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

Shirley Wu is back-to-back on The Work Item - we previously talked about her unexpected career in data visualizations, but for this episode we're switching things up a little bit and instead focus on building long-term career advantages based on Shirley's experience. This is an especially important topic in the era of AI, where folks have a lot of uncertainty about their career tracks and what it...

So, get this - how many times did you have one of your tweets go viral? Now, how many times did a tweet go viral for a project that you built around something that you really enjoy? And out of those times - how many times did a tweet go viral because Lin-Manuel Miranda himself retweeted you? Can't say that I am a member of that club, but luckily I know someone who is - Shirley Wu. Shirley is, what...

We're often operating under the false illusion that the career track we have now is the career track that we somehow have to follow under any circumstances - it's easy to snap to common conventions around progression, where you work, and how you work. But what if there's more to the "choose your own adventure" track that we do not know about? To get to the bottom of this question, I sat down with...

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 ver...

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. Throug...

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 organiza...

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 newslet...

This is the last episode for 2024. To make it special, it's a supercut of all the unconventional advice from every single guest that was on the show this year - Kent C. Dodds, Jerod Santo, Rob Walling, Adrienne Tacke, David Khourshid, Saron Yitbarek, Rachel Andrew, Katie Fujihara, Lena Reinhard, Miriam Suzanne, Kirupa Chinnathambi, Craig Hewitt, Jennifer Wong, Jason Lengstorf, Michael Kennedy, and...

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...

If you are listening to this show, you have likely heard of a programming language called Python. And if you are a Python developer, you've likely heard of a podcast dedicated to this programming language - Talk Python To Me. It was started by none other than Michael Kennedy, a Python Software Foundation fellow who managed to turn his expertise into a viable bootstrapped business. In this show, we...

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 develop...

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...

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 emba...

In episode 81, Den Delimarsky chats with Kirupa Chinnathambi, a product manager at Google who has built his own personal brand in what is now known as kirupa.com. Kirupa is a talented web developer, designer, writer, and packs so much knowledge in his blog that you can learn how to create great web-based experiences on that content alone. We discuss best ways to balance everything in one's life an...

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 disc...

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 recor...

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 Franc...

For today's episode, I had the privilege of sitting down with Rachel Andrew, arguably one of the more influential folks in the world of web development. With a career spanning over two decades, Rachel has left an indelible mark on the web developer community. From her groundbreaking work on CSS to her role as co-founder of Perch CMS (she spent 20 years as a freelancer and a business owner), Rachel...

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 C...

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 machin...

Welcome back to The Work Item. Today we're exploring the ins and outs of remote work, writing, and community engagement with a show veteran, Adrienne Tacke. I'm delighted to welcome Adrienne Tacke back to the show, especially considering that since our last recording we received quite a few follow-up questions. Just like last time, Adrienne brings a wealth of knowledge and experience to our discus...

If you've ever listened to Startups For The Rest Of Us (which, by the way, is approaching seven hundred episodes), you might already be familiar with the energetic host of the show - entrepreneur, bootstrapper, and podcaster extraordinaire Rob Walling. Rob and I chat about his early days as an employee, the transition from the more traditional path of working for someone to starting his own busine...

Today I got the pleasure to chat with Jerod Santo, the Managing Editor at Changelog Media. Picture this – a podcast that not only uncovers the intricacies of Jerod's career but also shares some unconventional lessons learned from his work. From navigating the ever-evolving tech landscape to spearheading Changelog, Jerod brings a wealth of experience that transcends your typical engineer expectatio...

Kent C. Dodds is a developer, educator, community organizer, and above all, a person that is passionate about making the world a better place by giving as many folks as possible the opportunity to learn web development. I sat down with Kent to chat more about his career, what bootstrapped his interest in programming, and what his takeaways from building his path as an entrepreneur are. Just like m...

Today, you're in for a treat as I sit down with Kenneth Auchenberg, a seasoned product manager - you might know him from his work at Microsoft on Visual Studio Code as well as on developer tools at Stripe. He is also a developer and overall a very nice person to know. Kenneth brings a wealth of experience to the table, especially when it comes to navigating the ins and outs of product management,...