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4 Pieces of Advice I Gave An Aspiring Writer/Performer

February 7, 2017

Yesterday I chatted with an aspiring writer/performer about how the hell she’s going to become a successful writer/performer. This motivated, passionate, go-getter went to my alma mater, Boston College (so very sorry Matt Ryan…). She found her way to me through my sister who was in her same a cappella group that has an alumni network she used to ask if anyone could help her become a writer/performer.  So, long intro short, she’s going to be fine.

I’m always impressed by slash jealous of 22-year-olds that know they want to pursue this path. I had an inkling but was too afraid/intimidated to dip my toe into those waters right after college. I took a job in marketing at a website even though my secret dream was to work on a TV show. I didn’t know anyone that worked on a TV show so I couldn’t figure out how I was going to make that happen. This Boston College grad didn’t know anyone that worked on a TV show either, but that didn’t stop her from finding someone and getting her first job on a well-known comedy show that shoots in New York.

I should have asked her for advice but instead I shared these four tidbits that have helped me along my way.


I know business cards are 100% 1995, but they’re purpose isn’t just to give your name, e-mail and digits to a new contact. An interesting business card makes you just a little bit more memorable in a world of two-second intros at crowded comedy clubs and improv shows. I used to have the Moo Mini cards from awesome business card printing company Moo.com.


People always commented on the size (these are so cute!), the feel of the paper (these are so smooth!) and the image I chose for the front (this is so clever!); it was a picture of an old cash register that said “thanks! please call again!” It gave me approx. three more seconds of conversation with a stranger and them one physical memory of my existence. Maybe they’d find it in their pocket later and remember to shoot me an e-mail? Maybe they’d throw it out, and upon doing so think, Jessie was nice. Either way it’s a little extra touch point in a world where we’re flying so fast that it’s impossible to remember anything. Worth it for $19.99 per hundred cards.


The very first thing I do when someone e-mails to ask if they can tell a story at SUNDAY NIGHTS SEX TALKS is Google their name. If I find that they have a personal website they are instantly more legitimate in my mind. This can be the simplest, one-page set-up with their name, face and brief bio but it’s something, which is more than nothing, which is impressive. You can set up a website for zero dollars via Square Space, WordPress or Wix. If you’re not tech-inclined you can find someone on Craigslist to do it for super cheap or, better yet, post to your Facebook that you’re looking for help and some friend of a friend will come to the rescue. If you’re going to put in the effort to set up a page I’d make sure it has these elements:

  • Photos of you – ugh, I know, but you’re a writer/performer so they’re necessary. If you’re just hoping to be a writer you can ditch the pictures
  • All of your social media info – you want people to see all you’re doing out in the world and, more importantly, follow you to get even more in touch
  • A brief bio – what are you about and what are you hoping to be about
  • Contact info – nothing is more frustrating than landing on a website that doesn’t tell me how I can get in touch with the person I’ve sought out
  • Bonus: where you’re performing next – if you’re at that stage, definitely list it all


Maybe it’s a writing group where you meet every Wednesday to drink wine and share 500 words? Maybe it’s an invite-only storytelling show that you run out of someone’s apartment and only 25 people can come because it’s all about working out stories? Maybe it’s a volunteer group but filled with writer/performers so you can give back to the world while you complain about your careers? It matters less what you do and more that you congregate regularly. Building community is critical in this field. You need friends to stay sane and you need friends to get jobs. It’s also nice to have a reputation among your larger community of growing writer/performers as that girl who has that Wednesday wine and 500 words thing. You’re not just about pulling your hair out while you try to write sketches for your UCB class; you’re about community, with a clever twist. I promise this will be worth the effort. Take it from that girl who runs that sex storytelling show where boys aren’t allowed. 


BROAD CITY was a web series. HIGH MAINTENANCE was a web seires. DRUNK HISTORY was a web series. And BURNING LOVE and CHILDREN’S HOSPITAL. Billy Eichner made FunnyOrDie videos. Issa Rae had a YouTube page. Lena Dunham got famous by shooting a film with money she borrowed from her parents. Yes, they had a lot of money but at least she used it to pursue her dream.

I know the money thing is hard when you’re trying to stay afloat in some of the most expensive cities in the world. I didn’t have enough money to shoot a web series or make a film so I started a storytelling show at a bar that gave me their back room for free. Podcasting is free. Facebook live is free. Cramming people into the biggest apartment among all your friends is free. Bottom line: don’t wait until you’re ready to do the thing you aspire to be doing now. I learned that the hard way. I should have started a Sex Talks podcast years ago to help grow my audience. I’m finally getting to it now because I didn’t think I was ready before. Screw that mentality. You’re never ready, which technically makes you always ready. Don’t think too hard about that sentence just go make some stuff.


There’s much more but that’s enough for now because calm down and enjoy your life is technically the most important advice I can provide. This is a marathon not a sprint. It is going to take time and a lot of patience. Start practicing that immediately. Also don’t drink too much. That never ends well.  

Good luck. God speed (whatever that means). And if you get there before me please remember this kind advice I provided and give me a job!

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