Streamlined Solopreneur: Build Systems so Your Business Supports Your Life

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 thoughtful one),...

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 hard to...

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 mind Using AI to do all of the writing for you. Using Claude...

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 refini...

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 realized it co...

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 solopreneur sho...

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 what tec...

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, logged of...

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 app Send feedback to https://streamlinedfeedback.com . Join...

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 productive, bu...

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 device Read more over at https://paperandsmoke.com ————...

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 — I'v...

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 noise? T...

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 stranded strange...

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 to solve...

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.com Is your tech stack helping you or just adding to the noise? Take my...

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 using i...

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.com Submit feedback: https://streamlinedfeedback.com

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 probably h...

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 things in...

“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 Pricing...

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 the real,...

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-yearly-theme...

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 automate their business so they can take time off worry-free. Each week, Joe Casabona shares practical systems, tools, and strategies to help you...

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 2025 When is it Time to Switch Tools? Paper & Smoke Book: Fahrenheit 182 Runner-up: The Anxious Generation Honorable Mentions: Neverwhere , Tiny Experiments , Listening to th...