How to Write for a Living

Season 5, episode 4 is here!Ashley Evans spent years devouring every book on creative resistance she could find, and still couldn’t bring herself to share her writing. Then a title gave her permission.Wannabe Wisdom, the diaries of a fake guru, is now three years and around 100 essays deep. She’s also a former actor, a hypnotherapist, a yoga teacher, and someone who has been murdered on screen in more creative ways than most.This was a warm, thoughtful conversation with plenty for anyone who has ever thought, “who am I to say this?”.What we covered:- How a writing workshop of over 100 strangers dwindled to five, and why those five gave Ashley the name that freed her to write.- The award she won in 2008 for the best death in a horror film, and why she won’t tell you where to find it.- The tools she used to quiet her inner critic, including a book on parts work she’d recommend to anyone.- The small punctuation choices that carry most of your personality, and why you’re probably funnier in person than on the page.- How she decides whether something is too personal to publish, and the gut check she uses right before it goes out.- The surprising story behind how Mary Shelley came up with Frankenstein, and what it says about creative blocks.- The note she wrote at 100 subscribers that went viral, and the image that changed how she felt about a small audience.Go and subscribe to Wannabe Wisdom, and if you’re a paid subscriber, keep an eye out for her new co-working sessions. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit thedavidmcilroy.substack.com/subscribe

Rob Riker has been on my radar for almost a year, popping up in comment sections all over Substack.This live was the first time we’d ever properly spoken. He’s built coaching businesses on Twitter, watched that platform change under his feet, and rebuilt on Substack around the one skill he’s most passionate about, which is building relationships. The chat was buzzing from start to finish.What we covered:- How Rob went from a social skills blog that barely made money to a coaching business that let him quit his nine to five, and why he pulled the offer when Twitter changed.- Why he thinks Substack has gone back to the way Twitter used to work, and what that means for who sees your notes first.- The simple reason adults struggle to make friends, and how the same problem plays out in your comments section.- His go-to move at a conference or party when you don’t know a soul, and why he skips the coolest people in the room.- The three keys to building relationships on Substack, and the one creators drop just as things start going well.- Why he deliberately seeks out writers with ten subscribers, and the maths that makes it worth it.- Where he thinks the internet is heading as bots multiply, and the in-person bet one of the biggest names in online business is already making.Go and subscribe to Rob’s publication on Substack and say hello in his comments. He’ll almost certainly say hello back. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit thedavidmcilroy.substack.com/subscribe

➡️ NEW FREE TRAINING: Are you failing, or are you just early? New free 38-minute training on the six signals that show you the difference. Comes with a downloadable scorecard so you finish with a concrete number, not just a feeling. Watch it here.Season 5, episode 2 is here!Drew English and I had never spoken before this live. We’d only traded messages, and it all began with a short video from him with nothing to sell attached. He’s a self-taught cinematographer, a former wannabe rock star, and the host of the No Set Path podcast. He talks about career chaos with total calm. What a great chat!What we covered:- How Drew went from wannabe rock star to Apple store employee to working cinematographer, with a used camera, YouTube University and a $5,000 summer job in the middle.- The podcast he started out of boredom in a basement during COVID, and the studio it grew into that he never has to market.- The simple message that got him into my DMs, and the one part he found hard about sending it.- Why he thinks plenty of people building a personal brand are actually building something else in disguise.- What happened to a six-figure cinematography career, and the hybrid way he’s rebuilding around the life he actually wants.- How he weighs paid work against showing up online, and the one thing that always comes first.- The sci-fi worlds, the surprising Paris film and the vintage hobby he uses to switch off, plus the reassuring thought he left us with.You can find Drew at No Set Path on Substack, where he also hosts the podcast of the same name. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit thedavidmcilroy.substack.com/subscribe

➡️ NEW FREE TRAINING: Are you failing, or are you just early? New free 38-minute training on the six signals that show you the difference. Comes with a downloadable scorecard so you finish with a concrete number, not just a feeling. Watch it here.Season 5, episode 1 is here!Virgil Brewster blows up launches for a living. He built a course business to seven figures with two partners, sold it, drifted into semi-retirement, and then got pulled back in when people kept asking him for help. He is easily the most energetic guest I’ve had on, and this one flew by.What we covered:- The story of Virgil’s very first online payment, back when he ran a boutique personal training business in Ibiza, and why he was convinced it had to be a scam.- What that first dollar does to your brain chemistry, and the two-second window of pure magic before your head starts chasing the next one.- How he balances raw ambition with being content where he is, including the millionaire at an event who taught him more than he expected.- His honest answer on avoiding burnout, from doing one task a day to the slightly terrifying activity he uses to quiet his mind.- Why he puts 5 to 10 percent of his income into learning, and the decade of trying to DIY it all before that penny dropped.- The two mistakes he sees people make with every launch, and why charging money for something half-built is the smartest thing you can do.- His glass-half-full take on where the creator economy is heading, and the one-liner he left us with that’s worth writing on your wall.Go and subscribe to Virgil’s publication, The Launch Room, and follow along with what he’s building. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit thedavidmcilroy.substack.com/subscribe

➡️ NEW FREE TRAINING: Are you failing, or are you just early? New free 38-minute training on the six signals that show you the difference. Comes with a downloadable scorecard so you finish with a concrete number, not just a feeling. Watch it here.The Season 4 finale is here!No guest this time. Just me and a shorter solo episode to close out season four. I answered some listener questions about podcasting and going live, gave a behind-the-scenes look at where the podcast is at, and walked through the changes coming next season. I even discovered a feature live on air that I had no idea existed…What I covered:- Where my podcast actually stands after two years, including the download count Substack quietly lopped over 20,000 off overnight.- Why my episode numbers look like I’ve recorded 421 of these when the real figure is nowhere near that.- The biggest change for season five, and why the recordings are opening up to everyone instead of just paid members.- The new perk paid members get, which means your question gets asked even if you can’t make the live.- My honest answers to listener questions on echo, cheap mics, and recording outdoors without it sounding like a wind tunnel.- Why I still find solo lives hard even now, and the simple fix that takes the pressure right off.- The evergreen traffic source I keep banging on about, and the feature I only realised existed halfway through this very episode.Season five kicks off next week with a cracking guest lined up. If you’re a paid member, keep an eye out for the prompt to send questions in advance, and if you fancy pitching yourself or someone else as a guest, my inbox is open. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit thedavidmcilroy.substack.com/subscribe