Streamlined Solopreneur: Helping solopreneur parents stop checking email at the playground

Joe Casabona — Business Systems Architect
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You didn’t start your business just to work through bedtime and answer emails at the playground. But if you're a solopreneur parent, that’s probably what it feels like. Imagine actually being present during family time. Picture taking real vacations without your laptop, making it to every school pickup, and having your business run smoothly while you focus on what matters most. I’m Joe Casabona, and I help solopreneur parents run their business in less time—without sacrificing quality or burning out. After hitting my own breaking point, I rebuilt everything around simple systems and automations that now save me 12+ hours a week. Each episode brings you real-world strategies, smarter workflows, and practical tools to help you reclaim your time and actually enjoy the freedom you set out to create. Because your business should support your life—not take it over.

  1. Can Your Business Survive Going ‘AI Vegan’ with Joe McKay

    4 DAYS AGO

    Can Your Business Survive Going ‘AI Vegan’ with Joe McKay

    I have a confession to make: I use my GPS every time I drive. It’s not that I don’t know where I’m going. It’s that I’ve told myself, “the GPS knows more than me – it has traffic data!”  Nick Bennett pointed out on LinkedIn that there was a time before GPS, when people knew how to read a map…or just get around. And that was a present in today’s guest’s mind when he made a big decision.  Joe McKay is a LinkedIn Ghostwriter who used AI for everything…until the day he decided he’d go AI Vegan.  Today we’re going to talk about what it meant for his business and his mind, and if you should try it too.  Want to go AI Vegan but worried you’ll be even less productive? Take the Business Systems Diagnostic and let’s see how we can fix your systems!  Top Takeaways: Joe found that, after a while, he was more concerned with whether or not people could tell if his writing was AI-generated, and less about what his customers…and their audience…actually needed. AI gives us the ability to do more, faster. But you’re making a choice – a bunch of prefab, low-quality stuff, or high-quality, hand-crafted work. But Joe and I have deeply considered what we’re losing by outsourcing to AI. Much like exercise, you need to actually do the knowledge work for you to stay sharp. Is AI dulling the skills we’ve staked our business on?Show Notes: Joe McKay on LinkedInJoe’s Beehiiv Nick’s GPS post on LinkedInAm I Outsourcing My Brain to AI? [Audio Note]I want to hear from you! Send your feedback to https://streamlinedfeedback.com.  *While I usually use AI to help me write the descriptions and takeaways, this time around, I decided to go AI Vegan, out of respect for Joe!  ★ Support this podcast ★

    45 min
  2. What do I even do? [Audio Note]

    6 DAYS AGO · BONUS

    What do I even do? [Audio Note]

    I spent the week at the beach thinking about my signature framework, but honestly, I’m struggling to define what I really want to do and how I want to help people. Despite all the different ways I currently serve clients - from podcast coaching to building automations - I’m frustrated that I don’t have a clear answer about my core purpose.  I’m asking for your input: if we had coffee together for an hour, what would you ask me for help with professionally? Write in at https://streamlinedfeedback.com  Episode description written by Claude AI ★ Support this podcast ★

    4 min
  3. The 3-Minute Brain Dump That Transformed My Work-Life Balance

    28 JUL

    The 3-Minute Brain Dump That Transformed My Work-Life Balance

    I used to lie awake at night thinking about tomorrow's tasks and couldn't be present with my family because my mind was stuck on work problems. Sound familiar? The game-changer wasn't better time management—it was creating clear boundaries between work mode and family mode. After years of working until the last possible second and then feeling mentally scattered during family time, I finally did something about it. Now I have a system that lets me be fully present with my kids while knowing nothing important will slip through the cracks. I'll walk you through my complete startup and shutdown routine system, from monthly planning all the way down to my daily brain dump. If you're tired of checking email at the playground or thinking about work during bedtime stories, this episode will show you exactly how to create the mental boundaries that actually work. Do you struggle to stop thinking about work when you’re with your family? Take the Business Overwhelm Diagnostic and get the plan you need to fix it. Top Takeaways Create intentional day planning - Use a startup routine to decide what you'll accomplish before opening email or social media, preventing reactive scrambling through your inboxBuild context-switching boundaries - Startup and shutdown routines act as mental flags that signal when work begins and ends, especially crucial for home-based solopreneurs without commutesImplement a brain dump system - The most important habit is unloading everything from your mind at day's end so you can be fully present with family without worrying about forgotten tasksShow Notes Free Startup and Shutdown Routine TemplatesWatch on YouTubeObsidianTodoistWhisper MemosZapierChatGPTTodoist integration for ObsidianGoogle Calendar integration for ObsidianToggl plugin for ObsidianAmanda GoetzChris LemaHave questions, comments, concerns? Send your feedback to https://streamlinedfeedback.com ★ Support this podcast ★

    25 min
  4. I’ve updated my /now page

    22 JUL · BONUS

    I’ve updated my /now page

    I just updated my /now page for the first time in a while, and it’s become much more comprehensive than before. I walk through all the new sections I’ve added - from current projects and media consumption to streaming services and personal details. There’s also a fun revelation about my five-CD changer playlist that’s surprisingly close to what I actually had back in the day. Check out my /now page here This description was written by Claude AI. ★ Support this podcast ★

    8 min
  5. The Hidden Cost of Switching Tools (It's Not What You Think)

    21 JUL

    The Hidden Cost of Switching Tools (It's Not What You Think)

    My dad's furious "never again" phone call to some faceless company stuck with me for decades. Fast forward to last weekend: I'm rage-quitting Dropbox after a seemingly small slight. Sound familiar? If you're a chronic tool switcher like me, you know that moment when you've had enough. But here's what nobody talks about—switching tools isn't just about clicking "cancel subscription." That’s why today I want to talk about what the actual costs are, and how to determine when to switch tools — when it will cause more clarity than chaos. Are tools just part of the problem? Take the Business Overwhelm Diagnostic Top Takeaways The hidden costs of switching tools go way beyond money—you're investing time to learn new systems, mental energy on decision-making, potential workflow disruption, and losing the knowledge you've built up with your current tool.Write a job description for your tools to evaluate if there's true feature parity between what you have and what you're considering—switching for the sake of switching rarely pays off.Test before you fully commit and consider how the switch affects your team members, contractors, and existing automations—I learned this the hard way when my editor's workflow got disrupted.Sometimes switching back is the right move—there's no shame in admitting a tool change didn't work out, especially if you can easily reverse course.Send feedback to at https://streamlinedfeedback.com Show Notes When do you burn it all down and start over?Why You’re Leaving Money on the Table with Email Automation with Kronda AdairDropbox VAT Tax PolicyGoogle Workspace Business Standard (Sorry I said starter during the episode)RSS.com ★ Support this podcast ★

    25 min
  6. Am I messing up not having a community? [Audio Note]

    15 JUL · BONUS

    Am I messing up not having a community? [Audio Note]

    I’m wrestling with a realization from Justin Moore’s 10K Brand Challenge - I don’t have a place for my audience to hang out and connect. I’m exploring options like Slack, Discord, and Circle, but feeling stuck on which platform makes sense for parent solopreneurs and my “chaos to clarity” framework development. This is a raw, unresolved brainstorm about community building and why I think it’s essential for my content strategy. This description was written by Claude. ★ Support this podcast ★

    5 min
  7. Stop Explaining What You Do and Start Showing It with Charlotte Crowther

    14 JUL

    Stop Explaining What You Do and Start Showing It with Charlotte Crowther

    Picture this: you're on a discovery call, your kids are making noise upstairs, and you're trying to explain what you do while mentally juggling dinner plans. Sound familiar? You're not alone—and there's a solution that goes way beyond just "trust me, I'm good." I sat down with Charlotte Crowther, the mastermind behind some of the most recognizable frameworks in online business, to uncover how signature frameworks can transform your entire business. From eliminating the dreaded "so what exactly do you do?" conversation to creating content that practically writes itself, Charlotte breaks down why visual frameworks aren't just pretty diagrams—they're business-changing systems. We dive into the hidden costs of winging it every time, why acronyms aren't always the answer, and how one simple visual can become the blood running through your business veins. Plus, you'll discover the one question every solopreneur should ask before creating their framework. Wondering how you can take your business from Chaos to Clarity? Take the Business Overwhelm Diagnostic. Special thanks to Kit for letting us use their studios! Learn more about them here. Top Takeaways: Frameworks are knowledge organizers, not just pretty visuals — they give structure to your expertise using both verbal and visual elements to help people understand faster and remember longer. Start with the outcome, not your content — instead of mining through your 100 newsletters for a framework, ask "what specific result do I want to enable?" then design backwards from there.Your framework becomes your business operating system — it informs your content strategy, sales conversations, course structure, and even team training, creating consistency across everything you do.Show Notes SignatureFramework.coSponsor MagnetUnveiling my Personal Brand with Hollie ArnettLeave Feedback at streamlinedfeedback.com ★ Support this podcast ★

    46 min

  8. 11 JUL · BONUS

    Why I’m Making My Podcast the Linchpin of Everything [Audio Note]

    I’m done letting AI dictate my content strategy and worrying about episode number parity while my downloads tank. After months of overthinking tactics, I’m simplifying everything by making my podcast the center of my content universe. Here’s how I’m cutting through the decision fatigue and getting back to what actually works: showing up generously for my audience. Article: How I Let AI Ruin My Podcast Content Strategy Send feedback at https://streamlinedfeedback.com This description was written by Claude AI. ★ Support this podcast ★

    9 min
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You didn’t start your business just to work through bedtime and answer emails at the playground. But if you're a solopreneur parent, that’s probably what it feels like. Imagine actually being present during family time. Picture taking real vacations without your laptop, making it to every school pickup, and having your business run smoothly while you focus on what matters most. I’m Joe Casabona, and I help solopreneur parents run their business in less time—without sacrificing quality or burning out. After hitting my own breaking point, I rebuilt everything around simple systems and automations that now save me 12+ hours a week. Each episode brings you real-world strategies, smarter workflows, and practical tools to help you reclaim your time and actually enjoy the freedom you set out to create. Because your business should support your life—not take it over.

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