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how do i know when it’s time to leave my job?
This is one of those questions people usually ask only when something real is already shifting. Here’s a simple way to tell if it’s time, without romanticizing quitting or gaslighting yourself into staying.
At the end of most weeks, ask yourself “Does this job give me more energy than it takes?”
If for months the answer is no, that’s not a bad week. That’s a pattern.
A good job should grow at least one of these: Skills, Reputation, Money, Freedom, Joy.
If none of those have moved in 6 to 12 months, you are standing still. Standing still in a moving market means falling behind.
Write down what you complain about at work.
If it’s one project, one person, one temporary phase, you can probably fix it.
If it’s the culture, the leadership, the way decisions are made, the values, that’s structural. You can’t fix that from your seat.
Ask “If I stay here 2 more years, will I be proud of that version of me?”
If you feel a quiet no in your body, listen to it.
You don’t need a dramatic crisis. Quiet misalignment is enough.
You are ready to leave when:
Staying feels safer than it should. Leaving feels scary but honest.
Fear is not the enemy. Stagnation is.
Pulled from Lenny’s podcast conversations about knowing when it’s time to leave a job.
this is a big one. You are not weird for asking it.
Here are the clearest signals that it might be time to go, pulled from people who have actually lived through it and studied it.
Andy Johns, ex Facebook, Twitter and Wealthfront, describes the real alarm system like this: When sleep, relationships, physical health, playfulness or social life start breaking down, that is not normal work stress. That is your nervous system saying something is wrong and needs to change.
He calls these flashing red alarms, not yellow ones.
If your sleep always sucks, if you are always tense, if your relationships are strained, that is your answer.
Source from Lenny podcast: When enough is enough with Andy Johns.
Andy also explains burnout as something that sneaks up on you.
Pressure, stress and anxiety build slowly. You normalize it. Then one day you realize you are panicking, numb or disconnected and you cannot fake it anymore.
If you keep thinking “I just need to push a little longer” and you have been thinking that for months or years, that is the boiling water moment.
Adam Grenier from Uber gives a simple test.
When you are just tired, you still enjoy other parts of life. You go to class, see friends, laugh.
When it is deeper than exhaustion, you cancel everything. Even things you used to love feel pointless.
If work is not the only thing that feels broken but the rest of your life is fading too, it is not just a bad job.
Andy walked away from a seven figure VC role after a heart scare and years of overachievement. His insight was brutal and honest.
He realized he was using achievement to feel lovable. Promotions and money kept coming, but inside he was worse, not better.
If your resume is going up while your energy and meaning are going down, that mismatch is a major exit signal.
One of the most common patterns in all these stories is this.
People know something is wrong long before they leave. They just keep negotiating with themselves. After the next project. After the next bonus. After the next quarter.
When your inner voice keeps coming back with the same message for months, that is not noise. That is data.
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