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

**Hilary Gridley** (0:00)
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.

**Claire Vo** (0:12)
How do you decide what to automate?

**Hilary Gridley** (0:15)
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.

**Claire Vo** (0:32)
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.

**Hilary Gridley** (0:39)
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.

**Claire Vo** (1:01)
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 Work OS. 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 codebase. 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 Work OS comes in. Work OS gets 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 Work OS to move faster and meet enterprise demands. Join them and hundreds of other industry leaders at workos.com.
Start building today. Hilary, 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?

**Hilary Gridley** (3:10)
A lot has changed. A lot has changed in my life, and in AI. Talking about custom GPTs almost feels so quaint now. It's like 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.

**Claire Vo** (3:39)
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?

**Hilary Gridley** (4:12)
That's right, we are upgrading.

**Claire Vo** (4:14)
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, we get 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.