Plenty of people have very practical advice about how to get a job or break into an industry, but I do not. Or not really. When I look back on work in my twenties, I see mostly dumb luck, good timing, and knowing the right people. In the interest of real talk, here are all my jobs — from college graduation onwards — and how I actually got them.
This is possibly discouraging but it is true.
Live-in nanny: When I graduated college I’d been working since I was 16 but had no idea what I wanted to do. I applied to Teach for America and didn’t get in. I asked for a one-way ticket to Rome for graduation, with a plan to return to a previous gig as a camp counselor then ‘see what happened’ from there. The night before my flight, I decided not to go. Not knowing what else to do, I trained to be an LSAT tutor with Kaplan, and whiled away the summer at my parents’ house. When I heard that a friend-of-a-friend had gotten a live-in nanny job through a website called greataupair.com, I decided to do the same. I had my BA, tutored kids in college, babysat during the summers, and spent my work-study senior year assistant teaching ESL, and thought I wanted to be a teacher. I made a profile — it was kind of like a dating website — and after a few phone interviews, I flew to New York for an in-person interview (on my own dime). I hung out with the kid for an afternoon, met the parents, and got the job. Later his mom told me she thought I sounded smart on the phone, and she liked that I wanted to be a teacher. I made $250 a week, plus free rent, meals, and an unlimited metro card each month.
Internship at 826NYC, unpaid: That summer after college I was spending a LOT of time on mcsweeneys.net and reading A Heartbreaking Work of Staggering Genius, which is basically made for 22-year-olds. I become by-proxy obsessed with the affiliated non-profit organization that Dave Eggers had started a few years prior, called 826. They had an opening for an “education intern” for when the nanny kid was at school. It felt like fate. I still remember sitting in my hometown Panera trying to write a sufficiently charming cover letter (in Gill Sans — edgy).
The woman who hired me, Miriam, was a year older than me and remains one of my best friends. Early on she admitted that she invited me to come interview there because they had never met someone who went to Notre Dame and they wanted to see what I was like. This may be the only time my degree actually got me a job. A job-ish.
Admin Assistant to Internet Rockstar: About a year into my nannying tenure I was losing my mind and plotting my exit. I applied to a bunch of MFA programs and got rejected by all of them (um, the first time). I applied to the New York Teaching Fellows program and didn’t get in. I applied to teach at a couple fancy private schools in the city and heard nothing. 826 considered hiring me but assumed I’d be leaving soon to go get my MFA so they hired someone else.
When John Hodgman, semi-famous friend of 826, emailed the staff asking if they knew anyone looking for part-time work, they passed my info along. His old friend Jonathan Coulton was looking for an assistant to answer email from his growing fanbase and do other admin work (update his calendar, upload concert recordings, mail swag, etc.). I jumped on it. We grabbed coffee and bonded over having no idea how to be an assistant or have an assistant. I think I got paid $18 an hour to work from home whenever I wanted to — usually around 12-15 hours a week. I did this while the kid was at school for the first six months or so, and then moved out when a cheap apartment opened up in Greenpoint.
Various Assistant-y Things for Internet Rockstar’s Friends: Did I have enough money to move out on my own and support myself? No, of course not, but I was young enough and desperate enough for privacy that I didn’t care. To make ends meet I spent most of 2008-2009 as a professional sitter — house, cat, children — for my boss’s friends. Creative professionals in their late-30′s who were newly successful and in need of help and probably feeling really weird about — this was my NICHE. I took their precocious kids to diners, I fed their aging cats, I luxuriated in their modestly decorated brownstone apartments. I wondered if one day I would be one of them.
I liked doing all of this low-pressure, high-gratitude work but I wasn’t exactly on retainer so for months there’d be none of it — no vacations! better babysitters! — and I’d be so so so so broke.
Tumblr: When I wasn’t working (which was…often) I was hanging out on Tumblr and writing about my feelings. When I dragged my friend to one of the first Tumblr meetups, I met some of the people who worked at Tumblr and had been reading my blog, and we became friends.
At the same time and unbeknownst to me, Tumblr as a business decided that a good way to get more users would be to encourage famous people to use the platform. DUH. They weren’t paying them but they were meeting with them and doing a lot of hand-holding, which was quickly becoming unsustainable for a group of 22, 23-year-old engineers.
Around this time I agreed to go out with someone who happened to had just left a VC firm that had invested in Tumblr. I did not exactly know what venture capital was at the time, and this guy and I did not exactly hit it off, but a few weeks in he forwarded me an email chain to show me that he’d suggested that Tumblr hire me for their new hand-holding role:
Meaghano has to have come to mind, no?
She’s Jonathan Coulton’s assistant…I can’t think of anyone better.
Meaghano – great call, Jacob on the Tumblr team is friends with her.
A few days later I got an email asking me to come in and interview. My boss asked me during the interview how I knew the VC guy and I think I told him the truth — we were dating. He laughed and said, “Well, he’s not the only one who suggested you for the role.” After we established that I was already a professional emailer and hand-holder, that I knew Tumblr like the back of my hand, I got hired as a contractor for $30 an hour. My first title was “VIP Concierge.” A few months later, once I had proven myself and once the company was sure they needed someone to fill that role, I was hired full-time.
Kickstarter: Kickstarter launched a few months after I started at Tumblr and I was enamored with it from the get-go. I met the co-founders when we decided to throw a party together at an upcoming internet conference (I know, it pains me to read that sentence, too). Before the party, I launched my own Kickstarter project with a friend– a book about sex — and came to their office so they could interview us for their podcast. We hung out at the internet conference, I complained about work, we joked about them “poaching” me from Tumblr but decided it was a bad idea. Without any real structure and being the only non-technical person in the office, I was flailing at my current job. When word got back to my boss that I was thinking about leaving to go work at Kickstarter — that was a fun conversation — we all pow-wowed and I ended up leaving.
I didn’t interview at Kickstarter so much as we got drinks and talked about what the job would be like — more work, less pay, but the structure and support and coworkers I needed. I remember putting my head down on the table and saying I needed to go home and do some math. The math sucked — I’d recently moved into my own place and a paycut meant I’d be broke for awhile — but then I remembered I’d already left my other job (‘quit-fired,’ I was calling it). What was I even debating? I took the job.
The Billfold: When I was at Kickstarter I struggled a lot trying to balance working full-time with writing. One of the few things I actually finished and submitted was a Rental History for the Billfold, which doesn’t seem like much but it made me happy. I knew the site and I knew Mike because he’d interviewed me when he worked for a different money site and I worked at Tumblr.
When I cashed out some Tumblr stock and quit my job at Kickstarter, I had no real plan except to take a year and write. A few weeks in, Mike Dang emailed me suggesting I write an essay about stock options — one I was actually already writing. I told him I would sent it to him when I was finished.
A few months later, alternately blissed out and panicked by my aimlessness, I was planning to apply to grad school and had no idea what I’d do if it didn’t work out (it didnt work out), when I got another email from Mike, subject line, “Want to Work With Me?” It felt like fate. We got coffee, I apologized for not sending him the stock option essay, we discussed the work, and, nervous, I asked him if I could ‘try it out’ for a few weeks.
And here we are! I am planning to let him know if I want the job any day now.
Want to share YOUR no-bullshit hiring history with us? Email me! My stuff is all over the internet already but you do not actually have to name the places you worked for or even your last name.