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.

#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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#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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#13 - Interview with Amanda Silver

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

09/27/20 • 60 min

In this episode of The Work Item we interview Amanda Silver, Corporate Vice President, Developer Division at Microsoft. We discuss the process of building great developer tools, the human element in product design, and career advice for the long run.

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#1 - Remote Work

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

03/15/20 • 56 min

In this episode, Courtny Cotten and Den Delimarsky talk about what it takes to work remotely, along with some tips and best practices.

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#8 - Interview with Charmaine Lee

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

07/19/20 • 60 min

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 experiences breaking into tech, building projects for fun, and being engaged in local tech scenes.

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#5 - Interview with Jin Yang

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

06/21/20 • 66 min

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 recommendations.

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

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

04/09/25 • 56 min

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 community leads for SaaS founders, they offer a refreshing counterpoint to the doom-and-gloom narratives trending on YouTube and other social channels about AI rendering software businesses obsolete.

Through Lianna's conversion-focused (and delightfully humor-filled) copywriting expertise and Colleen's technical background, they're equipping SaaS founders with marketing strategies that prove software businesses aren't just surviving the AI revolution—they're positioned to thrive alongside it.

What made our conversation so compelling was their evidence-backed optimism (a rare treat, I know) about the future of SaaS. While tech pundits predict AI will replace traditional software services, Lianna and Colleen articulate exactly why human-designed software solutions remain vital and how founders can use AI as an enhancement to what they're building rather than a replacement.

Our discussion covers both the challenges of the current landscape and the surprising opportunities AI creates for SaaS companies that want to ride the wave. We talk about their origin stories and how they continuously evolve their skills to stay ahead of the curve. I guarantee you that you'll walk away with immediately actionable tactics and insights regardless of your company stage, and perhaps most valuably, a renewed confidence that SaaS remains a business model with staying power.

You can find Lianna and Colleen on the following sites:

The podcast was produced by Den Delimarsky.

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

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

03/30/25 • 53 min

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 carries weight in boardrooms and across the industry alike. But beyond the fancy business cards and the seat at the executive table, what does it actually mean to hold the technical helm of an organization? Is it the promised land of pure architectural decisions and strategic vision, or something messier, more complex, and perhaps more rewarding in unexpected ways?

Today, we're peeling back the curtain on the CTO role with Taiwo Oyeniyi, who'll share his journey from engineer to executive. Rather than relying on generic career advice or job descriptions, we'll hear firsthand about the transition, the challenges, and the realities of the position. Taiwo will explore the skills that matter most (spoiler alert: they might not be the ones you're cultivating now), the hurdles he faced along the way, and how the role has transformed his relationship with technology.

You can find Taiwo on the following sites:

The podcast was produced by Den Delimarsky.

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

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

08/08/24 • 37 min

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. In this episode, I chat with Jennifer about her transition from a non-traditional career path into software, reasons to take on management instead of being an individual contributor, and why taking the road less traveled in terms of career progression might just be the recipe for long-term growth and success.

You can find Jennifer on the following sites:

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

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

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

03/07/25 • 54 min

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 to solve very specific problems. And often times, their problems are extremely hard to put a number on. Why did they abandon their cart right before checkout? What made them start creating a new newsletter but then abandon it but come back a month later? Not everything can be answered with a SQL query against the telemetry database.

Marisa Morby, a Principal Researcher at Observable, sat down with me to help me better understand what it means to be great (not just good) at user research, and how that can help produce a whole new range of unexpected product insights. And Marisa definitely knows what the impact of great user research can be on the product - she previously worked at such notable companies like Netlify, Gatsby, and Accenture Song, where she honed her skills and UX instincts.

You can also find Marisa around the web:

The podcast was produced by Den Delimarsky.

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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 90 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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