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Does one's intent factor into one's ability to rely upon an exemption in Halachah?

For example on Sukkoth, if I have no Sukkah and no intention of building a Sukkah (let's say at work, for one example and I've been bringing non-Mezonoth foods with me to eat for lunch or, for our purposes, "snack" every day; or for another example I am only going to be home for one or two days of the holiday so I don't bother to build one; or for a more extreme example, I just don't care to build one, although I am aware of the requirement to eat in one), and one day it rains, may I then rely on the exemption in Halachah that lifts the requirement to eat in a Sukkah?

Or, for another example, if I am lax/lazy and don't regularly wear Tefillin though I recognize that I ought to, and now it is Ḥol HaMo'ed and my rabbi/synagogue (assume no strong family Minhag, Ba'al Teshuvah, etc.) follows the opinion that one does not wear Tefillin on Ḥol HaMo'ed, may I rely on that exemption?

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You need a suka while at work? –  msh210 Oct 19 '11 at 18:34
    
Most people I know assume as much and bring "snack food" with them rather than "meal food" for lunch if they work in a building or a neighborhood without a Sukkah. I have been operating under the same assumption my entire life. –  Seth J Oct 19 '11 at 18:59
    
But these are not real-life examples for me - well, except for the Sukkah at work one. It's raining today, which made me wonder. –  Seth J Oct 19 '11 at 19:13
    
While your suka example makes sense to me — you're asking whether you may rely on the rain and eat out of the suka — I don't understand the t'filin example: are you asking whether you may rely on your family's custom and skip wearing t'filin? What's the alternative? — that you'd go against your family's custom and wear t'filin? That seems unlikely. –  msh210 Dec 7 '11 at 6:55
    
OK, let's say someone doesn't have a strong family Minhag, and is particularly lazy - and he no longer lives with his parents or in their community. His new Shul, which he attends infrequently during the week, has no set policy on Tefillin. He randomly decides on Sunday of Ḥol HaMo'ed he wants to go to Shul, but he feels lazy and doesn't want to wear Tefillin. Can he rely on the Minhag that he doesn't generally follow anyway? Perhaps this doesn't fit the rest of the question - if not, I can amend the question. –  Seth J Dec 7 '11 at 14:08
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It depends on the case. But you should not go out of your way to exempt yourself from a mitzva. If we're told "it's a mitzva to do ABC", then we should think proactively about trying to do ABC, not wheedling out of it. The diabetic needs to eat on Yom Kippur? We certainly understand. A healthy person who felt like going for a ten mile run, but boy now he's dehydrated and really needs a drink so he asks his rabbi? (I've read of this.) Well at this point his life comes first so he shouldn't fast. But why did he put himself there to begin with?

The Gemara says that a person who takes his four-cornered garments and purposely goes and rounds the corners, to get out of the obligation to put tzitzit on them -- such a person, well, when G-d is angry, you don't want to be them.

This was famously applied by Rabbi Moshe Feinstein with regards to taking trips for the fun of it on Chol HaMoed Sukkot. In theory, travelers aren't "home" and thus are exempt from eating in a Sukkah ("treat it like your home") -- so if I had to fly someplace over Sukkot (let's say I'm visiting family, or it's a business trip), fine I can eat bread or whatever on the plane. But to go say "hey I'll go do a day trip to the amusement park, and oh woops, I'm traveling -- honey! Pack the salami sandwiches! Sukkah shmookah!" is frowned-upon.

This is different than opting to eat non-grain products at work on Sukkot -- first of all, you have to go to work and there's no Sukkah, you're not purposely avoiding the mitzvah. Secondly it's not an "exemption" if you eat non-grain, it's that the only obligation in the first place is on grain products. (Now if you tailor your menu for all of Sukkot to avoid all grain and thus all sukkah-eating, that's a different story.)

The tefilin-on-chol-hamoed is again different; if your family practice says you should not wear tefilin then you shouldn't.

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Shalom, about your second paragraph, how does that jive with the many people who round one corner of a Bekeshe or other long frock coat as part of their distinctive, religious dress? –  Seth J Dec 14 '11 at 2:44
    
They still wear a four-cornered, fringed garment underneath it. The concern is someone who seeks to get out of the mitzva entirely. –  Shalom Dec 14 '11 at 6:31
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Intention matters... but so do the circumstances and the reason for the patur.

In the case of the Sukkah, we do not eat in the rain because it is unpleasant. If you find eating in the rain during sukkot unpleasant, then you should not eat in the sukkah even if you aren't eating even when it isn't raining. If, however, you normally don't eat in the Sukkah, and the rain inspires you to go ahead and do it (out of some desire for self sacrifice and it makes you feel good) then you should certainly take the opportunity to do Teshuva and eat in the sukkah in the Rain. But of course you don't have to if it is indeed unpleasant for you.

In the case of the Tefilin, it makes no sense to not wear tefilin during Chol Hamoed if you don't wear it the rest of the year. The Mishna says you wear Tefilin, and only for Kabalistic reasons, does it make sense to remove them for Chol Hamoed. Not wearing them during Chol Homoed is just a great opportunity for your Yetzer Harah to convince you to not do teshuvah.

Source: College Rabbi who dealt with this issue often.

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"If, however, you normally don't eat in the Sukkah, and the rain inspires you to go ahead and do it (out of some desire for self sacrifice and it makes you feel good) then you should certainly take the opportunity to do Teshuva and eat in the sukkah in the Rain." I don't believe that is correct. It is my understanding that rain negates the Sukkah's status as a valid Sukkah. There are things that are personal - if your Sukkah is attracting bugs and it is unpleasant to you but others might be ok with it, then you are exempt but the others aren't. –  Seth J Dec 12 '11 at 14:44
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I thought this was cute, the last line refers to not eating in the Sukkah in the rain.

Dr. Seuss on Sukkot

In terms of an answer about wither you get the mitzvah in the rain if you don't do the mitzvah when it is not raining:

The Mishna found here Sukka 18 - Daf 28b-29a tells us that we must view the Sukkah as a permanent home. This teaches us that part of the mitzvah is the ATTITUDE we have towards the Sukkah. This attitude is clearly lacking in your example and therefore it does NOT seem that one would be doing the mitzvah if they only cared about the Sukkah during rainy days.

Found in Rav Michael Siev's class' worksheet.

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