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Work · An honest evening, revisited quarterly

How to know when to leave a job

Leaving well means separating a bad week from a bad fit, using concrete signals instead of mood, and having a plan before you announce anything.

Most people leave two years too late or six months too early, because they never wrote down the actual criteria.

What nobody tells you

  • The job rarely gets dramatically worse right before you quit — it usually just stays quietly wrong until you finally notice.
  • Growth stalling is a harder signal to justify than a toxic boss, but it costs you more over a decade.
  • You'll never feel 100% ready to leave. Waiting for total certainty is how people stay five years too long.

The basics

  • There's a difference between a bad season (reorg, tough project, hard quarter) and a bad fit (repeated pattern with no end in sight).
  • Compensation, growth, autonomy, and people are the four levers — a job failing on one can be worth staying for; failing on three usually isn't.
  • Your resignation date and your actual decision date are different — decide first, then plan the exit.

The framework

The Trend Line Test

Don't judge a job by its worst week. Judge it by its trend over the last two to three review cycles across the four levers.

  1. 01

    Is your learning curve flattening, or still climbing?

  2. 02

    Is the gap between your pay and market growing or shrinking?

  3. 03

    Are the people and culture issues one-off or structural?

The playbook

0/6

The conversation — what to actually say

Deciding with a partner or close friend

“Here's my honest scorecard on pay, growth, autonomy, and people over the last year — and here's the trend, not just today's mood.”

Talking to your manager before deciding to leave

“I want to be direct: I'm not seeing the growth I need here. What would it take to change that in the next two quarters?”

The mistakes — what people get wrong

  • Quitting in the heat of one bad meeting — sleep on it for at least two weeks.
  • Staying purely out of loyalty to people, while the actual job keeps failing you.
  • Leaving without a financial runway or a next step, turning a career decision into a panic decision.
  • Assuming the grass is greener without doing any real diligence on the new place.

Ask yourself

  • If nothing changes in the next year, will I regret staying?
  • Have I actually asked for what I want here, or just assumed it's impossible?
  • What would I tell a friend in my exact situation?

Go deeper

  • Exercise

    The four-lever scorecard

    Rate pay, growth, autonomy, people quarterly and track the trend line.

  • Book

    Designing Your Life — Burnett & Evans

    Frameworks for testing options before committing to a change.

  • Practice

    Exploratory coffee chats

    Low-stakes conversations that convert vague dissatisfaction into real market data.

General educational information, not legal, tax, medical, or financial advice. Rules vary by country and change over time — verify with a qualified professional before acting.