Project Management is Boring

Jordon Keen

Project Management Is Boring focuses on the unglamorous work that actually makes projects succeed. We talk planning, requirements, meetings, stakeholder management, and execution—without pretending PMs are superheroes or that every problem can be solved with a new framework. Built for IT project managers, business analysts and professionals who value discipline, clarity and realism over buzzwords.

  1. Military Transition: Beating the Bot

    15 HR AGO · BONUS

    Military Transition: Beating the Bot

    Before your résumé ever reaches a human, it’s scanned, filtered, and judged by software that doesn’t understand military roles, leadership under pressure, or real-world problem solving. It only understands keywords. In this episode of Project Management is Boring, we break down how ATS systems work, why so many qualified veterans and professionals get screened out, and how small language choices can determine whether your application survives. We cover how to translate military experience into civilian terms, mirror job descriptions without losing authenticity, and avoid the silent rejection cycle that leads so many people to doubt themselves. More importantly, we talk about the emotional toll of applying into a system that gives no feedback—and how to stay confident when the process feels invisible and unfair. Because once you get past the algorithm, you’re back in human territory. And that’s where your real strengths shine.

    14 min
  2. Military Transition: Command Doesn't Work Here

    3 DAYS AGO · BONUS

    Military Transition: Command Doesn't Work Here

    In the military, authority is clear. Orders move. Responsibility is defined. When something breaks, you know who owns it. In corporate environments, that structure fades. Influence replaces rank. Progress depends on negotiation, relationships, and timing—not position. In this episode of Project Management is Boring, we break down why traditional command-and-control leadership from the military fails in modern organizations, why “just telling people” doesn’t work, and how projects actually move forward when nobody technically reports to you. We talk about managing sideways, leading without authority, navigating competing priorities, and building trust across teams that don’t share the same incentives. Most importantly, we show how veterans and structured leaders can adapt without losing their edge—by shifting from command to collaboration, from orders to alignment, and from rank to credibility. If you’ve ever felt responsible for results without having real power, this episode gives you the tools to lead anyway.

    17 min
  3. Military Transition: You Were Already a Project Manager

    31 JAN · BONUS

    Military Transition: You Were Already a Project Manager

    If you served in the military, you didn’t “switch careers” into project management — you translated it. In this first military-themed episode of Project Management Is Boring, we break down why so many veterans already have the core PM skills long before they ever open a PMBOK or sit for a certification exam. Mission planning. Risk management. Stakeholder coordination. Working with incomplete information under pressure. That’s project management — just without the corporate vocabulary. This episode is for veterans who feel like outsiders in tech and business, and for PMs who don’t realize how transferable military leadership really is. You were already doing the job. Now it just has a different name

    13 min
  4. Healthcare.gov - When Process, Politics and Code Collide

    28 JAN

    Healthcare.gov - When Process, Politics and Code Collide

    Healthcare.gov is often remembered as a broken website. In this episode of Project Management Is Boring, we unpack why that story misses the point. The failure wasn’t caused by bad developers or an impossible deadline — it was the result of fragmented ownership, unclear authority, ignored integration risk, and a leadership structure that made honest reporting nearly impossible. This episode walks through how dozens of vendors, competing agencies, and “green” status reports combined to hide real problems until launch day, when the entire system collapsed in public. More importantly, it shows why Healthcare.gov isn’t a one-off disaster — it’s a textbook example of how normal, everyday project management decisions quietly create catastrophic outcomes. If you’ve ever worked on a project that felt fine right up until it suddenly wasn’t, this story will feel uncomfortably familiar.

    26 min
  5. The Science of Saying No

    24 JAN

    The Science of Saying No

    In this episode of the Project Management is Boring podcast, we explore why refusing requests is one of the most powerful skills a project manager can have. Projects always run within boundaries—time, budget, scope, and resources—and saying yes to everything undermines those limits. We look at why saying no feels uncomfortable and how to do it effectively, using strategies grounded in logic and real-world examples. By learning to set clear boundaries, prioritize what truly matters, and communicate decisions confidently, project managers can protect their teams, reduce burnout, and keep projects on track. Saying no isn’t rejection—it’s essential project discipline.

    21 min
  6. The Email That Changed Nothing

    21 JAN

    The Email That Changed Nothing

    We’ve all sent it. The carefully worded status update. The polite nudge. The “just circling back” email that should have moved things forward. And then… nothing happens. In this episode of Project Management Is Boring, we break down why emails so often fail to create real movement — even when the information is correct, timely, and well-intentioned. This isn’t about bad writing or weak project managers. It’s about human communication friction. We talk about: Why emails feel like action — but often aren’tHow assumptions, attention, and workload distort messagesThe invisible cost of scale as teams growWhy “documenting the issue” is not the same as resolving itWhat effective PMs do instead of relying on inbox gravityIf you’ve ever wondered why your project is “communicated to death” but still stuck — this episode explains the gap between sending information and creating alignment. Because in real projects, the problem usually isn’t that people didn’t get the email. It’s that the email was never enough to begin with.

    19 min
  7. Risk Logs and Real Life

    17 JAN

    Risk Logs and Real Life

    Risk logs are supposed to make projects safer. So why do they feel like anxiety spreadsheets no one wants to open? In this episode of Project Management Is Boring, we look at risk logs as a mirror for human behavior — how we avoid naming uncomfortable risks, why we downplay what scares us, and how “everything is fine” quietly becomes a project strategy. We explore the psychology behind risk avoidance, the difference between documenting risk and actually managing it, and why the most dangerous risks are usually the ones no one wants to say out loud. If you’ve ever watched a project fail in slow motion while the risk log stayed perfectly up to date, this episode is for you. Timestamps: 0:58 - The Myth of the Perfect Risk Log2:44 - The Human Side of Risk6:07 - Risk Logs as a Mirror for Anxiety8:05 - Stories from the Trenches10:29 - Mitigating Human Risk14:10 - Risk as a Learning Tool18:50 - Humor in Risk Management20:00 - Closing Thoughts

    21 min
  8. Urgency and the Illusion of Control

    14 JAN

    Urgency and the Illusion of Control

    Everything feels urgent. Deadlines. Messages. “Just one quick ask.” In this episode of Project Management Is Boring, we unpack urgency culture — why constant speed feels productive, why it gives leaders a false sense of control, and why it often makes projects slower, riskier, and more fragile over time. We talk about how urgency replaces thinking with motion, how stress gets mistaken for leadership, and why the calmest projects are usually the healthiest ones. If your workday feels like a permanent fire drill, this episode is an invitation to slow down — not to do less, but to do better. Timestamps: 1:00 - Everything Is Always on Fire 4:07 - Urgency as a Management Crutch / Comfort Blanket 6:55 - How Urgency Destroys Planning 10:24 - Control Theater 13:23 - How Teams Get Trapped 16:28 - What Real Control Actually Looks Like 18:54 - Choosing Control Over Comfort

    21 min
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About

Project Management Is Boring focuses on the unglamorous work that actually makes projects succeed. We talk planning, requirements, meetings, stakeholder management, and execution—without pretending PMs are superheroes or that every problem can be solved with a new framework. Built for IT project managers, business analysts and professionals who value discipline, clarity and realism over buzzwords.

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