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

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. How do you decide what to automate? 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. 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. 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. Welcome back to How I AI. I'm Claire Vo, 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, Hilary 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. But there's a catch. These tools only work well when they have deep access to company systems. Your co-pilot 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. 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 kind of changed life now. So bring us up to date. What's been happening in the last year? 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 of change and I'm really excited to show you what I've been up to. 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? 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? That's right. We are upgrading. And what I love about what we're talking about before we started recording is, yes, what we're going to show is going to be a cool, like a 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. 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 a thousand more life admin things and logistics than I ever have been before. And I'm historically 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. 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. 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 it pulls all this kind of stuff. And I'm like, but you, 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 this sort of like the anti-systems system. That's, that's my philosophy in all of this. 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, I'm 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 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? 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? You're never going to guess in a million years. So I'll just tell you, this is Al Gore's desktop. That is not what I was expecting. I just looked at that 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. 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 extremely chaotic desktop. Because I think that is sort of like the state of how I felt about all the stuff I was trying to keep track of when I started setting up this system. 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. 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, you know, three priorities that I absolutely 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, where are the hours of the day when I'm most effective? 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, 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, 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. This one makes me laugh because I was complaining about how if I do certain types of work before bed, I don't, I stay up too late because I get into flow. Yeah. And so, like, noted. Thanks. Thanks a lot. So that's what it's pulling from. And then it goes ahead and it makes, 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 need to take a lot of screenshots. No, 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. 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. Amazing. I tweet for one person, Clara. That is Clara Vo. Amazing. Okay. So what I, what I like about this and what you've shown is, okay, so it's pulling from your preferences on schedule. It's got a, 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. Yes. And so I appreciate this because I don't want it to just take what I say literally. Because I say things all 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. 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. You know, I've had a, a executive assistant a couple 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. 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. But calendar management fails my test of, like, is this tedious life admin work? Like, oh, you got to 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 help me with that, I'm like, this is so obviously the right way 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? This episode is brought to you by Lovable. If you've ever had an idea for an app but didn't know where to start, Lovable is for you. 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, did I actually book that post office appointment? How did this all go? How do you do this, like, quality control loop on your Plan My Day agent? Yes. So another thing you will find about me when you're seeing these demos is I always resist the urge to have Claude, like, connect all a bunch of stuff in the background and get this information itself. Mostly because, like, 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. Like, freaks me out. But I do believe in my heart of hearts in the Yapper's 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. 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 multi-purpose tool, I can use it to do literally anything that involves my computer. It means that I'm then, like, talking to it all day about the things that I'm doing. And then Claude observes that and takes notes. And so I will 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, 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. 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 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 folder structure. And so it has my schedule that it has put into my calendar. And the other thing this has is 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. 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 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, the value of your time is very important. Then, 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. 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? 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, 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, 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. 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 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. 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 has chosen to double down on writing as a profession, you know, I tell everybody, look, my tweets are lovingly crafted with my human fingers because I don't think if I, if I get 10 times better at 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 those podcasts. Like, if this gets, you know, the interactions, the guest prep, 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 get folks a takeaway, it is take a couple 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 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 automate them? 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, 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. 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 can't evaluate that, you know, without the context of where you are on that learning curve. 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 skill set 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. 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, have to get this in the closer. So can you pop up that skill and what you, what you built? Yeah, I'd be happy to. So this is, okay, metal 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 show you what I mean by that. 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. Yes. What do I do? Hillary, save me. So the first thing I tried to do when I had this problem was, oh, I should just make a copy of my contacts 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 names and things like that. And then when I'm done, I just say reporting off and then it goes back. And so it doesn't, Getting over that fear, that initial hump, getting started, and just installing Claude code for non-code reasons. 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 do it every day 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. And the only reason I did was because I was using Cursor and I kept hitting 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 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. 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 the machine, Mr. Claude, Mr. Ms. Claude code. Where can we find you and how can we be helpful? 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 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. 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. Thank you for having me. Thanks so much for watching. 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