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.

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Top 10 The Work Item - Real Talk on Tech's Toughest Career Choices Episodes

Goodpods has curated a list of the 10 best The Work Item - Real Talk on Tech's Toughest Career Choices episodes, ranked by the number of listens and likes each episode have garnered from our listeners. If you are listening to The Work Item - Real Talk on Tech's Toughest Career Choices for the first time, there's no better place to start than with one of these standout episodes. If you are a fan of the show, vote for your favorite The Work Item - Real Talk on Tech's Toughest Career Choices episode by adding your comments to the episode page.

#69 - Product Management In The Era Of Generative AI, with Shyvee Shi

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

12/30/23 • 41 min

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:

The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.

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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!

#47 - 2021 Reflections, Creativity, and More, with Mayuko Inoue

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

12/12/21 • 59 min

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 friend on the show to talk about their journey through the past 12 months? In this episode, I am chatting with Mayuko Inoue about all things 2021, the best choices in comfort foods, McDonalds french fries, thoughts on the content creator career path, and more.

We wanted to make this episode very informal, yet informative. To borrow Mayuko’s intro to her own podcast, Muko’s Corner (which you should subscribe to) - sit down, get cozy, grab a cup of tea, and enjoy the show!

You can find Mayuko on the following sites:

If you haven’t yet seen Mayuko’s “A Day In The Life of a Software Engineer” and “Why Japan Fell Behind in the Tech Industry” - add them to your watch queue!

As a side-note, you can also check out my interview with Mayuko on her channel.

The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.

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#30 - Creativity in Code and Beyond, with Monica Dinculescu, Engineer Extraordinaire

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

04/18/21 • 58 min

Folks often forget that engineering is inherently a very creative process. Monica Dinculescu found her own niche where she can build impactful things and do it in some of the most unusual ways possible. An excellent engineer, creative thinker, and fellow Eastern European by origin, Monica joins me today to talk about the things she learned as she figured out her career path.

You can find Monica on the following sites:

Make sure to also check out Tim Holman’s work, that Monica recommended during the show!

The podcast was produced by Den Delimarsky. Music by Wataboifrom Pixabay.

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

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

10/31/24 • 64 min

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 former VP of developer experience at a web tooling startup (he was a head of developer relations prior to that too), that is aimed at helping everyone navigate the always changing landscape of developer tools and frameworks. Which, by the way, according to Jason do not matter.

In this show, we dive deep in Jason’s career path and focus on the less known aspects of climbing the career ladder - things like amassing political capital by doing great work, building visibility by meaningful means that can help cement your reputation, and being able to address business problems as a mechanism to build trust in your own leadership abilities.

You can find Jason on the following sites:

The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.

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#49 - Product Management in Government, with Director of Product Management for the City and County of San Francisco, Adrianna Tan

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

02/17/22 • 36 min

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. Not because I didn’t want to. Mainly, because I did not know that was even an option. As it turns out - it is, in fact, an option, and a pretty impactful one at that.

To learn more about this career trajectory, I chatted with Adrianna Tan, Director of Product Management for the City and County of San Francisco. She shares her journey as a founder of startups and non-profits, an avid hiker and an advocate for an open web, and how it all combines in her work.

You can find Adrianna on the following sites:

The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.

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#36 - Diving Into Open Source Engineering, with Jenn Creighton

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

06/13/21 • 57 min

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 requires a different set of skills altogether if you want to do it right.

To learn more about this, I sat down with Jenn Creighton, Senior Staff Open Source Engineer at Apollo GraphQL. Jenn has been building scalable web experiences at companies such as Ralph Lauren, Chartbeat, and ClassPass, and is now leading the work on one of the most interesting and active open projects out there.

You can find Jenn on the following sites:

The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.

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

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

05/28/24 • 43 min

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:

The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.

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

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

07/13/24 • 37 min

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:

And of course, make sure to check out Castos!

The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.

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#4 - Interview with Clint Rutkas

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

05/03/20 • 53 min

In this episode, Courtny Cotten and Den Delimarsky chat with Clint Rutkas about PowerToys - a fantastic set of utilities for Windows power users.

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

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

12/20/24 • 64 min

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 data-driven strategies with deep empathy for customers, making her a sought-after expert - from bootstrapped businesses to some of the most established companies. Whether you’re a startup founder or a seasoned marketer, I promise you that her insights will challenge your thinking and inspire quite a few new ideas.

In this conversation, Asia shares her journey from marketer to founder, unraveling the lessons she’s learned while scaling SaaS companies and guiding others to do the same. We’ll explore her philosophy on growth, the common mistakes founders make when trying to identify their growth levers, and the power of understanding your audience on a deeper level. This really ended up being a masterclass in sustainable growth and customer-first business foundations.

You can find Asia on the following sites:

Asia also recommended the following folks to check out:

The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.

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FAQ

How many episodes does The Work Item - Real Talk on Tech's Toughest Career Choices have?

The Work Item - Real Talk on Tech's Toughest Career Choices currently has 86 episodes available.

What topics does The Work Item - Real Talk on Tech's Toughest Career Choices cover?

The podcast is about Learning, Tech, Career, Founder, Entrepreneur, Discussion, Growth, Startups, Podcasts, Technology, Science, Business and Open.

What is the most popular episode on The Work Item - Real Talk on Tech's Toughest Career Choices?

The episode title '#82 - Stop Building SaaS Landing Pages - Craig Hewitt (Founder, Castos)' is the most popular.

What is the average episode length on The Work Item - Real Talk on Tech's Toughest Career Choices?

The average episode length on The Work Item - Real Talk on Tech's Toughest Career Choices is 51 minutes.

How often are episodes of The Work Item - Real Talk on Tech's Toughest Career Choices released?

Episodes of The Work Item - Real Talk on Tech's Toughest Career Choices are typically released every 14 days.

When was the first episode of The Work Item - Real Talk on Tech's Toughest Career Choices?

The first episode of The Work Item - Real Talk on Tech's Toughest Career Choices was released on Mar 15, 2020.

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

Den Delimarsky

Top 10 The Work Item - Real Talk on Tech's Toughest Career Choices Episodes

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FAQ

How many episodes does The Work Item - Real Talk on Tech's Toughest Career Choices have?

What topics does The Work Item - Real Talk on Tech's Toughest Career Choices cover?

What is the most popular episode on The Work Item - Real Talk on Tech's Toughest Career Choices?

What is the average episode length on The Work Item - Real Talk on Tech's Toughest Career Choices?

How often are episodes of The Work Item - Real Talk on Tech's Toughest Career Choices released?

When was the first episode of The Work Item - Real Talk on Tech's Toughest Career Choices?

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