Leesa Dean: The Squiggle that is Failure

Adventures in Digital Series Land #114
by Leesa Dean

jazzatthenewzealandschoolofmusicConfession #1: Sometimes (ok, a lot of the time) I wake up in the morning and feel like a failure. Why? Duh. Cause my career isn’t where I feel it should be. And, partly, cause I had a Quick! Easy! Fast! kinda-sorta success when I started out. And since then? Well, let’s just say I’m trying to catch up.  This is not about depression, btw. I’m not depressed. In fact, I’m a happy person and actually pretty optimistic about how things will turn out .

The Background: I made a big rookie mistake when I started:  I actually believed my agent/manager would get me work. So I didn’t spend every waking hour networking and writing writing writing. Yeah, I had more ideas. Yeah, I worked on some. And wrote a few spec scripts.  But since right out the box, I sold a spec script to a network (with virtually no experience under my belt), I thought it would just magically keep happening like that.

Spoiler alert: It didn’t.

My first deal was so over-the-top good–thank you 800-lb gorilla attorney and (former) manager!–that I literally thought I could retire in a few years. And could have, based on that contract.

The Hitch: Retiring in a few years was based on one teensy weeny little thing. My show had to go into production.  It didn’t and ultimately I was kicked to the curb with the rest of the writer debris. Sayonara former agent/manager! Don’t forget to write! JK, you never did in the first place.

It is very very hard to come from something seemingly MAJOR to, well, nothing.  But ultimately, the whole confidence imploding, trial-by-fire shitstorm experience got me one good thing: my hustle back. Cause you can’t succeed without it.

Confession #2: I thought I was fairly unique, you know, with the whole success to failure trajectory (well, except for country singers, meth-heads and some has-been rappers). That everyone else who had experienced the initial kind of success I did had go on to even mega-better things.  And I was waiting for, as Mark Duplass has said, “the cavalry”to come for me.  “Hey you! We heard you were really talented, you know, with that deal you had. Where’ve you been? Want a job in my writer’s room?” Nope, nada, zilch. (Yeah, I got over that notion pretty quickly.) Plus, not for nothing, it’s super isolating to toil away (yes, in obscurity). Especially when you’re working solo. Those Capital F plus Everybody’s Doing Better Than I Am and It Sucks To Be Me thoughts tend to creep into your psyche.

Turns out my story isn’t unique. In fact, it’s pretty common. Lately– mostly cause I’m in the last leg of production and second-guessing every single thing–I’ve been reading a lot of stories from super successful people who’ve detailed their own “failure” narratives. And you know what? It’s been incredibly empowering. Cause I’ve seen that my struggle is pretty much par for the course. Just read this brilliant/harrowing/ultimately kick-ass redemptive account by wonderful writer Nina Bargiel who went from being in the writer’s room on Lizzie McGuire to cleaning shoes in a gym. And, coming back. With a vengeance!

You know that meme that crops up every now and then on FB? The one what shows a mixed-up convoluted squiggle as the real trajectory of success?  It’s true.

And all the choices I’ve made post my original fall from grace were pretty much on point. (First thing: don’t stop writing/creating/hustling. Second thing: don’t depend on an agent to get you work. That’s really not how it works.) And failure is part of that equation.  It’s what separates the metaphorical men from the boys.

So that whole waking up in the morning and feeling like a failure thing?  Yeah, it still happens.  But I own it and know it’s only temporary.


Leesa Dean is the creator of CHILLTOWN TV, a digital series to reckon with. Learn more about Leesa and the series HERE

About 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.

One thought on “Leesa Dean: The Squiggle that is Failure

  1. ChilltownTV says:

    Thanks for posting, LB & Munchman!

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