Parashat Chukkat contains one of the most enigmatic episodes of the Torah: God asks Moses to ‘Speak to the rock before their eyes so that it may give water’ (Num. 20:8). But instead, ‘Moses raised his arm and struck [vayach] the rock with his staff twice’ (20:11).

Moses leads a life of righteousness, filled with compassion and tolerance for the downtrodden – from an infant sheep to a great nation. He has given everything for others, yet now he slips up in a moment of anger and is forbidden from achieving his dream of leading his people to the Promised Land.

Many commentators attempt to discern the exact reason why Moses is not allowed to enter Israel. We see that a small action can have tremendous consequences. But if one glances forty years into the past, the case becomes even more perplexing, as it seems Moses is acting this way based on precedent. The people were thirsty for water after having just emerged from the shackles of Egyptian slavery. God tells Moses, ‘Strike the rock and water will come forth from it and the people will drink’ (Ex. 17:6). What is the difference between these two parallel cases?

History seems to be repeating itself. Leaders often, perhaps mistakenly, act based on a past pattern rather than creating a more fitting response for the new and emerging needs of the future. While circumstances might be similar, conditions and contexts evolve over time. This is the core of Moses’ error.

Moses is a proactive personality who knows how to act with might to ensure what is right. He does not hesitate to jump in and take action when the situation calls for it. One of our first encounters with Moses as an adult is his active defence of a fellow Jew: ‘Moses saw an Egyptian man striking a Hebrew man, of his brethren…So he struck down [vayach] the Egyptian’ (2:11-12). Later, Moses sets the ten plagues in motion by ‘striking [vayach] the water’ (7:20) of the Nile and turning it into blood. This same action – striking – is repeated in the plagues of lice (8:13) and hail (9:25).

Moses knows his limitations and for this reason, when asked to lead the Jewish people, he responds, ‘I am not a man of words…for I am heavy of mouth and heavy of tongue’ (4:10). Perhaps this is what fuels his active – rather than oral – leadership.

Yet Moses fails to see the significant changes in the circumstances. In the first incident of hitting the rock, he is leading a generation born into slavery and emancipating them as a nation. Now, however, the stakes are very different. Now he is leading their descendants, an emancipated nation, into the Land of Israel.

The previous generation grew up surrounded by and responding to the physical strikes of slavery. This populace of the exodus therefore responds to that which they have become accustomed to - physical expression. The next generation, however, did not grow up in the same context. They are not familiar with, nor are they likely to respond well to leadership based on physical actions. They are more in tune with a leadership conducted through verbal expression and reasoning.

Under Moses’ leadership, the Jewish people have transformed from a nation of slaves into a nation of free people ready to enter the Land of Israel. This momentous transition is a major motif in this week’s parasha. When the Jews leave Egypt, an account of their singing is described only after a mention of their leader, Moses, ‘Then Moses and the people sang’ (15:1). At this point, however, on the brink of entering the Promised Land as a free nation, they sing independently with pride, ‘Then Israel sang’ (Num. 21:17). Whereas in the past, it is Moses who sends out messengers, now, with their newfound freedom and independence, it is the people themselves who send messengers to Sichon (21:21), asking to travel through his land. Similarly, when Moses sends spies, the people are themselves proactively involved in the conquering of the Amorites (21:32).

If Moses fails to recognise the needs of this new – and so very different – generation, perhaps a new leader needs to rise for the next stage of development of the Jewish people. Moses assists in building the family, but Joshua needs to take them home.

When contexts change, the responses of decision makers should evolve and adapt accordingly. It is therefore conceivable that Moses’ inability to enter Israel is not a punishment, but rather an unfortunate consequence of reality.

Each of us should create space in our own personal lives to reinvent ourselves as the different stages of life arise. We must realise that what inspired us in the past may not be as effective today, and the way that we acted then should not define who we are now. The past should be used as a springboard, not a mirror, to the future.