How to Know If You Should Actually Quit

Everyone fantasizes about quitting sometimes. Bad day, annoying colleague, stressful deadline—the thought crosses your mind. That's normal and doesn't mean much.

But what if the thought doesn't go away?

Here's how I think about the difference between venting and a genuine signal that it's time to leave.

Temporary vs. Structural Problems

Temporary problems are situational. A difficult project that will end. A colleague who's leaving. A busy season that has a finish line. These suck, but they resolve themselves.

Structural problems are built into the job. The culture won't change. Your growth has genuinely capped out. The work fundamentally doesn't use your strengths or interest you. These don't get better with time.

The question isn't "am I unhappy?" It's "is the source of my unhappiness likely to change?"

Before You Decide

Have you actually asked for what you need? A shocking number of people quit without ever telling their manager what would make them stay. More money. Different projects. Flexible hours. Internal transfer. You might not get it, but it's worth asking before you burn the option.

What would need to change for you to want to stay? If your answer is "everything" or "I don't know," that tells you something. If your answer is specific and achievable, try pursuing it first.

Are you running toward something, or just away? Quitting to escape is different from leaving for an opportunity. Both can be valid, but "away from" moves often disappoint because you haven't solved the underlying issue.

The Financial Reality

This isn't romantic, but it matters: do you have 6 months of expenses saved? Do you have health insurance figured out? Do you have dependents who rely on your income?

If your financial runway is short and you don't have another job lined up, you're not making a free choice. You're gambling. Sometimes that's the right call. But know that's what you're doing.

Red Flags That Warrant Action

Some situations justify leaving even without a perfect plan:

• Your physical or mental health is seriously deteriorating
• You're being asked to do something unethical
• The environment is genuinely toxic (not just annoying—toxic)
• You dread every single day with no end in sight

These aren't "grass is greener" situations. These are signals that staying costs more than leaving.

Making the Call

If the problems are structural, you've tried to address them, and you can afford to leave—it's probably time to go.

If you're reacting to a temporary situation, haven't advocated for yourself, or have no idea what you want next—slow down and get clarity first.

And remember: this isn't a permanent decision. You can change jobs again. You can even go back to a company you left. The stakes are real, but they're not as high as they feel at 2 AM.