When is the best time to change jobs? 💼
Always be prepared for that one unexpected reorg email where you'll be working on something you don’t want to work on or working for someone you don’t want to work for.
Hi everybody - something universal about all jobs is that you’re always one unexpected reorg email away from working on something you don’t want to work on or working for someone you don’t want to work for.
Being proactive about your career reduces that risk and gives you more control over where you end up long term, and in my latest video, I dive into this as part of answering many of your questions about my own career change.
If you liked this video, please do upvote it on YouTube and LinkedIn so that others can benefit from it 😇
Every Job Has an Expiration Date
One thing I believe is universally true…across tech and non-tech roles alike is that every job has an expiration date.
There comes a point where a role is no longer fresh. It’s no longer helping you grow. And staying in it becomes more detrimental than helpful. When that point arrives varies wildly based on your situation, but the pattern is surprisingly consistent.
I like to think about jobs the same way I think about a flight. You have the following stages:
In each stage, what you do and run into will be different:
Takeoff: You’re ramping up. Learning the people, systems, culture, and expectations.
Cruising altitude: You’re effective, confident, and operating at a high level.
Descent: Things begin to decline—sometimes slowly, sometimes abruptly.
Unless you’re the CEO (or about to be), every role eventually enters that descent phase.
The Best Time to Look for a New Job
This may sound counterintuitive, but the best time to look for a new job is when things are going well:
When you’re at cruising altitude:
You’ve learned what the role has to teach you
You’re delivering strong results
There’s little left for either you or the job to extract from one another
At that point, moving on is often a mutual decision, even if it isn’t explicitly stated.
The worst time to look for a new job is when things become chaotic, where you’re already entering the descent phase. Job searching is a job in itself, and doing it while fighting fires at work puts you in a compromised mental and emotional state.
It’s a bit like realizing milk has just passed its expiration date:
You might be fine drinking it, but do you really want to roll the dice?
Signs It May Be Time to Start Exploring
You don’t need to start looking the moment you hit cruising altitude, but you also don’t want to wait too long. Here are a few signals I’ve found useful:
1. You’ve maximized your learning
Nothing surprises you anymore. You can describe the system, domain, and failure modes in your sleep. New problems feel like slight variations of old ones. You’re teaching far more than you’re learning.
2. Your career path has peaked
This happens often in smaller companies—but it can happen anywhere. Your aspirations and the organization’s shape no longer align. There’s nowhere meaningful left to grow.
3. You sense trouble ahead
As you gain experience, your intuition gets sharper. If something feels off, it often is. One truth I strongly believe in is what I started this newsletter off with:
You are always one unexpected reorg away from working on something you don’t want to work on or working for someone you don’t want to work for.
These changes can happen overnight, without warning. And by the time they do, it’s often already too late to respond from a position of strength.
Maximize Optionality
The hardest part about being proactive is that comfort can feel convincing. But the goal isn’t restlessness. The goal is optionality. You want choices:
And the best way to create choices is to explore opportunities while you still have breathing room before urgency and nonstop fires remove whatever leverage you may have.
I find that this principle applies not just to careers, but to any situation where your future depends on a constrained set of options.
Wrapping it All Up
So, when is the best time to change jobs? The best time is when you can leave:
On a high note
On your own terms
With momentum rather than relief
In every role you take, always look to maximize both Learning and being able to collect Great Stories.
We often say a life well-lived is one filled with great stories. The same is true of a career. If you’re learning and building meaningful stories along the way, you’re increasing your odds of being both happy and successful in whatever comes next.
As always, if you have any thoughts or comments about this, feel free to contact me by posting on Twitter / X or on the forums.
Cheers,
Kirupa 😀