
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

Dec 31, 2023 • 48min
#70 - Building a Career In Developer Tools, with Kenneth Auchenberg
Today, you're in for a treat as I sit down with Kenneth Auchenberg, a seasoned product manager - you might know him from his work at Microsoft on Visual Studio Code as well as on developer tools at Stripe. He is also a developer and overall a very nice person to know. Kenneth brings a wealth of experience to the table, especially when it comes to navigating the ins and outs of product management, shaping a career around developer tools, and trying his hand at angel investing.
In our conversation, we'll dive deep into the developer-centric aspects of product management, explore effective strategies for making decisions, and build a better understanding of the crucial role of developer tools. Kenneth will share his hands-on experiences, offering practical insights into the day-to-day challenges and victories of building and managing tools that resonate with developers.
Plus, we'll peek into the world of angel investing from a developer's perspective, dissecting the process of spotting promising startups and contributing to the growth of new ventures.
You can find Kenneth on the following sites:
🐤 Twitter
💼 LinkedIn
📝 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!

Dec 30, 2023 • 42min
#69 - Product Management In The Era Of Generative AI, with Shyvee Shi
In today's episode, I sat down with Shyvee Shi, a seasoned product leader with a wealth of experience in steering products from conception to market success. Shyvee has been at the forefront of industry trends, contributing significantly to the evolution of product management practices.
In this very insightful conversation, we explore the fundamental role of product managers and the intricate dance they perform between market demands, user needs, and technological possibilities. But that's not all – Shyvee will also share her unique perspectives on how generative AI is poised to revolutionize the landscape of product management. We explore how it's reshaping the way product managers envision, create, and bring products to life in an ever-evolving digital landscape.
Whether you're a seasoned product professional or someone intrigued by the fascinating intersection of technology and product development, this episode is bound to spark your curiosity and broaden your understanding of the future of the discipline.
You can find Shyvee on the following sites:
📕 Book - Reimagined
💼 LinkedIn
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 29, 2023 • 56min
#68 - Why You Need An Executive Coach, with Eric Nehrlich
Recently I had the privilege of sitting down with Erich Nehrlich, a seasoned executive coach and thought leader in the realm of career development. Erich brings a wealth of experience and insights into the dynamics of leadership, organizational change, and the pivotal role that executive coaching plays in unlocking one's true potential.
In this episode, we're exploring the nuances of executive coaching, demystifying the process and shedding light on how individuals can break through the barriers that often hinder their career growth. Erich will share practical strategies and actionable advice on how to identify and overcome common roadblocks, enabling you to chart a path towards fulfilling your professional aspirations.
You can find Eric on the following sites:
📕 Book - You Have A Choice
📝 Website
💼 LinkedIn
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 21, 2023 • 35min
#67 - Building Design Communities, with Grace Ling, UX Designer at Electronic Arts, and Founder of Design Buddies
Grace Ling is a UX designer at Electronic Arts and the founder of the Design Buddies, one of the world's largest design communities. But among all the UX design and community work, Grace finds time to tackle many other ventures, like public speaking, content creation, 3D modelling, and traveling.
In this show, we discuss her recipes for balancing a large number of side hustles, overcoming challenges in bootstrapping a design community from scratch, and what's the best way to build a network early on in your career.
You can find Grace on the following sites:
💼 LinkedIn
📝 Blog
📷 Instagram
💭 Discord
🎨 Design Buddies
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 19, 2023 • 39min
#66 - Becoming The Best Product Manager You Can Be, with the CEO of Product School, Carlos Gonzalez de Villaumbrosia
What do you think are the top skills you need as a product manager? What is a product manager, to begin with? As a product manager myself, I could theorize a lot on these questions but instead I thought I'd ask someone who is not me, and has a wealth of experience in the field - the CEO of Product School, Carlos Gonzalez de Villaumbrosia.
Carlos and I dive deep into the product management field, discussing the differences between PM categories, what it means to become the best PM one can be, and what the outlook is for the next five years for those that want to break into the field.
You can find Carlos on the following sites:
🤵 LinkedIn
🎒 Product School
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 18, 2023 • 48min
#65 - Data, Impact, and Sustainability, with Jane Yang
Jane Yang is a Senior Advisor for Data Analytics at the Administration for Children and Families, as well as an Impact Fellow at the Federation of American Scientists. If there is one person you want to talk about data, quantitative analysis, and merging those with qualitative insights the right way, she would be at the top of the list.
In this show, we talk about ways to find the balance between your own passions and incentives in the tech industry, career seasonality, positive community impact, and recipes on measuring your own personal growth and sustainability.
You can find Jane on the following sites:
📝 Blog
😺 GitHub
Jane also maintains an extremely helpful repository for folks who want to break into the data science field: janejuenyang/welcome
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 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!
Remember Everything You Learn from Podcasts
Save insights instantly, chat with episodes, and build lasting knowledge - all powered by AI.