Tuesday Post: Challenges with Quitting a Project or Initiative

Happy Tuesday!

Every Tuesday I'd like to offer strategies for the week ahead and a thought to fuel your action.

You're two hours into a terrible movie. Your back aches, your phone is buzzing with texts, and the plot makes no sense. But you stay. Why? Because you've already "invested" two hours, and leaving now would mean admitting those hours were wasted.

This same logic ruins businesses, relationships, and dreams every single day.

Here's what I've learned after watching my own technology business die a slow, expensive death: we're all performing for an audience that isn't watching. We create elaborate narratives about how others are keeping score of our wins and losses, building entire identities around projects that were supposed to be experiments.

I spent seven years of weekends building a business that everyone associated with me. Saturday morning coffee runs became strategy sessions. Sunday dinners became investor pitch rehearsals. I wasn't just running a startup—I was the startup. And when people asked how it was going, I couldn't separate the company's performance from my own worth.

The fear of looking foolish kept me going long after the numbers stopped making sense. Every pivot became a "strategic shift." Every missed milestone became "market education." I was moving the goalposts in real-time, redefining success to avoid admitting failure.

The Hidden Mathematics of Quitting

Research shows that sunk cost fallacy influences 85% of project decisions. But here's the part that surprised me: the people who succeed aren't the ones who never quit—they're the ones who quit strategically and start again smarter.

Jeff Bezos captured this perfectly: "The smartest people are constantly revising their understanding, reconsidering problems they thought they'd already solved." Your GPS doesn't feel guilty about recalculating when it finds a better route. Neither should you.

The most successful people I know treat their projects like scientists treat hypotheses—with healthy skepticism and clear criteria for when to pivot. They install "smoke detectors" before the fire starts: predetermined metrics that signal when it's time to stop, reassess, or redirect.

The Paradox of Freedom

Here's the strange thing about quitting: it's hardest when you have the most options. When cash is tight, or deadlines loom, difficult decisions become obvious. However, when resources are abundant, we often keep everything "just in case"—like a closet that's bursting, but nothing gets donated because we have unlimited space.

This is why the most dangerous time for any project is when it's going moderately well. Not well enough to celebrate, but not poorly enough to quit. That's the valley where dreams go to die slowly, consuming resources that could build something better.

What the Scoreboard Actually Shows

Three months after I finally shut down my business, something unexpected happened. The people I thought were judging me started sharing their own stories of projects they'd held onto too long. The "failure" I'd been terrified of became the foundation for deeper conversations, better relationships, and, eventually, better decisions.

The scoreboard I'd been so worried about didn't exist. People were too busy managing their own cognitive dissonance to track mine.

Quitting isn't the opposite of perseverance—it's the prerequisite for a breakthrough. Every master craftsperson has a pile of unfinished projects, abandoned when they realized their energy could create something better.

The question isn't whether you'll face this choice. It's whether you'll recognize it when it arrives or spend years solving the wrong problem because you're afraid of admitting the right one.

The smartest move isn't avoiding the game. It's learning when to leave the table.

The best is ahead!

-Matt