NOTE: None of the following applies to Yom Kippur.
I am a chozeret b'teshuva who has found most of the mitzvot to be positive challenges: within my reach, if only over time.
However, one absolutely mainstream thing that I cannot, cannot, cannot do is keep Yom Tov.
My main problem is with observing the Laws of Yom Tov on random weekdays, sometimes for two (-three) days at a time, in addition to my commitment each Shabbos.
It drains me, it runs me down, it plunges me into depressions that last for months after Yom Tov. (The fall Yom Tov marathon is especially bleak, and Pesach is awful for its own reasons.)
I never get used to it, as with Shabbos, kashrus, etc., because it doesn't happen frequently enough. It's always a new, immensely painful drama.
My rov does not seem willing to write a new chapter of the Shulchan Aruch for me. Every Yom Tov, I try my own modifications of the law to see what could work. The only thing that has allowed me to get through Yom Tov unscathed is to keep only the Biblical prohibitions; that is, to avoid doing avodas, but not melachos. (For example, I might turn on my light switch and take a nice hot bath, but I don't do my weekday "laborious" job.) Yom Tov is genuinely enjoyable that way (as one might imagine). However, this involves so much secrecy and scurrying around that it feels dishonest and not exactly like a sustainable connection to religious Jewish life.
What do people actually do? Does everyone actually cheat? I can't imagine this is easy for everyone. Why don't I hear other complainers?
Answer
Yeah, especially when a diaspora yom tov is adjacent to Shabbat, it sometimes feels like a long slog. I sometimes feel like I'm fighting an uphill battle because I didn't do this from birth -- it isn't a life-long routine. Here are some things that help me. (Some of these are dependent on your family and community situations, which I don't know.)
Board games. While some games are hard to play without violating laws of melacha, many are just fine. In a comment somebody suggested Settlers of Catan; that's one of many. (This isn't Board & Card Games, so I'll refrain from giving you a list of recommendations.) My husband and I are board-gamers and have several games that work well for two players; in addition, we often have friends over. Secular friends aren't generally available on a Thursday afternoon (they're at work), but Shabbat afternoon we can often get a crowd. (And the Jewish board-gamers often are available on yom tov afternoon.)
Read.
Visit with others, particularly around meals. Extend those meals (in honor of the festival). So what if lunch lasts three hours -- where else did you have to be? If you've got the right kind of crowd, singing enhances this.
Try to organize a small study/discussion group on the Jewish topic of your choice. My congregation's Rosh Chodesh group reads and discusses short stories (by women) each month, as one "beyond torah" example.
Nap. The rest of my week is pretty busy; it's nice to get a break from that.
See also: How can I make a long summer shabbat a delight?
Do many other people "cheat"? That's going to depend on your community, of course, but odds are, no -- those who commit to torah commit to doing their best to fulfill the mitzvot as understood by tradition. I mean, you're being judged by the One who sees all, so sneaking around isn't going to help, right? Does everybody do it all perfectly? No. Is everybody completely happy with how they're doing? No. As for why you don't hear about this from more people: people do talk about these challenges sometimes -- discussions about the press of preparing for yom tov aren't uncommon, for instance. But my guess is that most people are not comfortable talking in detail about any struggles they're having in public, so even if people in your congregation do struggle, you might not hear.
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