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I did Wharton R1. It was my first application and was agonizingly long. I also did 70% of Kellogg to R1, but decided to postpone to R2.
I'm planning on doing Haas, MIT, Kellogg and Chicago for R2. I've started Haas +Kellogg and it's already easier, compared to Wharton R1.

If you're a bit experienced, it think it is doable to have 4 schools for R2, though it requires an effort and focus.
If this is your first application, you should consider prioritizing and maybe postponing to R3, if such round exist.
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I applied to 5 schools in R1 and had time to apply to a 6th. The further along the process you get, the tighter your story gets, so I think the essays for the 3rd or 4th school on were much easier. Keep in mind I started writing essays end of June, and the months of July and August I worked on essays at least 5 nights per week. It is a lot of work, but I am the type of person that would rather have two horrible months of writing essays and then never think of them again. If you are willing to put in the work, 4+ schools in one round is very doable.
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I did it last year and I did it again this year. While it certainly took a LOT of time overall, I agree with the other posters in this thread -- the more you do, the tighter your stories get, and the better your applications get. People have posted time and time again not to do your dream school first. Why is that? Because the more you're exposed to the application process, the more you've taken the time to tell your story and to find the best examples for certain essays.

For me, by the time I got to my last R1 application, my essays were completely different (and better!) than the ones I wrote for my first R1 application. The stories were told more concisely, with more conviction, with more color. And ultimately, I went back and redid the first few apps I did.

While the idea of applying to a lot of schools is painful, and definitely hurts your wallet, your writing does improve over time. If you take the time to plan out everything -- how many essays you have to write, what topics are covered, when all the application and deposit deadlines are -- you can come away with a finished product you feel good about ... regardless of how many schools you apply to.

DISCLAIMER: I have not yet been accepted anywhere this cycle. My opinion, while optimistic now, could very well change in a few months time if/when the dings start rolling in :)
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To echo what's been said, I don't think my essays have suffered whatsoever over the long haul, in fact I think they have gotten much much better. It's a shame that I did HBS and Wharton (the more competitive ones) first due to due dates, because the subsequent applications were much much better; I would say my ninth, Duke, was easily my best. If there is a legitimately large amount of schools you're interested in, go for it. My biggest tip would be to not try and recycle whole essays or even paragraphs, but sentences. I tried recycling some essays and tweaking them and they sounded like an incoherent mess not addressing the prompt. Trying to edit them to fit probably took more time than writing it 'fresh'. The biggest issue with the four schools you mentioned is that the due dates are in close proximity. Just work on them diligently in order of preference. If you run out of time on the fourth, throw it out, but try to have time for it. Just get them polished and ready for 'submit' well ahead of time so a hectic frenzy at the deadline doesn't make for silly mistakes.
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Thanks guys for such helpful advice. I appreciate it.

So I'm currently doing columbia, which i hope to submit by thanksgiving, and also haas round 2, which is due on november 29th. I was gonna do round 3 for haas, but everyone said that round 2 is better for traditional applicants. Haas' 5 essays are tough, and i'm worried about not being able to do them by the deadline (at least a good job). For round 2, I think wharton and sloan are pretty reasonable; tuck and kellogg however seem tough and specific in their questions.

Also, did any of you guys use an admissions consultant for your apps?
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No admissions consultants for me. Admissions consultants are good if you either have no idea where to start or are reapplying and don't know where you went wrong, IMO. For me, I felt I could budget my time appropriately and could glean enough information from resources like this forum to go through this process on my own.

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Totally doable. By the time you are through Round1, not only can you re-use some essays but you are also at a point where you know which stories will fit where so Round 2 should go faster/smoother. Here is a suggestion based on the essays I wrote for Round 1:

Review essay questions of all schools that you are applying to, start with the ones that you can re-use in other apps (or compress for the remaining). I usually found it easier to compress the longer essays into a word limit than expand on existing short limit ones. That way you have already word-smithed the essay, you just need to remove some pieces or re-use other pieces from it into other essays
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dawizard
Totally doable. By the time you are through Round1, not only can you re-use some essays but you are also at a point where you know which stories will fit where so Round 2 should go faster/smoother. Here is a suggestion based on the essays I wrote for Round 1:

Review essay questions of all schools that you are applying to, start with the ones that you can re-use in other apps (or compress for the remaining). I usually found it easier to compress the longer essays into a word limit than expand on existing short limit ones. That way you have already word-smithed the essay, you just need to remove some pieces or re-use other pieces from it into other essays
+1

I completely agree that compressing is easier than expanding.