The Hardest Project of My Career (and What It Taught Me)

Some of the most challenging projects, jobs, and relationships shape the way we move through life. They force us to grow, toughen up, and—if we’re lucky—walk away with some hard-earned wisdom. I’ve had plenty of these moments, both in and out of work. The kind that makes you question everything, push you to the edge, and somehow leave you standing stronger on the other side.

This is one of those stories—the kind that makes your blood boil years later. A project so mismanaged, so absurd, so full of preventable chaos that it turned into a masterclass in patience. It was supposed to be a career-defining opportunity. Instead, it became a test of how much incompetence I could endure before finally snapping.

Thrown Into the Deep End

Have you ever worked on a project that felt like the reason you were hired? That was this one—a massive website redesign for a prestigious museum. A $2 million scope. A high-profile client. A career-making opportunity. And how did we win it? Not through a pitch, not through a strategic discussion, not through any sort of alignment—just an RFP response that magically turned into a contract. No discovery, no conversations, just: Here’s the money, now go build it. It should’ve been a red flag, but I considered it a challenge.

I had just joined the agency as a senior PM and was immediately thrown into the biggest clients and projects they had ever scored. At the same time, I was still onboarding—getting to know the agency’s processes and procedures, which were very different from what I was used to. The team was also new to me. While they operated differently from my previous agency, they were clearly talented, and I was excited to work with them. And honestly, I was thrilled about the client.

Unfortunately, the feeling wasn’t mutual. They were duds from day one—unprepared, unorganized, and totally unready for what they’d signed up for.

The Slow-Motion Train Wreck Begins

From the start, everything was off. We couldn’t plan past discovery. They estimated the project would take two years, which—while ambitious—was technically doable. Instead, it took five. Five. Why? Because they hadn’t done even the bare minimum to prepare. No internal organization, no clear decision-making structure, no plan for how they’d manage their own involvement in the work. They just assumed we’d figure that out for them.

Their project manager was a nice person, deeply knowledgeable, and well-liked within the organization. But they had no authority. No real power to make decisions stick. And that meant every single step of the process was subject to the whims of various stakeholders with different priorities, opinions, and, apparently, an unlimited ability to derail the project. It quickly became clear that the PM was struggling, and in an effort to “fix” the issue, the museum did what many companies do in these situations.

They replaced them.

And that’s when things really went off the rails.

New PM, New Problems

Enter: the new project manager. New to the organization, eager to prove themselves, and, unfortunately, very convinced they knew more about the web than we did. Now, I’m all for an informed client, but there’s a difference between being knowledgeable and being a problem.

This person was a problem.

They wanted to revisit every single decision we had already made. They didn’t want to “align” or “adjust.” No, they wanted to redo months of work because they hadn’t been part of it. Meanwhile, the timeline was already obliterated, and the budget? Well, let’s just say we were hanging on by a thread.

So, I did what any good project manager would do. I pushed back—respectfully, professionally, and with clear reasoning.

Big mistake.

The Scapegoat Treatment

Instead of having an actual conversation with me about their concerns, they did what insecure people in power love to do: they escalated. Not to me. Not in a discussion where we could work through the issues. No, they called my boss—the owner of the agency.

I’ll never forget that moment. It wasn’t even face-to-face or over video. I had to go into a conference room alone and call him. And then I heard the words that still sting:

"They think you’re the problem. The project is suffering because of you. They don’t think you’re a good project manager."

Gut punch.

Thankfully, my boss actually knew the work. He had seen the status reports, documentation, emails, and late-night Slack messages. He let me vent before we came up with a plan. But I won’t lie—what came out of my mouth in that moment was not kind. I was livid. Honestly, I still am.

They weren’t holding up their end of the deal. They were disorganized and impossible to talk to, and now they were making me the scapegoat? The thought of continuing to work with them made my blood boil. But I knew I had to. And I knew I’d do it without stooping to their level—because that’s who I am.

(Side note: I hate that I took the high road. I deserved to tell them off. But I guess writing this is my catharsis?)

The Face-to-Face Showdown: When I Knew I Won

The next step? An in-person meeting. I had to travel to meet them (love that for me) and lay it all out: the budget overages, the timeline disasters, the receipts. And trust me, I had receipts—baselined project plans, status reports, emails, all the evidence proving I was doing my job.

I didn’t need any of it.

Because when we got in the room, they were… sheepish. Nice, even. They couldn’t say a damn thing to my face. And that? That pissed me off more than anything. I had spent months dealing with their disorganization, misplaced blame, and outright disrespect—and now that we were face-to-face, they just… folded? Instead of calling them out, I did the professional thing: I focused on solutions. It was the right move, but it still eats at me.

A moment in that meeting that still makes me laugh. The head of IT—who had been barely involved in the project—decided it was time to test my knowledge. He hit me with:

"Do you even know what a Work Breakdown Structure is?"

Oh, you sweet, condescending idiot.

Not only did I know, but I had our Work Breakdown Structure meticulously documented, complete with a forecasted launch date that his team had made impossible. So, I let him walk right into it. I calmly explained that we had a WBS in place since the day we signed the contract. I had a tidy Gantt chart outlining every phase, milestone, and dependency. Then, I did the best thing a project manager can do in that situation—I showed him his team's fingerprints all over every single delay and misstep. Right there, in real-time, he had to sit with the reality that their internal chaos was the problem. And for the first time, they started rethinking their stakeholder strategy. Something I'd been recommending and almost begging for, for months!

Did it change anything? Not really. But man, was it satisfying.

The Long Follow-Up: When the Tables Finally Turned

After that meeting, I kept doing my job—but I dropped the fake smiles. I don’t like working that way, but I do what the situation calls for. And these people? They didn’t deserve an ounce more of my goodwill.

That meeting vindicated me. It was clear to everyone that they were the issue. But, of course, they didn't get any better.

A few months later, the PM quit, and another came in, and I had to deal with the same BS all over again. But by then, I had figured out how to steamroll my way through, protect my team, and insulate our company from their endless indecision and dysfunction.

The project finally launched after five years of stalled communication and poor decision-making on the client’s part. For us, it was a letdown—not because the product wasn’t good, but because we had been on the cutting edge when we started and couldn’t bring them along with us. We spent years building something we’d probably never put in our portfolio.

For them, though, the launch was a big deal. They had to be excited—it was a massive investment in something a lot of people would use. I imagine they were also nervous because, deep down, they had to know how much they’d fumbled along the way. But by that point? It didn’t matter. We launched, we wrapped it up, and we cut off communication as soon as we could.

I probably celebrated—maybe even partied—but I honestly don’t remember. What I do remember is that I left that agency not long after. And while the project didn’t turn out the way I’d hoped, I was glad I saw it through.

The Lesson

Some people will never own their failures. They’ll dodge, blame, and hide behind emails and phone calls, but when it comes to actual accountability? Ghosts. And sometimes, no matter how much you want to, you won’t get your vindication. You won’t get the big dramatic moment where you drop the mic and watch them crumble under the weight of their own incompetence.

But if nothing else, this project was an education. It was my own personal master class in what I value, what I’ll tolerate, and how to manage a rotating cast of personalities without completely losing my mind. It taught me when to fight, when to step back, and how to navigate a mess without letting it consume me.

The punchline? Some projects break you down. But if you handle them right, they build you up into someone who can handle anything. And if that’s not enough? Well, at least you walk away with a hell of a story.