Writing a Book During a Long-Term House Sit With AI

Home > Blog > Writing a Book During a House Sit

I'm currently six chapters into writing a book, sitting on a balcony in Portugal in near-unbearable heat, and it has become one of the most genuinely fulfilling things I've done during a long house sit. Not because writing itself is easy for me, it isn't, but because of what the process has shown me about my own thinking once an AI was actually organizing it.

We're on a six-month TrustedHouseSitters sit right now, and this book is one of the direct results of having that much uninterrupted time. If you're not yet on the platform, a 25% discount on membership is available here. This connects directly to something we've written about before: boredom during a long sit isn't always a problem to solve, and this project is a real example of what can come out of it when you let it.

What the Book Actually Is

It's about how I actually live and fund this lifestyle. Mindset, genuine gratitude, how we spend and manage money, how we make money online, and the simple, practical steps behind all of it. The core idea I keep coming back to is that most people assume they need far more than they actually do to live a genuinely good life, and that realization can be uncomfortable for some people to sit with. I want the book to hand over the actual steps rather than just the feeling, something someone could genuinely act on rather than just find inspiring for an afternoon.

I'm keeping it simple on purpose. That's not a limitation, it's the point. A lot of what I have to say isn't complicated once it's organized properly. The complicated part has always been getting it out of my head in a form anyone else could follow.

The Actual Problem AI Solved for Me

Here's the honest version of how my brain works when I'm talking or writing freely: I go on tangents. I have a lot of ideas, genuinely good ones, but they come out in a scattered order, one thought leading somewhere else before the first one is finished. When I'm speaking, it makes complete sense to me. Translating that into something someone else can follow has always been the harder part.

What's changed everything is building a prompt that interviews me. It asks me questions on a specific topic, lets me answer in whatever order it comes out, and keeps going until it's pulled out everything I actually know or think about that subject. Then it acts as an editor, taking all of that and organizing it into something clear, still in my own voice, not a generic rewrite, but actually readable in a way my raw answers never quite are on their own.

Reading the result back has been a genuinely strange experience, in a good way. It's my own words, my own thinking, presented back to me in a form I didn't know I was capable of producing directly. The surprise wasn't that I had a lot to say, I already suspected that. It was realizing how much of it actually held together once something existed to hold it together for me.

The First Draft Is Never the Final One, and That's Fine

I want to be honest about this part too, since it matters if you're thinking about trying something similar. The first AI-organized version of a chapter is rarely the finished version. I read it, evaluate what's working and what isn't, and go back with specific notes on what to fix. It's a genuine back-and-forth, not a one-shot process.

The whole book is being built the same way: draft a chapter, review it, rewrite sections, and make sure earlier chapters connect properly to what comes later. If I mention something in chapter two, I want it to actually resurface in chapter five, not just sit there disconnected. That kind of coherence takes real editing passes, not a single AI output treated as finished.

Writing From a Balcony in 40-Degree Heat

The setting matters more than I expected it to. I'm writing this looking out over a genuinely stunning view, with a fan blowing on me because the heat, 38 to 40 degrees with full humidity, makes sitting still otherwise miserable. My sleep hasn't been great because of it, and my focus isn't always at its sharpest. And yet, despite all of that, it's been one of the most inspiring stretches of writing I've had.

Having this much time, and specifically having nothing forcing me to be anywhere else, is what's made this possible at all. A shorter sit wouldn't have given me the room to sit with an idea for a week, come back to it, and let it actually develop. Long-term house sitting, more than any other travel style we've tried, hands you exactly the kind of stretch a book like this actually needs.

A Starting Prompt If You Want to Try This Yourself

If you want to try building your own version of this, here's a template based on how mine actually works. This isn't the exact prompt I use, since mine has evolved through a lot of iteration, but it's a genuine starting point you can refine the same way I did.

1Write Your Ebook With AI: Quick-Start Prompt
2 
3Copy this into a new chat to start turning what you know into a real, chapter-by-chapter book. A simpler starting point, not the full system.
4 
5The One Rule That Matters Most
6 
7Never let the AI invent a story, number, or detail you didn't actually give it. If an answer sounds vague or generic, ask again before drafting anything.
8 
9Step 1: Tell It What This Book Is
10 
11Answer these yourself first, then hand them to your AI assistant:
12 
13What is this book about, and who is it for?
14Why are you the right person to write it: personal experience, research, or both?
15What's the one thing you want a reader to walk away believing or able to do?
16How deep do you want it: a focused, tight book, or a comprehensive resource?
17What tone fits: personal and story-driven, practical and instructional, or a blend of both?
18 
19Step 2: Get a Chapter Menu
20 
21Tell your AI: "Based on everything I just told you, suggest 10 chapters that could work for this book, each with a one-line description. Number them, and let me pick which ones I want." Choose the ones that fit. Put them in whatever order feels right, you can always reorder later.
22 
23Step 3: Interview, Then Draft, One Chapter at a Time
24 
25For each chapter, tell your AI: "Ask me 8 to 10 specific questions about this chapter before you write anything. I want real stories, real numbers, and my actual opinion, not generic advice." Answer fully. Only once you have, let it draft that one chapter, in your voice, using only what you gave it. Then move to the next chapter and repeat.
26 
27Step 4: Read the Whole Thing, Then Fix It
28 
29Once every chapter has a first draft, read the whole book start to finish. For each chapter, tell your AI what's off, what's missing, or what doesn't sound like you, and have it revise before moving to the next one.

Use this on a topic you actually know well, whether that's a full book or just one chapter's worth of material, and expect to go back and forth with it rather than treating the first output as done. A tool like Whisperflow or similar voice-to-text transcription software is worth pairing with this too, if talking through your answers comes more naturally to you than typing them.

I'm also in the process of packaging up a more complete, refined version of this system, the actual prompt I use, tested and developed over months rather than the starting template above. Once it's genuinely ready, we'll share more about it here. For now, the template above is a real, working starting point, and refining your own version of it is honestly part of what makes the end result feel like yours.

Conclusion

Underneath everything in this article is a fairly simple message, and it's one worth sitting with. When you have time, or when you're bored, that's not dead space to fill until something better comes along. It's an opening to look inward and actually focus on yourself, something most people rarely get the chance to do properly. Long-term house sits give you exactly this, real, uninterrupted stretches of time, and they exist in genuinely large numbers all over the world if you go looking for them.

Use that time well and you may find things about yourself you'd never really examined before, ways of thinking, ideas you didn't know you were carrying around, a clearer sense of how to actually say what you mean. That last part matters more than people expect. Finding the right words for what's in your head, whether that's a book, an app, a business, or just a better way of explaining yourself to other people, is its own genuine skill, and it's one this kind of time helps build. Sometimes what comes out of that process is worth sharing. Sometimes it's worth building into something other people would genuinely pay for. Either way, it starts with actually giving yourself the space to look inward in the first place, and a long house sit is one of the best environments we've found for doing exactly that.

Caro and I have completed 20 house sits across 12 countries, driven 19,000km across Europe in our 1998 VW T4, and saved over $26,500 in accommodation costs over three years of house sitting. If you're working on your own project during a long sit, tell us about it in the comments, we'd genuinely like to know what other sitters are building with all this time. DM us @housesittersguide if you have questions, we answer everyone.

Frequently Asked Questions

• Can you actually write a real book using AI during a house sit?

  Yes, though it's worth being precise about what that means. The ideas, stories, and opinions still have to come from you, AI didn't invent any of that. What it can do well is interview you to pull scattered thoughts out in a usable order, then organize them into coherent, readable prose in your own voice, which is a genuinely different problem than having the AI write the content itself.

• Is the first AI-organized draft usually good enough to use?

  Rarely, and that's normal. Expect to review each section, give specific feedback on what to fix or expand, and go through several passes before a chapter feels finished. Treating a first output as final is the most common mistake people make with this kind of process.

• Why is a long house sit particularly good for a project like this?

  The uninterrupted time matters more than the location. A long sit gives you the room to sit with an idea for days or weeks, come back to it, and let it actually develop, something a short sit or a normal working life rarely allows for. It's the same underlying reason long sits work well for learning a language using a similar AI-assisted approach.

• Do I need to be a good writer to do this?

  No, and that's part of the point. The process is built around how you actually think and speak, tangents and all, rather than requiring polished writing skills upfront. The organizing and editing is where the AI genuinely helps, not in replacing your actual ideas or voice.

• What tools are useful alongside the AI interview process?

  A voice-to-text transcription tool, something like Whisperflow, is worth using if talking through your answers comes more naturally than typing them. Beyond that, the core requirement is just a capable AI assistant and the willingness to go through multiple review passes rather than expecting a finished result immediately.

Related Guides