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We tend to treat the first six months in a role as a probationary period. Can you do the job? Can you ramp? Can you meet expectations? Are you a good fit?
That framing is so common we rarely question it.
But in my experience, the six-month mark is doing something else at the same time. It’s giving you enough information to decide whether this role, this team, and this company are actually a fit for you.
By six months in, you’re no longer onboarding. (Don’t get me wrong: there’s still a ton to learn, but you’re past the initial “I’m new here” phase.) You understand the org chart. You know how decisions really get made. You’ve seen how conflict is handled, how feedback flows, and which values are aspirational versus enforced.
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It’s usually around this point that I joke you’ve been there long enough to know where the skeletons are buried.
These typically aren’t catastrophic things. I’m talking about the tradeoffs the company has decided to live with and the cultural norms that don’t show up in interviews or onboarding decks, but shape daily life in very real ways.
The question at six months isn’t whether the skeletons exist. Every organization has them. The question is whether these skeletons are ones you can live with.
Some of them are benign. A messy process that mostly works. A product compromise that’s annoying but understandable. A leadership quirk you learn to route around. Over time, these fade into the background.
Others don’t, especially when it comes to how disagreement is handled. Sometimes it’s how decisions get reversed. Sometimes it’s the gap between what’s said publicly and what’s rewarded privately. None of these things are inherently “wrong,” but they can be very wrong for you.
This is the part we don’t talk about enough.
When someone feels unsettled around the six-month mark, we often frame it as a performance issue or a confidence dip. Maybe they just need more time. Maybe they haven’t fully adjusted yet.
Sometimes that’s true. But sometimes it’s a systems signal.
Growth changes companies. Teams evolve. Roles shift. The environment you joined is rarely the environment you’re actually working in six months later. I always joke that three things in life are certain: death, taxes, and reorgs every 6 months. These reorgs disrupt the flow of a company—often for the better, but the dust does have to settle.
At the same time, you’re not the same person you were when you accepted the offer. What motivates you sharpens. Your tolerance for certain dynamics narrows.
That misalignment doesn’t mean anyone failed. But ignoring it tends to come at a cost.
What I’ve found useful is treating the six-month mark as a two-way evaluation, even if it’s never named that way explicitly. Not in a dramatic “should I quit?” sense, but just being self-reflective.
Questions like:
What parts of this job give me energy, and which ones consistently drain it?
Which norms have I adapted to, and which ones still feel like friction?
If nothing materially changed here over the next year, how would that feel?
These aren’t questions you need to answer immediately. But they’re worth asking before you talk yourself out of what you’re noticing.
We’re very good at telling ourselves that discomfort is temporary, that we just need to push through, that this is what growth feels like. Sometimes that’s true. Other times, it’s how people slowly convince themselves to ignore information they already have.
The six-month mark isn’t about deciding whether to stay or go. It’s about clarity.
You finally have enough context to see the system as it is, not as it was presented. And once you see that clearly, you get to decide what you want to do with that information.
That decision doesn’t have to be urgent, but it does deserve to be intentional.