How to Write for a Living

Season 4, episode 11 is here!Bobby Umar has done a thousand keynotes across four continents, spoken at TEDx five times, and built half a million followers on Twitter. But it took multiple job redirections before he finally stopped waiting and figured out what he was actually all about. This was a really fun chat!What we covered:- Why Bobby thinks the difference between a personal story and a private story is the most important line any creator needs to understand.- What actually happened when he posted about his body image and binge eating disorder on LinkedIn, the last place anyone expected that kind of honesty.- The three things most people get wrong when they try to land a TEDx talk, and why the idea is usually the biggest problem.- What a TEDx talk actually does for your authority that no other single thing can replicate as quickly.- The red flag Bobby uses to know when someone is ready to pivot out of a job or a business, and why most people ignore it for years.- Why he thinks 90% of business owners are making the same two mistakes with their content right now.- What Bobby 2.0 looks like, and why he’s now working 30 hours a week instead of 60.You can find Bobby on Substack at The 1% Brand Brilliance, where he writes for small business owners. 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

Season 3, episode 24 is here!Angela Hollowell joined me to talk about her journey from photographer to filmmaker, why she publishes three times a week on her newsletter Please Hustle Responsibly, and what she learned running a documentary through the festival circuit.She shared why Substack is perfect for publishing but lacks the data tools serious businesses need, her approach to in-person podcasting that creates superfans, and the mindset adjustment that removes all the pressure from creating.What we cover:- The coffee mug gift strategy she uses for in-person podcast interviews that creates instant rapport- How she accidentally became a filmmaker after people kept asking if her camera recorded video- Why she wraps up an 18-month film festival run and now plans to write TV shows- Her featured post strategy that most Substack writers completely underutilise- The changeover from paid subscriptions to developing print magazines, in-person dinner parties, and digital products- Why the first things you create will be terrible and that’s completely fine 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

Season 3, episode 22 is here!I threw together this episode to answer questions from my Substack chat thread, where writers shared what’s actually slowing them down right now.As it turns out, the struggles are universal: too many platforms, not enough time, and the back-of-the-mind realisation that writing often isn’t enough - you have to market yourself too.What I covered:- When it’s okay to ruthlessly cut platforms that aren’t working)- The 80/20 rule for your first few months on Substack that nobody talks about- How to structure your day when you’re balancing soul-satisfying creative work with contracts that actually pay the bills- The broken expectation every writer hits: you can’t just write anymore, you have to be your own marketing executive too (and how to make that less painful)- Why you shouldn’t box yourself into a theme at the start- The TikTok strategy for finding ARC readers when you don’t know 50 people willing to review your book- Finding your value offer as a writer by asking yourself: what could you talk about on a soapbox for 30 minutes straight, and what would light you up seeing someone else achieve? 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

Season 3, episode 20 is here!Neera Mahajan joined me to talk about writing books fast, building authority, and turning a single book into a scalable business.She shared why most writers never finish their books, the difference between vanity projects and strategic assets, and how she helps creators write their books in 30 days through implementation over information.This one’s a must-listen for anyone struggling to finish their book!In this episode:- Why Neera started writing not because she was good at it but because she was bad, and how quitting her job to write full-time led to publishing 14 books that now serve as the foundation of her entire business model- The moment she realised three years of articles gave her nothing to show for the effort, and how one voice in her head telling her to write that damn book changed everything about her authority and income overnight- Why most writers fail to finish their books because they make them too big and drift in and out of the work, and the strict framework of 13 chapters maximum with 2,000 words each that actually gets books done in 30 days- The difference between vanity projects and strategic authority assets, including how a strategic book needs a clear audience, addresses one specific problem, and launches your tiered offer at the end instead of just existing on a shelf- Her four-level productivity system for writers that starts with calendar management and email inbox zero, and why she now surrounds herself with notebooks that travel from room to room capturing ideas before they disappear- Why her cohort focuses on implementation and daily accountability rather than piling on more information, requiring participants to write 500-1,000 words daily toward their book while working in a group settingCheck out all of Neera’s books here. 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

Season 3, episode 18 is here!My friend Jari Roomer from Write Build Scale joined me for a conversation about the most powerful growth lever on Substack.We talked about why collaboration matters more than ever, how to approach other creators without feeling awkward, and the specific strategies that brought us thousands of subscribers without spending a dime on ads.What we covered:- Why collaborations are the antidote to publishing in the void, and how they make the entire Substack journey more enjoyable while getting your work in front of audiences that already want what you offer- The guest posting approach that creates evergreen pathways for discovery months after you publish, turning one piece of content into a long-term subscriber magnet that keeps working while you sleep- Newsletter recommendations as the ultimate set-it-and-forget-it growth strategy, how Jari gained over 8,000 subscribers in 2025 from recommendations alone, and why most creators hesitate to reach out when it’s actually a win-win scenario- Going live on Substack as the collaboration format that builds the deepest connections, lets your audience see you’re a real person when things go wrong, and makes it easier for introverts who can share the talking with a guest- The exact DM approach that gets more yes responses to collaboration requests, including why you should offer multiple collaboration options and how to make it as easy as possible for someone to say yes- How to use AI as a ghostwriting tool rather than a crutch by recording 30-minute voice memos of your thoughts and stories, then letting AI handle the actual writing process while keeping your authentic voice intact- The ladder strategy for linking posts that guides readers to take the next step up rather than sending them sideways through your archive, and why fewer links actually create more conversions than overwhelming people with options 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

Season 3, episode 16 is here!In this week’s episode, Parker Worth and I chat about his journey from being a high school dropout to becoming a successful creator living in Brazil.Parker discusses the importance of storytelling in building a personal brand and the challenges of navigating the ever-changing landscape of online content creation, and emphasises the need for creators to build relationships and trust with their audience, write real-life stories that convert, and understand their audience’s pain points.What we cover:- Parker Worth’s journey from electrician to creator in Brazil.- The significance of storytelling in personal branding.- How to navigate the challenges of the online creator landscape.- Why building relationships and trust with your audience is crucial.- How using personal stories can lead to higher engagement.- Why understanding audience pain points is essential for content creation.- Why embracing fear can lead to significant personal and professional growth.Make sure to subscribe to Parker’s newsletter before you go! 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

Season 3, episode 14 is here!In this solo episode, I walk through exactly how to build a creator presence from absolute scratch with no fancy equipment, no complex strategy, just clarity and consistency.This is for anyone who feels like the smallest voice in the room but wants to create something real online.In this episode:- Why your personal brand is actually about how people feel when they encounter you, and how that feeling is what makes readers stick around long after they discover your work- The five traps that kill most creator journeys before they start- My recommendation to commit to one platform for six months minimum before spreading yourself thin across the internet- How to craft the one simple promise that becomes your positioning - a single sentence that tells people exactly who you help and what you do for them within five seconds of landing on your profile- The power of predictable touchpoints and why readers follow creators the same way they follow their favorite TV shows- Why confidence comes after consistency, not before it, and how showing up for 3 to 12 months with minimal response is actually part of the process, not a sign you should quit- The recurring format strategy that eliminates decision fatigue and builds loyalty through repetition, turning your weekly presence into something your audience genuinely misses when it’s not there 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

Season 3, episode 12 is here!This solo episode is a relaxed, open conversation about reviewing your 2025 creative work and getting intentional about 2026.It’s part reflection, part behind-the-scenes, part gentle push to simplify your process and double down on what genuinely works.What I’ve covered:- How to honestly review your 2025 wins, losses and “busywork” so you don’t drag dead weight into the new year.- Why I’m cutting weekly roundups after nearly 100 editions and what that kind of ruthless pruning makes space for.- The three pillars I’m betting on in 2026: audience growth, income expansion and personal brand depth.- Specific strategies I’ll be leaning on next year, from collaborations to live sessions to experimenting with new formats.- A wider look at income generation beyond paid subs, including digital products, sponsorships and coaching.- Why your voice, your quirks and your personal stories matter more than ever in the AI era.- An invitation to keep the process fun, simple and human while building a creator life that feels genuinely yours.And if you’re interested in working with me 1-to-1, just apply here. 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