Chutes and Ladders. So simple. Yet so profound.

I've spent quite a few hours recently playing this game. My children love it and I have no doubt why. It is one of the few games that doesn't require skill and yet is completely unpredictable. Everything can change at the very last moment, and that is exactly what is so exciting.

Everything can change at the last moment For those of you who haven't played in some time, I'll quickly summarize how the game works. The board has a starting point and an end. The goal is to get to the finish line first. Everyone takes turns spinning a little wheel that determines how many squares you can go. Along the board, however, are a number of boxes with ladders that allow you to jump ahead and skip over the lines; as well as a number of boxes with chutes, which if you land upon, you must slide back down and then make up the area you had already covered.

Now, in most games where you want to get to the end the quickest, you want to spin the highest number as many times as possible. But here things are different. Sometimes you actually want to roll a low number, such as one or two, rather than six. Even though six would get you farther in terms of spaces, if the ladder is on the second box, then you actually go much farther by rolling lower rather than higher.

What amazed me, however, was how my son reacted when he landed on a chute and ended up last. I thought he'd get really upset and not want to continue the game. After all, it seemed that he no longer had a shot at winning. But surprisingly, after taking a good look at the board, he was smiling! I was totally confused. I thought maybe he didn't understand how the game worked. What was there to be happy about? He was losing the game! So I tried to gently explain that the point of the game was to get to the end the fastest, not to end up by the beginning. But it turns out that I was the one in need of a real lesson, and not just in Chutes and Ladders, but in life.

He was excited about the opportunity that came with it My son looked at me sympathetically and then slowly and carefully explained his logic. Because he had landed on the chute and was back at the beginning, he had another chance – that none of the other players, all of whom were now ahead of him, had – to land on the largest ladder of the game. And if he was able to get that ladder, it would take him immediately to the top, bypassing everything and everyone along the way! Although he hadn't wanted to land on a chute, he was quite excited about the opportunity that came with it.


There are two roads to our goals in life. One is the "shorter longer way"; the other is the "longer shorter way" (based on an episode related in the Talmud, Tractate Eiruvin).

Often we are so focused on getting to the goal that we blindly run to the finish line. In the process, however, we don't always look at the bigger picture. And often, to get a sense of the larger scene, we need to take a step back.

Sure, something might be closer in distance, but as we all know, there are many other factors to take into consideration. You may have forgotten about the traffic on that route, or the construction along the way. It might be the shortest route distance-wise, but it will also take you the longest amount of time to get there.

On the other hand, there's the "longer shorter way." While it may seem that extra time is being expended, or that you are going in a circle when there was a possible straight line, this route comes from the understanding that by taking and investing the necessary time, in the end, while more distance might have been traveled, you will arrive at your destination sooner than any other route.

We shouldn't always want to roll the highest number in my life. While sometimes moving rapidly from square to square is the best method, we will more often get farther quicker by paying attention along the way, figuring out exactly where we want to land and how. By figuring out where life's ladders are stationed.

Recently a friend decided to take a pay cut. I was shocked. In this market, who chooses such a thing? Yet he had an explanation, and his move was both strategic and brilliant. He is in sales. He is also at the top of his field with little room for growth in his particular line of expertise. He started the job straight out of college and is a natural. But he quickly realized that if he wants to really move ahead, he needs to broaden his knowledge and skills. So he asked his company if they would allow him to keep his job but work less hours while he studied for his Masters in Business. In return, he would take a significant pay cut, not only because of the reduced hours, but a lower hourly salary as well.

His is defintely the longer, shorter way His move definitely is that of the longer, shorter way. He won't make it to the top quite as fast, but he is giving himself job security, both with this particular company and for other opportunities as well. And even though he is making less for now, his degree will ultimately allow him to make more. He is someone who noticed that he was better off spinning a two and eventually hitting that big ladder, than spinning a six over and over and over again, but with no ladders in the mix.

And then there are times in life when it seems that we are on top of the world, we are about to win the game, but then we land on that chute, and we plummet down and need to redo everything we just did. Other times we feel so far behind and that nothing is working out. But it is specifically when we are at the bottom that we have the opportunity to land on the biggest ladder of the game. And then, in seconds, everything can transform. We can instantaneously shift from being the last to being the first.

Yes, sometimes we miss the ladders and land on the chutes. But if we choose to, we can see it as a blessing in disguise. For, after all, we might just get another shot at the ladder we really want and need.

I recently lived this concept. Like many people, my family has been hit by the financial crisis and we had to be creative. Our income lessened while bills rose. Our speaking engagements – both my husband and myself are public speakers – were few and far between as everyone was struggling and organizations couldn't afford professional speakers. After some brainstorming and soul searching, I decided I would offer Torah-based creative writing workshops locally. It would bring in some additional income and was something I knew I could do. We had a friend who offered his restaurant as the space and I advertised through word of mouth and emails.

We can see a blessing in disguise The result of these classes is something hard to explain. They were truly life transforming. And not just for those who attended, but even more so for myself. I thought I had offered the classes in order to create a little more income; in the end, I would have paid for the opportunity. What I gained from the other women as we shared our writings and our struggles was priceless. These workshops were a gift that I didn't even realize I needed nor would have known how to give or receive. But I am so grateful for that chute as in the end it brought me to a much bigger ladder that I otherwise would have never found.


We are now in the month of Kislev. It is a month with long nights and short days. The majority of the twenty-four hours is spent in the dark, making it difficult to see what is around us or even sometimes what is immediately in front of us.

But we just need to remember that we are surrounded by ladders. And even if we suddenly find ourselves on the bottom,there are many paths, some unexpected, to making it right back up.