Leesa Dean: Guess Who’s Coming to Chilltown

Adventures of a Web Series Newbie - Chapter 19:  Five (More) Things


Adventures of a Web Series Newbie: Chapter 19 – Five (More) Things
by Leesa Dean

So, another week of being absolutely swamped and not attending a cool YouTube seminar. I have so much coming up–the TOP SECRET PROJECT, working on the relaunch and getting the whole Lele expansion into place, I literally don’t have the time for nearly anything.

And…I’m prepping for the Chilltown Season Finale. Yes, it’s coming up next week and it’s wonderful and sad and scary all at once. This has been an unbelievable six months (feels like I’ve been at this for years.) In July, I’m taking a few weeks to just write and put plans together and then hitting the ground running in full production mode.

Since the Season Finale’s coming up, a lot of people have been asking me what the biggest takeaway has been. I thought about it and realized: there is no one thing. So I decided to add to the list I already put together. Presenting:


1- You will never ever leave your house, becoming a virtual prisoner of the endless cycle of work slash promotion. Working harder than you ever even imagined. Even if you’ve an A-type personality extreme workaholic. No, I’m not talking about me. Ok. Yes, I am. It’s kinda like being in jail. But with better food and (probably not) better sex. No judgements.

2-Nearly everyone you meet will say, “AWESOME!” really loudly, whether in person or by commenting and using tons of exclamation points (!!!!!) Always. Especially, and embarrassingly, if they’re 45 year old dorky men attempting to sell to the tween market (which, sadly, is nearly everything in the YouTube universe.) The worst part? They also, inevitably, post inane aphorisms all day long on Facebook as if it’s somehow going to save them (see #4.) It won’t. P.S. I am now saying Awesome! all the time.

3- On the face of things, everybody’s crazily happy. Like you’re trapped in some inaneUp With People universe. Nobody, I mean NOBODY, is happy all the time. Especially if you’re slogging it out in the web universe. Yes, a large part of it *is* thrilling and fun and exciting but, unless you’re deluded, wildly successful from the beginning (i.e., experienced and/or funded) or annoyingly lucky, it’s usually a non-poetic mixture of highs and lows. Kinda like being bi-polar. But without the meds.

4- Rejection. Everybody knows it’s not an if, it’s a when. But with a web series, there’s a twist: you also have insane trolls on top of the regular soul-crushing variety. And it’s all, humiliatingly, in public. You don’t just fail. You fail big. 50 Shades of YOU SUCK, YOU F’ING LOSER!! big. Here are a few coping methods:

–laughing it off in public, crying your eyes out at home
–writing nasty comments/letters back and ultimately getting banned from YouTube (the bright side: if you get banned, at least it won’t affect your income cause you’re probably not making anything to begin with.)
–ultimately developing a thick skin.

I’m currently aiming for the last one and, surprisingly, partially succeeding. And finally,

5-Remember when you felt a mixture of pity, sadness and yeah, a little annoyance at the homeless musicians you saw over and over and over again on the subway (notable exception: the wildly talented & dope b-boys who took over the subway car I was on yesterday;  or her), doing the perp walk through the aisles begging for money? That is now YOU. But on the internet. The worst part? Getting chastised for “promoting” by people who turn around and do NOTHING but promote.

Author: ChilltownTV

I'm primarily a writer. Sold a few series to tv networks and production companies but never had anything get on the air. So I taught myself how to animate and completed 3 digital series, launching two. The first, Chilltown has been named one of "Five Web Series That Should Be on Your Radar" by ABCNews/Univision and a "Show to Watch" by Tubefilter. The second, Lele's Ratchet Advice Show, garnered a fanatic cult following. As a result, I now do Lele's 60 Second Wrap Up, a weekly comedic entertainment report (which I write & perform) that airs on urban radio stations Rhythm 105.9fm and the Just Wake Up Morning Show on WWRNfm.

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