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

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.

Growth Science Entrepreneur Business Technology Learning Ai Career Discussion Tech
Update frequency
every 13 days
Average duration
51 minutes
Episodes
93
Years Active
2020 - 2025
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#93 - What's It Like To Be A Data Visualization Wizard - Shirley Wu (Shirley Wu Studio)

#93 - What's It Like To Be A Data Visualization Wizard - Shirley Wu (Shirley Wu Studio)

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 something that you really enjoy? And out of those …

00:49:37  |   Wed 13 Aug 2025
#92 - You're Thinking Wrong About Your Career - Lenn Pryor (Executive Coach, Author)

#92 - You're Thinking Wrong About Your Career - Lenn Pryor (Executive Coach, Author)

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 circumstances - it's easy to snap to common conventions a…
00:47:19  |   Fri 25 Jul 2025
#91 - The Future Of Software Engineering - Simon Guest (CTO, Code.org)

#91 - The Future Of Software Engineering - Simon Guest (CTO, Code.org)

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 experiences is ran by someone who didn't really have…
00:58:12  |   Sun 01 Jun 2025
#90 - The Death Of SaaS Has Been Greatly Exaggerated - Lianna Patch & Colleen Schnettler (Co-Founders, SaaS Marketing Gym)

#90 - The Death Of SaaS Has Been Greatly Exaggerated - Lianna Patch & Colleen Schnettler (Co-Founders, SaaS Marketing Gym)

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 Patch and Colleen Schnettler. As coaches and commu…
00:56:22  |   Wed 09 Apr 2025
#89 - So You Want to Be a CTO - Taiwo Oyeniyi (CTO, Distrobird)

#89 - So You Want to Be a CTO - Taiwo Oyeniyi (CTO, Distrobird)

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 of an engineering career. That three-letter title …
00:53:16  |   Sun 30 Mar 2025
#88 - Best-Kept Secrets on Becoming a Great User Researcher - Marisa Morby (Principal Researcher, Observable)

#88 - Best-Kept Secrets on Becoming a Great User Researcher - Marisa Morby (Principal Researcher, Observable)

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 other side of the screen are real humans who want t…
00:54:28  |   Fri 07 Mar 2025
#87 - A Wrap-Up Of 2024 Unconventional Career Advice

#87 - A Wrap-Up Of 2024 Unconventional Career Advice

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 this year - Kent C. Dodds, Jerod Santo, Rob Wallin…
00:31:55  |   Tue 31 Dec 2024
#86 - The Only Real Way To Know Is To Talk To People - Asia Orangio (CEO, DemandMaven)

#86 - The Only Real Way To Know Is To Talk To People - Asia Orangio (CEO, DemandMaven)

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 reach new heights. Asia's unique approach blends…
01:04:16  |   Fri 20 Dec 2024
#85 - Building A Business From Python Expertise - Michael Kennedy (Founder, Talk Python Training)

#85 - Building A Business From Python Expertise - Michael Kennedy (Founder, Talk Python Training)

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 heard of a podcast dedicated to this programming lan…
00:59:07  |   Thu 14 Nov 2024
#84 - Tools Do Not Matter - Jason Lengstorf (Founder, Learn With Jason)

#84 - Tools Do Not Matter - Jason Lengstorf (Founder, Learn With Jason)

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 Jason. It's a project started by Jason Lengstorf, a…
01:04:46  |   Thu 31 Oct 2024
#83 - Don't Take The Easy Path - Jennifer Wong (Engineering Leader)

#83 - Don't Take The Easy Path - Jennifer Wong (Engineering Leader)

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 stuck with it for years since making that call. I…
00:37:42  |   Thu 08 Aug 2024
#82 - Stop Building SaaS Landing Pages - Craig Hewitt (Founder, Castos)

#82 - Stop Building SaaS Landing Pages - Craig Hewitt (Founder, Castos)

Craig Hewitt, the founder of the podcasting platform Castos, comes from generations of entrepreneurs, and his own journey builds on the experience and stamina of those that came before him. In this s…
00:37:29  |   Sat 13 Jul 2024
#81 - Making A Career Out Of A Hobby - Kirupa Chinnathambi (Product Manager - Google)

#81 - Making A Career Out Of A Hobby - Kirupa Chinnathambi (Product Manager - Google)

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 kirupa.com. Kirupa is a talented web developer, …
00:42:55  |   Tue 02 Jul 2024
#80 - Web Development Is Theatre - Miriam Suzanne (CSS Working Group, OddBird)

#80 - Web Development Is Theatre - Miriam Suzanne (CSS Working Group, OddBird)

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 her theater company and ended up building a career …
00:31:40  |   Wed 12 Jun 2024
#79 - How To Get Promoted To Tech Executive - Lena Reinhard (VP Engineering, CircleCI, Travis CI)

#79 - How To Get Promoted To Tech Executive - Lena Reinhard (VP Engineering, CircleCI, Travis CI)

We often talk about promotions and growth, but the moment the conversation shifts towards paths to staff or executive positions, the advice goes blank. There is very little actionable information out…
00:43:27  |   Tue 28 May 2024
#78 - I Left Hawai'i To Work In Startups, With Katie Fujihara

#78 - I Left Hawai'i To Work In Startups, With Katie Fujihara

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 joining a company right after college. Others get tir…
00:39:46  |   Tue 14 May 2024
#77 - Write About The Things You Learned, With Rachel Andrew (Google)

#77 - Write About The Things You Learned, With Rachel Andrew (Google)

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 development. With a career spanning over two decades, Rache…
00:40:52  |   Mon 06 May 2024
#76 - Be OK Talking About Money, With Saron Yitbarek

#76 - Be OK Talking About Money, With Saron Yitbarek

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 openly the hard decisions that go into things like…
00:47:42  |   Mon 08 Apr 2024
#75 - From Pandemic Pastime To Real VC-Funded Startup, with David Khourshid

#75 - From Pandemic Pastime To Real VC-Funded Startup, with David Khourshid

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. Today, we're breaking new ground around unconve…
00:33:43  |   Sat 30 Mar 2024
#74 - Books, Remote Work, and Q&A, with Adrienne Tacke

#74 - Books, Remote Work, and Q&A, with Adrienne Tacke

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 Tacke. I'm delighted to welcome Adrienne Tacke ba…
00:53:17  |   Fri 15 Mar 2024
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