Streamlined Solopreneur: Solo Ops to Stop Doing Everything Yourself

I’ve been testing Gemini, ChatGPT, and Claude to see which one actually helps me. Claude felt forgetful, so I dropped it. ChatGPT is still great at structured stuff, like rewriting transcripts. But for things I didn’t know how to start—like turning an outline into a flowchart or converting a school calendar into an ICS file—Gemini nailed it.

My takeaway? AI shines when I need guidance and structure. When I’m just being lazy, it gives me junk and reminds me I should probably just do the work myself.

Incidentally, ChatGPT did a better job at writing this summary…

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Streamlined Solopreneur helps overwhelmed solo business owners go from overwhelmed to having their time back.

Each week, Joe Casabona shares one practical idea — a system, tool, or strategy to help you get your time back without selling your soul to AI...and run your business without sacrificing the rest of your life, or your health.

Looking for a place to start? Take the Solo Systems Starter Quiz. 60 seconds, 8 questions, and I will tell you what system you should build first, and exactly how to build it. https://streamlined.fm/quiz 

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What is Streamlined Solopreneur: Solo Ops to Stop Doing Everything Yourself?

Overwhelmed? Feel like your business can't run for a day without you? You're not alone.

When you're a solo business owner, everything ends up depending on you. You're the only one who can do the work, answer the email, keep the plates spinning. So you're on the hook every day: nights, weekends, even the vacations you do manage to take. The overwhelm never really lifts.

But being a solopreneur doesn't have to mean doing it all yourself. With the right systems, parts of your business can run without you. That's what gets you your time back, and gives you the freedom to take a real break. And the freedom to do the work you actually want instead of the work you feel stuck doing.

Joe Casabona learned this the hard way. He went from so overwhelmed he had a panic attack to taking 4–6 weeks off a year, worry-free, and he's helped hundreds of solopreneurs build systems that give them their time back.

Every week, one clear idea to help you get your time back without hiring a team...or selling your soul to AI. Start listening, then grab the free newsletter at https://streamlinedsolopreneur.com.

I made a flowchart in Google Gemini yesterday, and it got me wondering if Gemini is the best of the chatbots. I've discontinued my subscription to Claude. I just didn't feel like, I feel like with all of these things get progressively worse the more you use them, and I felt that especially true with Claude.

Like Claude couldn't keep, and I know they just rolled out a new thing, but like it felt like it couldn't keep track of anything I was saying, like in conversation, outside of conversation, uh, and I know ChatGPT5 just rolled out, and so I was trying ChatGPT5 to build this flowchart, and it was just like a disaster, uh, and the reason I'm doing this flowchart is because of the work I'm doing with Charlotte Crother, uh, my signature framework, we basically worked out like, uh, how I best work with clients, sort of thing, and I've made it an outline, and she said you should make it a flowchart.

And I didn't really know where to start. So at first I asked ChatGPT, and I said I want to make, I want to turn this outline into a flowchart, make it detailed, ask me clarifying questions, which it did, and then it generated just like the most god image I ever seen. And I did the same thing to Gemini, and Gemini didn't really ask any clarifying questions, but it gave me a first draft, and I said what about this? And we went back and forth, and it made a mermaid script.

I guess Mermaid is for flowcharts. It's a free tool that I used, and I just copied and pasted what Gemini generated into Mermaid, and it looked pretty good, um, but I'm thinking about two things here, really, um, first of all, I don't know that Gemini is the best because this morning I had it like, uh, rewrite an SRT file as a transcript, and like it had citations, and I said just give me something I can copy and paste, and it still had the citation, so like ChatGPT is really good at that, um, but like as far as the, uh, like the more critical thinking stuff, maybe I don't really know how to word it.

I just know that like the two tasks that I feel like I needed the most help on, uh, Gemini was the best, that was like turning a Word document of a school calendar into an ICS file, did it flawlessly, whereas like ChatGPT just like couldn't fathom the question I was asking it, even though it did it for me last year. And then this like this flowchart thing, like so you know, I, I know that the ChatGPT AI bro advocates, your prompts are wrong, people would tell me my prompts are wrong, or that like, oh, different models are better for different things.

But like I'm not, I'm not trying to deeply understand all the models, right? Just like if you build a car, or if you know how to build a car, great, but like I drive a car, and when I want to go from my house to the cigar lounge, I expect it's going to get me there. I don't expect that it's going to be like, well, you didn't drive it the right way, or you didn't put the right gas in it. I expect this to be surface level, without understanding exactly how the engine works.

So as far as that goes, I've been really happy with Gemini, even more happy because it already comes with my Google Workspace account. But I'm not quite ready to say goodbye to ChatGPT yet. I do think it crunches on some data, um, pretty well, but I think like the more I'll be able to train Gemini, uh, the better it will be in the long run, I guess.

Like this is the other bummer is like I spent a lot of time training both Claude and ChatGPT, and now like those Claude projects are just gone, but like I didn't find them to be particularly good anyway, um, and like ChatGPT is just okay, and so now like I kind of retraining Gemini, I guess. What I'm really, I guess the main thing I'm saying right is this thing, this conclusion I've been barreling towards for a while now, which is like I had this very specific task where I wasn't really sure what to do and I needed some guidance and nudges in the right direction, and Gemini really helped me.

But when I'm being lazy and I know how to do the work and I ask AI to do it for me anyway, that's when I'm like, this is what AI has given me is garbage. And it like almost serves as just like a kick in the pants to do the right thing, like to actually do it myself. So I don't know. I've been enjoying Gemini. I think this like flowchart use case was really good.

I had an outline. I didn't know how to make the flowchart. I didn't really know where to start. And it was just like a good thing to rubber duck. And I think I ended up with a good flowchart. I guess Charlotte will tell me if this is totally bad or if it's decent. But I was pretty happy with the way it came out, not really knowing where to start a flowchart for this particular thing.

So let me know at streamlinedfeedback.com what's your current favorite AI chat thing. And thanks so much for listening.