Friday, April 11, 2025
Become a Patron!“[The early podcasts are] essentially unlistenable, unless you want to get a sense of how bad a person could be in early podcasting.” —Debbie Millman, host of Design Matters and author of Love Letter to a Garden
C’mon, really? Debbie Millman (@debbiemillman on IG) not only appeared here for Ep. 462, but it’s her third trip to CNF Pod HQ (her first and second are here and here). It’s when people return — and by all accounts seem happy to return — that validates the enterprise all the more.
Debbie has a new book out, Love Letter to a Garden (Timber Press), which is a bountiful book with her tight, concise, philosophical voice, much of it in her beautiful hand lettering. The book also has recipes from her wife, Roxane Gay. You may have heard of her.
As luck would have it, this new book also publishes in the lead up to Debbie’s podcast, Design Matters, turning … twenty! It can almost buy a drink. Think about that: she started Design Matters in 2005. I mean, the Red Sox had just won their first World Series in 86 years at that point in the fall of 2004. And we thought it couldn’t get worse than Dick Cheney and John Ashcroft! What a time!
Mmmkay, Debbie talks about the early days of Design Matters and how she saw herself as objectively bad and didn’t really hit her stride until 2012, and really mastered her point of view until 2017. That’s 7-12 years improving. The patience and perseverance is the point.
Debbie is the author of Why Design Matters and Self-Portrait as Your Traitor, The Remarkable Life Deck, among others. She’s the co-founder of the School of Visual Arts in Manhattan and has worked on brands like Burger King and Tropicana.
You’ll find her to be one of the most generous and genuine people in the creative space, so I hope you’ll check out more of her work and maybe buy a boo or two (in this economy?). No, seriously, consider supporting people who make our culture better.
If you dig this episode, share it, and tag me on IG @creativenonfictionpodcast or Bluesky @brendanomeara.bsky.social. And never forget to consider kind reviews on Apple Podcasts or ratings on Spotify. They all help and don’t cost a dime.
Debbie Millman, the Pod Mother, as I like to call her, has been hosting Design Matters for twenty years, a show where she beautifully crafts a conversation with people she deeply admires. Some are world famous, some only famous in a particular corner of the world, but all of them fascinating and dedicated to making things better, making beautiful things.
In past conversations, even on this very podcast, Debbie has said the arc of her career is often an exercise in failure. Zoom in close enough and that’s the arc of just about anybody who has ever made anything. What we so often see is the final result, not the years of anonymous slogging. She says:
“I don’t think I understood how bad I was, and so I just kept doing it. Part of the reason you can still listen to the old shows is to see that you can really, really be bad at something and get better over time.”
Which is the formula for doing anything creative: failure, or at least not being a master (yet), plus patience (do you have the perseverance and/or the resources to keep playing the game?), equals success, however you want to define that.
Part of what separates Debbie from many interviewers is the rigor she puts in before the mics turn on.
“Always prepare. Like, over prepare. I over prepare. And I know I over prepare. I don’t know that you could ever prepare too much. Some people are like, ‘Oh, don’t over prepare.’ I’m like, ‘How do you go about over preparing?’ The more you know, the better you’ll be.”
I liken this degree of preparation to the call sheet of an NFL head coach. You’ll see them holding up a laminated card with different colors on it. It basically has all scenarios and plays to call under those scenarios, and plays to call when the defense shows them curious looks. To be a skilled interviewer, you must be nimble. You steer it, but if the guest is veering in a particular direction, your extensive research allows you to tack in that direction. The call sheet may look rigid, but it’s actually quite fluid. Says Debbie:
“I’ve learned, and I’m continuing to learn, and we’ll probably always continue to learn, how to really listen. A lot of people, including myself, talk talk talk talk talk talk talk. Wait for somebody else to finish talking before we start talk, talk, talk, talk talk, talking again. And that, I think, is just human nature, and so that’s a consciousness I bring to conversations, to not have to be the smartest person in the room and not have to be the best questioner, just be as natural as possible. The looser you are, the better the conversation will be. And that’s sometimes hard when you’re talking to somebody you really admire and you’re really nervous, so you don’t want to mess up or look silly or whatever. That’s a conscious practice
Pair this conversation with Debbie’s previous visits to the show on Ep. 131 and Ep. 301, as well as Ep. 57 with Joe Donahue.
Debbie’s Recs from Ep. 462
The podcast Forever35
The TV show Adolescence
The novel All Fours by Miranda July
Parting Shot from Ep. 462: Give It Away Now
I had one parting shot teed up, but something kinda flew up my ass in my email that made me pivot this week’s jam, namely what should we paywall as creative types and what should be free to all.
I’m of the believe that 99% of everything should be free too all. I mean this as a blogger or producer. One of the six trillion Substacks I receive dealt with how this one pretty famous writer (by all accounts) makes a living as a writer. Before I opened it, I thought, I wonder if this is paywalled. It sure was! Pay me to find out how I make money.
This is different than, say, a magazine paying you for work, or a publisher paying you for your work, or a conference wanting you to be a keynote speaker. My feeling is if you give the bulk of your shit away, more paid opportunities come your way because you’re acting in service of the greater community and not trying to nickel and dime people who have few nickels and dimes.
It’s tricky to decide what should be free or what should cost something. Like, I made my book proposal available to $4 and $10 Patreon tiers and not the $2 tier or the free tier. Should that have been free? Or should something like a book proposal that took me a year to craft be made available only at a premium? I made my spreadsheet template of how I organize my work available to all tiers. The podcast will never have a paywalled version. My two newsletters will never be paywalled. I know the desperation of wanting seemingly privileged and walled-off information and not having the money to get some fucking answers. Not short cuts, just some fucking help.
It’s only through giving away just about everything I do that I’ve had speaking opportunities at conferences, or a book deal. I’m admittedly not the best, but people seem to dig what I have to say … maybe … It’s only because of this podcast that I started on a lark in 2013 that anything positive has happened to me at all, but it came from that germ of wanting to platform people who weren’t necessarily famous, people like me who had a lot to say but few places to say it.
Listen, I say all this shit not to pat myself on the fucking back. It’s just when I see people who by all outward accounts don’t need to squeeze money from desperate people squeezing money from them under the pretense that this little bit of advice might get them that agent, that publisher, that life-changing book deal, I find it off putting, even slimy and grifter-y.
If you have that big of a platform — hard earned at that — then you can actually afford to leverage your platform for paid gigs and better magazine articles or book deals and earn your money from the power brokers and gate keepers. You can act more like Robin Hood: amassing some money, maybe, but also knowledge that others desperate need because money shouldn’t be the reason a writer feels they can’t voice their story if you have experience that could open the door.
Now, I’m not saying you should be taken advantage of and bleed yourself out for people unwilling to do the work. A blog post should be free. But a 30-minute phone call might be the upcharge. Reading someone’s work and offering thoughtful and truthful notes, yes, upcharge.
There’s been a strong push toward each writer having to be this entrepreneurial silo of writing and editing services. Every writer has a shingle it seems. You better be specific if you want to stand out, but that’s another topic for another parting shot.
There’s no easy answer to this quandary. I want writers to make a happy buck however they see fit, but when writers who once railed against the gate keepers start gate keeping, you soon realize the insidious nature of systems and status roles, who is up and who is down, to quote Seth Godin. All I’m gonna say is before you think of dropping a “for paid subscribers only” button, ask yourself if ten years ago, or twenty years ago, you would have appreciated such a roadblock to the path you wanted to walk.
Many Moons Ago
400 Episodes Ago
300 Episodes Ago
Seyward Darby— Editing as Collaboration at The Atavist
200 Episodes Ago
Passion + Desperation = Bob Welch
100 Episodes Ago
- Should you choose to cite this transcript, check it against the original audio as these are not 100% accurate, despite my efforts at cleaning them up. And please cite me and the podcast linking back where possible. ↩︎
