How to find work you love | Bob Moesta (Jobs-to-be-Done co-creator, author of "Job Moves”)

How to find work you love | Bob Moesta (Jobs-to-be-Done co-creator, author of "Job Moves”)

Lenny's PodcastFeb 23, 20251h 24m

Lenny Rachitsky (host), Bob Moesta (guest), Christina Cacioppo (guest), Alison Reisner (guest)

The core idea and research behind the book *Job Moves*Four “quests” that explain why people change jobsEnergy drivers vs. energy drains and how to identify themDesigning and prototyping your next career moveTrade-offs between job features (salary, title) and experiencesJobcations and recovering from burnout or intense startup rolesUsing this framework for hiring, managing, and founder self-awareness

In this episode of Lenny's Podcast, featuring Lenny Rachitsky and Bob Moesta, How to find work you love | Bob Moesta (Jobs-to-be-Done co-creator, author of "Job Moves”) explores design your career like a product to find work you love Bob Moesta, co-creator of Jobs-to-be-Done, shares a practical framework from his book *Job Moves* for finding and designing a job you genuinely love. Drawing on 1,000+ in-depth career interviews, he explains why most people change jobs for the wrong reasons and end up worse off. The conversation introduces four core “quests” behind any job change, the importance of mapping energy drivers and drains, and how to prototype potential careers through targeted informational interviews. Moesta also shows how individuals and companies can reshape roles around human experiences—not just features like title and salary—to improve fit, retention, and long-term progress.

Design your career like a product to find work you love

Bob Moesta, co-creator of Jobs-to-be-Done, shares a practical framework from his book *Job Moves* for finding and designing a job you genuinely love. Drawing on 1,000+ in-depth career interviews, he explains why most people change jobs for the wrong reasons and end up worse off. The conversation introduces four core “quests” behind any job change, the importance of mapping energy drivers and drains, and how to prototype potential careers through targeted informational interviews. Moesta also shows how individuals and companies can reshape roles around human experiences—not just features like title and salary—to improve fit, retention, and long-term progress.

Key Takeaways

Understand which of the four career quests you’re on before moving

Most job changes fall into four quests: get out (escape a bad situation), take the next step (progress and growth), regain control (of time and workload), or realign (back to your strengths and what you enjoy). ...

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Focus on job experiences, not just features like salary and title

Features (comp, title, perks) are static, while experiences (how your days feel, how you’re treated, what you actually do) determine whether you stay and thrive. ...

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Map your energy drivers and drains to define your “job requirements”

Reflect on past roles, projects, and even school to list moments that gave you energy and those that exhausted you, then analyze *why*. ...

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Prototype career paths through wide, intentional informational interviews

Instead of blindly applying to roles, generate a wide set of possible paths that fit your strengths and quest, then interview people actually doing those jobs. ...

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Accept and consciously choose trade-offs instead of chasing a perfect job

No role checks every box; satisfaction improves when you deliberately choose what you’ll give up (e. ...

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Use jobcations and time off to reset your identity after intense roles

After high-burnout environments like startups, Moesta argues you often no longer know who you are outside that context. ...

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Companies should design roles around people’s strengths and experiences

Job descriptions are usually ad hoc lists of tasks and credentials, not descriptions of real experiences or outcomes. ...

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Notable Quotes

The moment you stop making progress in your career is the moment you start looking for another job.

Bob Moesta

Employees hire companies more than companies hire employees.

Bob Moesta

Most people change jobs and end up with a job that’s worse than the one they were at, because they don’t know themselves well enough.

Bob Moesta

Job descriptions are made up. They’re basically a list of stuff the manager doesn’t want to do.

Bob Moesta

If you can pull the ratio to 50/50 between energy drains and energy drivers, you don’t even know you’re working anymore.

Bob Moesta

Questions Answered in This Episode

How can I practically distinguish whether I’m on a “get out,” “next step,” “regain control,” or “realign” quest in my own career right now?

Bob Moesta, co-creator of Jobs-to-be-Done, shares a practical framework from his book *Job Moves* for finding and designing a job you genuinely love. ...

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If I mapped my last three years of work into energy drivers and drains, what surprising patterns might I find—and how would that change the roles I consider?

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Which trade-offs have I been unconsciously making (e.g., money over learning, prestige over balance), and which ones am I actually willing to choose going forward?

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How could I prototype two or three completely different career paths over the next month using informational interviews without risking my current job?

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If I’m a hiring manager, what would it look like to rewrite one of my current job descriptions around experiences and outcomes instead of years of experience and tools?

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Transcript Preview

Lenny Rachitsky

You just wrote a new book called Job Moves that I have right here. What's, kind of, just the big idea behind this book?

Bob Moesta

The moment you stop making progress in your career is the moment you start looking for another job. And so over the last 15 years, we've interviewed over 1,000 people, I've coached almost 1,000 people. Because I think there's a billion people a year who switch jobs, and ultimately most of them end up with a job that's worse than the one they were at, but they don't know how to find it. They don't know themselves well enough.

Lenny Rachitsky

There's a very tactical piece of advice in your book which is the idea of a jobcation.

Bob Moesta

When you're in a startup, it changes who you are. And the moment that you get out of that environment, you need to take the time to reset your mind and your body. I call it a jobcation, which is a job I can go do with one hand tied behind my back so I can rest and recover to go do something else. It's about actually being able to go to the gym and work out, and have some vacation. The moment you get comfortable with doing nothing, you know who you are again, and you can actually figure this out.

Lenny Rachitsky

You have this really interesting distinction in the book between job features like salary, and title, and job experiences.

Bob Moesta

It's very simple, uh, very similar to product. There's a difference between product features and product experiences, and what you start to realize is it's the experiences that keep you at your job. It's not just about the money, because you start to realize money is a surrogate for respect, or, "I've got bills to pay." Or, "I'm falling behind." Money has actually many, many different implications to it, 'cause everybody wants more money. But the question is why do you want more money?

Lenny Rachitsky

(instrumental music) Today my guest is Bob Mesta. Bob is the co-creator of the Jobs to Be Done framework and worked alongside Clay Christensen for many years. He's also started nine different companies. He's currently the co-founder and CEO of The Rewired Group. This is Bob's second visit to the podcast. In our first conversation, we got super deep on the Jobs to Be Done framework. In this conversation, we talk about his new book that he believes is gonna be even more impactful to the world than the Jobs to Be Done framework. The book is called Job Moves. It's basically a very tactical guide to finding a job that you love. I won't give it away, but if you're struggling to find a job, or hate the job that you are currently in and aren't sure what to do, or you want to get better at hiring and keeping amazing people, this episode is for you. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes, and it helps the podcast tremendously. With that, I bring you Bob Mesta. This episode is brought to you by Eppo. Eppo is a next generation A/B testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Miro, ClickUp, and DraftKings rely on Eppo to power their experiments. Experimentation is increasingly essential for driving growth, and for understanding the performance of new features, and Eppo helps you increase experimentation velocity while unlocking rigorous deep analysis in a way that no other commercial tool does. When I was at Airbnb, one of the things that I loved most was our experimentation platform, where I could set up experiments easily, troubleshoot issues, and analyze performance all on my own. Eppo does all that and more with advanced statistical methods that can help you shave weeks off experiment time, an accessible UI for diving deeper into performance, and out of the box reporting that helps you avoid annoying prolonged analytic cycles. Eppo also makes it easy for you to share experiment insights with your team, sparking new ideas for the A/B testing flywheel. Eppo powers experimentation across every use case, including product, growth, machine learning, monetization, and email marketing. Check out Eppo at geteppo.com/lenny and 10X your experiment velocity. That's geteppo.com/lenny. This episode is brought to you by Vanta, and I am very excited to have Christina Cacioppo, CEO and co-founder of Vanta joining me for this very short conversation.

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