreciated.
My old boss was me. My new boss is a nice guy from Brooklyn named Scott Lamb.
Turns out, I’m a really, really tough boss. My former editors like Megan Finley Horowitz will likely tell you I was also a really loving and kind and effective boss, but I was the absolute worst to myself.
My old boss worked me so hard that organs started rupturing.
My new boss is way nicer.
It’s such a fucking relief to have my life story untethered from my revenue stream
My writing style has always been narrative essay, with my life very much a part of every story. I started writing for magazines in 1997, started blogging in 2000, and wrote my first book in 2006. I got on social media in 2003, and shared my life through stories, photos, and then videos on Friendster, MySpace, Tribe.net, Flickr, Facebook, Instagram, among others.
In some form or another, I have been documenting and selling my life to readers and followers for close to 30 years.
[Let’s take a brief aside to say wtf how the HELL did I manage to not only do that for myself, but support a family by doing it? Sometimes, even I don’t understand my own career.]
What a profound relief it is to have my income and my personal life no longer entangled. It feels so expansive to just live my life for the sake of how it feels to be lived… instead of living my life while wondering how the Greek Chorus / peanut gallery will interpret it (and whether they’ll want to buy the book about it).
I love that my work for Medium is still focused on storytelling — but now it’s supporting other people telling their stories. My story can be as mundane as “I’m a middle-aged mom who works from her closet and walks the dog around her neighborhood.”
Turns out I can tolerate not being in charge
One of the biggest fears many entrepreneurs have about getting a job is whether one can tolerate the loss of control. I got a test this summer when, for the first time since 2009, I had to work on a project where I didn’t agree with the strategy.
Don’t get me wrong: I’ve worked on many projects over the years that I didn’t enjoy. But since I was the boss, I always knew what the strategy was, and agreed with it. (Because, well, it was my strategy.) Certain projects might be shitty, but I was in control of deciding that it was necessary shit.
This summer, for the first time, I was put on a project where I disagreed with the strategy. My boss patiently listened to my concerns (insert me waving my hands around squawking about resources will be stretched too thin! the operations team is already overworked! this is going to be a Trust & Safety catastrophe! a Saturday in August definitely is not the right time to do this!) and told me I needed to disagree and commit.
So I disagreed and committed. I focused on my tasks. I got everything done. I supported my colleagues. Then I put on a sequin dress and did my dang job.
And then Medium Day was a raging success and full of so many warm fuzzies and despite the fact that 10k people were there it was totally not a Trust & Safety catastrophe. I went very loudly on the record as saying that I was wrong.
Turns out, there’s a reason Tony Stubblebine is CEO and not me. I LOVE THAT FOR BOTH OF US!
Turns out, not being in control is not only something I can tolerate, it’s something I can learn from!
And man, I like learning things
I really, really like learning things, and one of the things that’s cool about working for Medium is that I get to learn A LOT. I learn from the publishers I’m working with on the Boost Nomination Pilot. I learn from the writers on Medium whose work I trawl daily.
And I get to learn so, SO much from my colleagues. Like, SO MUCH. These people include publishing industry luminaries who’ve worked with the likes of Anna Wintour, literal rockstars, amateur pyrotechnicans, former newscasters, numerous authors, and nerds of all stripes.
I’m working especially closely with my colleague Buster Benson, who’s starting to teach me about product management… something I’ve quietly done for years for my own little company but never really knew the name of nor thought about doing on a larger scale.
I’m learning about platforms and algorithms and how humans interact with AI and how to quantify quality. I work with people who want to dork out on what the attention economy has done to our brains. I work with people who want to share puppy pictures and talk about MFA programs and compare favorite authors.
I guess what I’m saying is that I like learning things, and also I like being part of a team. A team that I’m not in charge of… it’s someone else’s job to figure out the AWS contracts! It’s someone else’s job to deal with spammers and scammers! It’s someone else’s job to cut the paychecks! I only have to wear a few hats, instead of all the hats.
I have explored every single benefit
When most folks start new jobs, they figure out their health insurance and call it good. NOT ME. After all that self-employment, I was extremely excited to read the fine print about each job benefit that was offered by Medium, and take advantage of every single one.
I think that, in the last six months, I’ve used all the benefits that Medium offers — except life insurance. I think my favorite benefit is how the credits we receive for childcare can be applied to online education, and so I was able to get my kid 1:1 German tutoring. That was awesome.
I’m deeply aware that everything is always changing, and nothing is certain
I realize this story might sound a little starry-eyed ingenue, but I’m older than I look. I’m a pragmatist and realist because 25+ years into my career, I’ve worked for enough startups (Jobster, anyone?) to know that it can be a rollercoaster.
Even jobs for well-established corporations can be fleeting — my job at Microsoft in the mid-’00s was awesome one year, and then the next year, my role shifted to “manage this spreadsheet.” The following year, they laid me off at 8 months pregnant. (Don’t cry for me, Argentina: I used my severance to launch my publishing company!)
But here’s the thing: I didn’t come onto Medium to win (although sure, that would be cool). I came to Medium because it’s interesting. I came to learn. I came to work with people I admire and find fascinating.
Six months in, I am learning so, SO much. Where it goes from here is anyone’s guess, but I’m just grateful for all the learning.
[Update October 2023: I just got a new moved into a Product Manager role, which means I’ll be working more on the strategic side of things. I’m still running the Boost Nomination Pilot so not much will change there. As always, my focus will be working with my fellow indie publishers to help Medium build great publication tools.]
