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

Author: Den Delimarsky

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© 2025 by Den Delimarsky. All rights reserved.

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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.



94 Episodes
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#1 - Remote Work

#1 - Remote Work

2020-03-1556:14

In this episode, Courtny Cotten and Den Delimarsky talk about what it takes to work remotely, along with some tips and best practices.
#2 - Career Starts

#2 - Career Starts

2020-04-0529:29

In this episode, Den and Courtny are talking about their career starts.
#3 - Interview with April Speight

#3 - Interview with April Speight

2020-04-1201:03:33

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.
#4 - Interview with Clint Rutkas

#4 - Interview with Clint Rutkas

2020-05-0353:59

In this episode, Courtny Cotten and Den Delimarsky chat with Clint Rutkas about PowerToys - a fantastic set of utilities for Windows power users.
#5 - Interview with Jin Yang

#5 - Interview with Jin Yang

2020-06-2101:06:42

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.
#6 - Interview with Matt Swanson

#6 - Interview with Matt Swanson

2020-06-2801:07:13

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.
#7 - Interview with Dan Fernandez

#7 - Interview with Dan Fernandez

2020-07-0559:37

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.
#8 - Interview with Charmaine Lee

#8 - Interview with Charmaine Lee

2020-07-1901:00:42

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.
#9 - Interview with Philipp Cannons

#9 - Interview with Philipp Cannons

2020-07-2051:51

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.
#10 - Interview with Sara Chipps

#10 - Interview with Sara Chipps

2020-08-0952:43

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.
#11 - Interview with Eric Martel

#11 - Interview with Eric Martel

2020-08-2301:07:01

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.
#12 - Interview with Christina Weng

#12 - Interview with Christina Weng

2020-09-2058:41

In this episode of The Work Item we interview Christina Weng, product designer at Facebook, about building a career in user experience design from scratch.
#13 - Interview with Amanda Silver

#13 - Interview with Amanda Silver

2020-09-2701:00:35

In this episode of The Work Item we interview Amanda Silver, Corporate Vice President, Developer Division at Microsoft. We discuss the process of building great developer tools, the human element in product design, and career advice for the long run.
#14 - Interview with Richard Lander

#14 - Interview with Richard Lander

2020-10-1801:03:30

In this episode of The Work Item we interview Richard Lander, Principal Program Manager on the .NET team at Microsoft. Richard does a deep dive on communication, being a generalist vs. specialist, and growing one's career.
#15 - Tarun Gangwani on Innovation, Navigating Product Decisions, and Building Growth Engines

#15 - Tarun Gangwani on Innovation, Navigating Product Decisions, and Building Growth Engines

2020-11-0151:17

We sit down to chat with Tarun Gangwani, Senior Product Manager at Sanity.io. Tarun is a seasoned PM with tons of expertise to share about the product management domain. With previous experience at Twitch, where he oversaw the entire lifecycle of a developer using extensions and data services to create engaging and personalized viewing and streaming experiences, Tarun is talking about lessons learned, differences between startup and large company environments, along with the ways in which product managers can broaden the understanding of their products and customer needs.
#16 - Bill Kenney on Building Brands That Last

#16 - Bill Kenney on Building Brands That Last

2020-11-0801:02:45

This weekend, we go outdoors with Bill Kenney, co-founder of Focus Lab, a branding agency that is entirely remote. We talk to Bill about the importance of a good brand and what distinguishes professionals from amateurs in the field.
#17 - Christos Matskas on Going From Consulting to Corporate and Building Identity Tools

#17 - Christos Matskas on Going From Consulting to Corporate and Building Identity Tools

2020-11-1501:02:46

In a surprising twist, this week we chat with Christos Matskas on two topics - transitioning from consulting life to a corporate life, as well as about building identity tools and services in the cloud.
#18 - Megan Risdal on Building a Career at the Intersection of Data Science and Product Management

#18 - Megan Risdal on Building a Career at the Intersection of Data Science and Product Management

2020-11-2259:04

Right before the Thanksgiving break, we are releasing a fresh new episode with Megan Risdal, Product Lead at Kaggle. Megan took the multi-talented route to the career she has today, and enjoys every bit of it. In this episode, we talk about the importance of being a multi-dimensional professional in a product role, finding the best ways to collect customer feedback, and building communities at scale.
#19 - Wrap Up Episode For 2020

#19 - Wrap Up Episode For 2020

2020-12-2041:26

Den and Courtny reflect on the year we just went through, and discuss our plans for 2021. There is a lot to be thankful for, and we had quite a year kickstarting a new podcast from scratch. This also happens to be the last episode of our Season 1.
#20 - Scott Hanselman on Intentionality

#20 - Scott Hanselman on Intentionality

2021-01-1054:17

Our first episode of the year is with the one and only Scott Hanselman. We tried to come up with a catchy title, but the entire episode could be summarized in one word - intentionality. We discuss Scott's foray into TikTok, building your own definition of success, and fostering strong relationships with people around you.
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