How to turn Claude Code into your personal life operating system | Hilary Gridley

Hilary Gridley is an entrepreneur, former product leader, and new mom who previously appeared on the podcast discussing AI for managers. She returns to share how she's transformed her approach to personal productivity using Claude Code as her primary tool for managing both professional work and life admin. Hilary demonstrates her "anti-system system"—a philosophy that prioritizes simplicity over complex setup, allowing AI to learn preferences through observation rather than upfront configuration. What you’ll learn: How to capture to-dos instantly using a simple iPhone back-tap shortcut that requires zero app switchingThe “10x impact framework” for deciding what tasks to automate versus where to invest your human effortHow to use Claude Code’s observation capabilities to build a preference file that improves over time without manual setupWhy the “yappers API” (talking about what you’re doing while working) eliminates the need for complex OAuth integrationsA workflow for breaking down overwhelming tasks into 10-minute first steps that actually get completedHow to create Claude Skills by simply describing problems rather than writing code or following tutorialsTechniques for using “recording mode” to demo workflows without exposing personal information— Brought to you by: WorkOS https://workos.com/?utm_source=lennys_howiai&utm_medium=podcast&utm_campaign=q22025—Make your app Enterprise Ready today Lovable https://lovable.dev/—Build apps by simply chatting with AI — In this episode, we cover: (00:00) Introduction to Hilary Gridley (02:43) The opportunity cost of time as a new mom and entrepreneur (07:11) Philosophy of the anti-system system (08:05) Demo: Planning your day with Claude Code (10:00) Setting up simple iPhone shortcuts for task capture (11:48) How Claude organizes reminders and learns preferences automatically (16:19) Breaking down overwhelming tasks into manageable first steps (23:40) The yappers API: talking to Claude instead of building integrations (25:28) Daily logging and observation patterns (27:45) Quick summary (30:50) The power of screenshots (32:55) 10x impact framework for automation decisions (37:51) Applying the framework to different career stages (39:29) Building a “recording on” skill for anonymizing demos (44:11) Building a returns tracking skill from scratch (48:31) Building the muscle memory to reach for AI tools (50:18) Where to find Hilary — Tools referenced: • Claude Code: https://claude.ai/code • Obsidian: https://obsidian.md/ • iPhone Shortcuts: https://support.apple.com/guide/shortcuts/welcome/ios • Cursor: https://cursor.sh/ — Other references: • Figma file Hilary demo’ed: https://www.writerbuilder.com/howiai — Where to find Hilary Gridley: Substack: https://hils.substack.com/ Website: https://writerbuilder.com https://writerbuilder.com/ — Where to find Claire Vo: ChatPRD: https://www.chatprd.ai/ Website: https://clairevo.com/ LinkedIn: https://www.linkedin.com/in/clairevo/ X: https://x.com/clairevo — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  The opportunity cost of my time has never been higher. Also, as a new mom, it's never been harder. It has never felt harder to get out of my time what I want to because my attention is super fractured.

• 0:12Claire Vo?

  How do you decide what to automate?

• 0:15Speaker 00

  For any possible task, if I were 10 times better at it, would it have 10 times the impact? If the answer to that is no, then I just automate it. And if the answer to that is yes, those are the things that I want to put more time and effort into.

• 0:32Claire Vo?

  And you don't have to start with a big, complex Python script or anything like that. You just have to start with a problem statement.

• 0:39Speaker 00

  You learn by doing. And so every day, my Claude gets a little bit better at helping me manage my time, helping me do work because it is observing what is really happening. So we adjust as we go. And it takes the cost of maintaining the system and the cost of setting up the system to zero because Claude is just doing everything for me.

• 1:01Claire Vo?

  Welcome back to How I AI. I'm Clairveaux, product leader and AI obsessive here on a mission to help you build better with these new tools. Today, we have our first repeat guest, Hillary Gridley, who was on one of our most popular early episodes teaching us how to be a better manager with AI. Now she's an entrepreneur and a new mom, and she's back to show us her personal anti-system system for using AI to manage her day, her to-do list, and get everything done through that little alien in our computer, Claude code. Let's get to it. This episode is brought to you by WorkOS. AI has already changed how we work. Tools are helping teams write better code, analyze customer data, and even handle support tickets automatically.

• 1:46Claire Vo?

  But there's a catch. These tools only work well when they have deep access to company systems. Your copilot needs to see your entire code base. Your chatbot needs to search across internal docs. And for enterprise buyers, that raises serious security concerns. That's why these apps face intense IT scrutiny from day one. To pass, they need secure authentication, access controls, audit logs, the whole suite of enterprise features. Building all that from scratch? It's a massive lift. That's where WorkOS comes in. WorkOS gives you drop-in APIs for enterprise features so your app can become enterprise-ready and scale up market faster. Think of it like Stripe for enterprise features.

• 2:29Claire Vo?

  OpenAI, Perplexity, and Cursor are already using WorkOS to move faster and meet enterprise demands. Join them and hundreds of other industry leaders at workos.com. Start building today. Hillary, welcome back to How I AI. It's been almost a year and I'm going to flatter you a little bit. You were one of our most popular early episodes about how to be a better manager with AI. So I am super psyched to have you back on the show and show your new set of workflows and AI tools that help you in your changed life now. So bring us up to date. What's been happening in the last year?

• 3:10Speaker 00

  A lot has changed. A lot has changed in my life and in AI. Talking about custom GPTs almost feels so quaint now with what we talked about a year ago. But I also have a little baby now. I was pregnant when we were first recording that podcast. And so it's been really fun exploring these tools with a whole variety of new demands on my time and my life and just with the new capabilities that are available and how far these tools have come since then. So lots have changed and I'm really excited to show you what I've been up to.

• 3:39Claire Vo?

  And in addition to having a new member of the family, you're also focusing full-time on your own business, isn't that right?

• 3:45Speaker 00

  That's right.

• 3:46Claire Vo?

  So you've gone from being a product leader in an organization, thinking about how to manage employees and those constraints on your time, to being an entrepreneur. And again, the constraints on your time don't go away and you have lots of pressure and demands from both clients and the work that you need to do and your family. So you've built an entirely new system and we are upgrading from custom GPTs to something a little bit more advanced, isn't that right?

• 4:12Speaker 00

  That's right. We are upgrading.

• 4:14Claire Vo?

  And what I love about what we were talking about before we started recording is, yes, what we're going to show is going to be a cool, pretty complex way to automate your personal and professional life. And also, you have a philosophy on how complicated this can actually be to match your life. So tell us a little bit about how you think about the system of setting up your personal AI.

• 4:36Speaker 00

  The biggest thing that has changed for me since becoming a mom is I feel like the opportunity cost of my time has never been higher. Like, I just have no tolerance for wasting time in things that are not like either enriching my life, or helping me towards some goal, or spending time with my son, or whatever it is. But the problem is like, also as a new mom, I feel like it's never been harder, it has never felt harder to get out of my time what I want to, because my attention is super fractured. I'm tracking about 1,000 more life admin things and logistics than I ever have been before. And I'm historically

• 5:18Speaker 00

  not great with logistics and life admin. You know, I'm not sleeping as much, like, my brain's a little bit foggier. So it's been really fun for me to explore how AI can help me with that and help me sort of keep all the pieces together moving forward so that I can get more out of my time. Not in like a, you know, hyper productivity optimizer kind of way, but like, you know, like reclaim time so that I can go to the market and get a baguette and have some nice cheese and like enjoy life and not spend all my time juggling all of these logistical plates.

• 5:54Claire Vo?

  So what you're telling me is you're just prepping for the post AGI world where we're all just, all of our stuff is taken care of, we're living in an abundance world, abundance utopia, and we just have to figure out how to fill our time with robot baked baguettes and delightful leisure activities.

• 6:14Speaker 00

  I mean, I like to work. That's the thing. Like, I want to free up time to do work that makes me excited and that I love doing. But then I also want to go have a picnic. So it's, it's really, you know, the, within me, there are two wolves, and neither of those wolves are life admin. And so any help that I can get on that front is amazing. But the problem that I've seen with a lot of like systems, when I watch other people use AI and use Claude Code in this way, is like, it involves a lot of setup, and it involves a lot of organization. And like, they're like, look at this amazing system I built, where it pulls my top priorities, and you know, it pulls all this kind of stuff.

• 6:57Speaker 00

  And I'm like, you've already lost me, because the whole point of this is that I don't want to put work into maintaining a system. I don't want to do a bunch of setup. I don't want to like, like, I just want to get started and have my problem solved. And that's what I'm going to try to show you today, is how I approach that, in a way that, you know, we talked about a sort of like, the anti-system system. That's, that's my philosophy in all of this.

• 7:23Claire Vo?

  Well, and I think from a personal productivity perspective, there is this spectrum that I talk about, which is I think some of us are like, Notion boys, where we want like, tables and pages and linked assets and Kanban boards and all this stuff. And then some of us, and that's me, are just like a plain text file on my desktop that says things I need to do. And depending on where you fit on that spectrum, you're going to want to set up your AI in a different way. And I, like you, am a little bit more stream of consciousness approach to how I want to think about structuring my day, which is not at all. So I'm excited for you to show us, and a couple of the tips and tricks you use and things you've built, particularly with Claude Code, to get you there. So where are we going to dive in?

• 8:07Speaker 00

  All right. First, I want to show you something, to set the stage, which sort of gets into what we were talking about. This is a picture I took, like, I don't know, you can tell from the quality, it was probably 15 years ago. Do you know whose desktop this is?

• 8:22Claire Vo?

  No.

• 8:23Speaker 00

  You're never going to guess in a million years. So I'll just tell you. This is Al Gore's desktop.

• 8:28Claire Vo?

  But that is not what I was expecting.

• 8:31Speaker 00

  I saw it not in a million years. I went to see Al Gore talk and he flashed this up while he was loading up his PowerPoint. And I was like, this is the most amazing, like, what an amazing peek inside this person's brain. Uh, this person who's obviously accomplished so much and like, this is the state of their computer. And I don't like, that's not a criticism. Like, I felt seen and I felt like I finally have somebody who like, doesn't seem like they have it all together behind the scenes and is yet able to make it seem like they have so much together. So this is like, this one goes out to Al Gore and his, his extremely chaotic desktop. Uh, because I think that is sort of like the state of

• 9:15Speaker 00

  how I felt about all the stuff I was trying to keep track of when I started setting up this system.

• 9:21Claire Vo?

  I revise my statement. We're all on a spectrum of Notion Boy to Al Gore Desktop. That is my new definition for how organized we are relative to personal productivity.

• 9:31Speaker 00

  Exactly. So the first piece of this that I want to show you is just how I plan my day. And when I think about planning my day, like, again, it's not the like, big, uh, you know, three priorities that I absolutely need to make progress on, that I need help, uh, like, remembering and scheduling. I know what my big priorities are and I do them. The problem is all the stuff around them that I'm always forgetting. And so the first step of that is just, how do I make sure that nothing escapes the leaky sieve of my brain? For things that I have to do or ideas I have. So for things that I have to do, I just have a shortcut right on my phone, on, on the lock screen,

• 10:16Speaker 00

  where I just double tap the back of the phone. And then it pulls up a dictation box and I just say, reschedule pediatrician appointment, right? That's like, one of those things that I'm falling asleep and I'm like, oh my God, I have to reschedule the pediatrician appointment. So I tap the back of my phone, I say it out loud, and then it gets added into my inbox. This is no AI. We have not even reached AI yet. This is just a shortcut on your phone. You can set it up very quickly if you just go to shortcuts, add a dictate text. Uh, and then you also set up the accessibility backtap trigger. That is accessibility within your settings. You go down to touch, go to backtap.

• 10:57Speaker 00

  Click on, double tap, and then find your shortcut here. So, super simple to do.

• 11:02Claire Vo?

  If Apple's watching, I need a chatbot to navigate iPhone settings for me.

• 11:08Speaker 00

  I totally agree. So, I can actually, I can share this whole Figma file. That would be helpful for your listeners. I'll put it at writerbuilder.com/howaiai. And you can also share it in your, in your show notes. This is like so easy to set up, but it's just clicking around that like is very hard to do. So you can just follow the steps there if that's helpful. But now this is the fun part, which is hashtag how I AI. Do people still, I guess people don't still use hashtags.

• 11:36Claire Vo?

  I mean, it depends on, yeah, I'll, I'll, I'll throw a hashtag out there every now and then.

• 11:40Speaker 00

  Hashtag how I AI.

• 11:41Claire Vo?

  But I spell it out. I literally write hashtag.

• 11:46Speaker 00

  Perfect. So, okay, I'm going to open Claude code, which is where I run my entire life. Now, if you are new to Claude code, you are like, I don't understand. You are planning your life out of the terminal of your computer. That's confusing. Again, I'm just going to very quickly show you just to prove how easy it is. We're not going to dwell here. But you have your background, you just click this little magnifying glass, start typing terminal. Terminal pops up. You type in Claude, you hit yes. Don't ask questions.

• 12:20Claire Vo?

  Dangerously skip permissions.

• 12:22Speaker 00

  I, I don't dangerously skip permissions because I'm actually a bit of a scaredy cat, believe it or not. If you have never installed Claude code, it is also super easy to do. Just go to the Claude document. It'll give you a little line that you copy here. You copy that. You literally just paste it in, hit enter, the robot beep boop beep boops, and you're good to go.

• 12:43Claire Vo?

  Yep.

• 12:43Speaker 00

  So, that one goes out to everyone who hates setup and has thought that maybe Claude code has annoying setup, and that has kept you from using it. Not the case. All right. So now we are going to get into plan my day. So, all that I do is I type, plan my day, and I hit enter. And the robot starts beep booping again. Now, what it's doing here is following a set of instructions that I have given it. And I'll show you in a minute how I actually give it those instructions and how I set that up. But for now, I just want to show you like what it looks like and how it actually helps me plan my day. So it's pulling from a few things here. You can see it's pulling from my reminders. And basically, what's going on here is you remember I had that list of reminders

• 13:27Speaker 00

  that I was capturing from my home screen or my lock screen. Claude is in the background, taking those reminders and putting them into a doc where it's organizing them based on category, basically. And this is just a markdown file, so it's just a text file that Claude edits for me. I don't touch it. And it lives in a folder. This is a folder where I just keep everything that Claude ever needs. So this will come up a few times in my demos, but for the purposes of this part, it is just a folder with a text file in it.

• 14:00Claire Vo?

  And I have to ask for folks that want to go a little bit deeper. I see Obsidian, are you using Obsidian? How are you opening this? Are you opening this in cursor? Like, what is the system behind the system where literally just files?

• 14:12Speaker 00

  I, yes, I use Obsidian to edit markdown files. I do that more if I'm writing. I'll have Obsidian open in like the left two thirds of my computer and the terminal open on the right side of my computer. And I'm actively writing in the, in the text in Obsidian. And then I'm also going back and forth with Claude to talk about things that I want to edit. But I don't actually ever open this, so I'm just opening it here to show it to you. Like Claude is going and looking at it and it like, it's none of my business how Claude gets its work done.

• 14:45Claire Vo?

  I want to pause there because I have this opinion as well, which I think is really interesting, working with agents. And I'm thinking about OpenClaw, which is really funny. Which is, I think of my OpenClaw agents as employees and I would never You know, unless the law required, I would never go into their email and be like, how are they doing their work or into their to do to do list? I mean, like, how are they tracking their tasks? That's just not something I would do as an employer. And so it's really interesting how that parallel kind of moves over to agents, which is like, yes, it is actually none of my business how Polly gets it done. As long as she gets it done. Now, every now and then we got a spot check that she's following the rules or something goes sideways. It's nice to be able to inspect. But yeah, I agree with you. This is, this is their system, not mine.

• 15:30Speaker 00

  And it's, I mean, it's so task dependent. Like for most tasks, a 2% error rate is totally fine. And occasionally there are tasks where a 2% error rate is not totally fine. And then it's like, yeah, maybe you trust but verify a little bit more. But for the most part, for the vast majority of what I'm doing, the cognitive effort that it takes off of my plate to not have to even worry or think about this is 100 times more valuable than like, you know, a couple of times a month, one thing falls through the cracks. Like, I can live with that. It is certainly better than whatever was going on before any of this, when not only was I constantly thinking about all of this, but also like 50%

• 16:14Speaker 00

  of things fell through the cracks. Yeah. So like, it's just such an improvement.

• 16:20Speaker 00

  All right. The other thing that it is pulling from here is a list of preferences. So this is really great for me as a mom, because there's a lot of constraints in my day that make it hard to schedule things well, right? Like, I need to be pumping regularly. I need to be feeding my son. On the weekend when I don't have childcare, either my husband or I need to be with my child at all times. And so if the AI is going to make a helpful schedule for me, it is very important that it knows these preferences. Now, again, I don't like setting things up. So I never went in and was like, let's think about what my preferences are. Like, hmm, where are the hours of the day when I'm most affected?

• 17:04Speaker 00

  Like, I don't want to do that. So this has just been the AI observing me over time and changing based on things that it is observing about what I'm getting done, what I'm not getting done, what's actually happening. Which is great because it's actually my real behavior as opposed to me being like, you know, it's, I want to make sure that I get a walk-in for at least 60 minutes every single day. And if you tell that to the AI, it starts scheduling a walk-in. And it's like, if that never happens, it doesn't, you don't want that in your preferences. Even on your head, that's your preference. You know what I mean? So it just, it has all this stuff here that it has just been observing.

• 17:46Speaker 00

  This one makes me laugh because I was complaining about how if I do certain types of work before bed, uh, I don't, I stay up too late because I get in slow.

• 17:55Claire Vo?

  Yeah.

• 17:56Speaker 00

  And so, like, noted.

• 17:59Claire Vo?

  Yeah.

• 18:00Speaker 00

  Thanks. Thanks a lot. So that's what it's pulling from. And then it goes ahead and it makes, uh, or it pulls what's on my calendar. So it's like, all right, here's what your Wednesday already looks like. Here's what's already on your calendar. Let's pick one or two things. What do you want to get done? And I'll talk, like, I use dictation for this. I use dictation for basically everything. So me talking to my computer. I say, I definitely need to make progress on the baby passport. And otherwise, I want to use any block I have to prep for going on a podcast. Spoiler, it's this podcast. I needed, I needed to take a lot of screenshots.

• 18:37Claire Vo?

  I just have to, I have to pause and Hillary make you laugh, which is you and I are truly the exact same person. Same doctor's appointment, same schedule, same husband situation. We, one of us got to be watching the baby. Literally after this podcast, I am going to get the baby passport done. It takes so much effort. So this is, I am your audience of one for all of this.

• 19:03Speaker 00

  I tweet for one person, Claire, and it's.

• 19:05Claire Vo?

  That is Claire Voe. Amazing. Okay. So what I, what I like about this and what you, you've shown is, okay, so it's pulling from your preferences on schedule. It's got a, um, kind of a skill or a script to pull in your reminders. So it knows kind of what's a top priority. And then it's scaffolding out a day that should work for you to accomplish the things that you want to accomplish. And then it looks like it's making a recommendation on where to start.

• 19:33Speaker 00

  Yes. And so I appreciate this because I don't want it to just take what I say literally. Because I say things all of the time that I don't actually get done. Where every single day, I'm like, today is the day I'm going to get the passport for my baby. And then three days go by or three weeks go by and it hasn't happened yet. And a big reason in general that I have found I tend to procrastinate things is because I try to take off like too big of a bite at one time. And so I have this big task, which involves making an appointment, doing paperwork, going to the post office. Like it's, it's too much for me to fit in the margins of my day.

• 20:15Speaker 00

  And so what the AI has figured out about me nicely is that if it can just break that bigger thing down into the very first step, it can slot that into a 15 minute, you know, piece that I have free in my schedule. And then I actually start to make progress on these things that are otherwise just like weighing on me. So it says it here, you are not doing the passport. You are just making the post office appointment. That's it. 10 minutes off your plate. Tomorrow you can gather the documents and fill out the forms. Which is just like, it's such a small thing, but it's been so transformative for me in terms of how I actually make life admin feel like less of a just overwhelming burden.

• 21:00Claire Vo?

  You know, I've had a executive assistant a couple of times. And so I've seen and know a couple of these tips and tricks to getting administrative work done. One of which is just drop a task on your calendar to get done and block off time. And I think, you know, management by calendar is a really interesting use case for AI because like it or not, setting up calendar invites is pretty tedious. Like you have to write the title and the name and you pick a time. And when AI can just do that for you, it's, it's just a totally different form factor of to do list that I personally really like and have seen a lot from a couple of people who love to lean on AI for life admin.

• 21:39Speaker 00

  Yeah, I agree. I think two things are true. One, like, you cannot say you take something seriously if you are not putting your time into it. There are a lot of things that I say, like, oh, I care about this. I want to do this. And if you look at how I actually use my time, it does not reflect that, which is frustrating to me. And I agree with you that the solution to that is like, you, you have to block that time out, which is calendar management. The calendar management fails my test of like, is this tedious life admin work? Like, oh, you gotta go. Like, people who are like, I used to go in and add all these things to my calendar and take things off my to do list and put them on my calendar. Like, absolutely not. I was never doing that. But now that the AI can

• 22:21Speaker 00

  help me with that, I'm like, this is so obviously the right way to, to run your life and try to like, actually get better use out of your time. Both because it, you know, it helps you commit to what you're actually going to use that time for. But then, as you'll see, it becomes much easier to observe the delta between the things that I say I want to get done and what I actually get done, to figure out like, what, what is going on there? And how can I fix anything that is not reflecting what I actually want it to be?

• 22:59Claire Vo?

  Lovable lets you build working apps and websites by simply chatting with AI. Then you can customize it, add automations and deploy it to a live domain. It's perfect for marketers spinning up tools, product managers prototyping new ideas, or founders launching their next business. Unlike no-code tools, Lovable isn't about static pages. It builds full apps with real functionality, and it's fast. What used to take weeks, months, or even years, you can now do over the weekend. So if you've been sitting on an idea, now's the time to bring it to life. Get started for free at lovable.dev. That's lovable.dev. So, speaking of that delta, how do you loop back behind a day and say,

• 23:45Claire Vo?

  "Did I actually book that post office appointment? How did this all go? How do you do this quality control loop on your Plan My Day agent?

• 23:52Speaker 00

  Yes. So, another thing you will find about me when you're seeing these demos is I always resist the urge to have Claude connect all a bunch of stuff in the background and get this information itself. Mostly because I don't know what my tools are going to do when they're hanging out without me and I'm not in the room. It freaks me out. But I do believe, in my heart of hearts, in the Yappers API, which is when I'm looking at things on one screen and I am talking about what I'm seeing to another screen, and that helps me capture virtually everything I'm doing.

• 24:34Speaker 00

  So, because, as I said, throughout my day, I just have Claude open in the terminal on the right third of my computer, and then whatever I'm doing is in the other side of it. Because the terminal is such a multipurpose tool, I can use it to do literally anything that involves my computer. It means that I'm then talking to it all day about the things that I'm doing. And then Claude observes that and takes notes. And so I'll show you how it does that. Just a quick thing on this. As you can see, it just drops everything on my calendar for me. The hippo emojis are things that Claude adds, uh, which helps me kind of keep track. And then this is also helpful because back on my lock screen, I can always see what's coming up.

• 25:19Speaker 00

  So I always have that persistent reminder of how much time do I allocate for this? Have I, you know, do I need to move on to something else, which I am not good at? But the other thing that Claude does is it creates this, um, daily note for me. And again, this is just a markdown file. It lives in that same folder with all my other stuff. You can see here the, the folder structure. And so it has my schedule that it has put into my, uh, into my calendar. And the other thing this has is a log. And so I have told Claude, just observe what I'm doing. And then it has what I said I was going to do on the day. And then it has what I'm actually doing. And so I can check in periodically and say, like, what, you know, what are you observing?

• 26:03Speaker 00

  Like, what's working? What's not working? I have this end of day reflection that I like sometimes do, but sometimes don't. When I remember, then that can be helpful.

• 26:15Speaker 00

  I'll often ask it questions like, what, like, what are you seeing in terms of the gap between, uh, what I'm trying to get done and what I'm actually doing? Or even just like, what are your observations? Because I'm curious and I'm nosey, uh, and I want to know what the AI thinks about me. So like it, it pulls out these patterns, like, you know, that building is crowding out writing, uh, or that you're like doing a bad job time boxing something. Uh, or that you say, you know, most days list three priorities, but only number one gets real time. That's fine if you accept it, but then the real question is, are you picking the right number one? So this is when I said earlier that like, I don't really believe in spending time orchestrating this whole system that you use, uh, for your, um,

• 27:01Speaker 00

  You're a Claude. Part of that is because like you learn by doing. And so every day, my Claude gets a little bit better at helping me manage my time, helping me do work because it is observing what is really happening. If I had tried to orchestrate all of this upfront, I would have been wrong about most of it, right? Like, I thought that saying pick three priorities was a great way to do this. I thought that having this daily like reflection at the end of the day would be a great way to do this. Claude is pointing out that neither of those things are really working, so we adjust as we go. And it takes the cost of maintaining the system and the cost of setting up the system to zero because Claude is just doing everything for me.

• 27:45Claire Vo?

  I wanted to pause here because I think you just showed us so many rich things and I want to make sure that folks didn't miss a couple of the key points. And so, one, it's just like, reduce the friction, reduce the friction, reduce the friction, which is, you know, double tap the back of your phone to just capture to do lists, make it really easy for Claude code, which as you said, through the terminal can basically do anything your computer can do to access your to do list in whatever form, your calendar in whatever form. Don't go through the effort of defining your own preferences or building out these like complex prompts and instructions. Just say like, as we go, start tracking my preferences and it will start building out those files.

• 28:28Claire Vo?

  Create a file space for it to operate in, which, you know, this just can be a folder, markdown, markdown files. And then one thing that I want to make sure people didn't miss because I love this idea of the Yappers API, which is, you know, you could have gone through all this work and been like, okay, I'm going to build this web app. And this web app is going to like, oh, often to my Google, to my Google Drive and my calendar and all this stuff. And it's going to know when I'm working on documents and it's just going to be able to track everything I do per day. And you're like, no, bro, let's not do that. I will literally just as I write a blog post, say to Claude, I wrote a blog post. Or like, as I got the passport done, just say to Claude, I got the first part of the passport done. And this idea of we do not

• 29:10Claire Vo?

  Need, you know, we have so many debates on like MCPs and APIs and CLIs. It's like, literally just look at the screen and be a proxy for the software with your meatware, like use your mouth. And this is where I, we just had an episode with Figma and they're like, you know what? Nothing beats an opposable thumb. Like, nothing beats dragging a design around. And I still think nothing beats just eyeballs and language to describe what's going on in your life. And so keeping things really loose can be a really powerful way to get leverage out of technology without having to use technology at all in that interim step.

• 29:47Speaker 00

  Yes. Two things I believe. One is complexity has to earn its keep. And so if I like, I'll, I can show you some other workflows where I do have my Google connected. And as you can see, I did like, I eventually connected my calendar here. But I only do that after I've tried the jankiest version of the workflow for like, a week and been like, oh, yes, I'm going to continue using this. This is very valuable. And what I have found is I have a hit rate of like, maybe 20%. Like, a lot of things where I'm like, oh, I think it would be helpful to set up this type of workflow. I don't actually end up using it. And so if I spent all this time upfront, getting all of these things connected, like,

• 30:30Speaker 00

  A, it's a waste of time. B, if anything breaks, then it becomes a double waste of time because I have to troubleshoot a thing that wasn't even helpful in the first place. And so I'm like, I'm always trying to find the absolute simplest version of the thing. And then, like, and then I enrich it, and then I enrich it, and then I enrich it.

• 30:50Claire Vo?

  Well, and in addition to the Yappers API, I want to call it something else that we haven't seen in your flow, but we've seen in a couple others, like Jesse, Janee's OpenClaw Flow, which is, and I'm going to call it my mom sharing news API, which is screenshots. And so, yes, I'm not love you mom, but my mom likes to read articles and then like screenshot, like three pieces of the article and send it to me. And at first I was like, can you just like copy and paste me this text? And now I'm like, oh, mom's a genius. Like, that is actually the way to share context is just screenshot your calendar and say, hey, what would you do with with this if you're not ready to hook up the API? Or, you know, scribble a note while you're at the doctor's office and put it in and say,

• 31:34Claire Vo?

  hey, remind me about this next time we go to the pediatrician's office. I think just finding the lowest friction way for these AI assistants to get the information it needs to do a good job, whatever works for you, just use.

• 31:48Speaker 00

  I think that's 100% right. And I tell this to people too, when they say, I've come up with all these great ways to use AI in my personal life, but I can't use it at work because I'm restricted in terms of the permissions I have or the tools I can use. And I'm like, but no one's going to give you access to all of the data at your company if you have like a half baked idea for how it might be helpful. And so if you can make, again, like a janky version of this brilliant workflow that exists in your mind, that is like held together with screenshots and prayers and you talking, like prove that that is actually valuable and then bring that to whoever hold the keys

• 32:29Speaker 00

  to the castle at your company and like you will get the permissions that you need. The, the problem is like, if you haven't done your own proof of concepting and you're just letting yourself be blocked, even just to prove it, like you're kind of, you're kind of proving the problem, which is that you haven't really thought through the problem that you're trying to solve with this data.

• 32:49Claire Vo?

  Well, and I, you know, I think we could spend another hour and a half going through specific workflows, but what I want to really talk to you about next is how do you decide what to automate? And, you know, you opened our, our discussion with saying, there's just very high opportunity cost on your time, and I feel that when you can like experience the infinite love of looking into your newborn's eyes or schedule doctor's appointments, like you're clearly, you're the, the value of your time is very important. And layer on top of that, being an entrepreneur where there's like literally a dollar amount attached to your time that can only be created if you go to work.

• 33:31Claire Vo?

  It, it does feel existential to try to figure out the right things to automate and the right things to keep your human time on. So what are some of the frameworks you use to even just decide what to do?

• 33:43Speaker 00

  Yeah, let me show you. I have like a little diagram. So basically, the way I think about this is like for any possible task, if I were 10 times better at it, would it have 10 times the impact? And if the answer to that is no, then I just automate it. And if the answer to that is yes, like, those are the things that I want to put more time and effort into. And 10 times the impact here, like, in a work context, like if I'm managing a team and I'm trying to decide for people on my team, do I want you spending time on this or is this busy work? That framework works from like a,

• 34:27Speaker 00

  you know, if you get 10 times better at moving pixels around a PowerPoint deck, you're not going to be 10 times better at your job. But if you get 10 times better at, um, you know, like pulling important insights out of a body of user research that we can make better decisions about our product on, like, that I want you to focus on. And so that is something that I would not want to automate. But even within like a life context, to me, the impact there is it goes beyond work, right? It's like, I mean, I spent a year building a digital therapeutic to treat depression. And something that I deeply internalized from that was like, you have to carve joy out, or you have to keep joy into your life.

• 35:12Speaker 00

  You have to actively protect joy and all of the things that make being human fun and all the things that make your life worth living. So I also think about that of like, is this something that is going to bring me? Like if I were to really invest in baking this loaf of bread or something, is that something that's going to really enrich me and my life? Or is that something that's going to feel like a chore? And it can be very task dependent. It can depend on what mood that I'm in. But that's sort of the framework that I use. And even within a given task, like you can further break things down. So I said, like, even within this example of I'm giving a talk. And this, I can walk you through like how I would use AI to develop a talk. And for something like that. There are parts of it that are uniquely me and that are uniquely like if I get 10

• 35:56Speaker 00

  times better at this, my life will become 10 times better. And that is like how I come up with the ideas. That is how I craft a compelling narrative that people are going to like respond to and find interesting. That is not building the deck. And so like even within a given thing, you can always break it down into discrete parts and make decisions within those about where you are most valuable and where the AI is most valuable.

• 36:21Claire Vo?

  I think this is just such a useful framework because I agree, there are still things that I feel like it benefits me and benefits the work to not put AI in the process and writing is absolutely one of those. And so for you, as somebody who was chosen to double down on writing as a profession, you know, I tell everybody, look, my, my, my tweets are lovingly crafted with my human fingers because I don't think if I, if I get 10, 10 times better at a, at, you know, posting, I think I will have 10 times the impact. If I get 10 times better at writing long form content, it will have 10 times the impact. Same with this podcast, like if this gets, you know, the interactions, the guest prep,

• 37:06Claire Vo?

  all that stuff, it gets 10 times better, the content gets better. But like cutting, you know, cutting transcripts into like 10 step workflows, I can only get so much better at that. That's not where we're going to add the benefit. And so it's like you do have to do some of this automation. And so if I were going to give folks a takeaway, it is take a couple of tasks in your life where you're really either spending a lot of time or feel overwhelmed and break them down into this framework at two, at the double level. I love like, is the task itself at all in this category? Yes or no? And then if it's yes, what tasks within that category can be partitioned off and then, and then automate them.

• 37:50Speaker 00

  Yes. And one other thing I will add to that, especially if you are a manager of people and you are thinking about. How do I develop the people on my team? Keep in mind that this framework is very, uh, it can change depending where you are on learning curves. And so I don't actually regret all of the time that I spent moving pixels around PowerPoints, because it turned me into the kind of person who like, you could tell me, Hillary, you have to give a talk in 30 minutes. And I'd be like, no problem. I got it.

• 38:24Speaker 00

  But I didn't start there. And so for me, there's a lot of steps of the giving a talk that I've kind of reached saturation on in terms of more reps is not helping me get better. But for somebody on my team, they're often at the bottom of that. And so that thing of like, oh, I feel like I wasted all this time because I was moving pixels around a PowerPoint is like, you, you can't evaluate that, you know, without the context of where you are on that learning curve.

• 38:52Claire Vo?

  I think that's so important for people to hear because again, we're not saying formatting slides is not a valuable thing for a person to spend time on. It is not a valuable thing for you at this point in your career and your skillset to continue to spend, to spend the time on. And again, I'm just going to say, Hillary, you're the same person because yesterday I gave a presentation. And I mean, truly just in time, slide delivery. I was like seven minutes before going live in front of a thousand people. And my slides were very good, very good. Shout out to Gamma for helping me make some amazing slides right out the gate. Great, great use of AI. Well, Hillary, I, again, I think we could go through a million use cases. I know folks can, you know, go to your newsletter and follow you on social for use cases.

• 39:35Claire Vo?

  But I want to, I want to zip over to some lightning round questions. And the first one is less of a question and more of a request in the form of a question, which is, can you show us your recording mode skill? Because this is such an important use case for folks like me and folks like you who need to share AI workflows live on podcasts. I know riches and niches, but you showed me this before the show and I was like, we have to, to have to get this in the, in the closer. So can you pop up that skill and what you, what you built?

• 40:09Speaker 00

  Yeah, I'd be happy to. So this is, okay, meta lesson here is the amazing thing about AI, especially as a product person, is it completely changes the altitude at which you can solve problems. And so I think about this a lot when I think about how AI is amazing because it can help you build more ambitious things. It's not because you can move 10 times as fast or just like make 10 times as many things within the same paradigm that you were previously operating in. It's because it allows you to operate in completely new paradigms, which allow you to have like a 10x scope with the small effort. So I'll say what I mean by that.

• 40:50Claire Vo?

  Okay, so I'm going to start with, with the problem statement for you, which is, you are a lady podcaster with a lady podcaster guest on, and you want to show all your personal workflows on how AI makes your life with your kid and your husband better, and you don't want to dox yourself.

• 41:08Speaker 00

  Yes.

• 41:09Claire Vo?

  What do I do? Hillary, save me.

• 41:12Speaker 00

  So the first thing I tried to do when I had this problem was, oh, I should just make a copy of my context directory that is all blinded and anonymized. And then I was like, that is such a pain to basically create an entire demo environment for myself and have to like manage these two things. Double complexity fails my test. Instead, what I did is I just made a skill called recording on. And basically, when I do that, Claude, anytime it's going to pull up any identifying information, it just changes it before it puts it on my screen. And so it's still pulling from all of my files. It's still pulling from like all the real stuff. The workflows are all the same ones I follow, but it's just going to like change people's

• 41:56Speaker 00

  names and, and things like that. And then when I'm done, I just say, reporting off. And then it goes back. And so it does it. It also tracks like if it starts referring to, you know, this person as person A, it remembers that person A is like the same person. And then nothing, nothing gets changed. If it needs to fix anything that it messed up while recording a demo, it just fixes it for me.

• 42:17Claire Vo?

  And what I have to call out is this is such a cool way to demo Claude code, which I think is awesome. But now I'm thinking about folks that are maybe selling B2B software who have to demo their app. And my personal workspace, for example, on Chat, ChatP R D is the best demo app. It's so rich in information, but a lot of that we pull in, like customer insights and financial data and all this stuff. And I'm like, oh, my gosh, I need to have like a toggle for recording on mode where anytime I'm demoing live in my app, it does, it pulls from my production data sources, but anonymizes them in a way that I'm not sharing customer, customer data. Brilliant. 10 out of 10 idea. We're going

• 42:58Claire Vo?

  to clip this one for, for TikTok and put it on there. And I think this does just show there are like these micro problems that in hindsight, like what you say, double complexity to solve. I was trying to demo my OpenClaw and I literally had the OpenClaw make a web app of the conversation and redact the data because I couldn't scroll through my Telegram on YouTube and show all my kids' information. And so again, the ability to solve these tiny, tiny, tiny problems is so fun and so impactful with AI.

• 43:32Speaker 00

  Can I show you very quickly how I do it?

• 43:35Claire Vo?

  Yeah, please.

• 43:36Speaker 00

  Okay, so I sometimes see these like the skill libraries on the internet and no offense to these skill libraries, but it feels to me like the feeling of somebody taking their toy chest and like dumping it on my head and all this stuff falls on me. And I'm like, I don't know what this is and I don't want it in my space. And so a question I get a lot is people are like, oh, how you like, you know, like the workflow I set up, for example, for Plan My Day, like, how did you do that? And it's so simple, it's so easy, but it does not involve any of these like skills from the internet, which I don't even know what those are. Like, I like to say with all of this stuff, I always reason from first principles because I have no idea what I'm doing. And that's how I feel like when I talk to Claude, it's just me being like, I don't know how this works, fix it. I don't know how this works, fix it.

• 44:21Speaker 00

  Like, you don't need any specialized knowledge to do any of this. And so just to give you a quick example, like, one problem I hate have is returns, right? Like, I hate doing them, I forget about them, it's always at the bottom of my to-do list, and then I miss the deadline. So what do I do? I just tell Claude, like, "Hey Claude, I keep forgetting to return things on time. Also, I hate them. Just have to get that off my chest. I want you to come up with some solutions to make this easier for me. What do you got?"

• 44:52Claire Vo?

  I love that we're all trauma dumping on Claude.

• 44:55Speaker 00

  Exactly. The trauma of my return pile. So, you know, Claude asked me some questions. I do like the pattern of like, have Claude ask you questions, but my patience runs out after about three. So, you know, I'll tolerate a couple, and then I just say, "Use your judgment, figure out from here." So it basically asked me a few questions, and we kind of riffed back and forth on like, it trying to understand the shape of the problem, which is funny, people sometimes are like, "Oh, you're like, you're like product managing Claude." And I'm like, "No, Claude is the product manager. I'm the user."

• 45:33Claire Vo?

  I'm the product.

• 45:34Speaker 00

  Like, I'm telling Claude my problems, and Claude is solving them for me. So we're just kind of going back and forth, and I'm like, "All right." You know, I forgot what its first idea was. "Every time you buy something online, I can add a reminder to your reminders file with the return by date." Uh, yeah, great, cool, let's try that. "So, I like your first idea, but I don't want to have to tell you what I ordered. Can't you just figure that out?" So often I intang to Claude, "Can't you just do it? Like, can't you just figure this out?" My favorite question to ask people, too, people if I'm managing them, "What would have to be true for this to be yes?" And then Claude starts thinking, and Claude's like, "Oh, I could do all of this for you." So, you know, what would have to be true is I would need email access.

• 46:19Speaker 00

  And then we're kind of talking about that and I'm like, okay, I'm like, I'm into that. It offered to sort of integrate it into my daily workflow. But as I said, like, I like to kind of test run things a few times before I integrate them into something that's working. Because then if it breaks, the thing that was working is now broken. So I say, let's just run this a few times. I don't want to integrate it into my daily workflow yet. And it's like, okay, so you just need a script. Uh, it asks me a couple more questions. And eventually it just says, okay, I'm going to look at how your email address or your email access is set up. Here's what I'm going to build. Let me build it. Oh, yeah. Great question. I didn't even think about this. It was like, where, where do you have to go to do the returns? And I was like, I don't know, man.

• 47:04Speaker 00

  That's part of the problem is I never know where I have to go for the return. So it's like, okay, I'll take care of that for you too. And then basically what it does, like it built a skill. So it made slashed command returns. It writes a skill file, which is just the markdown file. It writes the script, which is the code that it needs to run to do all of this stuff. And here's what that looks like. This is the skill file, so it's just a markdown file. And it literally just has English instructions that a person could follow, but it's cloud following it. Uh, with some code that it will run to do all of this. This is actually funny. It like went in and polled, uh, return policies for like different retailers and like drop off info for Nike. Like, cool. Okay.

• 47:49Speaker 00

  And so that like just literally me just describing this problem to it. And now all of a sudden it just will do it for me.

• 47:56Claire Vo?

  I am going to steal this. I love this idea of let's presume I'm going to have to return something and work backwards from that presumption. As opposed to me getting in the panic mode at day 35 being like, pretty please, can I return this doors from rack? I really don't fit in it. Um, so I think that, again, that idea of like, you can preemptively solve problems you might have with AI in a very low cost way. Is super powerful and you don't have to start with a big, complex. Python script or anything like that. You just have to start with a problem statement. So I'm going to. Ask you that as our last lightning round question, which is, what would you say to folks? Because again, you started this saying like, you know, I don't really like a system. I'm coming to this with a beginner's mindset.

• 48:41Claire Vo?

  It's not that scary. And then we've spent the entire episode in like Claude code in the terminal and monospace font in dark mode. Like you are a life hacker right now, my friend. And so for folks, for like, you know, again, you want to demystify this a little bit. How do you, what, what do you say to people about, you know, getting over that fear, that initial hump, getting started and just installing Claude code for non-code reasons?

• 49:11Speaker 00

  I think the best advice that I have heard and that I try to give to people is just like, try to do one thing with it every day. And like, you just need to build the muscle memory so that you start to reach for it and you start to have your brain rewired so that you think, oh, the alien that lives in my computer could probably help me with this. And that seems so obvious, but it's like building any habit. Like you can intellectually understand it, but you still just need to, to do it every day and, and eventually it will start to feel like second nature to you. I was one of those people who was like, I'm never going to work in the terminal, like just a non-starter for me.

• 49:53Speaker 00

  And the only reason I did was because I was using Cursor and I kept hitting my, my limits on Cursor and then I would begrudgingly go over to the terminal and work in Claude code until my cursor reset. But then eventually I got used to the terminal and eventually it was like a week. And then I, once I got used to it, I realized the incredible power that it has. And then I just started playing around with it and then it became fun.

• 50:18Claire Vo?

  Amazing. Well, Hillary, this has been again, just a superstar episode showing how you can track your to-do list, your calendar, build yourself skills, just do everything, as you said, with that little alien in, in the machine, Mr. Claude, Mr. or Ms. Claude, Claude Code.

• 50:37Claire Vo?

  Where can we find you and how can we be helpful?

• 50:39Speaker 00

  Oh, amazing. Thank you for asking. You can find me on the internet. Best place to find me is Substack. I have a newsletter, hills.substack.com, where I write about

• 50:49Speaker 00

  All this stuff that we talked about here today. I have a course that I teach for managers on how to use AI and a few different events that I run for women, especially who want to get involved in AI. But the best way to keep track of any of that is just to follow me on Substack and I will post about everything there.

• 51:07Claire Vo?

  Amazing. Well, Hillary, I know your time is worth a lot, so I'm going to get you out of here. Thanks for joining How I AI.

• 51:12Speaker 00

  Thank you for having me.

• 51:15Claire Vo?

  Thanks so much for watching. If you enjoyed the show, please like and subscribe here on YouTube or even better, leave us a comment with your thoughts. You can also find this podcast on Apple Podcasts, Spotify, or your favorite podcast app. Please consider leaving us a rating and review, which will help others find the show. You can see all our episodes and learn more about the show at howiaipod.com. See you next time.