Why "Automate Yourself Out of a Job" is the Best Career Move You'll Ever Make


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 repetitive manual toil
  • Creating space to tackle more complex, impactful challenges
  • Continuously increasing your value by solving harder problems

Automation isn't about making yourself irrelevant. It's about making your old job irrelevant, and evolving into someone who creates even more value.

In an SRE's world, if you're still doing the same tasks you were doing six months ago, that's an issue; by now you could have automated those tasks and moved on to something more strategic.

Today, thanks to AI and other automation tools, this philosophy isn't just for engineers anymore. It's for everyone.

Why It Matters Now More Than Ever

The landscape of work is shifting fast. AI isn't "coming for your job" in some distant future. It's here, reshaping what work looks like today.

The people who thrive in this new world aren't the ones who resist change. They're the ones who use automation to catapult themselves into new opportunities.

Imagine being the person in your company, your industry, or your niche who:

  • Saves 20+ hours a week through smart automation.
  • Creates new value with the freed-up time.
  • Spots opportunities others miss because they're still buried in busywork.
  • Becomes indispensable not because of repetition, but because of reinvention.

That's the future. And it starts by automating yourself out of your current job.

What This Publication is About

This publication is for people who are ready to embrace that future. Together, we'll explore:

  • Real stories of people who automated part of their jobs and unlocked new career directions.
  • Tactical guides on how to start automating your work today, no matter what role you're in.
  • Mindset shifts to help you see AI and automation as fuel, not a threat.
  • New career paths and ideas born from the space automation creates.

We'll turn fear into fuel. We'll turn uncertainty into opportunity. We'll build the future we want, not just react to the future we're given.

Your Next Step

If you're ready to begin this journey, start by asking yourself:

"If I automated away 30% of my current workload, what higher-impact work would I pursue with that time?"

Your answer might reveal the first step toward your next career evolution.

Subscribe to join our community as we navigate this transformation together.

Welcome to "Automate Yourself”. Now is the time to automate yourself out of a job...and into the future. 🚀

Brought to you by Chill Labs

Chill Labs is a boutique consultancy dedicated to helping companies think strategically, solve complex business problems, and streamline their operations. We leverage Product Management and Software Engineering principles, including AI, to help businesses build products that users truly want and achieve sustainable growth. Reach out if you'd like to explore working together. Let's Chillaborate!

Thank you for reading!

Got a question for me or want to share something you're excited about? Just hit reply. I read every e-mail.

Chill Labs

Chill Labs is a boutique consultancy helping companies think strategically, solve business problems, and streamline operations utilizing Product Management, Software Engineering principles and AI. Combining a decade of experience running complex, globally distributed software products with expertise in product discovery, user research, and strategy, Chill Labs helps companies build products that users want and do so in a way that supports growth and scale. Dina Levitan, Founder and Principal at Chill Labs, based out of Seattle, WA, brings over 15 years of experience as a product and technical leader ranging from startups to companies like Google.

Read more from Chill Labs

Hi Reader, This month's idea comes from an Arthur Brooks talk I heard. One line stuck with me: never make the mistake of meeting a complex need with a complicated tool. In AI terms: it's very easy to start using a powerful tool to solve problems that aren't actually tool problems. What I'm Noticing When things feel uncertain (a hard decision, messy collaboration, fear of getting it wrong), we tend to reach for AI the same way people reach for their phone: as a way to calm the discomfort....

So You Want To Go Fractional Lightning Lesson

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...

From Parallel Play to Chillaborating

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...