Career change
Changing careers when questions outnumber answers.
A career change starts as a question you ask an AI late one evening, and then it doesn’t end for a year. Can I afford it. What am I actually good at outside this. What would I be walking away from. You come back to it after a bad week, or after a conversation with someone who got out, and every time you start the explaining over.
Most of it is open questions, for a long time
The hard part isn’t the deciding. It’s the long stretch before it, when almost nothing is settled and you can’t tell whether you’re getting anywhere. You ask about salary bands one night and retraining costs another. You talk yourself into it on a Sunday and back out of it by Wednesday. None of that is wasted — it’s how something this size actually gets thought through — but it leaves no trace you can point at.
Eight months in, there are forty-odd conversations behind you and still no way to answer the plainest question about your own life: what have I settled, and what am I still waiting on. So you re-ask the ones you already worked out, because re-asking is easier than finding. And the questions that actually matter — the ones you’ve been avoiding — never get written down anywhere at all.
Somewhere to put a question you can’t answer yet
When something firms up, you tell your assistant to write it down: “Save that to my career project — the income floor is $4,200 a month after tax.” When a question forms and you can’t answer it, you save that too. Giraffe puts both in one project, under headings that don’t move: what’s current, what you’ve decided, what’s still open, and the notes that fit nowhere else.
Months later a number changes — you finally look at the savings account, or a recruiter tells you what the band really is. You say so, and the new value takes the place of the old one. The old one is kept underneath it, with the date it was replaced. That is the difference between feeling vaguely better about your runway and being able to see that it went from four months to seven, and when. You read the whole thing in a browser, on your own, without opening an AI at all.
Eight months of it, in one project
Say you’ve taught high school biology for nine years and you’ve spent since last winter working out how to stop. An evening on what instructional design actually pays. A long one on whether the mortgage survives a $9k cut. A short one after a staff meeting in February that wasn’t really about the meeting. You didn’t decide anything in any of them, and the project still has something to show for all of them:
Leaving teaching
- Current
- Decisions
- Not another classroom. Two years of trying to fix this one from the inside settled it, and it closes every version of this that ends at a different school.
- No second master’s. A $38k degree to leave a job that pays $68k is the wrong way round, so every path that starts with one is off the list.
- Open questions
- Whether to tell Dana before I have something lined up. She gave Marcus the whole spring to hand off properly — but the day I tell her, I stop being someone she plans next year around.
- Whether a first-year pay cut of about $9k is survivable, or only survivable on the spreadsheet.
- Notes
- Four people who left teaching told me year one was worse than they expected and year two was better. None of them went back. That’s four people, not a study.
- Recent changes
The decision, when it comes, closes several questions at once
Two things on that card are settled, and each one shut a whole branch. Deciding against another classroom took every version of this that ends at a different school off the list. Ruling out a second master’s removed four retraining paths in one go. That is how these decisions arrive — not evenly, one a month, but rarely, and then in a lump that clears half the board.
Two things are genuinely open, and they have been open longest because they are the expensive ones: a conversation with a person, and a number you can’t model your way out of. That isn’t a failure of the project. It’s where you are, on a page, where you can look at it without holding all of it in your head at once.
Most weeks, reading it is the whole job. When you do want help with the next piece — what a $9k cut does to the year, or whether a posting is worth the evening — you pick it up in ChatGPT or Claude with nine years and a mortgage already written down, instead of explaining them from the top again. That is how Giraffe works.
Nothing decided yet is still worth writing down.