After 25+ years in IT, Chuck shares his unfiltered 2-year AI journey—from skeptic to AI-first. Why 2026 is the year IT professionals can't afford to wait on AI experimentation.

It's December 31st, 2025—the last day of the year and the final episode of 2025 for The IT XP. Chuck gets personal about his two-year journey with AI, from initial skepticism to becoming AI-first in his workflow and content creation.

This isn't a polished how-to guide. It's an honest account of experimentation, failures, and lessons learned across ChatGPT, Claude, Gemini, RunwayML, ElevenLabs, Sora, and emerging agentic AI tools.

🎯 WHAT YOU'LL LEARN:

- Why experienced IT professionals (25+ years) bring irreplaceable value in an AI-augmented world - The real difference between generative AI and agentic AI—and what it means for your career - How to overcome AI hesitation and start experimenting (even if you're skeptical) - Corporate Hardcore case study: Building a content brand using AI-generated characters and video - Coco Live case study: Managing a high-volume TikTok account with AI automation - The "clarity principle"—why AI reflects your thinking, not replaces it - Custom instructions mastery: How to make AI tools actually useful for your specific needs - Why your judgment becomes MORE valuable, not less, as AI adoption increases

🔥 KEY INSIGHTS:

"AI didn't replace me. It freed me to do the work only I can do."

Chuck breaks down the 70/30 rule: AI handles 70% of repetitive work, but the last 30%—judgment, context, validation—is where experienced IT professionals prove their value.

⚠️ THE HARD TRUTHS:

- Organizations are experimenting with "AI" solutions that aren't actually leveraging AI effectively - Instant gratification culture is killing long-term skill development - Junior engineers don't know what they don't know—experience matters more in an AI world - In 2025, not using AI doesn't make you cautious. It makes you slow.

📊 2026 PREDICTIONS:

1. AI agents go mainstream (it's already happening—Microsoft Ignite was wall-to-wall agents) 2. The IT skills gap flips: Demand shifts from cloud engineers to "AI orchestrators" who can direct AI to solve ops problems 3. Regulatory scrutiny intensifies: "The AI did it" won't fly in regulated industries

💪 THE CHALLENGE:

Start January 2nd. Pick ONE task you hate. Let AI take the first pass. You'll either save time or learn something. Either way, you're building the skill that matters most in the next decade.

This is a passion-driven episode from someone who's been in the trenches for 25+ years and sees the writing on the wall: experienced IT professionals have a choice. Adapt and leverage AI, or become "too expensive" without demonstrating new value.

🎙️ ABOUT THE IT XP:

10 years of unfiltered career advice, technology insights, and experience points for IT professionals. Not looking for top 10 podcast status—just trying to help one person avoid the mistakes Chuck made over 25+ years in corporate IT.

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🔗 MENTIONED IN THIS EPISODE:

- Corporate Hardcore (@CorpHardcore on TikTok) - Chuck's AI-generated corporate satire series - Coco Live Highlights (@cocolivehighlights on TikTok) - High-volume content automation case study - Tools covered: ChatGPT, Claude, Gemini, RunwayML, ElevenLabs, Sora, MCP servers

📅 Next Episode: Coming in 2026

If this resonated, share it with one IT professional still on the fence about AI. Let's make 2026 the year IT stops reacting and starts building.

After 17 years at a large utility company managing decade-long waterfall projects, Don Freeman made a radical pivot into the fast-paced world of Web3 startups—without ever applying for the job. In this episode of The IT XP, Don shares how his contributions to the Ethereum Foundation's web3.py library caught SonarX's attention and led to a complete career transformation.

We explore the stark contrast between enterprise and startup life, from 10-year projects to 10-day sprints, and why Don believes your GitHub commits might be worth more than your next certification. This isn't about quitting your job for crypto—it's about the power of learning in public and taking initiative.

Key Takeaways:

• The shift from 10-year waterfall projects to 10-day startup sprints (06:49)
• How documentation PRs evolved into a job offer from SonarX (04:30)
• Why "I've never found something I couldn't dig into and learn" is the ultimate career philosophy (07:42)
• The real difference between enterprise "decision trees" and startup autonomy (24:15)
• Why crossing team boundaries is the question enterprise people are afraid to ask (41:31)

About Don Freeman: Don Freeman is a software engineer who transitioned from designing power lines and managing enterprise systems at a utility company to contributing to open source Web3 projects. His journey from Linux enthusiast in the '90s to startup engineer showcases the power of continuous learning and public contribution.

Connect with Don:

LinkedIn: https://www.linkedin.com/in/donald-freeman/

GitHub: https://github.com/dbfreem

A 2025 Deloitte survey of 23,000 workers across 44 countries found only 6% of Gen Z aspire to senior leadership. Chuck—upper-middle management for over a decade—unpacks the real math behind the 94% rejection rate, shares war stories on emotional labor, and previews next week's dive into AI replacing managers entirely. Homework: map your role to IC vs. management paths and share what you find.

Chuck breaks down his first-ever Microsoft Ignite experience in San Francisco—from navigating the massive Moscone Center venue to cutting through the "Copilot everything" sales pitch. If you've wondered whether mega-conferences like Ignite are worth the hype (and the $400+/night hotel bill), this episode delivers the unfiltered reality check.

What You'll Get:

• Conference logistics reality: 20,000 attendees, government ID checkpoints, buses to Chase Center for the keynote, and the eternal search for the Marriott Marquis session rooms
• Talk quality assessment: Why "advanced" sessions felt disappointingly high-level, and when sales-focused content actually serves smaller orgs better than enterprise teams already deep in Microsoft partnerships
• Azure AI Foundry & security focus: Chuck's key takeaways from the tracks that mattered most—plus what the vendor floor really delivers (spoiler: lots of socks)
• The Copilot/Agent saturation problem: How Microsoft's 2025 strategy mirrors Dell Tech World '23's AI frenzy, and what it means for your actual infrastructure work

Bonus War Story (starts ~47:00): Chuck dissects a multi-day production outage where AI-armed stakeholders derailed troubleshooting—and shares the diplomatic strategies that kept tempers in check while solving the real capacity management issue. Critical lessons on handling aggressive personalities during high-pressure incidents, even when "Big Dick Todd" and "Big Dick Mary" show up with ChatGPT-fueled theories.

Who This Is For: Sysadmins, infrastructure engineers, and IT leaders who need to separate conference theater from actionable intelligence—and who've ever dealt with non-technical stakeholders "helping" during outages.

Key Timestamps:

• 00:00 – Ignite overview & Copilot saturation
• 02:15 – Venue logistics & San Francisco hotel costs
• 06:27 – Session quality: beginner vs. "advanced"
• 47:00 – Production outage war story: IOPS, firewalls & managing egos
• 52:21 – Handling aggressive personalities during incidents

Subscribe to The I.T. XP for weekly unfiltered advice on navigating IT careers, industry shifts, and the real stories behind the buzzwords.

When Amazon Web Services' US-East-1 region went dark in October 2025, half the internet felt it. In this episode of The IT XP, Chuck breaks down what really happened — from the DNS and DynamoDB race condition that triggered the AWS outage to the cascading effects across global systems.

He explains the technical side of DNS at scale in plain language, then connects it to bigger lessons for IT professionals: why multi-cloud strategies matter, how infrastructure teams can partner better with the business, and what aging technologists must do to stay relevant in the era of AI.

Whether you manage cloud platforms, build resilient architectures, or just want to understand why "it's always DNS," this is a must-listen.

The I.T. XP Returns: Navigating IT Careers in 2025—AI, Layoffs, and Staying Relevant

After a six-month hiatus, The I.T. XP podcast is back with unfiltered insights for IT professionals navigating today's rapidly changing tech landscape. Chuck returns to the audio format to tackle the biggest challenges facing sysadmins, IT engineers, and technology managers in 2025.

What You'll Learn in This Episode:

In this no-nonsense discussion, Chuck addresses the realities IT professionals face today: ongoing tech layoffs, AI transformation pressure from leadership, constant organizational restructuring, and the skills gap between operations and engineering roles. Whether you're a systems administrator, network engineer, or IT manager, this episode delivers actionable career advice for staying competitive.

Key Topics Covered:

• AI in IT careers: Why learning AI and automation is as critical now as cloud computing was ten years ago
• Offshoring myths vs. reality: What's actually happening with remote work and global IT teams
• Ageism in technology: Navigating career longevity as an experienced IT professional
• Proving your value: How to demonstrate human judgment and expertise in increasingly automated environments
• Career transition strategies: Moving from IT operations to engineering roles

Chuck also introduces his new project, Corporate Hardcore—a satirical take on workplace culture that uses humor to teach real IT career lessons.

Perfect for: IT professionals experiencing burnout from constant change, anyone concerned about job security in the age of AI, and technology workers looking for honest career guidance without the corporate spin.

Ready to hear the truth about IT careers in 2025? Listen now and join the conversation—share your own experiences and connect with IT professionals who keep the infrastructure running.

Subscribe to The I.T. XP for authentic conversations about real IT careers.

The Crowdstrike Falcon issue was an eye opener for a lot of IT organizations on the readiness of their BCP or DR plans. This isn't the first time we've seen this, but it's been a while where such a large outage has been seen across a number of different industries. I discuss how you can leverage this as an opportunity for you to be more visible within your organization and finding opportunities to get ahead in your career.

Crowdstrike PIR: https://www.crowdstrike.com/blog/falcon-content-update-preliminary-post-incident-report/

What is a post incident review: https://www.cybereason.com/resources/post-incident-review

Strap in as I take you back to my adventure at Western Governors University, where I crushed my Master of Science in Management and Leadership in one term (six months). Riding on the wisdom from a pivotal Reddit thread and armed with the solid gold insights from the Purdue OWL, I'm here to lay it all out bare: the good, the bad, and the brutally honest truths about speeding through WGU's competency based learning program. In this episode, I'm not just reminiscing about my academic grind during those intense months; I'm breaking down the strategies that could help you blaze through your own program even faster. But let's cut through the noise for a second, will this degree be your golden ticket to the executive suite? Probably not on its own.

Coming at you with nothing but the truth, I want to talk about what a degree really means for us folks who've seen a bit more of life. As we dive into the realities of adult education, career pivots in a mid-life context, and the looming shadow of AI in our professional lives, I'm here to show you not just how to earn that diploma, but how to make it truly count in the hustle of real life. So, for anyone out there contemplating hitting the books again, eyeing a career change, or simply curious about the evolving role of academic credentials in an age dominated by technology, you're in the right place. Remember, success isn't just about the accolades; it's about the drive and determination you bring to the table. Let's unpack how to get that degree to open doors and create opportunities, no matter where you are in life's journey. Join me, and let's get into it.

My MBA Journey: https://youtu.be/I3ibA8S1DyI

The Reddit Article that started me on this journey: https://www.reddit.com/r/WGU_MBA/comments/gmxkxo/mba_master_of_business_administration_course_mega/

My Favorite Online Writing Lab that shows you how to format your paper in different styles: https://owl.purdue.edu/owl/graduate_writing/introduction_graduate_writing/index.html

In this episode I discuss two paid platforms for your multi-cloud learning. These platforms I have leveraged in my own journey and I stand behind them. I know times are tough, but for those looking for a paid option to learn the various cloud platforms, these two may interest you.

A Cloud Guru: https://www.pluralsight.com/cloud-guru

Adrian Cantrill's Learning Platform (AWS and Azure only): https://learn.cantrill.io/