
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

Apr 25, 2021 • 1h 2min
#31 - Lessons In Leadership, with Chad Fowler, VP of Technology at DEVCON
Talking to Chad Fowler, you quickly realize what true leadership means. Chad has extensive experience leading large technical organizations such as LivingSocial and 6Wunderkinder, being a venture partner at BlueYard Capital, and now - helping make the Internet safer as Chief Product Officer at DEVCON. Did I mention that Chad also is a musician?In this episode, I talk to Chad about his work, lessons learned from music and travel and how those apply to life and career, and what is the approach to consider for one to carve out a path towards an executive role.You can find Chad on the following sites:🐤 Twitter📝 Blog🎶 Mahakala Music(Chad's record label)Make sure to also check out Chad's book - The Passionate Programmer.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!

Apr 18, 2021 • 59min
#30 - Creativity in Code and Beyond, with Monica Dinculescu, Engineer Extraordinaire
Folks often forget that engineering is inherently a very creative process. Monica Dinculescu found her own niche where she can build impactful things and do it in some of the most unusual ways possible. An excellent engineer, creative thinker, and fellow Eastern European by origin, Monica joins me today to talk about the things she learned as she figured out her career path.You can find Monica on the following sites:🐤 Twitter📝 Blog🛍 StoreMake sure to also check out Tim Holman's work, that Monica recommended during the show!The podcast was produced by Den Delimarsky. Music by Wataboifrom 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!

Apr 11, 2021 • 1h 15min
#29 - Building Things You Love, with Ben Sandofsky, Head of Development for Halide
From Pascal, to writing image processing code, if there is one word you absolutely can't use to describe Ben Sandofsky‘s career, it would be “uneventful.” He was one of the first mobile engineers at Twitter, had a stint helping build Periscope, and ultimately ventured into unexplored territory to finish a photo app he always wanted, that later became Halide.In this episode, I sit down with Ben to get a better understanding of the decisions he made in his career, and what were the critical turning points that made him start his own studio - Lux.You can find Ben on the following sites:🐤 Twitter📝 Blog📸 LuxWhile at it, you should check out Halideand Spectre- the must-have camera apps for iOS!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!

Apr 4, 2021 • 1h 1min
#28 - The Art of Engineering Management, with Rebecca Murphey, EM at Stripe
From all the questions I get asked, this one comes up quite often - “How do I become an engineering manager?” While I don't know the answer myself, I think I have an idea of who might have the insights on this topic.Rebecca Murpheytried a lot of things on her way to becoming an engineering manager at Stripe - from journalism to advertisement, and even learning how to fly.In this episode, I sit down with Rebecca to learn more about her path, what were the important lessons learned in her non-tech career that helped her be an efficient engineering leader, and what aspiring engineering managers can start doing today to figure out if this career track is for them.You can find Rebecca on the following sites:🐤 Twitter📝 BlogThe 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!

Mar 21, 2021 • 47min
#27 - How to Build a Career in Human Resources, with David Daniels
There is a certain air of mystery around careers in Human Resources (HR), and David Daniels, who is a veteran HR leader in tech, is here to bring some clarity about the work.David has extensive experience being in HR at Microsoft, Pinterest, and now - Snapchat. He shares his insights about going from education to leadership in some of the most prominent tech companies, fighting against the fixed mindset, and uncommon recommendations for folks wanting to get started with their careers.You can find David on the following sites:🤵 LinkedIn📝 BlogThe 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!

Mar 14, 2021 • 59min
#26 - How to Grow as a Product Manager, with Dan Olsen
There is no single, well-defined path to becoming a product manager. There are more questions than answers when it comes to figuring out which skills are necessary, what books or blog posts to read, or which courses to take.Dan Olsen, the author of “The Lean Product Playbook,” former product leader at Intuit, Friendster, Box, and the US Navy (he worked on submarine design) shares with us some insights on what it means to grow as a product manager.You can find Dan on the following sites:🐤 Twitter📝 Blog🎥 YouTube🤵 LinkedIn📅 MeetupMake sure to sign up for Dan's upcoming Lean Product Management online workshop on April 20, 2021.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!

Mar 7, 2021 • 1h 1min
#25 - How to Build a Career in Design and Pitch Gary Vee, with Jack Zerby
Jack Zerbyis not your typical designer. His experience producing music, working at Pentagram and Frog, building startups, pitching to Gary Vee, and now - building tools for creators at Gumroad, puts him square in the middle of a very uncommon career path.In this episode, I chat with Jack to learn more about what motivated him to grow his career, how to break into design, how to make the transition from a big company to a startup, and what does it mean to build compelling narratives in deck format.Make sure to check out Jack's upcoming Design for Decksworkshop to change the way you think about presentations.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!

Feb 28, 2021 • 52min
#24 - Building Communities with Jess Lee
Jess Leeis the co-founder of dev.to- a developer community that emphasizes the importance of a friendly approach to guiding folks through the tumultuous waters of software development.In this episode, we chat about Jess' career, the journey to founding Forem- the open-source platform powering large communities, and her experience building successful distributed teams.The podcast was produced by Den Delimarskyand Courtny Cotten. 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!

Feb 21, 2021 • 59min
#23 - From Servers, Phones, and Voice Assistants to Space with Charlie Kindel
Charlie Kindel is a tech industry veteran who helped bootstrap, grow, and manage teams that built home servers, phones, voice assistants, home automation software, and hopefully soon - space technologies. In this episode, we dive a bit deeper into Charlie's approach to product ideation and design, discuss the importance of having a principled organization, and ask questions about his most recent adventure around space.The podcast was produced by Den Delimarskyand Courtny Cotten. 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!

Feb 1, 2021 • 1h 7min
#22 - Paige Bailey on Building a Career In Artificial Intelligence and Machine Learning
Paige Bailey is one of the few Artificial Intelligence (AI) and Machine Learning (ML) experts who is able to convey complex technical topics in an easy-to-understand and relatable language. Her Twitter feed is full of AI/ML paper recommendations, open source projects, and insights about the ever-evolving tech space. What was her journey like to a career in a very complex domain? What does it mean to build an inclusive AI? This week, we sit down with Paige to learn from her experience.The podcast was produced by Den Delimarskyand Courtny Cotten. 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!