How to quit your job and completely fail as a PM contractor

Thinking about going contractor? Kate and Kim share how they each left corporate and made the leap—two very different stories (burnout vs acting early) with the same core truth: contracting is built on relationships, reputation, and value… not job boards and commodity rates. We cover how to know if you're ready, why sales is part of the job, what to watch out for (hello, 2008), and how to avoid racing to the bottom. Want us to teach the full process with scripts + steps? Head to http://pmhappyhour.com/be-free.  

As project managers, we spend a lot of time talking about tools, processes, and delivery frameworks—but far less time talking about the invisible structure that holds projects together: trust. In this Top Shelf Replay episode of Project Management Happy Hour, Kim Essendrup and Kate Anderson revisit one of the show's earliest and most enduring concepts: Trust Bricks. Originally recorded in 2018, this short but powerful episode explores how trust is built—not through grand gestures or heroic saves—but through consistent, everyday actions that compound over time. The core idea is simple: trust is predictability. When you repeatedly do what you say you'll do—whether that's sending meeting notes on time, honoring estimates, or showing up prepared—you lay one small Trust Brick at a time. Over weeks, months, and years, those bricks form a structure strong enough to withstand missed deadlines, bad news, or the occasional broken promise. Kim and Kate break down why Trust Bricks matter so much in project environments: Teams are more honest with you when they trust you Estimates improve when people believe they won't be punished for telling the truth Difficult conversations become easier when everyone believes you're on the same side Sponsors give you more latitude when your track record is consistent The conversation also explores what happens when trust breaks—and how the same Trust Brick approach can be used to rebuild credibility. Rather than trying to restore trust with a single "big win," the hosts argue that rebuilding starts small: partial deliverables, frequent check-ins, and deliberately meeting micro-commitments until confidence is restored. In the replay commentary, Kim and Kate reflect on how their thinking has evolved since the original recording. They discuss: The role of showing up consistently, even when no explicit promise was made How trust operates differently in virtual and remote teams Why strong performers can accidentally set expectations that lead to burnout How leaders vary widely in how much "trust damage" they tolerate before overreacting The episode also revisits the journey of Trust Bricks beyond the podcast, including Kim's experience delivering a TEDx talk on the topic and refining the framework into three enduring lessons: You are always building or breaking Trust Bricks—whether you realize it or not Missed expectations don't pause trust building; they actively tear it down Unspoken expectations are the fastest way to accidentally destroy trust This episode is a reminder that trust isn't soft, vague, or optional—it's a core delivery skill. If you want stakeholders who back you, teams who tell you the truth, and projects that don't require constant firefighting, it starts with sweating the small commitments. The next time you make a commitment—big or small—ask yourself: Am I laying a brick… or cracking one? Check out Kim's TEDx talk at trust-bricks.com or on the TED youtube channel Want more PM reality without the fluff? Join the PMHH membership for courses, templates, community, and direct access to Kate and Kim. https://pmhappyhour.com/membership

Kim and Kate settle in for a classic PM Happy Hour episode — the kind where the drinks are metaphorical, the conversation is wandering in the best way, and the insights sneak up on you. This one covers three big themes that hit close to home for project managers, leaders, and anyone who's ever had to keep a project — or a career — moving forward despite chaos. It starts with a deceptively simple question: How do you describe what a PM actually does for a living? Kim brings his favorite one-sentence description, and Kate immediately pokes at it (lovingly) to reveal the gaps between a tidy definition and the messy reality of day-to-day PM work. Together they break down the core functions that aren't on the job description: expectation-setting, alignment-building, timeline-translating, political-atmosphere-reading. Yes, PMs manage plans — but they also manage humans, assumptions, ambiguity, and the definition of "done," which shifts more than anyone wants to admit. The conversation hits on why this matters so much for stakeholder alignment, project success, and your own sanity. From there, the discussion pivots to fear in decision-making — specifically, how fear quietly creeps into choices that leaders and teams make every day. Kim shares a general's perspective on why big decisions get stalled ("people won't make hard decisions if it forces them to change"), and Kate adds their own real-world examples of hesitation disguised as caution. They unpack how fear leads to risk-avoidant behavior, analysis paralysis, unnecessary escalations, or decisions that look safe but actually create more work downstream. This part of the conversation digs into the psychology of leadership, the emotional drivers behind "bad" decisions, and how project managers can spot when fear — not logic — is driving a stakeholder's position. Along the way, they also reflect on why PMs sometimes avoid decisions themselves, even when they know the right call. Finally, Kim and Kate open up about what they've learned from going out on their own and being their own boss — the good, the bad, and the "wow, nobody warned me about this part." They talk candidly about leaving stable corporate paths, the discomfort of striking out solo, the thrill of autonomy, and the realities of running a business while also running your own mental health. Listeners get the inside picture of what independence really looks like: the freedom, the discipline, the failures, the self-doubt, and the eventual confidence that comes from owning your decisions and your livelihood. This segment offers honest lessons learned for anyone considering consulting, freelancing, starting a business, or just trying to build a healthier professional life. Through all three topics, the conversation carries the familiar PMHH rhythm: candid laughter, a little self-roasting, and the practical wisdom that comes from having been around the block more times than they're willing to count. It's not a tidy thematic episode — it's better than that. It's a Happy Hour catch-up that turns into real insight about project leadership, stakeholder psychology, career development, and the everyday challenges PMs face. If you've ever struggled to explain your job, watched fear take over a meeting, or wondered what life might look like outside the corporate bubble, you'll find something in this episode that feels uncomfortably familiar — and maybe a little inspiring. Want more PM reality without the fluff? Join the PMHH membership for courses, templates, community, and direct access to Kate and Kim. https://pmhappyhour.com/membership  

What happens when you drop a senior project manager into a room full of attorneys, tribal leaders, political operators, and massive personalities? In this Top Shelf Replay, Kate & Kim revisit one of the most beloved—and re-listened—episodes in PM Happy Hour history: "Stage Direction in the Boardroom" featuring master facilitator Sheila Morago. If you've ever wondered how elite leaders steer complicated, high-stakes conversations without losing their cool (or losing six months of work with one careless comment), this episode is your new playbook. Sheila shares the tools, tactics, and emotional intelligence behind managing senior stakeholders, building trust, engineering alignment, and yes…occasionally staging a fight to get everyone to "yes." Get ready—this episode is full of real-world policy drama, tribal gaming insight, negotiation theater, and powerful lessons for any PM trying to move from "task master" to strategic leader. Great Quotes From the Episode "Never ask a question you don't already know the answer to." "These aren't meetings—they're Kabuki theater." "Nothing brings people together like a common enemy." "If you don't let them vent early, they will vent later—and at the worst possible moment." "Policy takes years. Tech takes a week." What You'll Learn (Key Outcomes) 1. How Senior Leaders Actually Negotiate Sheila breaks down what it takes to orchestrate alignment among executives, attorneys, policymakers, and stakeholders—none of whom work for you, all of whom report to someone powerful. 2. The Secret Skill That Makes PMs Into Leaders How listening (really listening) becomes your most strategic tool at the senior level. 3. Managing High-Stakes Meetings Without Losing Control Why should one person guide the conversation? How to posit their positions to draw out quiet or hesitant stakeholders. How to keep the emotional temperature safe but not silent. 4. The Power of the 'Safe Zone' Why must you create a space where stakeholders can speak unfiltered, off-record, and without fear of political consequences. 5. Relationship-Building: The Long Game Happy hours, lunches, hallway conversations—how the "work between the work" makes the boardroom possible. 6. The Art of the Staged Fight Why conflict must be visible. Why letting people "win" (feel like they won) is essential. Why is the real battle scripted before the meeting starts? 7. Using Common Ground—and Common Foes When "we all want the same thing" works. When "the real enemy is over there" works even better. 8. How to Lock Down Decisions So They Don't Backslide Why immediate execution is key. How implementation momentum prevents second-guessing. 9. Lessons Kate & Kim Learned 8 Years Later Why parts of this episode hit harder after a decade of PM leadership. How letting emotions into the meeting leads to better outcomes. What PMs often overlook when they're new to senior-level facilitation. If you want to level up from "planner of tasks" to leader of leaders, this replay is essential listening. Whether you're negotiating policy, driving enterprise transformation, or just trying to get two teams to agree on anything—Sheila's battle-tested tools will help you steer the room, keep your cool, and bring people with you. ABOUT OUR GUEST, SHEILA MORAGO Sheila Morago is the Executive Director of the Oklahoma Indian Gaming Association. OIGA has 30 member tribes and numerous associate members.  Oklahoma now ranks third in the United States in gaming revenue, with 118 casinos ranging from small fuel stops to full resort casinos.   Prior to working for OIGA, Ms. Morago was Executive Director for the Arizona Indian Gaming Association. She has also served as the Director of Public Relations for the National Indian Gaming Association, based in Washington, D.C.  Ms. Morago began her career in tribal gaming in 1994 when she was appointed Director of Marketing for the Gila River Casinos, where she built the marketing department for this multi-million dollar enterprise and opened two successful tribal casinos.  Before joining AIGA, Ms. Morago was Vice President of National Relations for Initial Impressions based in Tempe, Arizona, where she was responsible for all political and public relations for tribal and non-tribal clients. In January 2006, she was named one of 25 people to watch by Global Gaming Business. She was named one of the "Great Women of Gaming" by Casino Enterprise Management in 2004, and inducted into the Indian Gaming Hall of Fame, presented by Indian Gaming Magazine, in 2012. And if you're tired of carrying the emotional labor for your entire project team, come get some backup and community. Join us at: https://pmhappyhour.com/membership  © Project Management Happy Hour

Kate didn't plan to measure their burnout by the number of bags of pink-and-purple Mother's animal cookies consumed at their desk…but here we are. Kim's clue was a rotating cycle of stomach aches and "maybe these aren't panic attacks but the room is definitely spinning." And our guest, Norlander Wilson, talks about showing up to work without showering or brushing her teeth for days because she literally couldn't. This one is about burnout at work — not the "I need a weekend off" kind, but the kind that rewires your nervous system and convinces you you're the problem. About our guest: Norlander Wilson is an experimental psychologist and an orbit disruptor by calling. She is the founder and CEO of Becoma, an operational strategy firm that helps leaders, creatives, and organizations move from survival mode into clearer systems and healthier energy. Through her work, Norlander blends psychology, strategy, and system design to challenge the patterns that keep people stuck and to create ways of working that don't require self-sacrifice. She's also the host of the podcast "She Don't Work Like That, No More," where she unpacks wounded leadership patterns and reimagines what it means to build, lead, and live without breaking yourself in the process. The theme today: burnout at work, and how project managers — the people everyone counts on — get trapped in it. Norlander doesn't sugarcoat it: "Burnout is a collective conversation, especially in an organization." She calls out how burnout starts at the top. If leadership pushes 100 hours, teams assume they should push 150. If leaders are exhausted, their teams are exhausted. Burnout isn't a personal failing; it's a system failure — and PMs often absorb the blast radius. Kate opens up about their 2024 breakdown: crying daily, losing appetite except for cookies, medical leave, and the creeping belief that if they just tried harder, they could fix everything. Kim shares his own burnout and the helpless feeling of watching teammates slide into it — seeing that "day-five-I-haven't-showered look" on Zoom and wanting to save them. And then there's the half-million-dollar moment. Kate negotiated nearly $500,000/year in compensation and turned it down because walking into the building made them feel sick. Not metaphorically — physically. "I'm not getting on that wheel unless I want to." Norlander validates it: "If it's profound burnout and everything triggers you at that job, yes, it's time to leave." She gives language PMs desperately need: Capacity check-ins, not productivity interrogations Systems that hold boundaries so you don't have to Stop parenting grown adults at work — "You are not an emotional container." Let people fail so they learn the consequence, not you Kim connects it to the "mouse on the wheel" experiment — the difference between choosing to run and being forced to run. The stress chemicals — literally — are not the same. Norlander's tools for burnout prevention and burnout recovery: Audit your systems quarterly Build boundaries into SOPs Protect scheduled joy like you protect deadlines Delegate to the system, not your nervous system Kate shares how protecting Tuesday riding lessons became non-negotiable. Not because horseback riding is magic (although…it kind of is), but because no one else will protect your time but you. Norlander's toast at the end is the line we're all putting on sticky notes: "When you do find your boundary… don't compromise it for anyone." If burnout at work is starting to feel familiar — if you're living on cookies, caffeine, and dread — pull up a chair. You're not lazy. You're not failing. The system is failing you. And if you're tired of carrying the emotional labor for your entire project team, come get some backup and community. Join us at: https://pmhappyhour.com/membership © Project Management Happy Hour  

Ever freeze up in a tough project conversation? Or worse—blow it up? In this episode of Project Management Happy Hour, Kim and Kate revisit their all-time favorite: Crucial Conversations by the team at VitalSmarts (now Crucial Learning). This book completely changed how they lead, negotiate, and manage conflict. Learn how to spot when a conversation turns "crucial," stay in dialogue instead of defensiveness, and use "don't-do statements" and "start with heart" to navigate conflict like a pro. We're not sponsored—just obsessed. If you lead projects or people, this book will change your life. 🍸 Pull up a stool at the bar—here's what we're talking about this round: 🍸 Every project manager has been there: a stakeholder meltdown, a team standoff, or that one sponsor meeting where your pulse hits 200. The question is—what do you do when the conversation turns crucial? In this PM Happy Hour throwback, Kate and Kim revisit one of their most popular and enduring episodes—based on the book Crucial Conversations: Tools for Talking When Stakes Are High by the VitalSmarts team (now Crucial Learning). They aren't paid to say this—but this book changed their lives and careers. Seventeen years after Kate's colleague first handed her this book, they still call it "the single most important leadership book for project managers." Forget the PMBOK—start here if you want to build trust, executive presence, and influence. You'll learn how to: Recognize when a conversation becomes crucial: differing opinions, high stakes, and strong emotions. Avoid the "fool's choice"—the false belief that you must choose between honesty and peace. Create a shared pool of meaning, so everyone's ideas and emotions contribute to better decisions. Use "Start With Heart" to keep your cool and focus on what you really want—for yourself, others, and the relationship. Apply "Don't-Do Statements" to set boundaries, de-escalate tension, and build empathy. From team conflicts to sponsor negotiations, this episode gives you practical, human ways to talk about hard things—and actually make things better. Kim and Kate share real-world examples from project meetings, resource battles, and even personal life to show how dialogue beats defensiveness every time. And they're not just quoting theory. Crucial Conversations is built on decades of behavioral research and communication psychology—and it's as relevant today as ever. Whether you manage projects, programs, or entire teams, mastering these techniques can level up your leadership, reduce drama, and get you promoted faster. 📚 Get the Book: Crucial Conversations: Tools for Talking When Stakes Are High by Kerry Patterson, Joseph Grenny, Ron McMillan, and Al Switzler Available anywhere books are sold (we're not sponsored—we just love it). JOIN THE HAPPY HOUR! Want even more? Join us at pmhappyhour.com/membership to get PDUsfor episodes, downloadable templates, access to our PM community, and 1:1 time with Kim and Kate.

Are you defining project success the wrong way? Most project managers are — at least according to PMI's Dave Garrett. Project Management Happy Hour hosts Kim Essendrup and Kate Anderson sit down with Dave — Senior Advisor at the Project Management Institute (PMI) and co-founder of ProjectManagement.com — for a frank and real conversation about PMI's new definition of project success to talk about how realistic it is, and what it means for the future of our profession. For decades, project success was judged by the "iron triangle" — scope, schedule, and budget. But PMI has officially redefined it: "A successful project is one that delivers value worth the effort and expense." Dave explains how this updated definition shifts the focus from checking boxes to delivering outcomes that truly matter — and how every PM can start measuring success through value creation instead of rigid constraints. The discussion digs into PMI's new M.O.R.E. framework — a practical mindset for modern project leaders: M – Manage Perceptions: Build trust and alignment with stakeholders. O – Own Success: Don't just deliver; ensure the value lands. R – Relentlessly Reassess: Constantly re-evaluate priorities and adapt to change. E – Expand Perspective: See the bigger picture across business strategy, customers, and society. Dave also shares lessons from his early startup days building Gantthead.com, the dot-com crash, and how those lessons apply in today's AI-driven project world. You'll hear how the rise of automation is making project management more human, pushing PMs to lead through empathy, influence, and strategic insight rather than process checklists. If you've ever struggled with the question, "Was my project really a success?"  this episode will give you a fresh, empowering way to answer it. Key Takeaways PMI's official definition of project success now centers on value, not just time, cost, and scope. The M.O.R.E. mindset helps PMs evolve beyond administrators into strategic leaders. AI will augment, not replace, project managers — freeing them to focus on human connection and business impact. "Success" is contextual: a delayed project that delivers exceptional value can still be a win. Guest Links Learn more about PMI's Project Success initiative: pmi.org/projectsuccess Connect with Dave Garrett on LinkedIn Explore PMI's AI resources: pmi.org/ai  Want even more? Join us at pmhappyhour.com/membership to get PDU certificates for episodes, downloadable templates, access to our PM community, and 1:1 time with Kim and Kate.      

Ever been dropped into a troubled project that's already gone off the rails? Welcome to life as "The Wolf." Inspired by the fixer from Pulp Fiction, Kim and Kate revisit one of our most popular episodes—now a PMI Global talk! —and break down how to step in, take charge, and rescue a broken project without losing your cool. Kim shares his new 3-part formula for project recovery: People first – You aren't just fixing a plan, you're fixing an organization. Calm – Calm is contagious, and you can only control yourself. Clarity & Courage – Seek out misalignment, bring truth to light, and have the guts to ask, "Does this project still make sense?" Of course, Kate keeps Kim honest, adding the perspective (and laughs) that make the tough lessons go down easy. If you've ever been handed a project that feels unsalvageable, this episode is your playbook. 👉 Want even more? Join us at pmhappyhour.com/membership to get PDU certificates for episodes, downloadable templates, access to our PM community, and 1:1 time with Kim and Kate.

Why bother with risk management when you can just deal with problems as they happen? In this episode, Kim and Kate dig into the heart of that question—and the answer might just save your future self a world of pain. You'll hear: Hard-hitting stats: 1 in 6 projects go 200% over budget (Harvard Business Review), 17% of major IT projects threaten company survival (McKinsey), and why 69% of projects don't succeed. Firefighting vs. fire prevention: why controlled burns (boring, thankless prep) prevent disasters while the "heroes" just put out fires. ROI of risk management: the surprising 20:1 return on time spent planning versus cleaning up issues later. Language hacks: how swapping "risks" for "obstacles" (credit to Dr. Josh Ramirez) can get your team—and executives—on board. Practical techniques: from whiteboarding failure points to slicing your project into risk categories, simple ways to start risk management without drowning in templates. Whether you're a seasoned PM or just tired of project disasters, this episode shows why risk management isn't about doom and gloom—it's about giving future you a fighting chance. JOIN THE HAPPY HOUR! Get access to all podcasts, PDU certificates, bonus content, exclusive member Q&A webinars and more from our membership! https://pmhappyhour.com/membership

Please. Let it end. PLEASE! A defining characteristic of a project is that it ends. Finally. Just finish it, right? If it were only that easy!  In another Top Shelf Replay, Kate and Kim revisit one of their classic past episodes, "The Closer." We play highlights from the original Closer episode as they talk about how to build up to a crisp conclusion to your project, making it a win for everyone. Then, Kate and Kim talk through their revised perspectives and learnings since the original airing of the Closer - and some of their hard learned lessons since then!    JOIN THE HAPPY HOUR! Get access to all podcasts, PDU certificates, bonus content, exclusive member Q&A webinars and more from our membership! https://pmhappyhour.com/membership