How to Become a One-Person Creative Wrecking Crew [Inside an Unthinkable Trello Board]
Editor’s Note: The team at Trello asked me to participate in their #InspireWithTrello campaign. I’ve been using their tool since 2012 (obsessively), and I was thrilled to do so. You can see tons of creators’ Trello boards on their Inspiration Page.
I pushed the door gently, and it crashed to the ground, debris flying everywhere around it. Granted, the door was pretty much hanging by a single screw. Also granted, the storm that just passed through had completely destroyed the house behind it, so I was basically standing inside a door jam, surrounded by a mess of rubble. But the door still fell of its hinges, and that felt like the last straw for me. I gazed at the disaster around me, paralyzed. My world was in ruins.
Alright, so I’m being melodramatic. I was really sitting in my office, thinking about my work. That disaster-scape wasn’t physical. It was mental. There was no storm. There was no door. But I felt like things were a total mess, like my work had been tossed violently around my brain, jumbling my thoughts together. I couldn’t think straight. I was stressed. I was pissed. I was ridiculously, woefully lost. How in the heck am I going to finish this project, let alone make it GREAT?
And then I remembered I’d put everything into Trello. Suddenly, there was no storm. There was no pile of rubble. I wasn’t standing alone like a sad-sack in a doorjam. I was belting out A-ha’s Take On Me, doing THIS:
See, I’m a creator. That’s what I do. That’s who I am. I make stuff to help other people who make stuff. Nothing brings me more joy. But when you’re a creator who ADORES the feeling of making stuff, you can easily rely too much on that burning desire you have to do great work to carry you forward. This seems fine, if not preferable to what most people do, turning the crank, never pursuing their aspirations. But there is a downside — almost a dark side, like clouds rolling in and thunder clapping in the distance. You can get SO. DAMN. EXCITED. that you simply ignore the need to stay organized or have a process. I dunno about you, but nothing can cause me stress quite like the desire to build something creatively great.
Over the last 3 years, the creatively greatest thing I’ve built has been the Unthinkable podcast. After digital media roles at Google and HubSpot and building a venture capital firm’s brand through content and community, I dove headfirst into podcasting with this show, first as a side project, then as a driver of leads for my speaking business, and now, as the flagship show for Unthinkable Media, where I work with B2B brands to create refreshingly entertaining shows about work.
Unthinkable sounds refreshingly entertaining for a show about work, but it’s an aggressive way to create one’s personal podcast. It’s highly produced, with narration, sound design, musical scoring, and lots and lots of slicing and rearranging interview audio. It’s a niche podcast that doesn’t have a simple niche to target. It’s not a marketing show or a career advice show, per se. It’s a show about conventional thinking at work and the people who dare to question it. (It is, after all, unthinkable.) It’s a show for people bothered by suck, fed up with average work, sick of obsessing over best practices — people who aspire to be exceptional by being the exception.
I’ve been lucky that this aggressively produced style has inspired a lot of listeners to subscribe, stick around, and interact with me. I’m grateful, too, for all the people and companies who welcomed me into their worlds and shared vulnerable moments and deeper thinking than a list of Tips and Tricks — companies like Slack (episode link), Disney/ESPN, Death Wish Coffee, InVision, Dollar Shave Club, and GRADO Labs.
Here’s an example of the show. “The Man Bun,” is our most-downloaded episode to date:
This is all a long way of saying, Unthinkable is a big, messy, awesome project. And while I’ve gotten some editing and coaching help (h/t to Andrew Davis and Josh Cole in particular), I’ve mainly done EVERYTHING on this program alone. Every stinking part of it.
(Cue door crashing to ground.)
And so, I am INSANELY organized about making this show, from the moment I spot an idea for an episode all the way through the moment I release an episode publicly, pour myself a good glass of bourbon, and high-five my dog. (I work alone in a home office in Queens with a beagle pup. He’s a terrible creative director. So demanding what with the whining and the clawing at me and the requests to “really make it pop.”)
Today, at the request of my good friends over at Trello, I wanted to provide a peek behind the scenes into how I organize the making of the show. My hope is that this can be useful not just for podcasters but for anyone building a big, messy, awesome creative project. Because NOTHING is better than following that burning desire to make something great. Just make sure you can focus that energy. Otherwise, well … (Cue door crashing to ground.)
Follow along as Episode 1 of Season 3, “Sound Comes First,” goes from idea to a final episode.
It’s the story of a remarkable family in Brooklyn that went from selling fruit to hand-building headphones for some of the most beloved brands and musicians on the planet. Although they compete with big, flashy brands like Samsung and Bose, they’ve never run a single ad. And that’s far from the most unthinkable thing that they do.
I went inside their company and discovered a rather ridiculous but ultimately heartwarming secret.
The full episode is linked inside the Trello cards, but you can also find it here:
- You can subscribe to Unthinkable on Apple Podcasts, Overcast, Stitcher, Google Play, Spotify, SoundCloud, or wherever you pod.
Click the image below to check out my Trello board.
Here’s the full link: https://trello.com/b/7BjapUTU/unthinkable-podcast-editorial-workflow
Founder of Marketing Showrunners, author of Break the Wheel, and host/producer of docuseries about creative work. I’m trying to create a world where people feel intrinsically motivated by their work. Previously in content marketing and digital strategy at Google and HubSpot and VP of brand and community at the VC firm NextView. I write, tinker, and speak on stages and into microphones for a living. It’s weird but wonderful.
Get in touch anytime: firstname.lastname@example.org // Speaking inquiries: email@example.com