Streamlined Solopreneur: Helping Solopreneurs Take Time Off Worry-Free

What will really happen if you don’t respond to that email right away? I used to work at an agency where I thought "dedication" meant being reachable 24/7. I skipped concerts, missed date nights, and even took a work call on Christmas Day. I was convinced that if I didn't respond immediately, I was failing.

The turning point? A pair of tickets to see Hamilton on my anniversary.

When my project manager told me I had to work t...

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

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Some of the results we seek benefit from repetitive work. Physical training, memorization, cooking, and practicing a big speech. But repetitive work can also limit us — especially if it keeps us from doing our most important, highest leverage work.

I recently found myself stuck in a cycle of repetitive work that was keeping me stuck and wasting my time. Here’s how I’m getting out of it, and how you can recognize and fix whe...

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

Simplify your tech st...

I remember when Nextel first launched its "push-to-talk" walkie-talkie feature back in the late 90s. It mostly resulted in people yelling into their phones at the mall, and it honestly made me hate the idea of talking to my phone in public for decades. But things have changed.

Between the rise of asynchronous communication and the power of AI transcription, I’ve found that talking to my phone is actually one of the best way...

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? Take my free tech stack asse...

I was recently stuck in an airport for 6 hours while my flight got more and more delayed. But instead of being mad about it, I realized something: this was a blessing of forced downtime.

And while I’m usually really good about taking time off, I know many solopreneurs who aren’t. We feel like we need to work or the business will crumble. I was there a few years ago.

But the good news is it’s not true. You can take time off a...

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 a problem.

If you’ve ever fe...

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 free tech stack assessme...

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 it. While most people are usi...

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 heard me say that gear doesn’...

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 the AI space. 

We ta...

“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. And Jonathan Stark...

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, the tangible, and the analo...

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-digital-detox/

Show Notes

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 the Law
• TV Show: Alex vs...

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 hired me, the changes we made, a...