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Jonathan Cutrell

Developer Tea exists to help driven developers connect to their ultimate purpose and excel at their work so that they can positively impact the people they influence.

With over 17 million downloads to date, Developer Tea is a short podcast hosted by Jonathan Cutrell, engineering leader with over 15 years of industry experience. We hope you'll take the topics from this podcast and continue the conversation, either online or in person with your peers. Email: developertea@gmail.com

Developer Tea

🎧 Episode Notes: Using a Nine-Block for Skill, Potential, and Energy Investment
Most career assessments try to paint a static picture of what you can do well with the least effort, but they often fail to provide a practical roadmap for your next career move. This episode provides a simplified, multidimensional version of a classic management tool to help you prioritise your growth:

Understand the Nine-block Matrix: • Visualise a grid where the x-axis represents your 
current performance • (how well you are doing now) and the y-axis represents your 
potential • (your capacity to grow to the next level).
The Energy Dimension: • Go beyond a 2D map by evaluating the 
energy cost • of each skill on a scale of 1–5; this helps you identify where you are on "autopilot" versus where a skill is draining you.
The Risk Factor: • Assign a 
risk or criticality score • to your skills to determine which are "fundamental" to your role (like software delivery) and which can be safely dropped to make room for more valuable growth.
Spot Opportunity Flags: • Identify areas where you have 
high potential but low performance and low energy output • ; these represent your best opportunities for rapid improvement with the least input.
Make the Counterintuitive Trade-off: • Learn why you might need to 
drop a skill you are already good at • if it has low growth potential, redirecting that energy toward a new skill that offers higher long-term value for your career.
Categorise Your "Bread and Butter" Skills: • Recognise those mid-level skills that ensure your reliability and help you get the job done but shouldn't be the primary focus of your intense energy and development.
📮 Ask a Question
If you enjoyed this episode and would like me to discuss a question that you have on the show, drop it over at: developertea.com.
📮 Join the Discord
If you want to be a part of a supportive community of engineers (non-engineers welcome!) working to improve their lives and careers, join us on the Developer Tea Discord community today! I am in there as well, and you can message me directly.
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Career Growth Accelerator - Assessing Yourself - Using a Nine-Block to Map Your Skill, Potential, and Energy Investment

This episode marks the 11th anniversary of the show, and I want to celebrate by continuing our Career Growth Accelerator series. Today, we’re moving beyond the "autopilot" mode that many engineers find themselves in and learning how to define goals that are uniquely yours so you can find the specific challenges that will actually move the needle.
🎧 Episode Notes: Going from Autopilot to Purpose
Many of us operate on instinct, chasing goals like "get a promotion" or "make more money" without understanding the "why" behind them. This episode is designed to help you interrogate those automatic responses and find a path that is optimized for what you uniquely value.

Break the Autopilot Loop: • Understand why common goals like "getting a promotion" are often just survival mechanisms intended to keep us safe within social norms rather than reflections of our true values.
The "Never Again" Pressure Test: • Use the mental exercise of imagining you will never get another promotion; if this causes visceral anxiety, it’s a sign that your goal is rooted in a sense of safety rather than self-actualisation.
Move from Post-Rationalisation to Purpose: • Instead of backwards-justifying the status quo, learn to be honest about what you truly desire—whether it's the affirmation of intelligence, the freedom of discretionary time, or a specific mission.
Create Instructive Goals: • Discover why a goal must be personal and specific to be useful; a generic goal provides no roadmap, whereas a unique goal acts as an instruction for what to do next.
Find Your True Challenge: • Once your goal is defined, identify the specific obstacle standing in your way that requires ingenuity and isn't already decided for you.
The "Asterisk" of Solvability: • Learn the most critical rule for picking a challenge: it must be something you can 
reasonably solve • given your current means to avoid falling back into paralysis and autopilot.
📮 Ask a Question
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📮 Join the Discord
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Career Growth Accelerator: Going from Autopilot to Purpose

This episode kicks off the Career Growth Accelerator series, focused on the specific hurdles faced by mid-to-senior level engineers, managers, and leaders who are looking to move to the next level. Before diving into specific strategies, I’m addressing the fundamental prerequisite for real growth: getting out of your own way. We often block our own progress because our ego conflates our self-worth with our career position, making it impossible to see the real problems or lessons we need to learn. In this episode, I share a vital mental exercise to help you disconnect your identity from your job title and begin diagnosing your career challenges honestly.

 • Understand why protecting your ego is one of the most 
dangerous ways to control your career • , leading you to discount valid reasons for stagnation or failure by focusing only on external factors.
 • Discover the fundamental shift needed: 
disconnecting your self-worth from your career aspirations • . Your position is merely a fact and has little bearing on your innate value or capacity to succeed more generally.
 • Learn how to use a 
distancing thought experiment • —viewing your situation as if it were an acquaintance’s story—to remove your ego from the diagnostic process and gain necessary clarity and perspective.
 • Explore why effective growth advice, whether for promotion or post-mortem analysis, requires focusing almost exclusively on the 
diagnostic aspect • ("What happened and why?") rather than building justifications based on your worthiness or past performance.
📮 Ask a Question
If you enjoyed this episode and would like me to discuss a question that you have on the show, drop it over at: developertea.com.
📮 Join the Discord
If you want to be a part of a supportive community of engineers (non-engineers welcome!) working to improve their lives and careers, join us on the Developer Tea Discord community by visiting https://developertea.com/discord today!
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Announcing - Career Growth Accelerator, Episode Zero - Getting Out of Your Own Way

Are you a mid-to-senior level engineer or leader who has hit a career roadblock or found yourself stagnated? I'm launching the new Career Growth Accelerator series, focused on the difficult, non-obvious hurdles that prevent you from moving to the next level.

In this foundational Episode Zero, I cover the critical prerequisite for growth: Getting Out of Your Own Way. Our ego often protects our self-worth by blaming external factors for failures, making honest diagnosis impossible,.

• Learn why protecting your ego is the most dangerous way to control your career.

• Discover the fundamental shift: disconnecting your self-worth from your career aspirations to gain clarity.

• I introduce a distancing thought experiment to help you diagnose the real problems blocking your path.

• Start focusing on the diagnostic aspect—What happened and why?—to build real momentum.

Subscribe now so you don't miss out on this series!

Announcing: The Career Growth Accelerator Series

When you hit a career roadblock, the methods that worked for you before often stop working. Today, I’m diving into why that happens, and why the first and most critical step in progressing past stagnation isn't doubling down on skills, but clearly defining the problem standing in your way.
Problem Definition As A Path for Career Growth
My goal on the show is to help driven developers like you find clarity, perspective, and purpose in their careers. This episode is for everyone trying to grow, especially if you have hit some kind of roadblock. Most career progression, especially early on, happens somewhat automatically through natural experience, domain expertise, and skill accumulation,. However, as you progress, you will hit missing rungs or roadblocks—things preventing you from progressing in promotions, positions, or specific projects.

When blocked, most people rely on the same things they did before, such as gaining experience, reading blogs, or building side projects, using a "scattershot approach" to try and guess what their managers want,. Unfortunately, relying on activity that previously got you ahead will not necessarily work later in your career,. As you climb the career ladder, the number of positions available decreases (the pyramid shape), meaning that even being highly qualified may not lead to the next role if it simply doesn't exist,.

If you haven't defined the problem, you have no way of knowing whether the actions you are taking will help you progress where you want to go. Instead of continuing the never-ending cycle of self-improvement, you need to step outside your own context and try to see the problem from an external viewpoint, like a consultant. Recognizing the core problem—like a lack of available roles—allows you to shift your focus away from only improving your skill set and toward solving that specific organizational problem, perhaps by expanding the necessary scope for the role to open up,. Redefining the problem may mean shifting your goal from getting a promotion to convincing someone to let you perform the activities associated with that higher role, which is a different process entirely. In almost every circumstance where you are blocked, there is a problem that you need to work on defining better; this is the first step towards moving past the roadblock,.

 • Explore why the natural career progression that works early on—driven by experience and skill accumulation—slows down and fails when you hit later-stage roadblocks,,.
 • Discover why relying on a "scattershot approach" of extra activity, like reading blogs or building side projects, is often ineffective when facing a structural block in your career path,,.
 • Understand that if a desired role doesn't exist within the company structure, becoming more skilled or qualified won't solve the organizational problem,.
 • Learn how redefining your career problem—for instance, shifting from needing a promotion to needing permission to do high-level tasks—can open up entirely new pathways for growth.
 • Challenge your self-improvement cycle by stepping outside your own context and defining your career roadblock as if you were an external consultant,.
📮 Ask a Question
If you enjoyed this episode and would like me to discuss a question that you have on the show, drop it over at: developertea.com.
📮 Join the Discord
If you want to be a part of a supportive community of engineers (non-engineers welcome!) working to improve their lives and careers, join us on the Developer Tea Discord community by visiting https://developertea.com/discord today! I'm also in the community, and you can message me directly there.
🧡 Leave a Review
If you're enjoying the show and want to support the content head over to iTunes and leave a review! It helps other developers discover the show and keeps us focused on what matters to you.

Problem Definition As A Path for Career Growth

We often look for ways to reduce the load on our brains, seeking shortcuts and optimizations to get ahead. Sometimes this works, reinforcing the belief that we can hack our way around every problem. However, this episode addresses the truth that many fundamental aspects of your career require something difficult, messy, slow, or inefficient, demanding deep thought and repeated failure.

This episode details the difficult truths about facing the most essential challenges in your career:

Understand the Hard Path: • Recognize that many aspects of your career, skill set, relationships, and hobbies require something difficult, messy, slow, or inefficient, demanding deep thought and repeated failure.
Identify Your Primary Obstacles: • Pinpoint the hard things you are procrastinating on, such as developing essential domain knowledge, deepening relationships with crucial co-workers or your manager, or getting the necessary "reps" of difficult building and practice.
The Path to Mastery: • Realize that becoming a great engineer (e.g., a great Python developer) is achieved not by reading books or finding perfect tools, but by 
building things over and over • . This practice includes receiving feedback from peers and applying what you learn under challenge.
The Pain of Decision: • Explore why it is difficult to even 
decide • to do a hard thing. By committing to the challenging path, you are choosing to 
cut off your optionality • and giving up the hope of finding an easier, lower-investment alternative.
Sustaining Commitment: • Understand that initial motivation or an energetic feeling will not carry you through the obstacle when the development process becomes awkward, slow, or frustrating. Staying committed requires reinforcing your 
core underlying reason • for doing the hard work.
The Reward: • Recognize that if you successfully address the hard thing you know needs doing, everything else in your life and career becomes easier.
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📮 Ask a Question
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📮 Join the Discord
If you want to be a part of a supportive community of engineers (non-engineers welcome!) working to improve their lives and careers, join us on the Developer Tea Discord community by visiting https://developertea.com/discord today! There are other engineers there going through similar things in their careers, and I am also in there, where you can message me directly.
🧡 Leave a Review
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You Know The Hard Thing You Need to Do Next - Here's Why It's Worth Doing Now

If you're looking to accelerate your career growth, this episode gives you what may feel like hard truths about the path forward. So many engineers fall into traps of overthinking, chasing minor optimizations (like 5% or 10% productivity boosts), or playing the games of politics and networking. While these sideline activities aren't necessarily useless, I want to help you focus on the "big engines" and "primary considerations"—the things that will make the monumental difference in your career building strategy.

• I explain why arguments based on nuance—such as trying to convince your manager that your work is valuable despite low throughput, or doing "glue work"—are often based on flawed strategies that cause your career to suffer and not grow easily.

• I use an allegory (discussing the primary path of treatment for low testosterone) to illustrate that many engineers are trying to fix a fundamental, mainline career problem with a sideline, nuanced solution, instead of focusing on the gold standard primary path.

• I debunk the skill collection fallacy: the misconception that broadening your skill set (learning more languages, frameworks, or techniques) provides the same level of career benefit as it did early on.

• Discover the fundamental path to growth: I advise you to set down new languages and skill sets and instead become a craftsman of a limited set of tools, fully understanding the domain, business problems, and how value flows through the organization.

• Learn why the most important factor that substitutes for very few other things is engaging in the deliberate practice of solving a sheer volume of problems encountered and solved over and over.

• I detail how to avoid the comfort zone: while solving problems is vital, you must ensure those problems progress with you by increasing complexity, scope, responsibility, or sheer volume of work, otherwise, your potential for growth will become limited and you will stall out.

• I caution that a lack of challenge (feeling no discomfort ever) can lead to boredom, disengagement, and eventual burnout, because your brain adapts, reducing the flow state you experience. I suggest finding ways to introduce discomfort that pushes you.

• Understand that the primary course of treatment for a failing or stalled career is simple: become incredibly good at your core set of responsibilities, making things like networking, resume writing, and managing relationships easier as a result.

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Career Fundamentals - Avoid Career Traps by Focusing on Primary Paths of Improvement

If you're an engineer looking to move into a senior role, you have likely heard that you need to demonstrate "ownership". Unfortunately, this crucial term is often poorly defined and leads to a major misconception: that ownership means being assigned a full project or a Tech Lead role. I want to dispel that myth and explain why ownership is actually a necessary behavior and mindset shift, applicable in almost every action you take, regardless of whether you’re leading a project.

 • Understand why ownership is a critical aspect of moving along your career track, especially for engineers moving from the associate or mid-level engineer role up to senior.
 • Uncover the misconception that ownership requires a specific scope of responsibility, such as owning a project or a deliverable.
 • Discover the crucial phrase that defines the ownership mindset: 
"What now?" • or 
"What next?" • which should guide you through every situation you encounter.
 • Learn why true ownership is not about inherently knowing every technical detail or executing every step, but about being willing to take responsibility and accountability for 
figuring out what happens next • .
 • Explore how a senior engineer's ownership behavior means translating identified problems (like those found in a retro) into action or decisions, thereby ensuring things continue moving forward and don't stall out.
 • I explain that engineers show ownership by 
choosing to opt in • to be held accountable for outcomes, rather than waiting for a manager to intervene or ask for a status update.
📮 Ask a Question
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📮 Join the Discord
If you want to be a part of a supportive community of engineers (non-engineers welcome!) working to improve their lives and careers, join us on the Developer Tea Discord community by visiting https://developertea.com/discord today!
🧡 Leave a Review
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Getting to Senior - Taking Ownership Without Leading Projects

Hey everyone, welcome to today's episode of Developer Tea. This is the second part of my interview with Bryan McCann, the CTO at you.com. If you haven't listened to Part One, I'd encourage you to go back, as it provides crucial context for our continued discussion. In this episode, we dive into how you can think about relating to and integrating the massive changes that AI is bringing to your job, whether you are a software engineer, manager, director, or product professional. Bryan and I discuss his interests beyond research, including art and organizational design.

 • Explore the two primary paths for developers in the long run: specializing as 
managers of AI tools • (like a product manager with engineering insight) or striving to be better than AI at 
building better versions of AI itself • (the "neurosurgeon" type).
 • Understand why refining your 
intuitions about what should be built • becomes increasingly crucial as automation makes execution easier.
 • Examine how 
conceptual biases • often become the bottleneck when interacting with powerful AI tools, such as focusing on very narrow tasks for a broad tool.
 • Learn how to approach AI failures: treat a failed output as an opportunity to dig in and figure out why, perhaps by asking the AI to write a better prompt or identifying a fundamental missing capability that could become a great startup idea.
 • Conceptualize AI as the earliest versions of 
magic • , where the manipulation of symbols (like embeddings) allows us to extend our influence into the world in a flexible and powerful way.
 • Discover principles of organizational design by studying how 
neural networks learn • , focusing on strong information flow, skip connections, and aligning with the objective.
 • Consider the idea that the next phase of human development might involve 
emulating AI’s learning mechanisms • (rather than expecting AI to become more human-like) to unlock the next phase of humanity and continue our search for meaning.
 • Hear Bryan’s final piece of advice for listeners: focus on 
learning • and working on things you are passionate about that will have the 
highest possible impact • .
📮 Ask a Question
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📮 Join the Discord
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Part Two - Bryan McCann, CTO of You.com, on AI, Engineering, Art, and Everything In Between

Hey everyone and welcome to today's episode of Developer Tea. It's been quite a while since I've had a guest on the show. Today, I'm joined by Bryan McCann, CTO at you.com. We dive into a wide-ranging discussion, exploring the philosophical origins of his career—from studying meaning and language to working in very early AI research. This discussion is less advice-heavy and more focused on kind of theory and discussion. I hope this is insightful for you and helpful as you crystallize your own philosophies on these subjects.

 • Explore the philosophical journey that led Bryan McCann from being a philosophy major interested in meaning to pioneering early AI research. Bryan views his current work as an extension of those original philosophical questions.
 • Discover how Bryan shifted from hitting a dead end in "armchair philosophy" to using computational tools to study language and try to make machines that could create meaning.
 • Understand why Bryan believes that meaning, in the sense he originally sought it, is an 
innately human thing • , tied to purpose and the narratives we use to shape our sense of reality.
 • Discuss the profound realization that AI breakthroughs might be akin to discovering electricity, suggesting we are tapping into a fundamental 
framework of meaning or connection • that has always existed.
 • Examine the concept of super intelligence and the "flywheel effect," where AI accelerates research and development, building better versions of itself and potentially surpassing the classic anthropomorphic vision of machine intelligence.
 • Explore Bryan’s other interests, including organizations, people, and art, which he sees as continuing the uniquely human 
search for meaning • .
 • Consider the idea that humanity's constant need to differentiate itself from machines may simply be a mechanism for survival, enabling our continued dominance.
📮 Ask a Question
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📮 Join the Discord
If you want to be a part of a supportive community of engineers (non-engineers welcome!) working to improve their lives and careers, join us on the Developer Tea Discord community by visiting https://developertea.com/discord today!.
🧡 Leave a Review
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Part One - Bryan McCann, CTO of You.com, on AI, Engineering, Art, and Everything In Between

Jonas Downey is the design lead at Basecamp. In this interview we discuss the ethics of designing and building constraints into your product that change human behavior.
✨ Sponsor: Redhat
Get access to Redhat's exclusive developer resources. Head over to https://developers.redhat.com/about to join for free today!
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Design Lead at Basecamp, Jonas Downey - Part Two

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