The Work Item - Real Talk on Tech's Toughest Career Choices
Den Delimarsky
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.
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.
Episodes
Mentioned books
Oct 31, 2024 • 1h 5min
#84 - Tools Do Not Matter - Jason Lengstorf (Founder, Learn With Jason)
Jason Lengstorf, founder of Learn With Jason, shares insights from his journey in tech, transitioning from musician to developer advocate. He discusses the importance of building political capital and visibility while tackling business problems to forge trust in leadership. Jason emphasizes that the tools developers use are less crucial than understanding desired outcomes, and highlights the unique challenges of being a founder versus an executive. Embracing setbacks and individuality is key to personal growth in a constantly evolving industry.
Aug 8, 2024 • 38min
#83 - Don't Take The Easy Path - Jennifer Wong (Engineering Leader)
In this discussion, Jennifer Wong, a seasoned engineering manager with roots in civil engineering, reflects on her unique journey into the tech world. She shares the thrills of quick project turnarounds in tech compared to construction delays. Jennifer emphasizes the value of user engagement and empathy over formal education in tech roles. She dives into the importance of mentorship and networking in transitioning to management, advocating for unconventional career paths as a key to long-term growth and success.
Jul 13, 2024 • 37min
#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 show, we chat about best practices for hiring developers for your bootstrapped startup, finding the right approach to deliver hard news, and how to ensure that your relationships aren't hurt as you embark on the entrepreneurship treadmill.
You can find Craig on the following sites:
📝 Blog
💼 LinkedIn
And of course, make sure to check out Castos!
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!
Jul 2, 2024 • 43min
#81 - Making A Career Out Of A Hobby - Kirupa Chinnathambi (Product Manager - Google)
Kirupa Chinnathambi, a Product Manager at Google and creator of kirupa.com, shares his journey from hobbyist to professional. He discusses the unexpected path that took him from web development inspired by a physics assignment to a successful career in product management. Kirupa highlights strategies for balancing work and life, the importance of supportive management, and how to turn interests into impactful careers. He also emphasizes building a community around personal passions and the role of luck in navigating career growth.
Jun 12, 2024 • 32min
#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 and a company around it. And not just that, but she also joined the CSS Working Group - the official standards body that determines how the CSS stack evolves.
In this show, we talk about her early discovery of the power of the web, how she joins creativity with technical prowess, and how CSS is really like poetry written in the browser.
You can find Miriam on the following sites:
🐘 Mastodon
🐘 OddBird (Mastodon)
🐦 OddBird Website
📝 Blog
💼 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!
May 28, 2024 • 43min
#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 there that can tell you how you can get to the highest echelons of leadership.
To get a clearer picture on this topic, I sat down with Lena Reinhard, a seasoned executive with an extensive track record at CircleCI, Travis CI, and more. Lena shares her insights on the best ways to accelerate career growth in the tech space, answer thorny questions, such as “Why are executives hired from the outside?” and provide some candid takes on why taking things slow sometimes can pay off in the end.
You can find Lena on the following sites:
🌍 Website
💼 LinkedIn
🎙️ Leadership Confidential 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!
May 14, 2024 • 40min
#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 tired of their corporate life and decide to try something different. Katie Fujihara, an engineer and a technical program manager amalgam, decided that her journey to the heart of “startup land,” San Francisco, would be an impromptu one - she just packed up her bags and set out on an adventure.
I am delighted to share with you this recording, where I talk to Katie about her early starts in Hawai'i, how working in engineering was not the end goal for her career journey, and what the best practices are for overcoming impostor syndrome.
You can find Katie on the following sites:
😺 GitHub
🤵 LinkedIn
🦜 X
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!
May 6, 2024 • 41min
#77 - Write About The Things You Learned, With Rachel Andrew (Google)
Rachel Andrew, a web development visionary with over 20 years of experience, discusses her transformative journey from aspiring dancer to tech leader. She talks about the power of mentorship and community in overcoming challenges in a male-dominated field. Rachel shares insights on leading a writing team, highlighting the importance of accurate documentation and collaboration. She also emphasizes the need for community-driven resources like MDN and Open Web Docs to enhance developer experience and her advocacy for inclusive web standards.
Apr 8, 2024 • 48min
#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 seeking funding, investing money into things that save you time, and scaling your own abilities with the help of, you guessed it, cold, hard, cash.
Saron Yitbarek, entrepreneur extraordinaire behind CodeNewbie and podcasts such as Command Line Heroes, generously accepted my invitation to chat and talk about all these things, and more. And of course, we talk about Saron's latest project - Big Cash Money 2024, something for folks that want to max out their income beyond just their salary.
You can find Saron on the following sites:
📝 Blog
💼 LinkedIn
📷 Instagram
💸 Big Cash Money 2024
🎙️ Code Newbie Podcast
🎙️ Basecs Podcast
🎙️ Command Line Heroes Podcast
🎨 Not A Designer 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!
Mar 30, 2024 • 34min
#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 unconventional paths of building an engineering career, entrepreneurship, and leveraging your audience as the potential first customers for your product. And of course - we talk a bit more about state machines (David is also the developer behind XState) and lessons learned from launching and growing a startup in the midst of a pandemic.
You can find David and his work on the following sites:
📕 XState
🕸️ Stately
😺 GitHub
🐤 Twitter
📷 Instagram
🧵 Threads
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!
