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cereal255
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You should be very competitive at Cornell and Michigan. I would drop Rochester and replace it with 1 more reach school of your choice. Considering you don't mind cold weather and rural/college town locations - have you considered Tuck?
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You have an unusual story and some schools definitely will value that more than others. You are on the short side of experience but Kellogg does have a reputation of appreciating folks with a different background more than many other schools. I would say that would be a school that would be worth a shot, its location is better than some of the others you are looking at and so is its brand...plus trust me your wife would love it. 6 schools would be reasonable and the Rochester should be a sure bet. I think Ross and Cornell are solid as long as you execute well and have a convincing story. You would be competitive at GSB, more so at Kellogg...HBS is an extreme long shot but with a very strange story you never know.
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Thanks again for your replies, this is really helping me calm down a bit about this whole process.

I took a look at Tuck and I'm definitely adding it to my list for round one...

I'm not so sure about Kellogg since as you say (and as I'm aware) I'm light on the experience side and if there's one thing that I hear about Northwestern on the various forums that I read it's that the school really values work experience more than most....

So my revised list:

Reach: Chicago(R1), Wharton (R2), Kellogg (Maybe R2)

Still Reach but slightly better shot: Cornell (R1), Ross (R2), Tuck (R1), UCLA (R2... if I can talk the wife into it)

Safety: Rochester (R2 if I don't get into Cornell R1)

This way my essays are spread out as well... I can only take so many of them at once. I'm also not considering any schools lower ranked than Rochester (I have ties to the Buffalo/Rochester area which is the only reason I'm applying)

I'm definitely tempering my expectations for this year since I don't have a lot of experience but it's certainly worth a shot and there's always next year...

Again, thank you so much for your input. Now to craft a strong goals essay...
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Great to hear you're applying to Tuck. Keep in mind that you have to complete a self-initiated interview on-campus in Hanover, NH prior to submitting your application. It should also help you see if the culture is for you or not. Tuck is a very tight-knit school.
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Well hopefully I'll be able to make it up to Hanover before the end of the month then so I can get my app in before the Early Action deadline... I don't know how Tuck was never on my radar. Thanks so much for suggesting it because it looks like it would be an awesome fit for me and since my wife keeps bugging me that she wants to move to Boston eventually it might be perfect for both of us.

I'm crossing my fingers it'll come down to Johnson vs. Tuck in a fight to the death... who knows how everything will play out but at least I have a more solid plan of attack now.
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I agree with the comments that you do have a special profile. I think with your profile you may even be more of a hit or miss type candidates, and I mean that has a good way, you can get a top-5 school but rejected from a 10-20's school. So definitely apply to the elites. Good GPA. GREAT GMAT's. Just play up your unique skills. Maybe look for way to reinforce your leadership skills, maybe quantative classes (I don't know your background but I would imagine liberal arts don't require to much hard math)
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cereal255
Well hopefully I'll be able to make it up to Hanover before the end of the month then so I can get my app in before the Early Action deadline... I don't know how Tuck was never on my radar. Thanks so much for suggesting it because it looks like it would be an awesome fit for me and since my wife keeps bugging me that she wants to move to Boston eventually it might be perfect for both of us.

I'm crossing my fingers it'll come down to Johnson vs. Tuck in a fight to the death... who knows how everything will play out but at least I have a more solid plan of attack now.

The Tuck alumni network is extremely strong in Boston and New England.
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GoBruins:

I've already taken 2 accounting classes at my community college and gotten As in both so hopefully that will allay some concerns. Hopefully my essays will also showcase how my current job also uses quant skills.