When Do You Quit?

Sometimes quitting is the smartest move you can make. I've done it often but not enough. The key is doing it for the right reasons. Whether you’re thinking about leaving a job, ending a relationship (should I fire them?), or abandoning a goal, the process matters. Here’s a straightforward approach to help you make the call.

Step 1: Get Honest About Your “Why”

Start by asking yourself the tough questions:

1. Am I quitting because I’m uncomfortable or frustrated? (Be honest)

2. Am I walking away from something bad, or toward something better? (BTW this is a question I’ve used to help me make most of my decisions in life. It’s money.)

Sometimes, quitting feels like failure when it’s actually a strategic move. Dr. Henry Cloud, in his book Necessary Endings, talks about the importance of “pruning” in life—cutting off what’s dead or no longer growing AND even the healthy, beautiful flowers to make space for new opportunities. If that’s the case for you, it’s time to sharpen those shears.

Step 2: Stop Romanticizing the Situation

Before you make a decision, strip away the rose-colored glasses. Is the job you’re clinging to really your dream, or are you just scared to admit it’s time to move on? Is the project you’re pouring hours into worth the effort, or are you trying to save face? Here’s the truth: just because you’ve spent time, money, or energy on something doesn’t mean you owe it more. That’s called a “sunk cost,” and it doesn’t deserve your loyalty.

Step 3: Balance Your Head and Your Heart

Quitting requires more than just logic or emotion—it’s about balance. If you’re running purely on emotion (frustration, burnout, or fear), take a step back. If you’re overanalyzing every little risk and ignoring how miserable you are, it’s time to tune in to your feelings.

Here’s a question I love to ask: Will your future self thank you for this decision? The answer will tell you what to do.

Step 4: Get a Reality Check from Others

Sometimes, you’re too close to the situation to see it clearly. This is where trusted advisors come in—friends, mentors, or even that brutally honest coworker who doesn’t sugarcoat anything. They’ll help you see what you’re missing.

Pro tip: If they’re all saying the same thing (“You’ve been complaining about this for months!”), it’s probably time to listen.

Step 5: Weigh the Risk of Staying vs. Leaving

There’s a risk to everything. Staying where you are could drain your energy and opportunities, but leaving might feel uncertain or scary. Here’s the trick: compare the risk of staying stuck with the potential reward of moving on. Spoiler alert: growth usually happens on the other side of discomfort.

Step 6: Decide and Move On

Once you’ve made the call, commit. Second-guessing yourself won’t help. And no, you don’t need everyone’s approval.

Final Thought

Quitting isn’t about giving up—it’s about moving forward. The most successful people know when to say, “This isn’t working,” and pivot. Whether you’re pruning the dead branches or stepping into uncharted territory, remember this: you’re not stuck. You’re choosing growth.

Now go make the tough call—and own it.