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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

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.
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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
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! 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
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 keep us focused on what matters to you.

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.

📮 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

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

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 keep us focused on what matters to you.

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
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!
🧡 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 keep us focused on what matters to you.

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
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!.
🧡 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 keep us focused on what matters to you.

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
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!.
🧡 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 keep us focused on what matters to you.

Part One - Bryan McCann, CTO of You.com, on AI, Engineering, Art, and Everything In Between

I'm tackling a massive challenge today: burnout. While the standard advice usually involves working less, I want to show you a practical dimension of burnout you have more control over, focusing on increasing your agency and autonomy to manage chronic workplace stress more effectively. Burnout is classified by the ICD-11 as a syndrome resulting from chronic workplace stress that has not been successfully managed.

This episode includes practical advice for understanding and addressing burnout by shifting focus from reducing work volume to increasing control and resources.

 • Understand the three dimensions of burnout as classified by the ICD-11: 
feelings of energy depletion or exhaustion • , 
increased mental distance/negativity • toward the job, and 
reduced professional efficacy • .
 • Discover why the amount of time you work is 
not • a direct input to burnout, meaning working less is often impractical and may not solve the underlying issue.
 • Learn the core philosophy for addressing burnout: 
In order to control stress, provide control • (meaning agency and autonomy).
 • Explore why stress is directly correlated to the ratio of demands placed on you versus the resources (including decision-making power, training, and tooling) you have to meet those demands.
 • I’ll give you practical ways to approach your manager to secure necessary resources, training, or mentoring to improve your professional efficacy and reduce job negativity.
📮 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!
🧡 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 keep us focused on what matters to you.

Going to War with Burnout - Less Hours Isn't Your Only Option

In this episode, I dive into the management mantra that "what is measured is managed" and explain why this simple assertion often leads to a complex trap. We discuss why the act of measuring team productivity is never neutral—it's an intervention that immediately changes behavior, often resulting in unintended consequences like gaming the metrics. We'll explore how to collaborate with your team to find measurements that truly drive desired behaviors.

 • Understand why the phrase "what is measured is managed" means that 
measuring something triggers management • of that thing, in varying degrees.
 • Learn why the act of measuring something is an intervention, especially when done with the intent of turning it into a target (e.g., increasing PRs or decreasing bugs), and how this action is shown to change behaviors around the thing being measured.
 • Discover how measurement can lead to unintended consequences, such as when tracking velocity via story points causes team members to inflate or deflate their estimates, making the measurement itself less meaningful.
 • Explore why giving ownership of metrics to the people acting to improve them makes sense, and how you can collaborate with your team to determine what kinds of measurements should be taken.
 • Recognize that if you want something to survive—such as paying down tech debt—you must 
feed it • with time, resources, and attention, ensuring your actions line up with what you claim to care about.
 • Understand that since your calendar and dashboards will get crowded if you measure everything, the exercise of choosing metrics is as much about accepting that you have to choose what you will actively manage and invest in.
📮 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!
🧡 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 keep us focused on what matters to you.

The Good and Bad of Choosing Measurements - Traps and Opportunities of Measuring What Matters

I want to dive into the concept of Deliberate Practice, which sets the greatest apart in fields ranging from sports to writing to engineering. I’ll explain why it’s much more than just repetition or experience, and why applying it to your career can lead to rapid improvement. Most importantly, I will provide concrete ways you can apply deliberate practice to level up your engineering and leadership skills, especially in areas that are traditionally difficult to practice, such as communication and strategic decision-making.

Differentiate Practice from Deliberate Practice • : Understand that while repetition is part of practice, deliberate practice specifically involves engaging in a 
very narrow set of activities • with the 
intentional goal of improvement • , requiring very quick feedback for continuous incorporation.
Identify Opportunities for Rapid Improvement • : Learn why deliberate practice is much more effective at achieving rapid improvement than simply engaging in repetition.
Apply DP to Leadership Skills • : Discover how to incorporate deliberate practice into roles like engineering manager, tech lead, or IC (Individual Contributor) leader, where the activity of practice is often harder to pinpoint.
Leverage Existing Work for Practice • : I suggest a mindset shift where you begin looking at existing responsibilities, such as one-on-ones, as opportunities for practice. For example, you can focus on improving your clarity when providing constructive criticism and ask for specific feedback on that aspect.
Generate Novel Value Through Practice • : Explore how engaging in deliberate practice activities—like recording a video to communicate a technical concept or creating documentation—serves the primary goal of practice, while almost certainly creating unexpected value for your team (often net neutral or positive).
Use Backwards Training for Strategy • : Find out how to practice strategic decision-making and forecasting by using "backwards training". This involves reviewing past decisions or work scopes, creating your own rationale or estimate, and then calibrating it against the known reality.
Simulate Difficult Conversations • : Consider leveraging Large Language Models (LLMs) to engage in deliberate practice around language-heavy skills, such as modelling sensitive or difficult topics, or practicing receiving harsh feedback.
📮 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!
🧡 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 keep us focused on what matters to you.

Engage in Deliberate Practice to Level Up Your Engineering Leadership Skills

I'm excited to be interviewing Ben Orenstein from Thoughtbot. Ben is a brilliant craftsman of a developer, and in this episode we discuss what it takes to be a craftsman. This interview is split into two parts, so be sure to check out the next episode for the second part!

Giant Robots Smashing into Other Giant Robots (podcast)
Upcase
Vim for Rails Developers
Vim resources on Upcase
Trailmix.life

Ben's personal site and writings can be found here

Ben on Twitter, @r00k: https://twitter.com/r00k and on GitHub, @r00k: https://github.com/r00k

19: Ben Orenstein from Thoughtbot, Part One

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