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

Den Delimarsky
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.

رؤية الكل
  1. #88 - Best-Kept Secrets on Becoming a Great User Researcher - Marisa Morby (Principal Researcher, Observable)

    الحلقة ١

    #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 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.

    ٥٤ من الدقائق
  2. #89 - So You Want to Be a CTO - Taiwo Oyeniyi (CTO, Distrobird)

    الحلقة ٢

    #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 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.

    ٥٣ من الدقائق
  3. #90 - The Death Of SaaS Has Been Greatly Exaggerated - Lianna Patch & Colleen Schnettler (Co-Founders, SaaS Marketing Gym)

    الحلقة ٣

    #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 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.

    ٥٦ من الدقائق
  4. #91 - The Future Of Software Engineering - Simon Guest (CTO, Code.org)

    الحلقة ٤

    #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 a plan to become a CTO. In the fourth episode of this season of The Work Item, I am talking with Simon Guest, CTO at Code.org. Simon walks me through how he actually became a CTO (not the LinkedIn version we commonly see), and what skills helped him succeed despite the fact that there was no pre-charted path he could follow. You'll be surprised to learn just how much serendipity and having the skills in the right place at the right time play a role in strapping one's career to a rocketship. We also talk about the future of coding, whether AI is truly going to make engineers obsolete, and what we can do to build a good career moat that sets us up for long-term success. And of course, if you've ever wondered what it takes to move into technology leadership, this conversation will give you a very realistic picture of what that path looks like.

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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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