The Upside Of Being Unreasonable by Jason Lengstorf 🔗 **Source:** [The Upside Of Being Unreasonable by Jason Lengstorf](https://www.youtube.com/watch?v=goVNPN6fVwQ) > [!note]+ Document Notes > tags: [career-development, entrepreneurship, creative-risk-taking] > author: Jason Lengstorf > source: YouTube > reference: https://www.youtube.com/watch?v=goVNPN6fVwQ > date created: 2024-12-19 14:30 > > # 🏷️ Title: The Upside Of Being Unreasonable > <!-- deep-read:sections start --> ## 🧰 Action Inbox - [H1] Evaluate your "unreasonable" ideas for potential — follow slow hunches #career-development - [H2] Plan fallback scenarios before taking career risks — risk mitigation strategies #entrepreneurship - [H3] Start doing the thing even when you don't know how — embrace adjacent possible #skill-development ## 🧭 Table of Contents - [📝 Summary](#-summary) - [📖 Main Content](#-main-content) - [🗒️ Notes](#️-notes) - [📚 References](#-references) - [🗣️ Paraphrase](#️-paraphrase) - [📰 Newsletter](#-newsletter) - [✅ Action Items](#-action-items) - [🧪 Hypotheses](#-hypotheses) - [📊 Methodology](#-methodology) - [❓ Questions](#-questions) - [🔮 Future Research](#-future-research) - [💡 Implications](#-implications) - [🧠 Learning Styles Assessment](#-learning-styles-assessment) - [📊 Accessibility Assessment](#-accessibility-assessment) - [🌍 DEIB Assessment](#-deib-assessment) - [✅ Logical Validity](#-logical-validity) - [🛡️ DARVO Analysis](#-darvo-analysis) - [🎯 Conclusion](#-conclusion) ### 🔗 References - [WebDev Challenge](https://webdevchallenge.com) - [Learn to Code with Jason](https://learnwithjason.dev) ## 📝 Summary - Jason Lengstorf shares his journey from tech executive to independent TV producer for developers - He advocates for pursuing "unreasonable" ideas when traditional approaches aren't working - The talk covers risk assessment, learning new skills, and finding work that brings joy in the process - Key message: Sometimes being unreasonable is the only reasonable choice when circumstances change - Bottom line: Follow your slow hunches and don't dismiss ambitious ideas without proper evaluation ## 📖 Main Content Lengstorf presents a compelling case for embracing unreasonable career moves through his personal story of leaving a VP role to start CodeTV. He defines "slow hunches" as ideas that develop over time through accumulated evidence and observation. His central thesis is that when established norms get disrupted (like remote work changing developer relations), traditional "reasonable" approaches become risky, while innovative approaches become necessary. The talk addresses common fears about career pivots: financial risk, lack of expertise, and fear of failure. Lengstorf advocates for thorough risk planning, embracing the "adjacent possible" (taking next available steps rather than seeing the whole path), and accepting initial poor quality as part of the learning process. A key insight is that sustainable success requires finding joy in the process itself, not just the outcomes. This intrinsic motivation enables long-term persistence through inevitable challenges. ## 🗒️ Notes #### ⏱️ [00:02:30](https://www.youtube.com/watch?v=goVNPN6fVwQ&t=150) — [H1] The half-million dollar ask that got rejected - Key idea: Lengstorf confidently requested $500K for an innovative developer relations program - Evidence: "I need a half a million dollars... He said no. He said the idea is great but this is a colossal risk" #### ⏱️ [00:04:15](https://www.youtube.com/watch?v=goVNPN6fVwQ&t=255) — [H2] Questioning what's so great about being reasonable - Key idea: History's greatest achievements were considered unreasonable at the time - Evidence: "Going to the moon was the opposite of reasonable... We choose to do these things not because they are easy, but because they are hard" #### ⏱️ [00:06:45](https://www.youtube.com/watch?v=goVNPN6fVwQ&t=405) — [H2] The concept of slow hunches - Key idea: Good ideas develop gradually over time through accumulated evidence - Evidence: "Charles Darwin... This was years of expeditions and journaling... before this theory of evolution sort of emerged" #### ⏱️ [00:08:20](https://www.youtube.com/watch?v=goVNPN6fVwQ&t=500) — [H2] The old developer relations playbook is dead - Key idea: Traditional DevTools marketing strategies stopped working after the pandemic - Evidence: "Webinars stopped getting as many registrations... fewer people were showing up at conferences... everyone is so sick of Zoom calls" #### ⏱️ [00:11:30](https://www.youtube.com/watch?v=goVNPN6fVwQ&t=690) — [H2] Sometimes being unreasonable is the only reasonable choice - Key idea: When norms get upended, traditional safe choices become risky - Evidence: "When all the norms... get upended, you have to change the game or you're going to end up suffering" #### ⏱️ [00:13:45](https://www.youtube.com/watch?v=goVNPN6fVwQ&t=825) — [H1] Quitting to start CodeTV - Key idea: After two years of trying to get company buy-in, Lengstorf went independent - Evidence: "At the end of 2022, I left my job and I started CodeTV... I make TV for developers" #### ⏱️ [00:15:20](https://www.youtube.com/watch?v=goVNPN6fVwQ&t=920) — [H3] You can just do things when no one's done it before - Key idea: Uncharted territory means no established authority to grant permission - Evidence: "When you're doing something that nobody's ever done before, there's not really anybody to tell you that you're wrong" #### ⏱️ [00:16:40](https://www.youtube.com/watch?v=goVNPN6fVwQ&t=1000) — [H2] Planning for realistic failure scenarios - Key idea: Fear of catastrophic failure is usually overblown; plan for likely outcomes - Evidence: "In order for this to be the outcome, I would have to make a whole lot of really bad decisions coupled with a whole lot of really bad luck" #### ⏱️ [00:19:15](https://www.youtube.com/watch?v=goVNPN6fVwQ&t=1155) — [H2] Managing risk until the biggest risk is not doing the thing - Key idea: Thorough planning can reveal that inaction is riskier than action - Evidence: "The biggest risk to me was not trying this... What if I bet on myself? What if I'd taken that shot?" #### ⏱️ [00:21:30](https://www.youtube.com/watch?v=goVNPN6fVwQ&t=1290) — [H3] The adjacent possible concept - Key idea: Progress happens step by step; you can't see the whole path at once - Evidence: "Every time you open a door, you gain access to a new set of doors... You can't go directly from humans discovering fire to humans discovering jet propulsion" #### ⏱️ [00:24:45](https://www.youtube.com/watch?v=goVNPN6fVwQ&t=1485) — [H2] Your taste will outrun your talent - Key idea: You'll envision better outcomes than you can initially produce, but that's normal - Evidence: "Your ability to see what something could be is going to be far superior to your ability to make a thing... you're never going to get better unless you make it" #### ⏱️ [00:27:20](https://www.youtube.com/watch?v=goVNPN6fVwQ&t=1640) — [H1] The success of WebDev Challenge - Key idea: The unreasonable bet paid off with a successful TV show for developers - Evidence: "This episode was wildly popular and I suddenly had a line of companies out the door who wanted to make these episodes" #### ⏱️ [00:29:45](https://www.youtube.com/watch?v=goVNPN6fVwQ&t=1785) — [H2] Finding joy in the process, not just outcomes - Key idea: Sustainable success requires intrinsic motivation from the work itself - Evidence: "The people who I know who make the most progress are finding a way to enjoy the process in itself... the act of doing the thing is the reward" #### ⏱️ [00:32:10](https://www.youtube.com/watch?v=goVNPN6fVwQ&t=1930) — [H1] Living out the original vision - Key idea: Lengstorf achieved exactly what he envisioned in his corporate role - Evidence: "I am literally living out my dreams right now... This is what I was trying to engineer my entire department into becoming" ## 📚 References - [WebDev Challenge Episodes](https://webdevchallenge.com) - [Jason's Streaming Content](https://learnwithjason.dev) - Steven Johnson - "Where Good Ideas Come From" ## 🗣️ Paraphrase - Traditional business approaches become risky when market conditions fundamentally change, making innovative "unreasonable" approaches necessary for survival - Career pivots require thorough risk assessment and planning, but catastrophic failure scenarios are usually less likely than gradual, manageable setbacks - Learning new skills happens through incremental progress ("adjacent possible"), where each step reveals the next possible steps rather than requiring a complete roadmap upfront ## 📰 Newsletter **Breaking Free from "Reasonable" Career Paths** Jason Lengstorf's journey from tech VP to independent TV producer offers valuable lessons for WordPress professionals considering bold career moves. When traditional approaches stop working—like the shift from in-person conferences to Zoom fatigue—sometimes the "unreasonable" path becomes the smart choice. Key takeaway: Follow your "slow hunches"—those ideas that build over time through accumulated evidence. But plan thoroughly: assess real risks (not catastrophic fantasies), identify your safety nets, and start small to build momentum. The WordPress ecosystem rewards innovation and creative problem-solving. Whether it's launching a plugin, starting a development agency, or creating educational content, remember that "you can just do things" when you're pioneering new territory. Resources: [WordPress.org Careers](https://wordpress.org/about/careers/), [Make WordPress](https://make.wordpress.org/), [WordCamp Speaker Resources](https://central.wordcamp.org/speakers/) ## ✅ Action Items #### DevRel - Developer advocacy: Create TV-style content showcasing real development workflows, sponsor reality-style coding challenges - Education: Develop narrative-driven tutorials that feel more like entertainment than traditional screencasts - Developer experience: Use storytelling principles to make documentation more engaging and memorable - Developer marketing: Shift from webinar-heavy strategies to content that developers actually want to consume - Community management: Foster communities around shared creative projects rather than just support forums #### WordPress - Core: Document decision-making processes as narrative case studies rather than dry technical specs - Community: Create reality-show style WordCamp content showcasing real project builds and problem-solving - Marketing: Develop entertainment-first content that happens to showcase WordPress capabilities - Training: Build learning paths that feel like engaging stories rather than traditional coursework - Documentation: Apply storytelling principles to make complex technical concepts more accessible ## 🧪 Hypotheses - Entertainment-focused developer content will achieve higher engagement rates than traditional educational formats - "Unreasonable" career moves become more viable when traditional industry playbooks are disrupted by external forces - Intrinsic motivation from process enjoyment predicts long-term success better than outcome-focused motivation - Gradual skill building through "adjacent possible" steps is more sustainable than attempting comprehensive upfront learning ### 📊 Methodology - A/B testing entertainment vs. educational content formats measuring engagement, retention, and conversion metrics - Longitudinal career studies tracking professionals who made unconventional pivots during industry disruptions - Survey research on motivation sources and their correlation with sustained performance over 2-5 year periods ### ❓ Questions - How can WordPress professionals identify when their industry's "reasonable" playbook is becoming obsolete? - What specific risk assessment frameworks work best for evaluating creative career pivots in tech? - How might the WordPress ecosystem better support and fund experimental content formats and community initiatives? ### 🔮 Future Research - Analysis of successful "unreasonable" career pivots in open source communities and their common characteristics - Study of entertainment-first technical content and its effectiveness for knowledge transfer and community building - Investigation of intrinsic motivation cultivation strategies for technical professionals in creative roles ### 💡 Implications - Practice: Encourages WordPress professionals to seriously evaluate unconventional career opportunities and creative projects - Policy: Suggests WordPress community funding should include experimental content formats and innovative community programs - Education: Indicates need for storytelling and entertainment skills in technical education and documentation - Funding: Shows potential ROI for investing in high-production-value developer content over traditional marketing channels ### 🧠 Learning Styles Assessment Reading level estimate: 9th grade (accessible to broad technical audience) #### 👀 Visual learners - Present: Video format with clear visual progression from early streaming setup to professional TV production - Improve: Additional before/after comparison slides, risk assessment flowcharts #### 🔊 Aural learners - Present: Engaging spoken narrative with clear verbal cues and storytelling structure - Improve: Background music or sound design to enhance storytelling moments #### 🗣️ Verbal learners - Present: Rich metaphors (adjacent possible as doors/rooms), clear definitions of technical terms - Improve: More analogies connecting career concepts to familiar experiences #### 🧩 Kinesthetic learners - Present: Actionable steps for risk planning, concrete examples of incremental progress - Improve: Workshop-style exercises for evaluating personal "unreasonable" ideas #### 🧠 Logical learners - Present: Clear cause-and-effect reasoning for why traditional DevRel stopped working - Improve: More detailed financial planning frameworks and decision trees #### 🧑‍🤝‍🧑 Social learners - Present: Community aspects of building a team and working with sponsors - Improve: Discussion prompts for sharing and evaluating career ideas with peers #### 🧘‍♀️ Solitary learners - Present: Self-reflection prompts about personal risk tolerance and career satisfaction - Improve: Structured self-assessment tools and private journaling exercises #### 🌿 Naturalistic learners - Present: Evolution metaphor with Darwin's gradual theory development - Improve: More ecosystem thinking about career development and industry evolution ### 📊 Accessibility Assessment #### Screen reader semantics - Present: Clear heading structure, descriptive timestamps for video navigation - Improve: Alt text for any visual examples, transcript with speaker identification #### Keyboard navigation - Present: Standard YouTube video controls work with keyboard - Improve: Chapter markers for easier navigation to specific topics #### Contrast and readability - Present: High contrast text in notes, clear heading hierarchy - Improve: Ensure any embedded graphics meet WCAG contrast standards #### Text resizing and reflow - Present: Responsive text formatting in notes - Improve: Test video player accessibility at 200% zoom #### Media and captions - Present: YouTube auto-generated captions available - Improve: Professional transcript with speaker identification and timing cues #### Forms and interactions - Present: No complex interactions required - Improve: Ensure any embedded links have descriptive text ### 🌍 DEIB Assessment #### Cultural breadth - Present: US-focused tech industry perspective with some acknowledgment of broader applicability - Improve: Examples from other geographic regions and cultural contexts #### Inclusive language - Present: Gender-neutral language throughout, avoids technical jargon without explanation - Improve: Acknowledge that not everyone has a partner's income as safety net #### Neurodiversity support - Present: Clear structure with consistent heading patterns, chunked information - Improve: Content warnings for financial anxiety topics, multiple processing formats #### Representation - Present: Single speaker perspective, primarily tech industry focus - Improve: Diverse examples of "unreasonable" career pivots across industries and backgrounds #### Psychological safety - Present: Acknowledges fear and anxiety around career changes, emphasizes personal choice - Improve: More explicit recognition that some have fewer safety nets and higher risk tolerance requirements ### ✅ Logical Validity #### Strong reasoning - Deductive strength: Strong logical progression from changed market conditions to need for new strategies - Inductive strength: Good use of personal experience and historical examples to support broader principles - Causal reasoning: Clear cause-and-effect analysis of why <!-- deep-read:sections end --> ## 📺 Video ![](https://www.youtube.com/watch?v=goVNPN6fVwQ) --- # 📄 Full Transcript *Auto-generated from YouTube captions · timestamps roughly every 30 seconds · [watch on YouTube](https://www.youtube.com/watch?v=goVNPN6fVwQ)* **[00:05]** So, I know it's late. I know it's the end of the day and uh have a feeling everybody is feeling a little oversted with information. You've been uh you've been watching a lot of brilliant talks and I guess let's just let's just first give another round of applause for all the amazing speakers today. It's been really good in here. So, I think it's safe to assume that uh your brains are probably full. So, I'm not going to talk to your brains. Instead, I'm going to see if I can fill **[00:35]** your heart. So, to start, if you will trust me, I would love it if we could do a little bit of visualization together. So, please close your eyes. All right. Now, imagine yourself in a meeting with your company CEO. You've grabbed the meeting room. You're both in that cramped little spot. Somebody stole the chair, so one of you is sitting on an ottoman. And he's looking at you like, "Why are we **[01:05]** here?" And you've got a project in mind. You've been doing a lot of research on this. You just need the budget to pull it off. So, imagine yourself in this meeting. You're about to ask the CEO for money. Are you picturing it? How's your heart rate? Okay, now hold that image in your minds and imagine yourself saying these words. I need a half a million dollars. Everybody's blood pressure. Okay. All right, open your eyes. **[01:37]** I need a half a million dollars. So, this was a sentence that I found myself saying to my own CEO back in 2021. I'd been working on this hunch for several years at that point and I was confident that it was the right decision and that this was the program that we needed to pursue. I had laid out my pitch. I had given strong reasoning for why this was the course of action that we needed to take. I just needed the funding to pull it off. **[02:09]** So I looked and I confidently asked for what I needed to make this happen. and you are never going to believe what happened next. He said no. Um he said the idea is great but this is a colossal risk. He said what if it fails? And then he said something that has been echoing in my head since 2021 which is be reasonable. Surely there's another way to get these **[02:40]** results that's less ambitious. Surely there's something we can do that is more budget friendly. And aren't there tried andrue strategies that we can use to accomplish the same thing? How can we minimize the risk on this? It feels so risky to make this choice. It all just feels too big. And so I had to sit there and and listen to this and and getting shut down did suck, **[03:12]** but I tried. I tried to see it from everybody else's perspective. It is a big risk, but it kept gnawing at me. I kept thinking about this and and I I was sure my vision was really clear on this and and my hunch was strong. I knew that this was the right thing to do. Given the goals that we wanted to accomplish, given the state of the market, given the things that were important to our company, this was what we were supposed to do. And it got me wondering **[03:43]** what's so great about being reasonable, right? It is not reasonable to make art. It's not reasonable to go out and do really ambitious architecture projects. Going to the moon was the opposite of reasonable. They didn't say this mission is a proven safe path to hitting all of our OKRs. No. They said, and I quote, why choose this as our goal? And they **[04:15]** may well ask, why climb the highest mountain? Why fly the Atlantic? We choose to do these things not because they are easy, but because they are hard. Choosing to do hard things calls on our best impulses. It challenges us to do more, to be more. And sure, there are easier things that we could do. We could take safe paths. We could do less risky things. But how **[04:48]** good does it feel to explore, to grow, to affect change, to make something that has never existed before? Right? That's that's something special. So, this talk is a story and it's specifically a story about me being unreasonable. And I'm going to make the argument that being unreasonable is a good thing sometimes. And I'm going to talk about how I've turned unreasonable, being unreasonable, into a career that's allowed me to do **[05:21]** all the things that I like to do. It's tailor made to my specific set of skills and interests and fixations. But I do want to caveat. There's nothing wrong with being reasonable. My goal is not to convince you that being reasonable is a problem. But while I'm telling the story, I'm going to share some of the lessons that have helped me get to where I am. And I hope they're useful. But remember, this is a story. I'm not giving advice. I'm not telling you how you should live your **[05:51]** life. I'm telling you what I did to live my life. What worked for me is not guaranteed to work for anybody else. My goal is just to encourage you to examine ideas. Give them time to develop before dismissing them as unreasonable because maybe sometimes being unreasonable is the way to make the biggest impact. Okay. So, so where were we? Be reasonable. Okay. Fine. one no is not the end of the line. We can regroup. We can we can think this **[06:23]** through. So the basis of the refusal was that there were better, more proven options available to get the same results. But I didn't know if I believed that, right? Because I'd been developing what uh Steven Johnson described in where good ideas come from as a slow hunch. And so a slow hunch is this idea that forms over a long time. It starts as a vague sense of like there's something happening here. It's this little voice in your head that says, you know, I think I think I'm seeing something, but I don't know what it is yet. And over **[06:53]** time, as you get more information, more evidence, that starts to consolidate into an idea. So Charles Darwin, who's up on the screen here, is is a good example of the slow hunch. He didn't just sit down and have a Eureka moment and go, "Ah, I understand evolution." This was years of expeditions and journaling and referencing his own research and talking to other people before this theory of evolution sort of emerged. He was chasing something that seemed real, but he wasn't sure what it **[07:24]** was. He just knew he wanted to keep going. And he kept taking these really longass boat trips to figure it out. So, I'd been sitting with my own slow hunch for a couple of years. And I work in developer relations. That's uh that's what I was doing before I went independent. And I did that for a long time. And I was becoming increasingly certain of of one thing. The old ways are dead. DevTools companies used to have this really solid playbook. We could sponsor local meetups. We could sponsor every conference we could find. We could put **[07:56]** on webinars and then we just sit back and we'd watch the leads roll in. Now, who's working in a dev tools company right now? Not as many hands as I thought to. Okay. Is this talk? This is maybe not a talk for y'all. Should I leave? Um, but so that that playbook was not working. When I was at Nellifi, we were trying to do this. And what we were seeing is that the things that had worked before were not working. Now, **[08:26]** webinars stopped getting as many registrations and the registrations we did get weren't turning into new signups. It didn't matter how many ad bucks we threw at it. It just wasn't converting. And fewer people were showing up at conferences. Remember, this is 2021 and the remote conference experience, as we've all been through, is is rough. Um, and for sponsors, the remote conference experience is is utterly terrible. Uh, and I really want local meetups to be strong, but they just haven't come back now in the way that they were before the pandemic, **[08:58]** right? And so, right now, it's not a place where I would bet the company's future. And then the entire playbook basically got smashed down into some variation of hop on a Zoom call. And everyone is so sick of Zoom calls. So I think it's going to get better, but I don't think it's going to get better right now. And so that kind of means we need to try something different. Bud companies are in austerity mode. How many people got their education budget slashed over the last few years? Right? **[09:29]** How many people aren't able to get the company to cover a conference? How many people have pulled back seen their companies pull back on a lot of the spending that they were doing that allowed us to do all all these fun things, right? It's it's becoming less and less common to be able to do that. And that means that for right now, if you are a company, it is very difficult to count on these old things that used to work despite them being the established patterns. Right now, I'm talking about Devril, but this applies **[10:00]** in a lot of ways. We're watching AI, as as we just heard, eat the world. So, all these things that used to work aren't working the same as they worked before. So, even though they seem safe, they are established patterns. They are tradition, tradition's not safe when things have changed in significant ways. So, we needed to do something very different. And the more I looked at the the information that was available to me, the more I felt confident that what I felt like we should do was the right **[10:32]** decision. It was the right path forward. And so that kind of got me thinking that sometimes being unreasonable is in fact the only reasonable choice. So despite how wacky it sounded, my plan wasn't really absurd. It was just different. It was something outside of the established norms, but I felt like it was the clear and logical choice given the landscape that we're in, giving the options that were available to us. And so when all the norms determine what's reasonable and **[11:02]** acceptable get upended, you have to change the game or you're going to end up suffering. And that means that sometimes playing it safe becomes the riskiest option. But I kept trying. I kept pushing. 21 turned into 22. I got myself about two years in and I started to realize if I want to do this, I'm gonna have to do it myself because I just couldn't get through. You know, the budget would get approved and then it would get let's **[11:33]** wait until next quarter. Uh we we had the budget but we moved the budget because we needed to do this other thing. And I just realized like it was never going to be prioritized. It's it was too big of a swing. Company didn't move that way. I needed to I needed to do it on my own. So, I quit my job as a tech executive and I decided to go pursue my dreams of making it big in Hollywood. Well, sort of. I was in Portland. Um, so at the end of 2022, I left my job and I started Code TV. And I will be honest, **[12:05]** um, I don't exactly know what Code TV is. If you, if you ask me to give you an elevator pitch for what my company does, I'll tell you I make TV for developers. There's a lot that goes into that. It's, you know, it's hard to describe and so I typically don't. Um, I just knew that this direction, this TV for developers direction was the right choice given the landscape that we were in because people didn't want to watch Zoom. They didn't want to go to local meetups. They **[12:36]** weren't getting travel budget to go to conferences, but they were watching a ton of TV and talking about it on social media. So, I figure if we make something interesting, people will watch it and they'll talk about it on social media. And given the options, I don't really have any better ideas. You and and we just didn't really see anybody coming up with anything different. So, this was the this was the way I felt confident. And so, that starts to ask these **[13:07]** questions. I'd quit my job to go try to do this thing that was weird, deeply weird. So, what if you're not allowed, right? And and the thing was is like I didn't have permission. There's no real path being followed here. There's no certification that I can get. There's no degree that I could get. Like, as far as I know, this is the the company is kind of the it's not the first of its kind making TV. It's not the first of the kind doing developer stuff, but I'm pretty sure it's the first one that's **[13:37]** kind of mashed it all together into one thing. And that's kind of terrifying because you're off on your own. You're you're in uncharted waters. But the flip side of that is that when you're doing something that nobody's ever done before, there's not really anybody to tell you that you're wrong. You don't need to get permission. You can just try it. You can just do stuff. There's no one to stop you, right? And as a good friend of mine is known to say, you can just do things. Um, if you don't know who Aaron Francis is, you should take a photo of this and **[14:08]** and tag him in it because I love to use his work without credit. So, you can just do things. But at this point, a reasonable person might very reasonably ask as I'm preparing to leave my job and strike out on a new adventure, "What happens if you fail? Because after all, I've been building this career for myself, right? Here's me. I've been building this life. And I **[14:39]** was making great money. And that great money had allowed me to buy a house. And in that house, I was able to entertain my great group of friends. And if I got this wrong, I was going to lose the money. And if I lost the money, I might lose the house, which might lead to me losing my friends. And then I'd be alone. And then I would die, but I wouldn't have money for a coffin. So they'd just put me in a dumpster. And I'd be forgotten and lost and not even a footnote in history. **[15:12]** And I mean, okay, maybe sure this is theoretically possible, but in order for this to be the outcome, I would have to make a whole lot of really bad decisions coupled with a whole lot of really bad luck. So, the more likely outcome is a lot less than this, right? So, instead of playing out the doomsday scenarios and giving into that knee-jerk fear that what if I screw up and everybody hates me and I lose all the loved ones in my life, start thinking through what really goes wrong, right? What happens? what can actually go wrong and and what **[15:43]** are the fallbacks? So, I started planning and this is long before I quit my job, by the way. This wasn't like I quit my job and was like, "Oh, shit." Um, this is how I got ready to quit my job. I started thinking about it. So, I love longhand. I'm a really big fan of a notebook and a pen. Who else is with me on this? Notebooks and pens. Oh, yeah. There this the whole time I've been asking questions hoping to see that many hands. So, we're back, baby. Okay. So, it helps me think. I love writing out longhand. I um this is **[16:13]** this is one of the things that I think is so important is, you know, we we don't want summaries. Making the summaries is the point, not having them, right? This is why I don't put AI agents in my meetings because consolidating information is thinking. Reading a summary is not thinking. Um so, I start writing down my plan. I start thinking through all the boring details. I'm looking at budgets. I'm looking at how much I can realistically charge for my work. I'm looking at whether or not I think it'd be possible if I'm able to charge that much for my work. Can I raise those prices in a in a year, in **[16:45]** six months? Um, how many projects do I actually have on the table? Like, if I say I'm ready to go, who can I actually call right now and say, "Hey, it's time. It's happening. Let's do this." And do I have runway? How much money have I saved up? Like, how long can I do this before I need to get a paycheck or I have to, you know, something goes really wrong? And what are my safety nets? Like for example, my wife also works. So I've got a little bit of a fallback here where my wife is in tech. So if everything goes wrong, I can kind of mooch off her for a **[17:15]** little while while I figure out what my next plan is, right? And and ultimately what it became was this game of managing risks until the biggest risk was not doing the thing. because I started to look and I was like, "Okay, so if I do all of this stuff and I'm I'm looking at this plan and now what happens if I only get half of what is in this plan? You know, I I think I can get this many things, but what if I get half? Can I live? Can I continue?" And the answer was yes in this scenario that I was working on. And so it became really **[17:46]** clear really fast that the biggest risk to me was not trying this. Because if I think about what my purpose in life is, what's really important to me? It ultimately boils down to minimizing regret, right? Like what is the meaning of life? Well, to me, the meaning of life is to be on my deathbed looking back and not having a single thing that I say, "Man, I wish I would have tried that." Right? And if I didn't try this, I think it was going to be one of those things that I'd be like, "What if I bet on myself? What **[18:17]** if I'd taken that shot?" Right? So, I had to do it. So, we covered risk, right? But a reasonable person might very reasonably ask, "Do you actually know how to make a TV show?" And I didn't. So, uh, I'd been streaming on Twitch, but anybody who streamed on Twitch and also watched television knows that there is a vast difference between a live stream and a TV show. So, I didn't **[18:48]** really have any of the requisite experience to do the thing that I wanted to do. However, I had this theory. TV shows are made by people, and I am a people. So, I could figure this out. It was possible, right? By the transit of property, I can get there. Um, and as a quick aside, this was probably the single biggest blocker for me in making this leap because I spent the entire first year not making the thing. I was **[19:21]** doing safe things because I was scared that I would try to do it and do a bad job. I kind of wanted to figure it all out before I even started. And and I'll talk more about this in a second, but ultimately it doesn't work that way. So I had to look at what can I do to move forward. Now I had to be okay with not knowing how to get to my destination. I just knew what I could do next. I knew what the next step was and I trusted that that next step was going to give me a new vantage point that would help me **[19:52]** determine the step that comes after that one. That had to be good enough because there was no way to see all the way to the end. So there's this concept that I love called the adjacent possible. And the the core of it is that progress is can be seen as a room with doors in it. And every time you open a door, you gain access to a new set of doors. And you you can think of each of those doors as like a new possibility. And you can't **[20:25]** open all the doors at once. You have to open the doors in the room you're in before you can open the doors in the next room. Right? You can't go directly from humans discovering fire to humans discovering jet propulsion. Right? It's kind of like that old Mitch Hedber joke. Like I know they say that Seven Up is lemon and lime, but there's more to it than that. Um, so I don't know how to do a lot of the things that I need to do to take this leap. But I did know that if I kept taking steps forward and I kept learning **[20:56]** the next thing, the thing that was obviously missing, it would it would expose what the next step was after that because I would see what I could do and what I couldn't do and I would know what I needed to learn next. And so it's a little scary. It's always overwhelming, but going after big ideas usually means you're not going to see to the end. And you just have to take the next possible step and know it's not going to be the last. So maybe we're okay on risk. Maybe we trust ourselves to learn. But again, a reasonable person might very reasonably **[21:28]** ask, "What if you suck at this?" After all, this is a new thing. Haven't done it before. What if I try and just terrible? This is This is a killer for so many ideas. I mean, can it like I'm going to ask for hands again. How many people here have have had a good idea and you've chosen not to do it because you were worried it would suck, right? This absolutely froze me in my tracks. What if I look like I'm bad at **[21:59]** this? What if I look terrible? Fortunately for me, I had a little bit of practice. I used to be in a band and I would play on stage and we would videotape every show from the back of the room so that we could see what we looked like on stage. So, I had seen myself dance in women's jeans and eyeliner, and I knew I couldn't look stupider than that. So, I looked back at where I started. This is one of my very first live streams. And as you can see, this is a **[22:31]** uh Zoom call sharing the screen. Don't have any overlays. There's no design here. You can see my my video up in the top right. I had no lighting using the MacBook camera. I didn't have a microphone. There was no no production value whatsoever in this thing. I just started because I didn't know better at the time. I I didn't know that you could get a good microphone or a good camera. I was like, well, I think streaming is going to be better than trying to do just webinars because I can maybe reach more people and then we can pull clips out. I had ideas, right? **[23:04]** So, even when you suck, you can just do it anyways as my wife always says. So being scared isn't going to go away, but it gets easier with practice. It gets easier to do scary things if you show yourself that you can do a scary thing and survive. So I kept doing it for for years and years. This is maybe two or three years into my streaming journey, maybe a little bit more. And and now you can see I've got some design. There's some **[23:35]** interactive bits there. We've got uh you know, the chat is there. my my camera and microphone are way better. Um, I'd figured out how to get the Zoom window hidden so that you couldn't see that I was just like sharing a screen. All these little changes. And I still wasn't really where I wanted to be, but I I knew that there was a place to go. But again, I was kind of frozen by this idea of like, I want to make a TV show. This isn't a TV show. This is nowhere near a TV show. And so I kept putting off **[24:06]** taking this swing at the thing that I really wanted to do until I realized that I was never just going to get somebody to hand me that half million dollars to do the thing that was in my head. If I wanted to do this, I was going to have to figure out what's the actual minimum viable product here. What's a thing I can do that's not very expensive? Or in my case, what can I do that doesn't cost money? And so I resisted it for a really long time, but eventually I ended up taking the same approach where I got my friends together. We gave ourselves a time **[24:37]** limit. We had 30 minutes to plan and four hours to build this app. We all recorded, you know, our screens as we demoed to each other. And we showed each other the apps we were building. And I was simultaneously very proud of this. This was the the very first episode. I call this season zero of WebDev Challenge. Um, but also it sucked. It was remote. It was It had the weird like live delay that you get when you've got people talking to each other from around the world, you know, like Sarah's calling in from Europe and you just **[25:08]** don't get that warmth of a of a human interaction when people are 300 milliseconds delayed in conversation. So, I had to to sort of embrace this idea. I heard an interview with Ira Glass where um he said that your taste is going to outrun your talent for a long time. When you when you first start out, your ability to see what something could be is going to be far superior to your ability to make a thing. And you're always going to be able to **[25:39]** imagine what it could be, but you're never going to get better unless you make it, right? So, I decided I was going to keep going. I made a few of these of the the remote version and then I was able to leverage that and say, "Hey, look, people like this, right? It was getting good views on YouTube. People are enjoying it, but I want to do this in person." And I found a partner. I talked to Data Stacks. They were great. And they decided they were going to fund half of what I wanted to do. I was like, I guess I'll I'll take it. Let's do it. **[26:11]** And uh and so I ended up doing this in-person reality TV show where I was able to put in half of my own funds. This was the bet I took on myself was that I was going to pay for this because I believed that if people saw it, they would do the thing, right? And this first episode went live in June of 2024. And and fortunately, this hunch that I'd been working on since before 2021 was proven right. This episode was wildly popular and I suddenly had a line of companies out the door who wanted to **[26:42]** make these episodes. I ended up in 2024 making 10 episodes of this show. And in 2025, we've made 12 and we're going to end with I think 13 for the year. Right? This is pretty much my entire income now is making stuff like this. And as you can see, this is very different from a live stream. We've got a whole crew. We've got three camera people. We've got our sound mixer. We've got a gaffer doing lights. We've got a team of editors. We've got, you know, we're **[27:13]** we're everything. We're flying people in. We're doing logistics. I have an corporate expense account with a hotel chain. Like, what the hell, right? Like, so many things have happened that I never could have guessed I would need to know. Um, I have corporate sponsors. I have like Ben Q sent me a bunch of monitors for free and Uplift Desk sent me desks because these videos are so successful that they just want to be in them, right? Never could I have dreamed that that was a thing that was possible. **[27:44]** And so with every episode, I'm always looking at like, how do we take this 1% further? How do we how do we see let's be even more unreasonable? What what could we do next? Right? And so it's been a very visual reminder that if you want to get good at a thing, you have to do the thing. And you can't just do it once. You have to do it often. And intentionally, deliberate intentional practice of doing a thing is how you're going to get better at the thing. And there's no shortcuts. This is terrible news. I know. I'm sorry. And in light of **[28:14]** this, a very reasonable person might very reasonably ask, "But what? It is hard." And it is hard. But you know what else is hard? It's like our jobs. Like I worked at IBM. I worked in startups. I've worked as as an agency. It's always hard. I burned out in big tech. I burned out in startup tech. I burned out in an agency. And now I'm burning out in this. It's always going to be hard. There's no there's no shortcuts. **[28:45]** But the thing that sucks here is that I do think if it feels hard, if it if you are looking at it and every day you're thinking,"I don't want to do this." I actually don't know anybody who's sustainably pushed through something that they thought was hard and and stuck through it, right? Like maybe there are people who have the internal fortitude to just hate it for years and and get the thing that they want, but that's **[29:16]** never been how it works for me. It's got to be a different thing. The people who I know who make the most progress are finding a way to enjoy the process in itself. Like the act of doing the thing is the reward for the thing. And that allows you to get to the outputs, the results, these big uh big outcomes. But those are sort of a pleasant side effect instead of being the only reason you do stuff. And I think this is where I started to realize why this thing was different from the other things that I **[29:47]** was doing. Because previously I would sort of look at my jobs and I would think about the the project I was working on and I would think about it as all right well if I just suffer through this project then I'm going to get that promotion and then I can hopefully have a little more autonomy over what I'm working on. And then I would get it done. I wouldn't get the promotion. then I'd look at the next project. Okay, we're doing this again. We're going to get through it. We're going to get the promotion and then I'll finally be okay. And it just never became true. Um, if you can make it into a thing where doing the thing is its own reward, and this **[30:18]** doesn't have to be my big silly thing. This can be what you work on dayto-day. This can be the types of projects you volunteer for at work. This can be the stuff you do with your family outside of work. doesn't have to be my thing. But if you can find the thing for you and find a way to do it so that it brings you joy in the doing, then you're going to do incredible things and it'll never feel hard, right? It'll be hard and you're going to be working and you're going to know that you're working, but it won't feel like you're dragging **[30:49]** yourself toward victory, right? You're just going to do it because it's enjoyable to do it, even if it's hard. And and so this has led to one of the most incredible things in my life, which is that I have all of these special interests. I really like code. I really like open source. I also really like figuring out how to tell stories. I like to write. I like to make goofy with my friends. I like to do all of these interesting things. And because I was willing to do this unreasonable thing, I' I've found out that I'm able to just **[31:19]** have a bunch of creative people around me and work with companies that understand the vision that I have. And I get to make I made this for work. >> Get a load of this one. This bloke's looking to rewrite his entire code base in Rust. >> But wait, I need thread safety at compile time. You got cheeses, mate. [Music] **[31:49]** >> I got paid for that. >> And so again, you can just do things, right? You can just do things. Um, and I I followed a hunch and I invented a job for myself and I chose to trust that unreasonable voice in my head that said this is the right thing to do. And as a result, I am literally living out my dreams right now. When I was sitting in my VP job at Netlefi, I would daydream about this being my job. This is what I was trying to engineer my entire **[32:20]** department into becoming. This is what I was asking for the money to do. And today, I get to do it right. And now, are there parts of this that stress me to holy hell? Is my, you know, is my hair turning gray? Yes, very much so. But I'm still I wake up and I'm excited to do this work. And and so what I want to just implore everybody to do is to give your unreasonable ideas a little more time. If you've got that thing in your head, you you've been thinking **[32:51]** about this for a while, you feel like you've got something that you can offer, pay a little more attention to it. Don't just dismiss it out of hand as being too much, too risky. Give it some time. Give it some effort. and uh follow that slow hunch cuz there's truly no way to fail except giving up. Thank you.