Hi Reader, This month marks 4 years since I started Chill Labs and went fractional. What I’m Noticing It wasn’t because I wanted less work. It was because I wanted better, more interesting work. Work with people I choose. Going fractional was my first act of “automating myself” as an entrepreneur. Not with AI, but by redesigning how I work. Now, I use them in tandem: I work with a portfolio of clients, and I automate the parts of work that don’t need me. That’s the Automate Yourself...
about 1 month ago • 1 min read
Hi Reader, You don’t learn this stuff by reading more. You learn it by doing. And doing it with other people. What I’m Noticing AI is moving fast, and a lot of people are trying to keep up all on their own. Solo learning looks productive. New tools, new prompts, new threads. But it often turns into parallel play: everyone is experimenting separately, and nobody is getting meaningfully better together. I see this in teams all the time. Five people “trying AI”. Each person learning different...
about 1 month ago • 2 min read
Hi Reader, This month on Automate Yourself, I sat down with Yves Junqueira, a former Google SRE and founder of Pipeboard. We explored how automation is transforming what's possible for solopreneurs and small teams, and Yves shared insights from his journey building AI tools that help businesses do more with less. What we covered: - The automation mindset from Google: How Yves's SRE background shaped his approach to building systems that scale without constant human intervention - Empowering...
about 2 months ago • 1 min read
Issue #4 Why Most Automation Fails (Lessons Learned from Google SRE) A framework for understanding processes before you automate them The Two-Month "Simple" Task "Just move the cluster to the new datacenter. How hard could it be?" That was my thinking when I started what seemed like a straightforward automation project at Google. We needed to move SmartAds' click-through rate prediction system, a critical ML pipeline that helps decide which ads to show users. The manual process existed,...
4 months ago • 4 min read
Issue #3 How One CEO Multiplied His Impact with 40+ AI Agents Ever wonder what happens when someone actually runs an entire marketing department with AI agents? My guest this week, Jacob Bank, is doing exactly that. I'm thrilled to share the second podcast episode of the “Automate Yourself” podcast, featuring Jacob Bank, CEO of Relay.app and former Google Product Management director. Jacob’s journey from academia to leading AI-driven innovations across multiple startups and Big Tech shares a...
6 months ago • 3 min read
Issue #2 I Can Do Anything Now: How AI Renewed One Netflix Developer's Love for Engineering In a rapidly evolving tech landscape, the ability to adapt and leverage new tools is more crucial than ever. The latest podcast episode of “Automate Yourself Out of a Job and Into a New Career,” hosted by Dina Levitan and Chill Labs, features a compelling conversation with Deonna Hodges, a senior software engineer at Netflix and a passionate advocate for AI and automation. Deonna’s journey offers a...
7 months ago • 5 min read
Issue #1 Why "Automate Yourself Out of a Job" is the Best Career Move You'll Ever Make There's a saying that we used a lot in Google's Site Reliability Engineering (SRE) team: "Automate Yourself Out of a Job." Counterintuitive? Absolutely. At first glance, it sounds like terrible career advice. But dive deeper, and you'll discover this philosophy might be the most powerful career strategy for our times. The Origin Story In Google's SRE culture, this mantra means: Systematically eliminating...
8 months ago • 2 min read
