

The Work Item - Real Talk on Tech's Toughest Career Choices
Den Delimarsky
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.
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.
Episodes
Mentioned books

Dec 12, 2023 • 42min
#64 - Diving Into Industrial Design, with Anson Cheung
Anson Cheung is a San Francisco-based industrial designer with more than ten years of experience shipping hardware. It's not often that we talk to someone who produces physical things, and naturally I was excited to learn more about what Anson works on and how we can discover pathways into an industrial design career track. In this show, we discuss Anson's origins, working with a large design firm vs. going solo, and what are some ways in which an aspiring industrial designer can hone their craft without investing thousands of dollars.
You can find Anson on the following sites:
🤵 LinkedIn
📝 Website
📰 Design Things Newsletter
The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.
Feedback
If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

Nov 8, 2023 • 45min
#63 - Beyond Just Engineering Skills, with Adrienne Braganza Tacke
Adrienne Tacke, a Senior Developer Advocate at Cisco and author, dives into the nuances of career growth in tech. They discuss the importance of intentional career paths and effective mentorship, particularly for underrepresented groups. Tacke shares insights on balancing roles and managing imposter syndrome while navigating remote work challenges. Fascinatingly, she also reveals her unexpected journey from aspiring pastry chef to tech advocate, using food analogies to explain complex concepts like APIs. It's an engaging blend of personal story and professional wisdom!

Oct 23, 2023 • 36min
#62 - Building Sustainable Practices, with Jason Fried
Jason Fried is the co-founder and CEO of 37signals, the company behind Basecamp and Hey. I chat with Jason about his path to entrepreneurship, the lack of value in a lot of meetings, and generally building sustainable practices that enable businesses and their employees to thrive.
You can find Jason on the following sites:
💼 LinkedIn
📝 37signals Blog
📝 ShapeUp
📝 Jason on world.hey.com
✉️ Hey
🏔️ Basecamp
The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.
Feedback
If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

22 snips
Oct 9, 2023 • 55min
#61 - Career Moats And Beyond, with Cedric Chin
Welcome friends to the fourth season of The Work Item podcast. I am starting the yearly series with some fantastic guests, and today is no exception.
To start us off, I am chatting with Cedric Chin - the founder of the CommonCog blog and business series. You might've read some of Cedric's writing on career moats before (I know I have). Cedric has a wealth of experience in managing engineering teams and has embarked on a quest to build a deep understanding of business and development principles from the ground-up.
We're glad you're here, listening to this show. Enjoy!
You can find Cedric on the following sites:
🐘 Mastodon
📝 CommonCog Blog
📰 Commonplace Newsletter
🎙️ Commonplace Expertise Podcast
The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.
Feedback
If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

Dec 28, 2022 • 48min
#60 - Defining A Force Multiplier, with Sam Saccone
When we choose our career path, we often try to optimize for one specific bucket - you're a product manager, or a project manager, or a UX designer, or any other variation of an expertise area in tech. Sam Saccone defies the expectations of a single role and instead believes in being a “plumber” - doing whatever work is necessary to enable others to do their own version of great work.
I sat down with Sam to learn more about his path to a Senior Staff Engineer at Google, what it means to brute-force your way through problems, and what the best avenues are to become a force multiplier for your team.
You can find Sam on the following sites:
🐘 Mastodon
🐤 Twitter
📝 Blog
The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.
Feedback
If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

Dec 22, 2022 • 39min
#59 - Building On Your Own, with iOS Developer Donny Wals
Leaving your full-time job behind and starting your own business based on your own brand is a somewhat scary proposition. And yet, this is exactly what Donny Wals, a prolific iOS developer and technology teacher, is doing. In this episode I sat down with him to talk more about his work, what was his thinking in going solo, and what one needs to learn quickly in an ever-changing technology space.
You can find Donny on the following sites:
🐤 Twitter
📝 Blog
💼 LinkedIn
📸 Instagram
The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.
Feedback
If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

Nov 2, 2022 • 59min
#58 - Becoming a Game Studio Co-Founder, with Moon Studios' Gennadiy Korol
Working on games is hard. It's even harder to go from an engineer to a founder of a game studio that is able to produce two blockbuster titles in a row. In today's show I chat with Moon Studios co-founder Gennadiy Korol about his work on Ori (if you're near an Xbox or a PC - the game is worth your time), learning the complexity of graphics engineering, and navigating the uncertainty that comes from starting a zero-to-one effort where you have nothing to fall back on.
You can find Gennadiy on the following sites:
🐤 Twitter
You can learn more about Gennadiy's work as well:
📝 Moon Studios
🐤 Moon Studios - Twitter
📝 Ori - The Game
The podcast was produced by Den. Music by Wataboi from Pixabay.
Feedback
If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

Oct 29, 2022 • 38min
#57 - From Turbo Pascal to CodePen, with Chris Coyier
If you are a web developer, chances are that you used CodePen more than once. You're also probably very familiar with CSS-Tricks for, well, more than just CSS tricks. The man behind these experiences, Chris Coyier, actually started his journey some time ago with a programming language called Turbo Pascal - many steps removed from web development. I sat down with Chris to talk more about his career, lessons in getting CodePen out into the world, and so much more.
You can find Chris on the following sites:
🐤 Twitter
📝 Website
The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.
Feedback
If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

Oct 10, 2022 • 28min
#56 - Reverse Engineering The Halo API with Alexis from HaloDotAPI
If you ever played any of the Halo games, you probably know that there is a wealth of data being exchanged between the game and Halo services. This includes stats and so much more. If you've ever wanted to use those stats, you also probably ran into HaloDotAPI - a Halo API wrapper for Halo Infinite and Master Chief Collection. Behind all of this work is one individual - Alexis, or Zeny_IC (on both Twitter and Xbox Live).
Today I chat with Alexis about his early roots, what led him to explore reverse engineering as a viable career path, as well as what it took to actually figure out the Halo API.
You can find Alexis on the following sites:
🐤 Twitter - Alexis
🐤 Twitter - HaloDotAPI
The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.
Feedback
If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!

Aug 27, 2022 • 42min
#55 - Open Source and Web Development, with Monica Powell
What does one need to do to make open-source code more approachable? How do you figure out which teams to join for maximum positive impact on your communities? And how do you build communities? These questions and more are the topic of my conversation with Monica Powell, software engineer extraordinaire, who also happens to be a GitHub Star - an exclusive group of contributors recognized for their outstanding work in the open-source software space!
You can find Monica on the following sites:
🐤 Twitter
📝 Blog
The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.
Feedback
If you haven't already, make sure to subscribe to the show and leave a review or a rating, wherever you are getting your podcast. I really appreciate your feedback and am working to make this podcast more useful for you, the listener, with every episode. Ratings and feedback make it so others can easily discover and enjoy the insights you listen to here!