Well hello there and thanks for such a nice question. Recently I’ve been getting this question more and more on Tumblr and via email, so I thought I’d try to answer it here even though I worry I don’t really have anything insightful to say. So please bear with me, nice people who have asked me about my job and how I ended up doing what I do.
This is going to be so long and navel gaze-y, I am already embarrassed.
Let me start by telling you that when I graduated college I had zero idea what I wanted to do. I applied - and didn’t get - a job working for Planned Parenthood (I majored in Women’s Studies) in Boulder, CO, and so I decided to move to NYC and live with my friend Teresa (after a brief stop in Nepal for two months of trekking with my then-boyfriend). I was in Nepal for 9/11/01 and my parents made me come home early. It was a weird time. I moved to New York that October.
I think part of figuring out what you want to do is doing a ton of things that turn out to be NOT what you want to do. Once I got to NYC I worked full time doing retail at Patagonia and then interned two days a week at a documentary film company. I had done some film stuff in college, so I figured “maybe this is what I want to do?”
It wasn’t, and it was great to learn that. But that January I also started improv comedy classes at the Upright Citizens Brigade and it turned out that improv was EVERYTHING I wanted to do. So I did improv, all the time. Classes, practice groups, etc. It was the first time in my life I had ever felt sure of something. It was a very freeing experience.
Meanwhile I had to keep making money. So when $10.50/hour wasn’t cutting it (after over a year and a half of working in retail), I took a HORRIBLE job at a financial company. It was a production assistant job assembling their quarterly financial reports, but it involved an understanding of numbers and a passion for finance, of which I have neither. Plus, my boss was a cold, insane woman who refused to let us take lunch breaks. I thought it was going to be the kind of job I could do mindlessly to get insurance and a paycheck and then do comedy at night, but it ended up being the cause of consistent, brutal panic attacks for eight straight months, until I quit.
During this time I got on a UCB Harold team and was performing a ton. I knew I wanted to “do comedy” but I didn’t know what this meant, really. I thought the next step was to write sketches, but I hated it and was terrible at it. I also thought I should be auditioning for commercials but I stunk at this too, and never enjoyed it either. So, I floundered a bit.
Eventually I got a job as a temp receptionist at a really great company called Jack Morton that produced corporate events, where my future husband Anthony and our friend Charlie Todd both worked. Eventually I became a production assistant for two really wonderful women. I met a lot of amazing, creative people and got to do some really cool stuff (like go on tour with Oprah Winfrey for three weeks, a personal life highlight), even though I knew it wasn’t what I wanted to do exactly, because I wanted to “Do comedy.” I also had figured out I wanted to write, but I wasn’t sure what. So I started a blog (Thank you Will Hines, for setting up my first blog) and I wrote about Lindsay Lohan and The Bachelor and whatever else came to mind.
Remember how I mentioned trying a bunch of things and realizing it’s not what you want to do? Well, I did a lot of that. I wrote sketch comedy, like I mentioned above. I tried to anyway. It always felt awful and I never enjoyed it. And while my musings on pop culture were equally as bad, I loved doing it. So I just kept doing that. (And my friends who liked writing sketches and kept doing that are now all TV writers and screenwriters and my heroes.) Eventually I quit my job to intern at Metro Newspaper, under their Entertainment editor. I emailed a friend (thanks Dorothy) who worked there and they needed someone, and that was that. I was 25 at this point, or maybe 26? I don’t remember, but I was the same age as the people who had actual jobs there. I was terrified and kind of embarrassed being an “old intern” because I’m inherently a self-conscious, insecure person but I learned a ton, got a lot of small clips out of it and even was paid to write two pieces. I had to take work again as a freelance production assistant to make ends meet but I was writing for real, and it felt very exciting.
Then a friend (thanks Charlie) helped me connect with the team at College Humor, and I wrote some stuff for them too. I started writing their weekly celebrity gossip column (thanks Streeter and Sarah). They were even nice enough to hook me up with a book editor who needed someone to ghostwrite a book by Flava Flav (thanks Ricky). I had no idea what I was doing and it showed and I handed in a 35 page proposal and no one ever called me again about it, but it was a good learning experience.
I wrote something that ended up in the Gawker book that no one bought, but I was really proud to be included in it, so that was cool. (I think I have Chris Gethard to thank for this connection.)
Right before I turned 27, my mom was diagnosed with terminal cancer. So I quit my production assistant job and moved home full time-ish and had a variety of meltdowns, including one where I seriously considered applying to Social Work grad school. I didn’t. But I did end up getting into grad school for creative writing and was all set to go, when I found my job at VH1 and decided to do that instead.
(Also during this time: a friend who was an editor at NY Mag hired me to do some TV show recapping/writing, which was awesome. Thanks Dan.)
Here’s how I got my job writing at VH1: I was up at 1AM on a random night at my parents’ house a month after my mom died. I was drinking wine and terrified to leave my dad and go back to NYC, and I was trolling Craigslist for jobs (IDK) and I came across a job listing for a “morning blogger” at VH1. I distinctly remember thinking “If I could blog for a living at VH1 I would be the happiest person alive.” I applied and interviewed a bunch and it took 2 months and I actually even tried The Secret, I wanted this job so badly. They hired me and it was the best thing that ever happened to me, career-wise, not just because I was actually WRITING ABOUT POP CULTURE FOR A LIVING OMG but because it literally saved me during the most depressed, horrible time in my life. So thanks, everyone at VH1 past and present.
I’ve been at VH1 ever since. I started as a blogger, then became an Editor and then Sr. Editor, and now my job is some magical hybrid of writer/correspondent/producer/person who gets to freak out about things she likes for a living. I’ve been very fortunate to work with people who are not just sane (this is a rare thing to find in life, seriously), but supportive and nurturing and generally great. It is a job like any other job and it comes with its challenges and frustrations, but overall it’s been the bee’s knees. It’s been wonderful in the sense I’ve been able to say “Hey, can I try this?” and they have said, more or less, “Sure.” This is a huge gift.
I’m sorry I’ve now written out my 12 year job history for you, but it’s help me conclude a few things:
1. Allow yourself to try things and fail and try and fail some more. Even when it is embarrassing and horrifying and feels awful. This is really hard for me and I wish I did this more.
2. Be open to opportunities, even if it seems like it doesn’t totally fit with what you want to do. I benefitted so much from working at Jack Morton and learned so much, and am still in touch with amazing people who I met there. It wasn’t directly related to what I wanted to do, but it taught me a ton. And I got to meet Oprah! And her dogs! (Yes, SOPHIE.)
I even learned a lot working at that awful financial company working for that cruel woman. Like - what kind of boss do I aspire to be and what kind of work environment do I hope to foster and also, people should be allowed and encouraged to take long lunch breaks, for Christ’s sake.
3. Find a community of people who support you, challenge you and help you grow creatively. The Upright Citizens Brigade Theatre is one of the greatest things to ever happen to my life. I saw this without any sort of irony. Every single person who helped me make a job connection or gave me career advice or introduced me to someone else are people I know somehow through UCB (and I tried to mention all of them above because I am tremendously grateful for their help). It is an amazing place to learn about all aspects of comedy and experiment and try things. Also: a great place to make friends and meet life partners.
I’m not saying everyone needs to go to UCB, but find your UCB. Find the place where people have your back and you can learn from them through out your whole life.
4. Don’t be afraid to ask for help and make connections. I hate the idea of networking and I have no idea how to do it, but I do like the idea of genuinely connecting with other humans. I think people like to help other people. When you need it, ask.
5. Do what you want to be doing, even if you aren’t getting paid for it or doing it for a living. I have been writing about pop culture, entertainment, celebs, and many other weird things for a very long time, because I enjoy it so much. I’ve had blogs on Typepad, Wordpress and now Tumblr. I wrote for a Phish tour newsletter called Surrender To The Flow. In a perfect world, what you love will eventually be the thing that pays your bills, but it doesn’t have to be and that doesn’t make it any less valuable or meaningful, or mean you aren’t good at it.
6. Be patient with yourself and your goals and your life. Sometimes things take time. Sometimes, time is what you need. Be nice to yourself.
7. A lot of times, we never know what we want to do in life. Also, what you want to do in life changes through out your life. So just do what you like in the present. You might start out doing one thing and end up doing something completely different, and that is awesome.
8. Read things. I don’t know, this just seems like pretty good life advice overall.
9. When stuff stops being fun, stop doing it. It is never worth being miserable. Seriously.
10. For writers, specifically: write what you know. This is thrown around a lot, but seriously: If you are obsessed with TV and British men, write about TV and British men. The reason I’ve written WAY too much about the Twilight fandom is because I know it so well (because I am in it). Sometimes this feels “too easy” and we think writing/creative pursuits have to be hard, and thus we assume we must be doing it wrong. But this advice has never steered me wrong, and thus I am passing it on to you.
Well, this is possibly the TL/DRiest thing I’ve ever written in my life, but I appreciate people asking me about this stuff. There’s no clear path to anything, I don’t think. My whole career/creative journey (barf) has been long and weird and unexpected and I imagine that’s how it is for most people. That’s also what’s made it fun.
In conclusion: good luck, go for it, have fun and kick ass.