When to apply for permanent positions while having a lengthy postdoc

Some thoughts:

• How do you know when you are "ripe" for the tenure-track market?

The easiest thing to do is to try. If you get interviews, then you are ripe. (But the reverse is not true! The way the market is, in many fields you may be ripe but still not get interviews.)

The second easiest thing is to ask your postdoc mentor.

("Wait, but I am working for them! Wouldn't they want to keep me there?" Having a postdoc placed into a well-regarded tenure-track position is good for your mentor's reputation. It is in his/her interest to maximize your chances of getting a permanent position.)

• Will I be shooting myself in the foot applying this year for a position that may have a position in my last year of postdoc?

Yes and no.

If you are obviously underqualified now, your application file will be passed over and forgotten by the time you try again in two or three years.

If you are somewhat qualified, but not the tops, they may remember your earlier application. Then in addition to judging you on how you compare to other applicants the committee may also try to compare your new file with their impression of your file from before. In other words, you need to show growth in the intervening years.

If you are good enough to get a position now, why not take it?

• If I take a permanent position early, will this make it much more difficult to obtain a better position later?

Only your personal investment and inertia at your new permanent position.

I would advise against the thought of "shopping" for the best position at this early stage in your career. Unless you are one of the superstars, your goal should be just to get a job first. Worry about better opportunities when they actually happens. Or as the saying goes: A bird in hand is worth two in the bush.

• How can you tell what level one should look to shoot for when applying early and not wanting to take too low of a position on your (personal) ranking?

Realistically, the calculation goes something like this:

• Final year at postdoc: apply for everything, take whatever you get.
• Year -2 at postdoc: If I get this job, I stay employed for three more years! I'll happily take a pay-cut for that.
• Year -3 at postdoc: I have two more years to polish my files. Let's just feel the water and only apply to places I would really want to work at.

If you are really unsure: more than two years from the end of your postdoc you can afford to be a bit more picky (and err on the side of thinking that you are a superstar). You really don't want to be offered a position that you have to reject because your postdoc is "better".

One last comment: if you are good enough to attract a tenure-track offer during the earlier part of your postdoc from a large enough institution, there is a non-zero chance that you can ask for a later start date in order to "finish things up at your current position".

Here are my thoughts on the matter. (The OP and I know each other, and I think by now he has figured out to take me seriously but not too seriously.)

The worst part of the academic job market is the randomness and uncertainty. In any given year, there will be a pool of desirable positions and a pool of candidates who desire them. The second pool is unfortunately much larger than first: more than an order of magnitude larger. But within that pool there is a much smaller subpool of candidates whom most people agree are deserving of a position of the desirable sort. More or less by definition, this subpool has approximately the same size as the pool of desirable positions: but what sucks is the "approximately." So every year on the job market there are candidates that don't get the desirable positions essentially because they lost a game of musical chairs.

Because of this phenomenon, having longer postdocs is a mighty gift. The difference between a two year postdoc and a three year postdoc is already considerable (and the difference between a one year postdoc and a two year postdoc is almost cruel). I advise all postdocs who are interested in research jobs in mathematics to do everything in their power to arrange to apply for jobs while they still have the option of one more year on their postdoc. This smooths out the randomness and uncertainty considerably, and as @Ben Webster says, it's actually better than that: when you apply for jobs in year N and don't get them, you get very useful information for year N+1. Ideally you will get specific feedback on your application itself, but even if not: if you apply for 20 jobs in year N and get 3 interviews, then you should be okay applying for not many more jobs in year N+1. If you apply for 20 jobs and get no interviews, you better apply for a lot more jobs in year N+1.

The main counterargument that I can think of against applying for jobs is that it takes a lot of time to do it in a solid way. Most people that I know do not apply for jobs in the first year of a three year postdoc, in part because they're slightly traumatized from their recent job application cycle, their research program is just starting to take off (that's when you should graduate!) and they really want to burn midnight oil on that rather than more job applications.

A five year postdoc: wow, that's nice. I would suggest not applying for anything in the first year and spending your second year expecting not to apply but keeping an eye out for perfect jobs (including jobs that people are trying to recruit you for). Whether to apply for jobs in your third year depends on how well your research has been going recently: if you just landed a big result or big publication that you don't see yourself topping for a little while, maybe do it. If you feel like you need the time to build up to where you want to be, maybe don't do it. I would strongly recommend that you apply for jobs in each of your last two years.

How do you know when you are "ripe" for the tenure-track market?

This is the wrong question. The right question is "What value do I get out of doing this postdoc, and what value would I get from a tenure-track position now?" In general, getting a bunch of papers, colleagues, research methods etc. in place now will massively help you with tenure, but great / perfect opportunities won't come every year. So great / perfect: apply now; good: expect there will also be good most years and wait til your fourth year. You probably want to apply twice, so I'd do fourth & fifth year, unless somewhere you really want to go invites you to apply earlier. Don't waste time applying and reading advertisements every year!

If I take a permanent position early, will this make it much more difficult to obtain a better position later?

Yes. You have to prove yourself in that position before people will look at you. Also, you will get no novel research done the first two years you are teaching.

How can you tell what level one should look to shoot for when applying early and not wanting to take too low of a position on your (personal) ranking?

Fourth year: only apply the places you want. Fifth year: apply everywhere.