A calendar like this is a great idea in a lot of ways, and (I'm guessing) a lot of us have internalized a calendar something like this. Deadlines for Kalamazoo or MLA or CCCC are at such and such a time each year, grant deadlines are at always at a similar time, and so on. I try to inform my students about deadlines in the field, too, so that they can develop a similar yearly calendar if they haven't already.
This student obtained, in total, some $200,000 of research funding in graduate school (in cultural anthropology–a field that does not have massive grants), in addition to her basic TA funding package. She had several publications before finishing, and secured a tenure track position at an R1 institution in her first year on the market. She is solidly on track for tenure, and this past year she won another major research fellowship that gave her a year’s leave time for new fieldwork on a second project.
And Kelsky is also right that, as they say about the lottery, you can't win if you don't play. If you do submit to a conference or put in a grant proposal, there's a chance you'll be rejected, but if you don't submit anything, there's a 100% chance you won't get to present at a conference or get funded.
The only thing I'd add to this plan is this: it helps with a good outcome, but it can't guarantee one, because the ultimate results are often not in your hands. You have to be flexible.
- Grants don't always happen; in fact, grants usually don't happen. The NEH funds about 6% of applications for individuals. What if, as is likely, you're among the 94% that didn't get funded? What's your Plan B? It's like being a prospective college student, in a way: what if you don't get into Stanford or your equally competitive first choice?
- Publications don't always happen, either, or at least not on a schedule and timeline that's going to facilitate the outcome you want. Your article may get rejected more than once, or your research plans may be disrupted due to a lack of funding (see above).
- Your writing might not take the direction you've planned, either. Maybe what you thought was a straightforward topic with a clear timeline turns out to be more complex than you thought, or you need more research than you thought, or you just plain need to think longer and harder about it than you originally planned.
- Opportunities can arise that aren't in your plan. Serendipity happens, but rarely on a schedule (or else it wouldn't be serendipity). Are you going to say yes, and, if so, how does that affect your plan?
- Sometimes life intervenes: you get the flu, or have a baby, or your family gets sick and you have to care for them.
- Also, money isn't a part of this plan. What if you have to teach more to make more money so that you can go to conferences, or you can't afford to go to a major conference because it's being held overseas or far away? A conference costs, on average, at least $1500 unless you can drive to it; research trips cost more; and if you're turned down for a travel grant, how will you accomplish these goals?