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

By Den Delimarsky

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Image by Den Delimarsky

Category: Technology

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Subscribers: 7
Reviews: 0
Episodes: 94

Description

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.


Episode Date
#94 - Exploiting Your Unfair Advantages - Shirley Wu (Shirley Wu Studio)
Oct 20, 2025
#93 - What's It Like To Be A Data Visualization Wizard - Shirley Wu (Shirley Wu Studio)
Aug 13, 2025
#92 - You're Thinking Wrong About Your Career - Lenn Pryor (Executive Coach, Author)
Jul 25, 2025
#91 - The Future Of Software Engineering - Simon Guest (CTO, Code.org)
Jun 01, 2025
#90 - The Death Of SaaS Has Been Greatly Exaggerated - Lianna Patch & Colleen Schnettler (Co-Founders, SaaS Marketing Gym)
Apr 09, 2025
#89 - So You Want to Be a CTO - Taiwo Oyeniyi (CTO, Distrobird)
Mar 30, 2025
#88 - Best-Kept Secrets on Becoming a Great User Researcher - Marisa Morby (Principal Researcher, Observable)
Mar 07, 2025
#87 - A Wrap-Up Of 2024 Unconventional Career Advice
Dec 31, 2024
#86 - The Only Real Way To Know Is To Talk To People - Asia Orangio (CEO, DemandMaven)
Dec 20, 2024
#85 - Building A Business From Python Expertise - Michael Kennedy (Founder, Talk Python Training)
Nov 14, 2024
#84 - Tools Do Not Matter - Jason Lengstorf (Founder, Learn With Jason)
Oct 31, 2024
#83 - Don't Take The Easy Path - Jennifer Wong (Engineering Leader)
Aug 08, 2024
#82 - Stop Building SaaS Landing Pages - Craig Hewitt (Founder, Castos)
Jul 13, 2024
#81 - Making A Career Out Of A Hobby - Kirupa Chinnathambi (Product Manager - Google)
Jul 02, 2024
#80 - Web Development Is Theatre - Miriam Suzanne (CSS Working Group, OddBird)
Jun 12, 2024
#79 - How To Get Promoted To Tech Executive - Lena Reinhard (VP Engineering, CircleCI, Travis CI)
May 28, 2024
#78 - I Left Hawai'i To Work In Startups, With Katie Fujihara
May 14, 2024
#77 - Write About The Things You Learned, With Rachel Andrew (Google)
May 06, 2024
#76 - Be OK Talking About Money, With Saron Yitbarek
Apr 08, 2024
#75 - From Pandemic Pastime To Real VC-Funded Startup, with David Khourshid
Mar 30, 2024
#74 - Books, Remote Work, and Q&A, with Adrienne Tacke
Mar 15, 2024
#73 - Put The Passion Aside And Go For The Market, with Rob Walling
Feb 12, 2024
#72 - Give People What They Came For, with Jerod Santo
Feb 05, 2024
#71 - Going Solo As A Developer Educator, with Kent C. Dodds
Jan 29, 2024
#70 - Building a Career In Developer Tools, with Kenneth Auchenberg
Dec 31, 2023
#69 - Product Management In The Era Of Generative AI, with Shyvee Shi
Dec 30, 2023
#68 - Why You Need An Executive Coach, with Eric Nehrlich
Dec 29, 2023
#67 - Building Design Communities, with Grace Ling, UX Designer at Electronic Arts, and Founder of Design Buddies
Dec 21, 2023
#66 - Becoming The Best Product Manager You Can Be, with the CEO of Product School, Carlos Gonzalez de Villaumbrosia
Dec 19, 2023
#65 - Data, Impact, and Sustainability, with Jane Yang
Dec 18, 2023
#64 - Diving Into Industrial Design, with Anson Cheung
Dec 12, 2023
#63 - Beyond Just Engineering Skills, with Adrienne Braganza Tacke
Nov 08, 2023
#62 - Building Sustainable Practices, with Jason Fried
Oct 23, 2023
#61 - Career Moats And Beyond, with Cedric Chin
Oct 09, 2023
#60 - Defining A Force Multiplier, with Sam Saccone
Dec 28, 2022
#59 - Building On Your Own, with iOS Developer Donny Wals
Dec 22, 2022
#58 - Becoming a Game Studio Co-Founder, with Moon Studios' Gennadiy Korol
Nov 02, 2022
#57 - From Turbo Pascal to CodePen, with Chris Coyier
Oct 29, 2022
#56 - Reverse Engineering The Halo API with Alexis from HaloDotAPI
Oct 10, 2022
#55 - Open Source and Web Development, with Monica Powell
Aug 27, 2022
#54 - From Apple to Netflix, with Carola Nitz
May 20, 2022
#53 - Find Your Mentor And Complementary Skills, With Nicole Zhu, Senior Engineer At Vox Media
Apr 21, 2022
#52 - Grow Your Career in Data Science, with Nick Wan, Director of Analytics for Cincinnati Reds
Mar 25, 2022
#51 - Finding Your Engineering Passion, with Vicente Plata of 500 Startups LatAm, Shopify, and More
Mar 11, 2022
#50 - Problem And Product Management, with Isaac Hepworth
Mar 04, 2022
#49 - Product Management in Government, with Director of Product Management for the City and County of San Francisco, Adrianna Tan
Feb 17, 2022
#48 - The Story of Working In Developer Relations, with Dan Shaw
Feb 06, 2022
#47 - 2021 Reflections, Creativity, and More, with Mayuko Inoue
Dec 12, 2021
#46 - From Journalism to Developer Engagement, with Christina Warren
Dec 05, 2021
#45 - Startups, Growth, and A Quest to Build People-focused Companies, with Jennifer Kim
Nov 28, 2021
#44 - So What Is Product Marketing, with Isaac Levin
Nov 14, 2021
#43 - Ins And Outs Of Developer Advocacy, with Brian Douglas
Nov 07, 2021
#42 - Building The World You Want To See, with Jeff Atwood
Oct 31, 2021
#41 - Why Big Tech Is Not For Me, with Chloe Shih
Oct 24, 2021
#40 - Engineering and Team Empathy, with Amro Mousa
Oct 17, 2021
#39 - Focus on Delivering Value, with Dan Shaw
Oct 03, 2021
#38 - Becoming a Polymath, with Salman Ansari
Jul 11, 2021
#37 - Be A Builder, With Jack Zerby
Jun 27, 2021
#36 - Diving Into Open Source Engineering, with Jenn Creighton
Jun 13, 2021
#35 - From Pre-Med To Product Management, with Janine Co
Jun 06, 2021
#34 - Busting Career Myths with Laurie Barth
May 30, 2021
#33 - Engineering In A News Organization And Beyond, with Nicole Tibaldi
May 16, 2021
#32 - Camille Fournier on Engineering Management Paths
May 09, 2021
#31 - Lessons In Leadership, with Chad Fowler, VP of Technology at DEVCON
Apr 25, 2021
#30 - Creativity in Code and Beyond, with Monica Dinculescu, Engineer Extraordinaire
Apr 18, 2021
#29 - Building Things You Love, with Ben Sandofsky, Head of Development for Halide
Apr 11, 2021
#28 - The Art of Engineering Management, with Rebecca Murphey, EM at Stripe
Apr 04, 2021
#27 - How to Build a Career in Human Resources, with David Daniels
Mar 21, 2021
#26 - How to Grow as a Product Manager, with Dan Olsen
Mar 14, 2021
#25 - How to Build a Career in Design and Pitch Gary Vee, with Jack Zerby
Mar 07, 2021
#24 - Building Communities with Jess Lee
Feb 28, 2021
#23 - From Servers, Phones, and Voice Assistants to Space with Charlie Kindel
Feb 21, 2021
#22 - Paige Bailey on Building a Career In Artificial Intelligence and Machine Learning
Feb 01, 2021
#21 - Mayuko Inoue on Building a Content Creator Career Path
Jan 17, 2021
#20 - Scott Hanselman on Intentionality
Jan 10, 2021
#19 - Wrap Up Episode For 2020
Dec 20, 2020
#18 - Megan Risdal on Building a Career at the Intersection of Data Science and Product Management
Nov 22, 2020
#17 - Christos Matskas on Going From Consulting to Corporate and Building Identity Tools
Nov 15, 2020
#16 - Bill Kenney on Building Brands That Last
Nov 08, 2020
#15 - Tarun Gangwani on Innovation, Navigating Product Decisions, and Building Growth Engines
Nov 01, 2020
#14 - Interview with Richard Lander
Oct 18, 2020
#13 - Interview with Amanda Silver
Sep 27, 2020
#12 - Interview with Christina Weng
Sep 20, 2020
#11 - Interview with Eric Martel
Aug 23, 2020
#10 - Interview with Sara Chipps
Aug 09, 2020
#9 - Interview with Philipp Cannons
Jul 20, 2020
#8 - Interview with Charmaine Lee
Jul 19, 2020
#7 - Interview with Dan Fernandez
Jul 05, 2020
#6 - Interview with Matt Swanson
Jun 28, 2020
#5 - Interview with Jin Yang
Jun 21, 2020
#4 - Interview with Clint Rutkas
May 03, 2020
#3 - Interview with April Speight
Apr 12, 2020
#2 - Career Starts
Apr 05, 2020
#1 - Remote Work
Mar 15, 2020