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From http://mitadmissions.org/blogs/entry/50_things,

#4. Take naps in the middle of the afternoon with reckless abandon.

I think I understand reckless and abandon, but what does reckless abandon mean here?

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@Maulik V is basically correct, but it's important to note that the author's choice of phrase, "reckless abandon", is very ironic and wry; it's meant humorously. The phrase "reckless abandon" typically is applied to actions that are, well, very active. The word "reckless" comes from the same root as "reckon" (to account, to tally, to figure), and means "without thought to the consequences", or "thoughtless" in the pejorative sense. Things to which "with reckless abandon" are most typically applied are operating motor vehicles and handling fire arms – things that if not done carefully are dangerous to innocent by-standers. One might make edits on a database in production "with reckless abandon", especially if it involves "DELETE *".

So to instruct people to nap with reckless abandon is meant to be clever and funny in its incongruity. Perhaps to a slight degree it also is meant to gently tease the reader not to be too scandalized by the idea of napping -- saying with sarcasm that it's not like napping is driving a car with your eyes closed.

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Straightforwardly he means...

Take rest (in the afternoon) without getting worried! [with devil-may-care attitude!]

Here it is...

reckless (adj) -showing a lack of care about danger and the possible results of your action.

And...

abandon (n) - The trait of lacking restraint or control; reckless freedom from inhibition or worry.

Putting reckless, the speaker/author just wants to emphasize.

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I thought I understand what reckless abandon means after reading the two answers, but today, when I read another example from XP's retirement triggers another wave of deserters,

I use Chromebook to browse the web with reckless abandon

I found that my understanding was completely wrong (I thought "with reckless abandon" is use to describe things that are most typically like operating motor vehicles and handling fire arms – things that if not done carefully are dangerous to innocent by-standers). So I'm searching for better answers myself now:

From https://ca.answers.yahoo.com/question/index?qid=20080425132954AAMMJm4

  • To do or say something without regards for the consequences (Jackie C)
  • Basically it means to abandon all sense of responsibility or consequence and just take the plunge despite the possible outcome (Aunt Susan)

From http://www.urbandictionary.com/define.php?term=Reckless%20Abandon

  • It's idiomatic English, means roughly "without care or regard for consequences".
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  • No, you were right originally. This is another example of using the phrase wryly, for humor.
    – Codeswitcher
    May 6, 2014 at 5:46
  • Ok, I'll pick base on the vote then.
    – xpt
    May 6, 2014 at 13:59
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My football coaches in high school used this phrase when telling players how to "pursue the ball(carrier)".

a complete surrender to natural impulses without restraint or moderation; freedom from inhibition or conventionality:

to dance with reckless abandon.

(Source: Dictionary.com)

With "freedom from inhibition" being attached to a positively connotated "lack of reason"/mindlessness/wu-xin/uninhibitedness/recklessness.

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