Uncomfortable Comfort

Sukkot can be one's practice of happily doing Hashem's Will even when uncomfortable! Living outside one's comfort zone has far-reaching implications - read Pinney Wolman's insight from battling mosquitos and heat!

3 min

Pinney Wolman

Posted on 27.09.23

Sukkot has always been one of the tougher holidays for me. I don’t mind building the Sukkah too much; it’s the eating in and sleeping in parts where I have trouble. From the schlepping of everything in and out of the house, to the mosquitoes and bees, I don’t really enjoy mealtimes. Gone is the quick morning breakfast with the kids when we have to do it in the Sukkah. As for sleeping in the Sukkah, count me out for now. I hate camping, from the bugs and wildlife, to the uncomfortable sleeping bags. The thought of sleeping in the Sukkah has yet to appeal to me. I’ve always said I can handle a day of outdoor activities like hiking and canoeing if at the end of the day I end up in my hotel room with a comfortable bed and heat or air conditioning.

So there I was again, this past Sukkot, trying to find joy in the mitzvah of Sukkah. I feel a lot of pressure to enjoy it, both because I know that’s what true Judaism is about and because I want my kids to see me enjoying it so they’ll want to follow in my footsteps. But due to my admitted fastidiousness, I failed miserably over the first three-day holiday. I was impatient with my kids’ behavior, snapping and yelling at them when their own complaining became too much to bear. I was uncomfortable sitting at the table, constantly feeling phantom mosquito bites, on the lookout to squish the next would-be lethal attacker. I overate to help pass the time and take attention from my own unease.

During the third day of Chol Hamoed, I finally decided to address the situation with Hashem in my hitbodedut. I asked Him the age-old question my Yezter has always had: Our Sages have always taught that sitting in the Sukkah is to remind me to trust and believe in Hashem’s care only. How is sitting in the Sukkah supposed to accomplish that when You don’t even keep the mosquitoes away?! I asked Him to please show me how I could find meaning and joy in this holiday for my own growth and development.

During this moment, Hashem turned my thoughts towards my recently increased interest in Aliyah. Ever since getting into Emuna, I’ve intellectually agreed that part of my endgame would be moving to Israel. But my wife has no interest in moving and I’ve always been happy to accept that. I had recently asked myself, “Why am I not more interested in moving to Israel? Why don’t I bother her more about moving?  And most specifically, “What would it take for me to want to move?” Instantly, I knew the answer to that last question. Fifty million dollars. The sad truth is that I know if I won the lottery and had no money concerns, I would be bothering my wife more about getting out of the U.S.

With this answer, I realized what I was really lacking was financial trust in Hashem. Since then, He has been helping me grow in that area but that’s for another article. What struck me during this Chol Hamoed hitbodedut session was that I homed in on the original amount of money I had named: fifty million dollars. Why so much? Wouldn’t even a million or two more than enable us to move without too much worry? Hashem helped me realize that part of my fear was connected to my quality of life. Part of me didn’t want to move because I really love all the materialism and high quality of living I’m enjoying here in Teaneck. Part of me believed Hashem would make sure we survived in Israel. We would have food, clothes, a place to live, etc.

But I’m not ready to give up my four/five-star level of living. That’s why I wanted such a large sum of money beforehand. It would give me the false sense of security that I could live in Israel according to the standards I’m used to.

In summary, my issue is that I’m not comfortable doing Hashem’s Will when I’m uncomfortable.  As I’m thinking about all this in my hitbodedut, Hashem popped the thought into my brain, “This is the point of Sukkot!” Sukkot can be my practice of happily doing Hashem’s Will even when I’m uncomfortable! I leave the comfortable environment of my house to learn how to serve Him in discomfort! Halacha (Jewish law) even seems to support this because the rule is that whoever is distressed by being in the Sukkah is absolved from doing so! It’s like Hashem is saying, “Practice being outside your comfort zone and when it becomes too much, get back inside.”

I thanked Hashem for this insight into how to better observe this important holiday. I’m pleased to report that I enjoyed myself much more during the last days of the holiday, knowing they were helping me train for a higher level in service to Hashem.