It’s Elul now, this is our Back to School edition and Rosh Hashana is not far away. I was looking for something related to teshuva and Elul to write on but when I sat down to write on deadline day again, the only thing that came to mind for me is a recent hike I did. I don’t often write about hiking in this space and I usually leave the hiking columns to our veteran columnist and Teaneck neighbor Danny Chazin, who is far more experienced with Tri-State area hikes and trails.

However, I would like to share a personal hiking experience this week that I hope you may relate to and could possibly have a meaningful Elul / pre-Rosh Hashana message or perhaps just a minor inspirational message. This story really starts on Chol Hamoed Pesach 2021 with COVID having canceled many events and programs. So we decided as a family, minus our son Zev, to do a challenging hike right on the Hudson River and the NY/NJ border called the Giant Stairs Palisades hike. I researched the hike online and completely ignored all of the many comments about how challenging and difficult the hike was and how taxing it could be for the out-of-shape, etc. but simply because we knew of other family members and friends who had survived this hike and were in about the same or worse shape as I was, I felt it shouldn’t be a problem. My attitude was this: if those inexperienced and out-of-shape family and friends could do it, so could I, of course. So off we went!

The hike starts at the State Line Lookout spot just off the Palisades Parkway and I quickly realized that wearing regular sneakers was not a good choice for this hike. My feet and toes started aching and screaming almost immediately. But it got worse when we reached the unique feature of this hike, which is called a “boulder scramble,” which I have learned is one of the largest and longest in the entire Northeastern U.S. A boulder scramble in hiking parlance is the portion of a hike in which you are navigating on, around and through a mountainside of boulders ranging in size from small houses to basketballs, and any slight misstep or poor landing could have very serious consequences.

In truth, I wasn’t prepared mentally for it and I wasn’t my 20-year-old self anymore. (I am not even sure I was my 20-year-old-self even when I was in my 20s.) Navigating these boulders was very challenging for me and I was plum exhausted as we hit the end of the mile-long boulder field. And just as we were about to finish the last of the boulders, I landed poorly and watched my ankle bend into an unnatural position as I slid down too fast on a large rock. I was in major pain and knew immediately that this was a very bad sprain or worse…and I blamed my exhaustion for the misstep.

Without getting too detailed, let’s just say that it was a very difficult journey to finish that hike and climb the hill back up to the car. I had to turn down the many offers of graciously offered emergency assistance from basically everyone who passed me on the trail at this point (I did not look good.) and worst of all, my kids got the chance to see their father struggling and in pain on a very steep trail back. It was painful, deeply unpleasant, and wholly embarrassing and not the way I would have chosen to spend a Chol Hamoed outing. When we got home, I collapsed from exhaustion and pain and resolved never to do this hike again. I was in pain for about 6-8 weeks after Pesach but thankfully, the sprain went away, but the memory lived on.

Although I tried to put it behind me, my mind kept returning to the idea that on a certain level, I needed to do this hike again and prove to myself, and maybe to my wife and family, that I wasn’t afraid of it…and that I could do it without hurting myself. My mind just couldn’t let this idea go and it kept resurfacing, despite some efforts to quell it. And since I occasionally like a good, meaningful, and worthy challenge, I began to share these thoughts with my wife. Of course, once I voiced my thinking to my wife earlier this summer, she offered to support me, and I was now required to go ahead with it. (I had kept this to myself for over a year and as long as I didn’t say anything, I didn’t have to do it.)

So this past Sunday, with my wife and youngest son along, I did the Giant Stairs Palisades Hike again. Equipped this time with proper hiking shoes and the positive attitude of “I can’t let my wife and child down again,” I managed to finish this hike without any injuries and with my self-esteem and self-worth more or less intact. I tried so hard to be super-careful with every step I took while “scrambling” on those boulders. It was as challenging and as exhausting as I remembered it but I enjoyed every minute of it, and especially getting to the end in one piece, with only minor naps and breaks required along the way.

It felt so good to pass other hikers and not have them offering to call 911 for me, and it felt good that I wasn’t too far behind my much more fit wife and son. I was, and still am, really proud that I was able to do it.

I share this personal anecdote with you, our readers, because I see in my small personal success this past Sunday something similar to what we face as individuals and as a community every year before Rosh Hashana. Our complicated lives are really just a series of challenging and ongoing boulder scrambles, with many steps and decisions to choose and sometimes treacherous consequences if the wrong step is taken. Yet we know that we have to keep scrambling through and keep pushing forward. And as indicated by my limited physical success, its clear that we can strive to do a bit better the second or third time around. With better preparation, equipment, and a better attitude, this year’s attempt to fully engage with the davening and tefillot and the teshuva process can succeed or minimally, be stronger, than in the past. Bottomline, we can do the same challenging hike and climb again – literally and spiritually – and achieve a better result and outcome.

Welcome to our Back to School Edition!