Streamlined Solopreneur: Helping Solopreneurs Automate to Take Time Off Worry-Free

No One Will Die if You Don’t Respond to Email Right Now Oct 13, 2026 745 Do you really need to answer every email right away? You definitely don’t. That’s a story we tell ourselves. But the truth is no one is sitting at their inbox waiting for your email. And in today’s episode, I tell you how you can start letting go…but more importantly, why you need to.Are you ready to get your 25 hours back? Book a free strategy call — no strings attached.Show NotesSolo Op

Is AI Really Saving You Time and Money? [Friday Wrap-Up] Oct 9, 2026 2717 This week I talk about whether AI is really saving us time and money, and how using Claude to rebuild my WordPress theme between sections made this newsletter take longer than usual. Then Cal Newport on AI's jagged abilities, and a recommendation for "Chronically Cautious" by Braden Bales on YouTube. Plus this week's systems tip: the Stream Deck + XL.I'm working on a new cohort around how

4 Questions Before You Vibe Code a Tool Replacement Oct 6, 2026 1220 Should you replace your software subscriptions with tools you vibe code? I've replaced several of mine, but I'll never replace others. Here's how I decide, using four questions: skill, expertise, tools, and the one that matters most, dependency.Want help figuring out what to replace and building it to last? Join the waitlist for my upcoming cohort on how to vibe code your own tools: strea

What I Learned at Ecamm's Creator Camp [Friday Wrap-Up] Oct 2, 2026 965 This week I share what I learned after speaking at Ecamm's Creator Camp: why listing the simple automations I use landed better than I expected, and how my "AI is for tasks, not craft" line ended up on the quote board. I also go through four questions I'm asking myself now.Should I go back to Instagram? What should my YouTube pillars be? Do I need a simple digital product? And when should

What Would You Do With 25 Hours? Sep 29, 2026 668 My clients spend more time with their families, serve their community, and even have time to write their book. What would you do with 25 extra hours a month? While building a system is how you get there, today I want to focus on what you get.Are you ready to get your 25 hours back? Book a free strategy call — no strings attached.Show NotesSolo Ops RoadmapFree Strategy CallHow I Saved Laur

Should I Burn It All Down? [Friday Wrap-Up] Sep 25, 2026 673 This week I talk about converting casabona.org from a 20-year-old WordPress site to a flat-file site in two days — and whether my mailing list needs the same "burn it all down" reset. Then Apple's final Friday Night Baseball broadcast of the year, shot on the iPhone 18 Pro Max, and a recommendation for my Italian music playlist on Apple Music. Plus this week's systems tip: Cue for Apple M

Stop Figuring Out the Same Task Every Single Time Sep 22, 2026 554 I hate lunch. I’m never prepared for it, so I just end up wasting a bunch of time before picking the fast, easy thing. If I did some meal prep, this wouldn’t be a problem.But many solo business owners do the same thing with their work. They sit down, they shrug their shoulders, and wonder what to do. Everything takes more time because it's not written down.That’s why today I'm walking thr

Pick Two: Voice Memo Apps Sep 15, 2026 719 This week I'm doing a Pick Two for Voice Note apps (plus the one I’m not using, and a bonus transcription app)#1 is Whisper Memos, which I happily pay for because of one killer feature.#2 is Audio Pen, which gives me system-wide dictation: press a key, talk, and the text lands wherever my cursor is. That's what I use for long prompts to a large language model.Wondering which system to sta

I'm Getting iPhone Duo [Friday Wrap-Up] Sep 11, 2026 660 This week I talk about the iPhone Duo — my first real foldable — and why I'll trade away the telephoto lens, action button, and fast charging (and swallow a $2,100 price plus the end of the annual upgrade program) for a big anti-glare screen that folds into my pocket and takes an Apple Pencil. Then an episode of Ditching Hourly with Nick Richtsmeier on doing things that don't scale and fo

Telling AI to Write It Doesn't Mean You Wrote It Sep 8, 2026 548 When I was 17, my high school organized a two-week trip to Italy and Ireland for $900. My dad offered to pay for it. I said, "Why do I need to go when I can just look at pictures online?"Seventeen-year-old Joe, you were so, so stupid. I’ve since learned that photos aren’t the experience. Just like ideas aren’t the fully fleshed-out thought.On top of a passionate credo about why we need to

Should You Stop Teaching to Get Clients? [Friday Wrap-Up] Sep 4, 2026 882 This week I talk about a Steve Thompson video that's had me rethinking my whole approach — the idea that teaching tactics on YouTube actually costs you clients, because when you hand people the solution they assume they can do it themselves. After a rough summer where teaching hasn't yielded new business, I've decided to make September an experimental month: teach less, shift beliefs more

Conscientious AI Usage: How I Built a Quiz in Two Hours Sep 1, 2026 804 There was a time when building a quiz as a lead magnet seemed insurmountable to me. The setup, the configuration, the routing — not to mention how much those tools cost. It never felt like the juice was worth the squeeze.LLMs have changed that. So today I'm walking through exactly how I built my Conscientious AI Usage quiz, and how you can too.Take the quiz at quiz.lovehate.ai — find out

Writing With AI Isn't Like Using a Calculator [Friday Wrap-Up] Aug 28, 2026 809 This week I talk about why writing with AI isn't the same as using a calculator for math — financier Stanley Druckenmiller defended his AI-written WSJ critique of Scott Bessent by calling it "using a calculator," and I break down why that misunderstands math, calculators, and words. Then the unraveling of Ashley Flowers' true-crime podcast empire, and what a founder pulling 3 a.m. alarms

When to Use Automation vs. When to Use AI Aug 25, 2026 861 AI and Automation are not the same thing. But people seem to use the terms interchangeably. Tools like Zapier and Make are deterministic automation — you know the input, you know the output, and it's incredibly consistent. Large language models are what I'm calling interpretive automation. Run the same thing multiple times and you can get different outputs.Both can do similar things. I do

Are You Practicing Conscientious AI Usage? [Friday Wrap-Up] Aug 21, 2026 867 This week I talk about Conscientious AI Usage (a term my mastermind group gave me). Then a Six Colors article on Anthropic's lexical watermark and why making LLM output worse might be a net good, and a recommendation for Halo 3 on Game Pass. Plus this week's systems tip: building an "Are You Suffering From AI Brain Rot?" quiz with Claude in a couple of hours between meetings.Links:What is

How to Start Thinking in Systems Aug 18, 2026 438 A few years ago, I was helping my friend Jeff rebuild an automation — getting his intake form to talk to his CRM and his project management tool. Halfway through the screen share, he stopped and said, "So you just think like this?" That's when it hit me: not everyone's brain defaults to systems. Mine does…but I wasn't born with it. I learned it.That's what this episode is about. A lot of

Am I wrong about AI-generated YouTube thumbnails? [Friday Wrap-Up] Aug 14, 2026 529 This week I talk about whether I'm wrong about AI-generated YouTube thumbnails — I've told my designer to never use AI on them, but if a thumbnail's only job is to get the click, does it matter? Then Casey Newton on Mark Zuckerberg's AI manifesto and why "superintelligence is a dragon" is the analogy that actually fits, and a recommendation for Schmigadoon! on Apple TV. Plus this week's a

The Lie That AI Is a Magic Shortcut Aug 11, 2026 638 I was talking to an acquaintance recently who told me how he has AI agents write his articles for him. He sends a voice note of an idea, and every morning it picks the ideas, writes the drafts, sends them to him, he requests edits, and then it writes and publishes them. So I asked him: at what point do you feel uncomfortable putting your name on this? And he couldn't even see the issue.He

Resetting Claude Every 3 Months? [Friday Wrap-Up] Aug 7, 2026 515 This week I talk about a piece of advice from Boris Cherny, head of Claude Code — that you should reset your prompts, projects, and skills every time a new model ships — and why I'm not doing it. Then a recommendation for Destiny of the Republic, Candice Millard's book on James Garfield, and why I've started walking a mile every morning without headphones. Plus a quick promo: I'm speaking

You Don't Have to Fix Everything — Just Start With One Thing Aug 4, 2026 468 Back in 2016, I ran…well, *completed…*a Disney half marathon. And the thing about Disney is they make it impossible not to find the starting line. Buses from the resort, signs, gates, pre-race emails. Everything points you to where to start.And if I didn’t know any of that, I wouldn’t just start running. I would start simple…like asking a cast member when the race is, and go from there.Bu

"No One Can Do It Like Me" Is a Lie (And It's Costing You) Jul 28, 2026 583 For most of my life, I believed that if I wanted something done right, I had to do it myself. I held it all the way until I had a panic attack and had to stop doing everything myself. I made changes, and you know what?I learned that being a solopreneur doesn't mean doing everything yourself. It means you own the business and work on your own terms — not that you personally execute every t

The Simplicity of Yellow Legal Pads [Friday Wrap-Up] Jul 24, 2026 674 This week I talk about rediscovering the humble yellow legal pad after years (and hundreds of dollars) sunk into fancy notebooks and fountain pens. Then a piece by Kashmir Hill about discovering an AI-generated biography of herself for sale on Amazon that she never authorized or was contacted about, and a recommendation for the summer drinks series on Cocktails with Suderman.Plus this wee

Welcome to The Streamlined Solopreneur Jul 22, 2026 146 Imagine you finally logged off. It's the first real vacation you've taken in years. The coffee's hot (or iced), the phone's in the other room, and for once, nobody needs you. This is why you went solo in the first place. Work you actually care about, on your terms. The freedom to close the laptop and just… be there. The business hums along without you standing over it. You breathe.And the

How I Produce a Week of Content in 90 Minutes Jul 21, 2026 820 I was at a retreat with my mastermind group. We were going over our big takeaways, and my friend Cat reminded me of something: I output more content than most people. Her point was that when someone sees you doing what looks like a lot, it can feel completely unreachable, so they shut off to your message entirely.So today, I want to pull back the curtain. I put out two podcast episodes a

When is implementation the problem? [Friday Wrap-Up] Jul 17, 2026 653 This week I talk about when implementation itself becomes the blocker — how working on a new welcome sequence in Kyle Adams' Newsletter Power-Up Cohort reminded me that I rarely get stuck deciding to act, but I do get stuck overcomplicating the build, and why I need to iterate for myself the way I do for clients. Then a FanGraphs piece that reframed how I react to fans booing at the All-S

Why Your Solopreneur Business Feels So Complicated Jul 14, 2026 554 One of my favorite shows is Scrubs, and there's one episode that's stuck with me for nearly 2 decades, and I think about it nearly every day. In it, the team can't diagnose a patient showing every sign of Lyme disease, because they can't find the tick bite. Every test comes back negative. Then Dr. Cox shaves the patient's head, finds the bite, and mentions Occam's Razor: the simplest solu

Is Claude Winning? [Friday Wrap-Up] Jul 10, 2026 657 This week I talk about whether Claude is quietly winning the AI war — at least among business owners and tech nerds — after every speaker at Ecamm Creator Camp reached for Claude and nobody mentioned ChatGPT or Gemini, and why its "constitutional" rule-following makes me more comfortable using it. Then my take on finishing The Odyssey (the Emily Wilson translation) on a plane into Chicago

How Solopreneurs Stop Being the Content Bottleneck Jul 7, 2026 789 Imagine making yourself a bowl of cereal. But instead of grabbing a bowl from the cupboard, you head to your backyard, throw a brand-new bowl on the pottery wheel, and while it dries, you drive to the store to buy a fresh box of cereal. Then you do the whole thing again the next morning. Sounds ridiculous, right? But that's exactly what we do with content when we create every piece from s

I almost did something horrible: get back in Instagram [Friday Wrap-Up] [Friday Wrap-Up] Jul 3, 2026 969 This week I talk about almost re-joining a platform I know I'd hate. Then a look at Disney's next-gen audio-animatronic transforming from a pirate to a skeleton, and why it's a reminder that technology can still serve great storytelling. And a recommendation for the LEGO Game Boy set for a low-key long-weekend build.Plus, the Automation of the Week. Links:2026 Summer and Fall Speaking Eve

The 4 Systems Every Solopreneur Needs to Take More Time Off Jun 30, 2026 1233 A few months ago I was doing a series of research calls, and the same piece of feedback kept coming up: "I read all your stuff, this sounds awesome, but I don't even know where to start." That was maybe the most important thing I've heard since I moved away from web development. So I finally decided to solve it.That's why I built the Solopreneur System Starter Kit, and today I walk you th

I bought a tiny game controller for automation [Friday Wrap-Up] Jun 26, 2026 764 This week I talk about my latest Mac automation tool: the 8BitDo Micro, a $15 tiny game controller I picked up during Prime Week and mapped to complex key combos and Raycast actions — and why these little tactile hardware automations are easier on your brain than memorizing keyboard shortcuts. Then a MacStories write-up that inspired the whole experiment, walking through real use cases fo

How to Automate Your Business Without Losing Critical Thinking Jun 23, 2026 1352 Lately, I've been hearing horror stories about how people use AI. Not "AI wrote me a program" stories — I mean people who can't decide what to make for dinner, write their own feedback on a contractor's work, or come up with a single question for a webinar without asking a chatbot first. I call it AI Brain Rot, and getting really bad.So I walk through the three warning signs you might be

Is speaking worth my time, Zuck doesn't get people, HotD [Friday Wrap-Up] Jun 19, 2026 1006 This week I talk about why this is my heaviest speaking year since before the pandemic — and how I'm deciding whether all that travel and prep time is actually worth it, given the real cost of crafting talks and getting clients from them. Then a story about Mark Zuckerberg telling Meta employees to "have fun again" after brutal layoffs, including the absurd perk of a permanent desk. And a

What to Do Before You Automate a Task Jun 16, 2026 1479 Here's the problem: most solopreneurs don't know exactly what they do. They can't explain it, so they can't build systems around it. And when we try to build systems without explaining them, they end up with bad, ineffective systems. Because when we explain, we scrutinize.How do you fix it? Pick one task you do often, fire up a screen recorder, and narrate how you do it and why. Recording

Siri's big update, and a CRAZY LEGO scandal [Friday Wrap-Up] Jun 12, 2026 994 This week I talk about WWDC and the big Siri update Apple just announced and why Apple's measured, context-aware approach feels like the right application of AI. Then the wild, still-unfolding Reckless Ben vs. Bricks and Minifigs saga, where a consigned Star Wars LEGO collection turned into a legal nightmare, and a recommendation for my own Alphabet Playlist: one album from one band for e

Where AI Actually Works in Solopreneur Systems Jun 9, 2026 1092 I talk a lot about the wrong ways to use AI. But a rainy weekend gave me a few free hours and two pet projects that I used Claude Cowork for— and the results actually impressed me.The first: I used Claude to vibe-code a custom Obsidian theme from scratch. No CSS, no digging through the inspector — just a few prompts and some back-and-forth until it looked exactly the way I wanted.The seco

Why Summarize Everything, Ben Sasse, and Lou Gehrig [Friday Wrap-Up] Jun 5, 2026 986 This week I talk about why summarizing everything isn't actually reading more — summaries rob you of the experience, the context, and the ability to form your own opinion, and I'd rather read one primary source than 14 summaries I'll forget. Then a heavy but admirable piece from The Dispatch on Ben Sasse facing terminal cancer with poise, and what it teaches us about being present with ou

The Automation That Lets Solopreneurs Leave Work at Work Jun 2, 2026 1134 I left work early recently to volunteer at my daughter's ice cream social and sit through her spring concert without checking my phone once. And if you’re a solopreneur, you know that’s a big deal. It’s all thanks to my startup and shutdown routines. And I know I’ve talked about them on the show before, but something interesting has happened over the last year.As LLMs and AI tools have be

Saturday Mornings, The Creative Act, and Pop Punk [Friday Wrap-Up] May 29, 2026 853 This week I talk about my surprisingly productive Saturday mornings — and why I'm hoping that same quiet, distraction-free focus carries into summer with all three kids out of school. Then The Creative Act by Rick Rubin, which pulled me out of a months-long reading slump in just a few days, and a recommendation for my early-to-mid 2000s pop punk discography playlists on Apple Music.Links:

"I'll Remember It" Is a Lie: 3 Ways Solopreneurs Can Capture Tasks Faster May 26, 2026 770 Have you ever gone to the grocery store without a list? You walk down every aisle, grab whatever looks good, spend way more than you planned — and somehow still get home without the one thing you actually needed.Running a one-person business without a real task capture system feels exactly the same.When everything falls on you, important work slips through the cracks. And without a plan,

Do you work while driving? [Friday Wrap-Up] May 22, 2026 530 This week I talk about how I used 4 hours of solo driving to and from a mastermind retreat in Baltimore — and why I chose to turn everything off instead of grinding through business prep. Then a wholesome story about a teen umpire who handled a coach's meltdown with poise, and a recommendation for SNL's The Rundown series on YouTube.Links:Solopreneurs and forced downtimeA teen umpire toss

Inbox Zero for Solopreneurs: The Exact System I've Used for 8 Years May 19, 2026 1030 Have you ever seen a 5-digit notification badge? It’s most stressful things I see on someone's phone. And I get it — as a solopreneur, email feels urgent. What if a client needs something? What if you miss a deal?But after nearly a decade of refining my approach, I've built a technical system that keeps my inbox at (or close to) zero — without having to check it constantly.In this episode

Do LLMs employ variable rewards, Spike Lee's hat, and a chilling video [Friday Wrap-Up] May 15, 2026 798 Welcome to the Friday Wrap-Up for May 15, 2026. This is a short newsletter where I talk about 3 things: What’s on my mind this week, Recommended Reading, and Recommended Media. Here's what's on my mind...Earlier this week I found myself fighting Claude on something I felt was a pretty basic problem — one that I had used it to solve before. I kept going back and forth with Claude. I would

The Best Newsletter Tool for Solopreneurs (and Why) May 12, 2026 737 Does having a mailing list feel like too much for you? Like it’s adding “one more thing” to your list as a one-person business?That's what I hear constantly when I coach solopreneurs. Either they don't have a newsletter because it feels like too much work, or they have one, but they're paying for a plan they don't actually need. And in almost every case, it's not a strategy problem. It's

Don't Miss Out on What You're Doing, Deleting Second Brains, drop dead [Friday Wrap-Up] May 8, 2026 901 Are you so concerned with FOMO that you're Missing Out On What's There, rendering your real life MOOWT? That's what's on my mind today. Plus, a great article about why it might actually be bad that you're storing every little thing in your second brain, and a fantastic performance from SNL. Finally, a pay small tribute Yankees legend, John Sterling, who passed away earlier this week. Get

Why Your Solopreneur Business Feels Overwhelming (Fix This First) May 5, 2026 1244 The most overwhelming room in my house is the sunroom. Three small kids, all their toys, total chaos. One day, I was sitting in there feeling overstimulated and realized it would take about five minutes to clean it up. So we did — and suddenly it was a great place to hang out again.A lot of solopreneur businesses are like that sunroom. They're not broken. They don't need a massive overhau

What Solopreneurs Can Learn From Star Wars May 4, 2026 1041 I have a confession to make: The first Star Wars movie I ever saw was Episode 1: The Phantom Menace. I was 13, and it just hit the dollar theater when my friend invited me to see it with him. He realized I had never seen the Original Trilogy when I was surprised that Qui-Gon Jinn died (spoiler, I guess). We fixed that quickly, but this movie, despite being considered the worst Star Wars m

Single-Purpose Apps, AI Won't Take Your Job, Ted Lasso is Back [Friday Wrap-Up] May 1, 2026 791 Are single-purpose apps going to replace SaaS? I've been building small, focused tools with AI to replace subscriptions that solve my problem, just not quite my way, and I'm not the only one. Also: a well-researched piece on why AI isn't actually coming for your job, and some very good news for Ted Lasso fans.On My Mind: Single purpose apps/the age of personalized software.Recommended Rea

The One Thing Solopreneurs Shouldn't Automate (And What to Automate Instead) Apr 28, 2026 924 Using AI to write your book is like using a car to run your marathon. Sure, you covered the distance — but nobody's impressed.Here's what I'm seeing with solopreneur automation right now: people are handing off their most important work to AI without thinking about what that signals. When you let a language model write your first draft, come up with your ideas, or do your thinking for you

Trading Algorithms + Claude MYTHos [Friday Wrap-Up] Apr 24, 2026 1005 This week I've been deep in my SEO and content strategy, and it got me thinking: am I just trading one algorithm for another? I left social media to stop chasing feeds, but now I'm optimizing for Google, YouTube, and even AI search. Here's where I landed. Also: Cal Newport's take on Claude Mythos (spoiler: no, it's not terrifying), Ryan Holiday's Discipline is Destiny and what it has to s

Why Solopreneurs Should Read Discipline is Destiny Apr 21, 2026 899 What if the best business advice you ever got came from a book about ancient philosophy?I've been on a bit of a reading bender this year — physical books, old ideas, things written long before the age of notifications and hustle culture. And when I picked up Ryan Holiday's Discipline Is Destiny, I wasn't expecting it to hit so close to home as a solopreneur.But it did.Here are 3 lessons I

What is AI Brain + Recommendations [Friday Wrap-Up] Apr 17, 2026 1005 AI brain is when you've come to rely on AI for even the most basic things -- and after a week deep in Claude Max, I felt it creep back in. I'm sharing the three warning signs I've identified so you can catch it early, plus how bad sleep and brain fog made it worse. I've also got recommended reading from Mike Schmitz on using Claude to script YouTube videos (not my approach, but a thoughtf

Vibe Coding for Solopreneurs: When It's Worth It and When It's Not Apr 13, 2026 1274 I understand the temptation of using AI to write your own apps. I’m sick of the endless subscriptions, feature bloat, and raising the subscription price to accommodate the feature bloat. But it may not be all it’s cracked up to be.It can definitely be a huge timesaver (I've used it to build WordPress plugins and write Obsidian Dataview code), but it can also be a huge time suck.It can be

Thoughts and Recommendations for April 10, 2026 [Friday Wrap-Up] Apr 10, 2026 758 I'm trying a new format this week called the Friday Wrap-up, where I tell you what's on my mind, and recommend some articles and videos. The hope here is to curate some more timely resources to help you think about your solopreneur systems, and how to work better so you can take more time off! Here's the Wrap-Up for April 10, 2026. On my mindUsing AI to do all of the writing for you.Using

How to Plan Your Week as a Solopreneur (My Exact System) Apr 6, 2026 824 I can’t imagine something more overwhelming than sitting down on Monday and having no idea what to work on, despite knowing you have a bunch of work to do. But that’s how many solopreneurs start their week.Even worse, when you don’t know what to do, it’s easier for other people to hijack your time, you waste time by deciding in the moment, and it’s hard to measure success.I’ve spent years

Task Journaling for Solopreneurs: How to Finally Understand Your Own Productivity Mar 30, 2026 783 Most task managers only tell you half the story. They show you what you checked off, but they have no idea that you moved that one task four days in a row, or that you cleared three things on Tuesday because you felt guilty, not because they were actually done.I've used pretty much every task manager out there; Todoist is my favorite and I still use it every day. But a while back I realiz

3 Lessons Solopreneurs Should Take From the Olympics Mar 23, 2026 997 I loved watching the Olympics this year — more than usual. Part of it was the great stories and incredible performances. But a big part of it was that it was a celebration of human accomplishment.I believe firmly that AI can’t replace the actual good, worthwhile work we do…and the Olympics is a shining example of that. So for this episode, I wanted to share 3 lessons I think every solopre

Stop Fighting Your Tools: How Solopreneurs Can Build a Better Tech Stack Mar 16, 2026 2059 In 1998, I got genuinely frustrated with my mom for not knowing how to right-click. I thought technology was just… obvious. It took me an embarrassingly long time to realize it was only obvious to me because I'd grown up with it. Not everyone has that background — and assuming they should is how a lot of solopreneurs end up feeling like their tools are working against them.That's exactly

Email Boundaries for Solopreneurs: 3 Steps to Stop Letting Your Inbox Run Your Life Mar 9, 2026 856 What will really happen if you don't respond to that email right away? I used to think "dedication" meant being reachable around the clock — skipping concerts, missing date nights, even taking a work call on Christmas Day. Then a pair of Hamilton tickets on my anniversary changed everything. My project manager told me I had to work through the weekend just to get paid on time. I said no,

I Used AI to Code an iOS App [Audio Note] Mar 6, 2026 821 I had Strep Throat this week, and when I got sick of being cooped up in bed, I decided to do something interesting: use AI to code an iOS app.I have a lot of thoughts that probably require a part two to this note, but for now, I walk through the requirements, how the process was, and why this could be worth my time. Screenshots from the appSend feedback to https://streamlinedfeedback.com.

Why Repetition is Killing Your Productivity as a Solopreneur (And How to Fix It) Mar 2, 2026 978 Not all repetition is bad. Practicing a speech, drilling a recipe, building a training habit — that kind of repetition compounds over time. But there's another kind of repetition that doesn't build anything. It just eats your day, week after week, while your most important work sits untouched.I recently caught myself stuck in exactly that cycle. The kind where you're busy, you feel produc

Why I'm Buying Music Again in 2026 [Paper & Smoke] Feb 25, 2026 691 I bought a modern iPod — not because I needed one, but because I realized I didn’t actually own most of the music I thought I did.It began with my daughter’s intense love of music. I’m committed to keeping smartphones out of my kids’ lives until they’re teens, and that meant finding a way for her to enjoy music without an internet-connected deviceRead more over at https://paperandsmoke.co

How Talking to Your Phone Can Make You a More Productive Solopreneur Feb 23, 2026 871 I grew up watching people yell into their Nextel phones at the mall in the late 90s, and it put me off talking to my phone for years. There was something deeply embarrassing about it — like you were performing for everyone around you just to send a message.I've completely changed my tune.As someone who does a lot of thinking away from my desk — on walks, in the car, between school pickups

Why I’m Returning the remarkable 2 [Audio Note] Feb 18, 2026 478 I tested the reMarkable 2 with the Type Folio keyboard hoping for a distraction‑free, E‑ink writing experience. It’s a great device but I found it wasn't great for my workflow. Here’s why. Plus, a new experiment. Let me know your thoughts at https://streamlinedfeedback.com. Visit https://streamlinedsolopreneur.com/ for more insights. Is your tech stack helping you or just adding to the

The Solopreneur's Guide to Taking More Time Off Worry-Free Feb 16, 2026 1319 I got home at 3 a.m. after a week of back-to-back conference days and Disney park days with my brother. I was exhausted. And my flight had just been delayed six hours. But somewhere around hour three in that airport, I realized something: this was the most downtime I'd had in weeks. No kids. No client work. No next thing to rush toward. Just me, a restaurant, a book, and two other strande

Your Members Don't Want More Content Feb 9, 2026 2668 Memberships and Communities are a great way to stop selling hours for dollars. But you need to do it right. I recently sat down with my good friend Becky Pierson Davidson to talk about why so many communities fail and how she helps solopreneurs turn "ghost town" memberships into thriving, seven-figure assets It hinges on this: people don’t want a library of 150 hours of video; they want t

Working on Interoperability with the reMarkable 2 [Audio Note] Feb 5, 2026 372 I picked up reMarkable 2 to see how I liked typing on an eInk device. I share some initial impressions, but am facing a bigger, more interesting problem: how to I make it play nicely within my current writing ecosystem? Get all of the episodes at https://streamlinedsolopreneur.com/Send feedback to https://streamlinedfeedback.comIs your tech stack helping you or just adding to the noise? T

What do we lose by relying on AI too much? Feb 2, 2026 1041 What do Michelangelo, Shakespeare, Marie Curie, Ben Franklin, and Virginia Woolf all have in common? They all created long-lasting, humanity-impacting work…without the use of AI.See, there are lots of people who will tell you that you need to use AI or get left behind. Those people are wrong.In fact, I think the way to stand out is to not use AI. At least, not in the way everyone else is

January Accountability Report for Digital Detox [Audio Note] Jan 30, 2026 430 It's the end of January and my Year of Digital Detox is in full swing. Here's how I'm doing with it so far. Read about The Year of Digital Detox: https://casabona.org/2026/01/2026-yearly-theme-digital-detox/Subscribe to Paper & Smoke: https://paperandsmoke.comSubmit feedback: https://streamlinedfeedback.com

Why Gear and Tools Actually Matters Jan 26, 2026 1269 I was recently trying to do something that should have been simple: sharing my work calendar with my wife so she knows when I'm actually free for family time. I found myself digging through "secret" settings pages, checking her phone, then mine, and getting increasingly frustrated.It made me realize how often we settle for "fighting" our tools instead of letting them support us.You’ve pro

How AI Can Actually Help Your Critical Thinking, not Hurt It Jan 19, 2026 2586 I’m deeply worried about humanity losing our critical thinking skills. We’ve seen it degrade in the social media era, and now we’re seeing people wholesale outsource it in the AI era. But what if we can actually enhance our critical thinking with AI? I’m too much of a skeptic to tackle this topic on my own, which is why I brought in Christian Ulstrup, who’s doing some truly interesting th

How to Serve More People and Scale Your Income Jan 12, 2026 3252 “What’s your exit strategy?” Someone actually asked me this when I was starting my business. I didn’t have one. I’m not in it for the exit. But the question went to something deeper: how are you going to make actual money? Because the problem is most solo business owners charge hourly. Or they need to hire to scale. OR they need to sell the business. But there’s a better way: Value-Based

New Podcast: Paper & Smoke [Trailer Drop] Jan 9, 2026 244 I am no Luddite. I have three pieces of technology that monitor my health and wellness. I’ve come to rely on many devices.That is why I am doing a digital detox.This is Paper and Smoke. It’s a look at how real-world craft happens, through the lens of a technologist going through digital detox. In a society increasingly online (and outsourcing thinking to AI), Paper and Smoke celebrates th

The Year of Digital Detox (2026 Yearly Theme) Jan 5, 2026 1759 There comes a time in everyone’s life when they’ve consumed too much of something, and they find the very notion of consuming more sickening. This is the very basis for my yearly theme. 2025 was finally the year were I felt my overconsumption of technology was getting the best of me. So this year, my theme is digital detox. Read the full article here: https://casabona.org/2026/01/2026-yea

An End of the Year (Beginning of the Year?) Update Jan 1, 2026 215 We're almost at the end of Christmas break and I decided to record a quick update on how it's going...plus test my new camera. Check out the (somewhat unflattering) video here: https://youtu.be/HvSTnzOP01g ————Streamlined Solopreneur helps solopreneurs stop doing it all themselves, with simple systems that give them their time back.Each week, Joe Casabona shares one practical idea — a sys

My Favorite Tech, Apps, and Media of 2025 Dec 31, 2025 1717 It's one of my favorite episodes of the year: my Favorites of the year! I'll go through all of my favorite media and tech of the year, as well as some close runners up and honorable mentions. Links below! My Favorites of 2025When is it Time to Switch Tools?Paper & SmokeBook: Fahrenheit 182Runner-up: The Anxious GenerationHonorable Mentions: Neverwhere, Tiny Experiments, Listening to t

How I Saved Laura Brazan More Than She Spent on my Coaching Dec 29, 2025 2321 Knowing when to get help is so, so, so crucial to prevent burnout. Laura Brazan knew this, which is why she decided to hire me for coaching. During our few months together, I was able to save her a ton of time, help her create process automations, and consolidate her tech stack. She even said that she’s saving more than she paid me! In this interview, we look at where she was before she h

Replay: My Favorite Christmas Story Dec 25, 2025 414 I knew from a young age, I wanted to play the drums. I got my first small kit when I was five, and when my friends and I started a "band," heavy quotes, I played paint buckets. When I was 15 years old, I knew I needed a real kit.This is the story of how I got it, and how one man's incredible kindness had a profound effect on me.Show NotesRead the Story at Casabona.orgSubmit feedback at ht

3 things you need to do before 2026 Dec 22, 2025 1235 I started my Christmas vacation the minute my kids got out of school. I can do that because I’ve built a business that doesn't chain me to my desk. But if I’m being honest, I don’t take those two weeks off just to bake cookies and watch movies—I use that downtime to make next year even better.When the house is quiet, I run a full self-assessment on my business to figure out how I can furt

Pick 2 (Revisit Edition): Bear Notes and Blinkist Dec 15, 2025 806 It’s a soon-to-be classic Pick 2 episode, where I pick 2 apps or tools I’m using and tell you about them. I say soon to be classic because I’ve wanted to do this for a while, and I’m finally going through with it!This week, it’s 2 apps I’ve used before and stopped using, but I’m revisiting. They are:Bear NotesBlinkistThanks to AppStories for the ideaWant to get the tools, apps, and automa

Streamlined Solopreneur: Helping Solopreneurs Automate to Take Time Off Worry-Free

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