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

Aug 23, 2020 • 1h 7min
#11 - Interview with Eric Martel
We're back after a week-long hiatus with an interview. This time, we chat with Eric Martel, Director of Artificial Intelligence and Machine Learning at Eidos-Montréal. We re-visit some of the gream games of the past, talk about console development considerations for modern games, and dig into how artificial intelligence and machine learning are going to revolutionize the engineering process.
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 9, 2020 • 53min
#10 - Interview with Sara Chipps
In this episode of The Work Item, we interview Sara Chipps, Director of Public Q and A at Stack Overflow. Sara is also the founder of JewelBots, a company that provides electronic building kits for young inventors. We chat with Sara about community feedback, engineering management career tracks, and building tools for STEM inclusivity.
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!

Jul 20, 2020 • 52min
#9 - Interview with Philipp Cannons
In this episode of The Work Item, we interview Philipp Cannons, CEO and founder of PMFIT.AI - a startup that aims to accelerate product success. Philipp talks about his experience starting a business from scratch and building a deep understanding of large organizations.
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!

Jul 19, 2020 • 1h 1min
#8 - Interview with Charmaine Lee
In this episode of The Work Item, we interview Charmaine Lee, product manager intern at Microsoft, and a friend of the show. Charmaine talks about her experiences breaking into tech, building projects for fun, and being engaged in local tech scenes.
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!

Jul 5, 2020 • 60min
#7 - Interview with Dan Fernandez
In this episode of The Work Item, we interview Dan Fernandez, VP of Product for Developer Services at Salesforce. Dan, a tech veteran, talks about product management, skill stacking, and building great developer experiences.
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!

Jun 28, 2020 • 1h 7min
#6 - Interview with Matt Swanson
Today, we had the honor of having an in-depth conversation with Matt Swanson, a software engineer at SEP, on engineering best practices, design systems, and managing complexity.
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!

Jun 21, 2020 • 1h 7min
#5 - Interview with Jin Yang
A virtual fireside chat with Jin Yang, VP of design at CapitalOne. We discuss leadership, building great teams, and wrap up the show with food place recommendations.
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!

May 3, 2020 • 54min
#4 - Interview with Clint Rutkas
In this episode, Courtny Cotten and Den Delimarsky chat with Clint Rutkas about PowerToys - a fantastic set of utilities for Windows power users.
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!

Apr 12, 2020 • 1h 4min
#3 - Interview with April Speight
In this episode, Courtny Cotten and Den Delimarsky chat with April Speight, Senior Developer Advocate at Microsoft, about social media, writing Python books for kids, and more.
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!

Apr 5, 2020 • 29min
#2 - Career Starts
In this episode, Den and Courtny are talking about their career starts.
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!