The Work Item - Real Talk on Tech's Toughest Career Choices
Episodes
#93 - What's It Like To Be A Data Visualization Wizard - Shirley Wu (Shirley Wu Studio)
13 Aug 2025
Contributed by Lukas
So, get this - how many times did you have one of your tweets go viral? Now, how many times did a tweet go viral for a project that you built around s...
#92 - You're Thinking Wrong About Your Career - Lenn Pryor (Executive Coach, Author)
25 Jul 2025
Contributed by Lukas
We're often operating under the false illusion that the career track we have now is the career track that we somehow have to follow under any circumst...
#91 - The Future Of Software Engineering - Simon Guest (CTO, Code.org)
01 Jun 2025
Contributed by Lukas
Every year, millions of students try coding for the first time through Hour of Code. But most people don't know that the technology powering those exp...
#90 - The Death Of SaaS Has Been Greatly Exaggerated - Lianna Patch & Colleen Schnettler (Co-Founders, SaaS Marketing Gym)
09 Apr 2025
Contributed by Lukas
In this week's episode, I sat down not with one, but two brilliant guests - the duo behind the brand-new venture known as SaaS Marketing Gym, Lianna P...
#89 - So You Want to Be a CTO - Taiwo Oyeniyi (CTO, Distrobird)
30 Mar 2025
Contributed by Lukas
Chief Technology Officer - a few people I've talked to in the past year expressed some degree of interest in reaching, what seems like, the pinnacle o...
#88 - Best-Kept Secrets on Becoming a Great User Researcher - Marisa Morby (Principal Researcher, Observable)
07 Mar 2025
Contributed by Lukas
User research is an underappreciated art - we in tech are so used to being immersed in an ocean of quantitative data that we can forget that on the ot...
#87 - A Wrap-Up Of 2024 Unconventional Career Advice
31 Dec 2024
Contributed by Lukas
This is the last episode for 2024. To make it special, it's a supercut of all the unconventional advice from every single guest that was on the show t...
#86 - The Only Real Way To Know Is To Talk To People - Asia Orangio (CEO, DemandMaven)
20 Dec 2024
Contributed by Lukas
Today, I'm thrilled to be joined by Asia Orangio, the brain behind DemandMaven, a growth agency dedicated to helping SaaS companies and their founders...
#85 - Building A Business From Python Expertise - Michael Kennedy (Founder, Talk Python Training)
14 Nov 2024
Contributed by Lukas
If you are listening to this show, you have likely heard of a programming language called Python. And if you are a Python developer, you've likely hea...
#84 - Tools Do Not Matter - Jason Lengstorf (Founder, Learn With Jason)
31 Oct 2024
Contributed by Lukas
If you've been immersed in the tech world for some time, you probably have heard one specific YouTube channel mentioned more than once - Learn With Ja...
#83 - Don't Take The Easy Path - Jennifer Wong (Engineering Leader)
08 Aug 2024
Contributed by Lukas
Jennifer Wong is a seasoned engineering manager who started her journey in civil engineering. The fast pace of the tech industry drew her in, and she ...
#82 - Stop Building SaaS Landing Pages - Craig Hewitt (Founder, Castos)
13 Jul 2024
Contributed by Lukas
Craig Hewitt, the founder of the podcasting platform Castos, comes from generations of entrepreneurs, and his own journey builds on the experience and...
#81 - Making A Career Out Of A Hobby - Kirupa Chinnathambi (Product Manager - Google)
02 Jul 2024
Contributed by Lukas
In episode 81, Den Delimarsky chats with Kirupa Chinnathambi, a product manager at Google who has built his own personal brand in what is now known as...
#80 - Web Development Is Theatre - Miriam Suzanne (CSS Working Group, OddBird)
12 Jun 2024
Contributed by Lukas
One of the things that Miriam Suzanne realized early in her developer journey is that web development is a tool - she wanted to build a website for he...
#79 - How To Get Promoted To Tech Executive - Lena Reinhard (VP Engineering, CircleCI, Travis CI)
28 May 2024
Contributed by Lukas
We often talk about promotions and growth, but the moment the conversation shifts towards paths to staff or executive positions, the advice goes blank...
#78 - I Left Hawai'i To Work In Startups, With Katie Fujihara
14 May 2024
Contributed by Lukas
One's journey from their early career to working at startups in Silicon Valley can take many forms. Some folks take the more traditional route of join...
#77 - Write About The Things You Learned, With Rachel Andrew (Google)
06 May 2024
Contributed by Lukas
For today's episode, I had the privilege of sitting down with Rachel Andrew, arguably one of the more influential folks in the world of web developmen...
#76 - Be OK Talking About Money, With Saron Yitbarek
08 Apr 2024
Contributed by Lukas
One of the things that is a bit taboo to talk about, both in the tech industry and outside of it is money. People just aren't comfortable discussing o...
#75 - From Pandemic Pastime To Real VC-Funded Startup, with David Khourshid
30 Mar 2024
Contributed by Lukas
In this episode of The Work Item, I had a conversation with David Khourshid, founder of Stately.AI. You might know him as @DavidKPiano on social media...
#74 - Books, Remote Work, and Q&A, with Adrienne Tacke
15 Mar 2024
Contributed by Lukas
Welcome back to The Work Item. Today we're exploring the ins and outs of remote work, writing, and community engagement with a show veteran, Adrienne ...
#73 - Put The Passion Aside And Go For The Market, with Rob Walling
12 Feb 2024
Contributed by Lukas
If you've ever listened to Startups For The Rest Of Us (which, by the way, is approaching seven hundred episodes), you might already be familiar with ...
#72 - Give People What They Came For, with Jerod Santo
05 Feb 2024
Contributed by Lukas
Today I got the pleasure to chat with Jerod Santo, the Managing Editor at Changelog Media. Picture this – a podcast that not only uncovers the intri...
#71 - Going Solo As A Developer Educator, with Kent C. Dodds
29 Jan 2024
Contributed by Lukas
Kent C. Dodds is a developer, educator, community organizer, and above all, a person that is passionate about making the world a better place by givin...
#70 - Building a Career In Developer Tools, with Kenneth Auchenberg
31 Dec 2023
Contributed by Lukas
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 Visu...
#69 - Product Management In The Era Of Generative AI, with Shyvee Shi
30 Dec 2023
Contributed by Lukas
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 s...
#68 - Why You Need An Executive Coach, with Eric Nehrlich
29 Dec 2023
Contributed by Lukas
Recently I had the privilege of sitting down with Erich Nehrlich, a seasoned executive coach and thought leader in the realm of career development. Er...
#67 - Building Design Communities, with Grace Ling, UX Designer at Electronic Arts, and Founder of Design Buddies
21 Dec 2023
Contributed by Lukas
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...
#66 - Becoming The Best Product Manager You Can Be, with the CEO of Product School, Carlos Gonzalez de Villaumbrosia
19 Dec 2023
Contributed by Lukas
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 the...
#65 - Data, Impact, and Sustainability, with Jane Yang
18 Dec 2023
Contributed by Lukas
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 Ame...
#64 - Diving Into Industrial Design, with Anson Cheung
12 Dec 2023
Contributed by Lukas
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 som...
#63 - Beyond Just Engineering Skills, with Adrienne Braganza Tacke
08 Nov 2023
Contributed by Lukas
In this episode, I am talking to Adrienne Tacke, an author, engineer, and teacher. We discuss the intentionality in one's career trajectory, approache...
#62 - Building Sustainable Practices, with Jason Fried
23 Oct 2023
Contributed by Lukas
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 lac...
#61 - Career Moats And Beyond, with Cedric Chin
09 Oct 2023
Contributed by Lukas
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. ...
#60 - Defining A Force Multiplier, with Sam Saccone
28 Dec 2022
Contributed by Lukas
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, o...
#59 - Building On Your Own, with iOS Developer Donny Wals
22 Dec 2022
Contributed by Lukas
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 wha...
#58 - Becoming a Game Studio Co-Founder, with Moon Studios' Gennadiy Korol
02 Nov 2022
Contributed by Lukas
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 ro...
#57 - From Turbo Pascal to CodePen, with Chris Coyier
29 Oct 2022
Contributed by Lukas
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 ...
#56 - Reverse Engineering The Halo API with Alexis from HaloDotAPI
10 Oct 2022
Contributed by Lukas
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 ...
#55 - Open Source and Web Development, with Monica Powell
27 Aug 2022
Contributed by Lukas
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 com...
#54 - From Apple to Netflix, with Carola Nitz
20 May 2022
Contributed by Lukas
Carola Nitz is a seasoned engineer who has been involved in a variety of complex projects - from VLC, to Apple Maps, and now working at Netflix on the...
#53 - Find Your Mentor And Complementary Skills, With Nicole Zhu, Senior Engineer At Vox Media
21 Apr 2022
Contributed by Lukas
There are a few things in your engineering career that you should focus on relentlessly, but few as impactful as finding yourself a guide through the ...
#52 - Grow Your Career in Data Science, with Nick Wan, Director of Analytics for Cincinnati Reds
25 Mar 2022
Contributed by Lukas
I don't talk about data science enough on this show. To remedy that, I brought in a remarkable analytics and data science expert - Nick Wan, who is a ...
#51 - Finding Your Engineering Passion, with Vicente Plata of 500 Startups LatAm, Shopify, and More
11 Mar 2022
Contributed by Lukas
Vicente Plata is doing way more than one would expect from an engineering leader - not only is he an engineering manager, but he also advises startups...
#50 - Problem And Product Management, with Isaac Hepworth
04 Mar 2022
Contributed by Lukas
Today I chat with a good friend, mentor, and an all-around great person - Isaac Hepworth. Isaac is the person you should go to if you want to learn mo...
#49 - Product Management in Government, with Director of Product Management for the City and County of San Francisco, Adrianna Tan
17 Feb 2022
Contributed by Lukas
Despite starting a career in product management at one of the big companies, I've never considered to do the same job but working for the government. ...
#48 - The Story of Working In Developer Relations, with Dan Shaw
06 Feb 2022
Contributed by Lukas
This is the brand-new start of the third season of The Work Item podcast, and to make the kick-off even better I sat down with our good friend of the ...
#47 - 2021 Reflections, Creativity, and More, with Mayuko Inoue
12 Dec 2021
Contributed by Lukas
The end of 2021 is almost here, and it's time to wrap up the second season of The Work Item. And what better way to do that than to invite a good frie...
#46 - From Journalism to Developer Engagement, with Christina Warren
05 Dec 2021
Contributed by Lukas
The myth of the superhero programmer - we often hear about it, but it's rarely the reality. Being a superhero on a team takes more than just technical...
#45 - Startups, Growth, and A Quest to Build People-focused Companies, with Jennifer Kim
28 Nov 2021
Contributed by Lukas
The decision to join a startup or a big company is not an easy one, as one has to consider many factors that go beyond just the financial side of thin...
#44 - So What Is Product Marketing, with Isaac Levin
14 Nov 2021
Contributed by Lukas
You've probably heard of the many types of PM - project managers, product managers, and even program managers. But did you also know that there is a P...
#43 - Ins And Outs Of Developer Advocacy, with Brian Douglas
07 Nov 2021
Contributed by Lukas
Developer Advocacy is a relatively new field, but when it comes to knowing how to navigate it, Brian Douglas' knowledge is second to none. As Director...
#42 - Building The World You Want To See, with Jeff Atwood
31 Oct 2021
Contributed by Lukas
Whether you are new in the tech industry or are a veteran developer, chances are that you've used a product that Jeff Atwood worked on. I'm talking ab...
#41 - Why Big Tech Is Not For Me, with Chloe Shih
24 Oct 2021
Contributed by Lukas
Despite what your LinkedIn feed might tell you, a career in FAANG is not the only way to grow in tech. Or even get started in tech, for that matter. T...
#40 - Engineering and Team Empathy, with Amro Mousa
17 Oct 2021
Contributed by Lukas
Management, and especially engineering management, is way more than just telling others what to build. Talking to Amro Mousa, an engineering manager a...
#39 - Focus on Delivering Value, with Dan Shaw
03 Oct 2021
Contributed by Lukas
In the sea of shiny technology objects (I am talking frameworks, tools, libraries, and many others), Dan Shaw has been pretty opinionated - focus on d...
#38 - Becoming a Polymath, with Salman Ansari
11 Jul 2021
Contributed by Lukas
From the early days - when we are growing up, to when we go to school, we tend to be involved in a lot of activities. From sports, to music, painting,...
#37 - Be A Builder, With Jack Zerby
27 Jun 2021
Contributed by Lukas
Last time I chatted with Jack, I had pages of questions I still wanted to ask - with this episode, I attempt to address that backlog. And the more I t...
#36 - Diving Into Open Source Engineering, with Jenn Creighton
13 Jun 2021
Contributed by Lukas
There is a bit of a chasm between requirements for building open source projects and those that are designed to be closed. Not surprisingly, it also r...
#35 - From Pre-Med To Product Management, with Janine Co
06 Jun 2021
Contributed by Lukas
I often hear about folks moving from engineering to product management and back. Others make the transition from marketing and sales to product manage...
#34 - Busting Career Myths with Laurie Barth
30 May 2021
Contributed by Lukas
There are thousands of blog posts, tutorials, and videos that tell you what engineering careers are about, how you should be thinking about your dream...
#33 - Engineering In A News Organization And Beyond, with Nicole Tibaldi
16 May 2021
Contributed by Lukas
What lessons can you take away from a music degree and bring into engineering management? How do engineers work with folks in the newsroom at one of t...
#32 - Camille Fournier on Engineering Management Paths
09 May 2021
Contributed by Lukas
Setting your sights high for a career in engineering management might be an appealing endeavor, but it also means that you will be making a lot of ass...
#31 - Lessons In Leadership, with Chad Fowler, VP of Technology at DEVCON
25 Apr 2021
Contributed by Lukas
Talking to Chad Fowler, you quickly realize what true leadership means. Chad has extensive experience leading large technical organizations such as Li...
#30 - Creativity in Code and Beyond, with Monica Dinculescu, Engineer Extraordinaire
18 Apr 2021
Contributed by Lukas
Folks often forget that engineering is inherently a very creative process. Monica Dinculescu found her own niche where she can build impactful things ...
#29 - Building Things You Love, with Ben Sandofsky, Head of Development for Halide
11 Apr 2021
Contributed by Lukas
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 “unev...
#28 - The Art of Engineering Management, with Rebecca Murphey, EM at Stripe
04 Apr 2021
Contributed by Lukas
Rebecca Murphey tried a lot of things on her way to becoming an engineering manager at Stripe - from journalism to advertisement, and even learning ho...
#27 - How to Build a Career in Human Resources, with David Daniels
21 Mar 2021
Contributed by Lukas
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...
#26 - How to Grow as a Product Manager, with Dan Olsen
14 Mar 2021
Contributed by Lukas
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 ...
#25 - How to Build a Career in Design and Pitch Gary Vee, with Jack Zerby
07 Mar 2021
Contributed by Lukas
Jack Zerby is not your typical designer. His experience producing music, working at Pentagram and Frog, building startups, pitching to Gary Vee, and n...
#24 - Building Communities with Jess Lee
28 Feb 2021
Contributed by Lukas
Jess Lee is the co-founder of dev.to - a developer community that emphasizes the importance of a friendly approach to guiding folks through the tumult...
#23 - From Servers, Phones, and Voice Assistants to Space with Charlie Kindel
21 Feb 2021
Contributed by Lukas
Charlie Kindel is a tech industry veteran who helped bootstrap, grow, and manage teams that built home servers, phones, voice assistants, home automat...
#22 - Paige Bailey on Building a Career In Artificial Intelligence and Machine Learning
01 Feb 2021
Contributed by Lukas
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 eas...
#21 - Mayuko Inoue on Building a Content Creator Career Path
17 Jan 2021
Contributed by Lukas
Mayuko Inoue made a bold step by defying the stereotypical career path of a software engineer, and became a full-time content creator. Her videos on Y...
#20 - Scott Hanselman on Intentionality
10 Jan 2021
Contributed by Lukas
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 summa...
#19 - Wrap Up Episode For 2020
20 Dec 2020
Contributed by Lukas
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 k...
#18 - Megan Risdal on Building a Career at the Intersection of Data Science and Product Management
22 Nov 2020
Contributed by Lukas
Right before the Thanksgiving break, we are releasing a fresh new episode with Megan Risdal, Product Lead at Kaggle. Megan took the multi-talented rou...
#17 - Christos Matskas on Going From Consulting to Corporate and Building Identity Tools
15 Nov 2020
Contributed by Lukas
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 abou...
#16 - Bill Kenney on Building Brands That Last
08 Nov 2020
Contributed by Lukas
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 importanc...
#15 - Tarun Gangwani on Innovation, Navigating Product Decisions, and Building Growth Engines
01 Nov 2020
Contributed by Lukas
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...
#14 - Interview with Richard Lander
18 Oct 2020
Contributed by Lukas
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 com...
#13 - Interview with Amanda Silver
27 Sep 2020
Contributed by Lukas
In this episode of The Work Item we interview Amanda Silver, Corporate Vice President, Developer Division at Microsoft. We discuss the process of buil...
#12 - Interview with Christina Weng
20 Sep 2020
Contributed by Lukas
In this episode of The Work Item we interview Christina Weng, product designer at Facebook, about building a career in user experience design from scr...
#11 - Interview with Eric Martel
23 Aug 2020
Contributed by Lukas
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 a...
#10 - Interview with Sara Chipps
09 Aug 2020
Contributed by Lukas
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 com...
#9 - Interview with Philipp Cannons
20 Jul 2020
Contributed by Lukas
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. Phili...
#8 - Interview with Charmaine Lee
19 Jul 2020
Contributed by Lukas
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...
#7 - Interview with Dan Fernandez
05 Jul 2020
Contributed by Lukas
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 pro...
#6 - Interview with Matt Swanson
28 Jun 2020
Contributed by Lukas
Today, we had the honor of having an in-depth conversation with Matt Swanson, a software engineer at SEP, on engineering best practices, design system...
#5 - Interview with Jin Yang
21 Jun 2020
Contributed by Lukas
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 r...
#4 - Interview with Clint Rutkas
03 May 2020
Contributed by Lukas
In this episode, Courtny Cotten and Den Delimarsky chat with Clint Rutkas about PowerToys - a fantastic set of utilities for Windows power users.
#3 - Interview with April Speight
12 Apr 2020
Contributed by Lukas
In this episode, Courtny Cotten and Den Delimarsky chat with April Speight, Senior Developer Advocate at Microsoft, about social media, writing Python...
#2 - Career Starts
05 Apr 2020
Contributed by Lukas
In this episode, Den and Courtny are talking about their career starts.
#1 - Remote Work
15 Mar 2020
Contributed by Lukas
In this episode, Courtny Cotten and Den Delimarsky talk about what it takes to work remotely, along with some tips and best practices.