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Thoughtfully Critical
Chris Wahl
19 episodes
1 week ago
Hosted by Chris Wahl, an industry veteran with nearly 30 years of experience, this podcast contains 15 minute stories diving into the challenges and opportunities of modern systems, platform design, cloud architecture, and team building.
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Technology
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All content for Thoughtfully Critical is the property of Chris Wahl and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
Hosted by Chris Wahl, an industry veteran with nearly 30 years of experience, this podcast contains 15 minute stories diving into the challenges and opportunities of modern systems, platform design, cloud architecture, and team building.
Show more...
Technology
Episodes (19/19)
Thoughtfully Critical
The Strategic Imperative of CI/CD

In this video, I dive into one of my favorite topics: CI/CD (Continuous Integration and Continuous Delivery), also known as pipelines. Whether you're new to automation or looking to level up your DevOps skills, I'll break down the core concepts, share real-world examples (including some fun unicorn analogies!), and give you practical tips to start building your own pipelines. If you're ready to make your workflow smoother, more efficient, and more collaborative, this episode is for you. Let me know in the comments what tools or resources you're using, and let's keep learning together!

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4 months ago
17 minutes 3 seconds

Thoughtfully Critical
Building Better, Stronger Systems

Join me on Thoughtfully Critical as I share insights and practical strategies for effective systems design. Drawing from years of experience building large-scale systems, I outline a three-phase process: Prototype, Scale, and Polish, to achieve elegant and maintainable solutions. Discover how to navigate common pitfalls, the importance of iteration, and how to transform raw ideas into robust, scalable systems. Perfect for anyone looking to advance their career in systems architecture or build better, more reliable solutions. Comments and community sharing encouraged!

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5 months ago
28 minutes 34 seconds

Thoughtfully Critical
DevOps in the Modern Era

My journey through the world of DevOps! From the early days of breaking down silos between developers and operations to the current complexities of cloud-native environments. I'll talk about my personal experiences, the challenges we faced, and how the role of a DevOps engineer has evolved.


More: https://wahlnetwork.com/2025/05/13/the-evolution-of-devops-and-why-it-matters-now-more-than-ever/

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5 months ago
22 minutes 49 seconds

Thoughtfully Critical
Subscriptions Gone Wild

It's quite ironic that businesses exist to help you cancel subscriptions, which are essentially recurring payments you've likely signed up for. The core issue often stems from a lack of awareness or proactive management on the user's part. We willingly subscribe to services, sometimes forgetting about them or not realizing the cumulative cost over time. The idea of then paying another subscription fee to manage and cancel these original subscriptions highlights this irony. You are essentially subscribing to a service to unsubscribe from other services.

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5 months ago
15 minutes 31 seconds

Thoughtfully Critical
The Meteoric Rise of Online Platforms

At the heart of the digital advertising model lies a fundamental tension between the desire for effective, data-driven targeting and growing user demands for privacy and control over their personal information.

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6 months ago
14 minutes 41 seconds

Thoughtfully Critical
The Truth About System Maintenance Everyone Ignores

Today, I start with some spring positivity before diving into two main topics. First, I share my strong preference for wired tech over wireless in the wired vs. wireless debate, highlighting the frustrations of device charging. Then, I discuss the often overlooked but crucial topic of maintenance, stressing its importance throughout the lifecycle of a system, from deployment to eventual retirement. I also touch on the challenges faced by companies failing to adapt their maintenance strategies over time.

📙 Chapters:00:00 Introduction01:05 Wireless vs Wired02:30 Maintenance07:57 Updates

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7 months ago
8 minutes 50 seconds

Thoughtfully Critical
Three Essential Habits from a Systems Perspective

In this episode, I share impactful advice that has shaped my career success, primarily through a systems perspective. This presentation revolves around three crucial habits that can enhance your thinking and approach to your career and life. From maintaining a comprehensive portfolio, documenting your solutions publicly, to upholding a single source of truth—these strategies not only streamline your workflow but also ensure consistent improvement and clarity in your professional journey. Join me as I delve into practical examples and insights that you can implement for your long-term success.

Thoughtfully Critical is a weekly podcast created by Chris Wahl. You can find out more about Chris by reading his newsletter at⁠⁠ ⁠⁠⁠⁠⁠Wahl Network⁠⁠⁠⁠⁠⁠⁠⁠. Please subscribe and leave a review to help shape the conversation.


Timestamps:

00:00 Introduction

02:42 The Importance of a Portfolio

06:32 Enhancing Your GitHub Profile

09:50 Documenting Solutions Publicly

12:24 Maintaining a Single Source of Truth

16:09 Final Thoughts and Encouragement


Links & Resources:

When Shit Hits the Fan Podcast

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7 months ago
16 minutes 41 seconds

Thoughtfully Critical
My Approach to Rebuilding Connections & SCaLE 22x

I share insights from my recent solo business trip to California. I attended the Southern California Linux Expo (SCALE 22), visited Rubrik's headquarters, and reconnected with old friends. We'll explore the unique challenges of planning a self-funded business trip, the inspiring environment of SCALE 22, and the importance of reconnecting with loved ones.

Thoughtfully Critical is a weekly podcast created by Chris Wahl. You can find out more about Chris by reading his newsletter at⁠⁠ ⁠⁠⁠⁠⁠Wahl Network⁠⁠⁠⁠⁠⁠⁠⁠. Please subscribe and leave a review to help shape the conversation.


Timestamps:

00:00 Introduction

01:00 Planning a Solo Business Trip

02:30 Experiences and Reflections from the Trip

04:42 Reconnecting with Friends and Former Colleagues

09:12 Attending the Southern California Linux Expo

14:37 Final Thoughts and Personal Reflections


Links & Resources:

SCaLE Page

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7 months ago
16 minutes 44 seconds

Thoughtfully Critical
My AI Tools & Their Impact

I dive deep into various AI tools, market conditions, and exciting topics around AI. I start by discussing the Descript editing tool, its capabilities, and how it streamlines podcast creation. Then I cover Cursor, a fork of VS Code, and its role in automated coding with insights into its privacy and security features. Additionally, I touch on Gartner's Hype Cycle and its stages, offering perspectives on where AI stands today. Finally, catch a preview of upcoming content and an announcement about attending the Southern California Annual Linux Expo.

Thoughtfully Critical is a weekly podcast created by Chris Wahl. You can find out more about Chris by reading his newsletter at⁠⁠ ⁠⁠⁠⁠⁠Wahl Network⁠⁠⁠⁠⁠⁠⁠⁠. Please subscribe and leave a review to help shape the conversation.


Timestamps:

00:00 Introduction

01:13 New YouTube Content and AWS Course

01:58 Exploring Descript for Content Creation

06:44 Cursor: AI-Powered Coding Tool

12:44 Gartner Hype Cycle and AI Expectations

14:50 Upcoming Conference and Conclusion


Links & Resources:

AWS and Terraform Essentials Course on YouTube

AWS and Terraform Essentials Course on SlideShare

Cursor Security Page

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8 months ago
15 minutes 56 seconds

Thoughtfully Critical
My $3600 College Computer Catastrophe

A pivotal experience from 1999 involving a PowerMac G4, college, and a costly mistake. This isn't just a trip down memory lane; it's a raw and honest look at a time when a 'personal supercomputer' dream turned into a financial and technical nightmare. I'll detail the financial pitfalls I fell into, the hard lessons I learned about companies and marketing, and how I ultimately took control of the situation. If you've ever felt misled by a company or made a costly tech purchase, this episode offers valuable insights.

Thoughtfully Critical is a weekly podcast created by Chris Wahl. You can find out more about Chris by reading his newsletter at⁠ ⁠⁠⁠⁠⁠Wahl Network⁠⁠⁠⁠⁠⁠⁠. Please subscribe and leave a review to help shape the conversation.


Timestamps:

00:00 Introduction

00:27 The Road to Chicago and a Budding Mac Fan

06:05 The PowerMac G4 Dream and Disaster

10:53 Major lessons learned

12:23 Building My Own & Escaping the Lemon


Links & Resources:

Quote: " My biggest issue was counting on future earnings to pay for current costs. Bad idea."

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8 months ago
17 minutes 27 seconds

Thoughtfully Critical
Tools, TACOS, and Terraform

Let’s explore the complexities of choosing and adopting new technical tools in your tech stack. We’ll discuss the importance of evaluating a tool's overall value, including its benefits, drawbacks, and long-term implications. We delve into the essential components of getting buy-in from your team, writing comprehensive Architecture Decision Records (ADRs), and the pros and cons of making versus buying tools. Additionally, we scrutinize the use of Terraform Automation and Collaboration Software (TACOS) and infrastructure wrappers like Terragrunt and Atmos, weighing their potential benefits against the added complexities they introduce.

Thoughtfully Critical is a weekly podcast created by Chris Wahl. You can find out more about Chris by reading his newsletter at ⁠⁠⁠⁠⁠Wahl Network⁠⁠⁠⁠⁠⁠. Please subscribe and leave a review to help shape the conversation.


Timestamps:

00:00 Introduction

01:02 Evaluating the True Value of a Tool

01:33 The Ripple Effect of Tool Adoption

02:09 Tool Sprawl and Its Impact

03:07 Building vs Buying Tools

04:31 Getting Team Buy in and Documentation

08:14 Exploring Terraform Automation and Collaboration Software

13:11 The Case Against Infrastructure Wrappers

14:52 Conclusion and Final Thoughts


Links & Resources:

Reshape your AWS CloudFormation stacks seamlessly with stack refactoring on AWS Blog

Quote: " Tools should enable you to do your job better, not become the job itself."

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8 months ago
15 minutes 29 seconds

Thoughtfully Critical
1980's Adventures

I'll take you on a nostalgic journey back to the 1980s. We'll explore the early days of computing and gaming, talk about the Apple IIe and Bulletin Board Systems (BBSs), and delve into the exciting world of making games. Whether you're a seasoned tech enthusiast or simply curious about the origins of the digital age, this episode is for you.

Thoughtfully Critical is a weekly podcast created by Chris Wahl. You can find out more about Chris by reading his newsletter at ⁠⁠⁠⁠Wahl Network⁠⁠⁠⁠⁠. Please subscribe and leave a review to help shape the conversation.


Timestamps:

00:00 Introduction

03:02 The Apple IIe

05:38 Bulletin Board Systems

08:36 Making games

10:32 Where to start


Links & Resources:

⁠BASIC Computer Games on Wikipedia

Quote: "Never stop asking 'why?' and 'how?' The tech and gaming worlds thrive on innovation, and curiosity is the engine of that. Don't be afraid to tinker, experiment, and push the boundaries of what's possible."

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8 months ago
15 minutes 11 seconds

Thoughtfully Critical
Paying Technical Debt

We're diving deep into the concept of technical debt. I'll explore what it is, where it comes from, and most importantly, how to manage it effectively. I'll discuss strategies for using technical debt as a tool without letting it become a burden, and how to balance the need for progress with the importance of maintaining a healthy codebase. Join me as I navigate the complexities of technical debt and keep projects on track.

Thoughtfully Critical is a weekly podcast created by Chris Wahl. You can find out more about Chris by reading his newsletter at ⁠⁠⁠⁠Wahl Network⁠⁠⁠⁠. Please subscribe and leave a review to help shape the conversation.


Timestamps:

00:00 Introduction

04:33 Leveraging debt

05:26 Tracking and paying debt

11:09 Where to start

13:31 Getting your team involved


Links & Resources:

Identifying and Paying Off Technical Debt on Wahl Network

The other infinite loop that all coders fear by CommitStrip

Frequency Reduces Difficulty by Martin Fowler

Quote: " Good ideas on paper don't always translate into good ideas in reality. It's best to nip those debt issues in the bud early. "

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9 months ago
15 minutes 18 seconds

Thoughtfully Critical
Consulting Life Realities

From the shocking realities of technical debt in major companies to my first big win as both designer and implementer, this is my origin story as a "Technologist as a Service." I share key lessons for aspiring consultants, including the importance of listening, writing, and networking.

Thoughtfully Critical is a weekly podcast created by Chris Wahl. You can find out more about Chris by reading his newsletter at ⁠⁠⁠⁠Wahl Network⁠⁠⁠⁠. Please subscribe and leave a review to help shape the conversation.


Timestamps:

00:00 Introduction

01:45 The Consulting Life

05:26 Learning to Design and Deliver

11:09 Key Lessons for Consultants


Links & Resources:

Technologists as a Service by Wahl Network

Every engineer should do a stint in consulting by Forrest Brazeal

Quote: "I don’t need to be the expert in all things; I just need to know who the experts are."

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9 months ago
13 minutes 47 seconds

Thoughtfully Critical
Keymakers of Platform Engineering

How do platform engineers become the "keymakers" of modern technology? In this episode, I break down the principles of platform engineering through the lens of product development—prototyping, scaling, and abstracting. You'll learn how to design platforms that empower teams to build, test, and deploy at scale while maintaining consistency and reliability across environments. From modular design to service contracts and pipelines, this episode dives into creating platforms that truly unlock success.


Thoughtfully Critical is a weekly podcast created by Chris Wahl. You can find out more about Chris by reading his newsletter at ⁠⁠⁠Wahl Network⁠⁠⁠. Please subscribe and leave a review to help shape the conversation.


Timestamps:

00:00 Introduction

04:16 Where to start

07:32 Scaling the platform

11:16 Abstracting the platform


Links & Resources:

How to Improve Documentation Practices in Engineering Teams on Wahl Network

⁠Platform Engineering⁠ topics on Wahl Network

The Matrix Reloaded IMDB Page

Quote: "Platforms are the right way to build if you want it done right."

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9 months ago
15 minutes 44 seconds

Thoughtfully Critical
World of Warcraft

Lessons in leadership, collaboration, resilience, and knowing when to pivot—drawn from the highs and lows of leading World of Warcraft guilds and raids—prove that even unexpected experiences can shape your career and life.


Thoughtfully Critical is a weekly podcast created by Chris Wahl. You can find out more about Chris by reading his newsletter at ⁠⁠⁠Wahl Network⁠⁠⁠. Please subscribe and leave a review to help shape the conversation.


Timestamps:

00:00 Introduction

01:08 Raid leader

05:05 Guild leader

08:25 The pivot


Links & Resources:

World of Warcraft: Official Site

Dragon Kill Points (DKP)

Zanzer’s Z Hunter Mod: Archived Mod Information

Quote: "Don’t take your situation for granted. It can always get worse, and you rarely know you're in the good times until those good times are gone."

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9 months ago
14 minutes 33 seconds

Thoughtfully Critical
Strategic Kaizen

Understanding every layer of an organization—its processes, people, and challenges—unlocks the path to strategic leadership and impactful solutions, blending the power of Kaizen with practical insights for crafting technology strategies and building cohesive teams.


Thoughtfully Critical is a weekly podcast created by Chris Wahl. You can find out more about Chris by reading his newsletter at ⁠⁠Wahl Network⁠⁠. Please subscribe and leave a review to help shape the conversation.


Timestamps:

00:00 Introduction

00:55 Nissan and kaizen

04:02 Returning to college

08:36 Learning the business


Links & Resources:

Gemba Kaizen: A Commonsense Approach to a Continuous Improvement Strategy on Amazon

Office Space IMDB Page

Deep Work⁠⁠⁠ by Cal Newport on Amazon

Quote: “Surround yourself with good people and success will follow.”

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9 months ago
13 minutes 30 seconds

Thoughtfully Critical
Deep Work

Redefining goals, eliminating distractions, and embracing deep work pave the way for intentional growth, impactful leadership, and a career built on focus and meaningful progress.


Thoughtfully Critical is a weekly podcast created by Chris Wahl. You can find out more about Chris by reading his newsletter at ⁠⁠Wahl Network⁠⁠. Please subscribe and leave a review to help shape the conversation.


Timestamps:

00:00 Introduction

03:49 What is deep work?

06:50 Why pursue deep work?

10:59 Where to begin


Links and Resources:

An Intentional Focus on Deep Work

Deep Work⁠⁠ by Cal Newport on Amazon

Start With Why by Simon Sinek on Amazon

Quote: “If you want to win the war for attention…let that terrifying longing crowd out everything else.” – Cal Newport

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10 months ago
14 minutes 5 seconds

Thoughtfully Critical
Welcome to Thoughtfully Critical

This debut episode dives into the transformative journey of leading a multi-million dollar program—facing fear, building teams, and harnessing the power of mentorship and collaboration—while setting the stage for a podcast dedicated to exploring leadership, tools, and frameworks that drive meaningful change.


Thoughtfully Critical is a weekly podcast created by Chris Wahl. You can find out more about Chris by reading his newsletter at ⁠Wahl Network⁠. Please subscribe and leave a review to help shape the conversation.


Timestamps:

00:00 Introduction

04:45 Podcast goals


Links and Resources:

Timothy Cain on YouTube

Quote: “If you want to go fast, go alone. If you want to go far, go together.”

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10 months ago
7 minutes 3 seconds

Thoughtfully Critical
Hosted by Chris Wahl, an industry veteran with nearly 30 years of experience, this podcast contains 15 minute stories diving into the challenges and opportunities of modern systems, platform design, cloud architecture, and team building.