The Work Item - Real Talk on Tech's Toughest Career Choices

Updated: 07 Mar 2025 • 88 episodes
theworkitem.com

The web is full of podcasts that dole out generic career advice - “Follow your passion!”, “Keep learning!”, “Set clear goals!” This is all good if you’re just starting out, but the pointers start to lose their luster quickly as you progress and start hitting invisible walls in your growth. All of a sudden, it’s harder to get promoted, opportunities to advance become more ambiguous, and the choices in front of you aren’t as obvious as they were when you first started your job. What does it take to get to the Staff engineer level? If you want to become an executive in the future, what should you do now to maximize your chances of hitting that goal? Should you have a time-bound career map or focus on unique opportunities that pop up serendipitously? Should you try your hand at entrepreneurship, and if so - how do you build a robust safety net? For these questions and more, The Work Item is the podcast where I attempt to answer them with help from folks that went through trial by fire. They are not social media thought leaders - they are actual practitioners who have first-hand experience dealing with some of the more thorny challenges in this industry. With folks like Jason Lengstorf (Founder, Learn With Jason), Craig Hewitt (Founder, Castos), Saron Yitbarek (Founder, CodeNewbie), Rob Walling (Founder, MicroConf), Cedric Chin (Founder, CommonCog), Jason Fried (CEO, 37signals), Gennadiy Korol (CEO, Moon Studios), Mayuko Inoue (iOS Engineer, Apple), Camille Fournier, and many, many more you will get extraordinary insights that will help you unlock your career potential beyond the basics you’ll learn elsewhere.

Show episodes

User research is an underappreciated art - we in tech are so used to being immersed in an ocean of quantitative data that we can forget that on the other side of the screen are real humans who want to solve very specific problems. And often times, their problems are extremely hard to put a number on. Why did they aband

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This is the last episode for 2024. To make it special, it’s a supercut of all the unconventional advice from every single guest that was on the show this year - Kent C. Dodds, Jerod Santo, Rob Walling, Adrienne Tacke, David Khourshid, Saron Yitbarek, Rachel Andrew, Katie Fujihara, Lena Reinhard, Miriam Suzanne, Kirupa

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Today, I'm thrilled to be joined by Asia Orangio, the brain behind DemandMaven, a growth agency dedicated to helping SaaS companies and their founders reach new heights. Asia's unique approach blends data-driven strategies with deep empathy for customers, making her a sought-after expert - from bootstrapped businesses

64 min
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If you are listening to this show, you have likely heard of a programming language called Python. And if you are a Python developer, you've likely heard of a podcast dedicated to this programming language - Talk Python To Me. It was started by none other than Michael Kennedy, a Python Software Foundation fellow who man

59 min
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If you've been immersed in the tech world for some time, you probably have heard one specific YouTube channel mentioned more than once - Learn With Jason. It's a project started by Jason Lengstorf, a former VP of developer experience at a web tooling startup (he was a head of developer relations prior to that too), tha

64 min
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Jennifer Wong is a seasoned engineering manager who started her journey in civil engineering. The fast pace of the tech industry drew her in, and she stuck with it for years since making that call. In this episode, I chat with Jennifer about her transition from a non-traditional career path into software, reasons to ta

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