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. Seven of Eight

    3 DAYS AGO

    Seven of Eight

    This episode examines a deceptively small technical detail that triggered one of the most expensive software failures in financial history: a deployment that updated seven servers out of eight. At first glance, this kind of issue sounds like a minor technical oversight. In many environments it would be. But inside high-speed distributed systems, partial deployment is not a small problem — it is systemic instability. Episode 2 explores how organizations verify that software deployments actually produce the environment they intended to create. Each segment breaks down a different layer of deployment governance: the difference between deployment and verification, how “definition of done” determines what counts as completion, why distributed systems require absolute symmetry across nodes, and how organizational culture can normalize incomplete verification when releases usually succeed. The episode then connects these ideas to modern infrastructure environments — including container orchestration and cloud-based deployments — where partial alignment across systems can introduce security vulnerabilities, performance anomalies, or unexpected behavior at scale. Together, these segments build toward a central insight: Deployment is not complete when the process runs. Deployment is complete when the environment is proven to match the intended state. Verification is the discipline that turns intention into certainty. When organizations treat deployment success as an assumption instead of a requirement, they allow unstable system states to exist. And in fast systems, unstable states do not remain small. They compound. Episode 2 ultimately argues that deployment verification is not a technical afterthought — it is a project management governance mechanism. By defining what “done” actually means, project managers help ensure that activation only happens after alignment has been proven. Because in distributed systems, seven out of eight is not close. It’s a fracture waiting to propagate.

    22 min
  2. A Normal Morning

    5 DAYS AGO

    A Normal Morning

    On August 1st, 2012, Knight Capital lost $440 million in just forty-five minutes. There was no cyberattack. No rogue trader. No dramatic villain. Just one incomplete deployment. One server out of eight. Legacy code that was believed to be dormant. In this season opener of Project Management Is Boring, we walk through what actually happened — and why the failure didn’t begin when the market opened. It began earlier. In assumptions. In configuration drift. In routine work that felt safe. This season examines the quiet systems that prevent fast environments from unraveling — deployment verification, technical debt governance, rollback discipline, authority clarity, and more. Because project management isn’t cinematic. It’s procedural. And in high-speed systems, that’s exactly what keeps the morning ordinary.

    20 min
  3. Season 2 Trailer

    SEASON 2 TRAILER

    Season 2 Trailer

    In August 2012, Knight Capital Group pushed a routine software update to its automated trading system. Seven servers were updated. One was not. In 45 minutes, the company lost $440 million. No cyberattack. No sabotage. No dramatic villain. Just a missing update, an untested rollback, and automation moving faster than humans could react.

    1 min
  4. Military Transition: The Emotional Ambush

    18 FEB · BONUS

    Military Transition: The Emotional Ambush

    Leaving the military isn’t just a career transition. It’s an identity shift. In uniform, everything is defined — your rank, your role, your mission, your tribe. The structure is built in. The feedback is constant. The purpose is clear. Then one day, it’s gone. In this episode of Project Management Is Boring, we explore the emotional side of transition that no one briefs you on: the loss of identity. Why high performers often struggle the most. Why landing a job doesn’t automatically fix the discomfort. And how to intentionally rebuild purpose in civilian life. Because transition isn’t just about employment. It’s about redefining who you are — and choosing your next mission.

    23 min
  5. Military Transition: Certs are Just Badges, But You Still Need Them

    14 FEB · BONUS

    Military Transition: Certs are Just Badges, But You Still Need Them

    Most veterans treat certifications like a trophy case—collecting as many as possible to "prove" they belong in the civilian world. But in this episode, we’re calling it what it really is: a bureaucratic game of market logistics. We break down why certifications aren't a measure of your competence—you already have that—but a translation layer for HR systems that can't read a military record. We explore the concept of "Horizontal Stacking," moving away from the "panic stack" of random badges and focusing on the one or two "Entry Keys" that actually unlock interviews and change your compensation band. If you're tired of feeling "invisible" to hiring algorithms, it’s time to stop out-certifying your anxiety and start aligning your experience with the civilian "language pack." Learn how to use these boring credentials as a strategic maneuver to land well, get inside the room, and let your actual leadership take over.

    19 min
  6. Military Transition: Project or Charlie Foxtrot?

    11 FEB · BONUS

    Military Transition: Project or Charlie Foxtrot?

    Why do IT projects feel so wrong to people with military experience? In this episode of Project Management Is Boring, we break down why veterans instantly spot dysfunction in civilian projects—unclear objectives, fuzzy authority, missing logistics, and weak communication. What looks like “flexibility” in IT often feels like a mission with no commander’s intent, no contingency planning, and no ownership. We compare failed projects to failed operations, unpack why veterans get frustrated in corporate environments, and show how military habits like risk awareness, clear roles, and early planning aren’t rigid—they’re exactly what modern projects need. If you’ve ever sat in a meeting thinking, “This would never pass a brief,” this episode explains why—and why that instinct is your edge during the transition into project management or IT.

    17 min
  7. Military Transition: Beating the Bot

    7 FEB · 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
  8. Military Transition: Command Doesn't Work Here

    4 FEB · 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
See All (22)

Trailer

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.

Information