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Chicago Booth has only one essay for first-time applicants this year, and it is their traditional open-ended question.  How should you approach it?

Chicago Booth values adventurous inquiry, diverse perspectives, and a collaborative exchange of ideas.  This is us. Who are you?  There is no prescribed minimum or maximum length.  We trust that you will use your best judgment in determining how long your submission should be, but we recommend that you think strategically about how to best allocate the space.  Acceptable formats are PDF, Word and Powerpoint.

Give Booth some credit.  Before the 'no-page-limit', 'open-ended' prompt was adopted by HBS (and suddenly, shockingly became all the rage) they firmly held to this approach year after year.  Other essays would come and go, but Booth's open-ended essay has been around for a long time.

That's not to say there have not been changes.  Booth used to constrain the length to 4 Powerpoint Slides or pages, which naturally gave rise to a certain kind of storytelling (Stern still does this).  Now, of course, since Booth has eliminated this requirement, it would be a bad idea to repurpose a Stern essay for Booth -- too obvious.  Likewise, just because HBS has you writing open-ended essays now does not mean that you can just reuse the sentiments (or worse yet, the entire essay) for Booth.  Quite frankly, Booth and HBS are not concerned with the same things, and a fit for one school will not be the same as for another.

Also, do not underestimate the value of a good multimedia presentation!  Most people look at multimedia as 'a lot of work' or 'not in their wheelhouse'.  Well, yeah, that's exactly the point.  By going that extra mile, securing some help with your multimedia component, and putting together something well thought out that takes good advantage of the medium, you will already be setting your candidacy apart from dozens of others in your bucket.  You want differentiation?  This is your chance.
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