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I really enjoy being Jewish, most of the time, but let's be honest, sometimes it can be difficult to enjoy Judaism. Sometimes it's the little things, like having to wait those extra minutes to eat dairy, and sometimes it's the big things, like not wanting to abide by a million rules every single day. Furthermore, as a parent, I know it's important to model exciting and enthusiastic Judaism for my kids, not just bland rule adherence. Not to mention my fear of Devarim 28:47 - תַּחַת, אֲשֶׁר לֹא-עָבַדְתָּ אֶת-יְהוָה אֱלֹהֶיךָ, בְּשִׂמְחָה, וּבְטוּב לֵבָב--מֵרֹב, כֹּל.

Rolling all these things up I realize how important it is to enthusiastically enjoy Judaism. But I'm also finding it harder and harder to do. What are some tried-and-true suggestions for how to combat this based on your own expertise or sourced statements from our tradition?

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That reminds me of the anecdote from Rabbi Emanuel Feldman's book, Tales Out of Shul. A woman once told him, "Rabbi, I'm really not enjoying this week of mourning."

Not everything in life (or Judaism) has to be enjoyable. Nor is it meant to be. At least not in the immediate gratification, self-centered sense of the word. Sometimes your enjoyment should not be based on your enjoyment, but on someone else's enjoyment.

Really, enjoyment of life (or Judaism) depends on your outlook. You can think "Oy, I've got jury duty" or you can think "Thank G-d I live in a country where there are juries, and not a country where the courts are a sham or even nonexistent." You can think "Oy, I can't eat that tasty chazzer" or you can think "Wait a second, G-d recreates me every moment. He's given me a mission and hence, a purpose. I'm an essential part of the greatest achievement humankind will ever be part of! And all I have to do is not eat the ham and have a steak instead? Score!"

Also, shop around. Different flavors of Judaism have different perspectives on things. Listen to a mussar shiur, or a chassidus shiur. Ask a Sephardi, an Ashkenazi a Yemenite, etc., what perspectives their traditions give on things that annoy you. Don't be afraid to learn more about different perspectives.

TL;DR
This is not a Judaism issue, it's a life issue. It's all about perspective. Everything that appears to be non-enjoyable is really a matter of looking at it the wrong way. Learn positive perspectives from others.

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    I was one work project away from writing something very similar. My only addition is that changing various things in your life might make you happier in general. – Charles Koppelman Dec 28 '12 at 20:36
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I changed my views on how I see Judaism. I find Judaism exciting and interesting because I went to a completely new place with it. If you can find a Jewish practice that gets you excited then go and do it. I found that participating in Shabbat activities with my host family got me more excited. I joined a program that teaches Jewish value through sisterhood and arts and crafts. I made learning and my religion more exciting. I infused my Jewish life with something that I love and enjoy doing like arts and crafts.

Another great way is to put the excitement with your kids. That little wait to eat dairy, think about how you are letting that meat you ate recently digest and you won't feel sluggish when your child asks you to play. Keep that bit in mind. I love child activities that make it simpler. I don't talk down to kids. They are really capable. I put the spin of the ultimate superhero with G-d in mind when teaching my cousin about Judaism. Now whenever I think about G-d I think of that character that can do anything and I will start laughing, no matter how many times I have done it, I will. I love the dancing and I love putting the positive on the laws. That is another thing that can help. There is the negative and positive side to each law. Instead of I can't... put I can only do... This is just what worked for me when I needed a spark in Judaism. I had to become a kid again.

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Sometimes it's important to get things into perspective in order to understand what the Creator would actually want from us at a particular point in time. Instead of driving yourself crazy about every last chumrah and picking up new "minhagim", think about whether you really know why Hashem gave us specific commandments.

For example, an important of the mitzvah of welcoming guests is escorting them home, or at least to your gate. Now just trying to do that by rote can get bothersome and tiring. I know from experience that it can be hard to have the discipline to walk outside with them every time someone leaves your home. However, if you stop to think for a moment beforehand, the guest has walked all the way here and now they are going to walk all the way back, on their own, before going to sleep in an empty house probably (this is the kind of guest you should be inviting). The least you can do is walk with them some of the way. Now it doesn't seem such a pain to walk out of your house when you least feel like it. By understanding the reason that the chachamim prescribed that, or the way they understood the mitzvah, you get a greater appreciation and even want to do more!

It is this reflection that is imperative in Judaism. Hashem wants you to have a healthy mind and body, in addition to following His commandments with all your heart.

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You can read Rabbi AbrahamJ. Twerski's books

Or Listen to the lectures of Rabbi YY Jacobson Each one of them is a treasure..

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    Rabbi Twersky was once asked how he could write (at the time) 27 self-help books. He replied, "I didn't write 27 self-help books, I wrote one self-help book 27 times." – not-allowed to change my name Dec 28 '12 at 14:18
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B"H It's a privilege to be Jewish. Think about what our ancestors gave up, including their very lives, so that you could live to do these mitzvos. Think how much nachas and satisfaction they would derive from watching you do even one trivial and boring and tedious mitzva. How much more pleasure, then, does G-d take from watching it?

The "ultimate accounting" thing seems bizarre, since the world is apparently unjust. But I have no doubt that there is a secret accounting that goes on above and below our knowledge. The pleasure for your mitzvos is somewhere else, but it really exists. If you can believe that, it is yours.

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