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Walking the unkown path takes courage

There is an interesting moment towards the end of Moshe's life. After forty years of leading the Jewish people, Moshe knows that he will not be the one to take them into the Land of Israel. That responsibility will fall to his student and successor, Yehoshua. As he prepares Yehoshua for what lies ahead, Moshe tells him, “Be strong and courageous.” It is a powerful instruction, but there is something interesting about it. Yehoshua was probably as prepared for leadership as anyone could possibly be. He had spent years beside Moshe, observing one of the greatest leaders in Jewish history. So why did he still need to be told to have courage?


Moshe and Yehoshua came to leadership and leadership skills from very different places. Moshe had almost no precedent to follow. There had never been a leader of the Jewish people in the circumstances he was about to face. From the moment he first approached Pharaoh, he was learning this kind of leadership on the job. In fact, his first attempt to help the Jewish people seemed to make their lives worse. Pharaoh responded by increasing their workload while demanding the same output. Moshe then had to lead a nation out of slavery, through the splitting of the sea and into the wilderness. Along the way came complaints about food and water, the Golden Calf, the tragedy of the spies, Korach's rebellion and countless other challenges. There was no handbook explaining how to lead millions of former slaves through the desert while transforming them into a nation. Moshe had to confront each new challenge as it arrived.


Yehoshua had something Moshe never had. He had Moshe. He had spent years watching his teacher lead. He had seen Moshe under pressure. He had watched how he responded to criticism, disappointment and rebellion. He had seen moments of extraordinary success and moments of terrible failure. Yehoshua therefore entered leadership carrying decades of accumulated experience, even though much of that experience had been gained by observing someone else. Yet Moshe still tells him, “Be strong and courageous.” Perhaps that is because preparation can teach us how others dealt with yesterday's challenges, but it can never completely prepare us for tomorrow's.


Yehoshua was not being asked to become another Moshe. The Jewish people themselves had changed. Moshe had taken responsibility for a nation emerging from generations of slavery and back-breaking labour. They had spent their lives being told what to do by Egyptian taskmasters and suddenly had to learn what it meant to live as free people. Yehoshua, however, would lead a new generation. They had grown up in freedom. His challenge was no longer to take the people out of Egypt, but to take them into Israel. He would have to inspire them to cross the Jordan, confront powerful enemies, conquer the land, divide it amongst the tribes and begin building a functioning society. The lessons Yehoshua had learned from Moshe were invaluable, but the circumstances he faced would never be identical to those of his teacher.


This is true in our own lives as well. We should learn from those who came before us. We should seek mentors, study successful people, listen to our parents and teachers, read books and learn from the experiences of others. One of the great advantages we have is that we do not need to make every mistake ourselves. We can learn from what others got right and from what they got wrong. But eventually, preparation reaches its limit. There comes a point when nobody can tell us exactly what to do because nobody has ever lived precisely the life we are living.


A parent can learn a great deal from the way they were raised, but their children are different people growing up in a different generation. A business leader can learn from someone who built a successful company twenty years ago, but the market, technology and expectations of customers may have completely changed. A community leader can study how previous generations responded to their challenges, but today's community may face problems those leaders never imagined. Even within our own lives, something that worked brilliantly ten years ago may no longer be the right answer today. Wisdom means learning from experience without becoming trapped by it.


Perhaps this is why Moshe does not tell Yehoshua, “Don't worry, you are completely prepared.” Instead, he tells him to be strong and courageous. Experience does not eliminate uncertainty. Preparation does not guarantee success. Courage is necessary precisely because we cannot know exactly what will happen next. We sometimes imagine that confident people act because they are certain of the outcome. More often, they have simply accepted that certainty is unavailable. They gather the information they can, seek advice, prepare carefully, make the best decision available to them and then move forward.

There are times in life when preparation itself can become a hiding place. We tell ourselves we need to do another course, speak to another person, conduct more research or wait until circumstances become clearer. Sometimes that is wise. But sometimes we already know enough to take the next step and what we are really waiting for is the feeling of complete confidence. That feeling may never arrive. Yehoshua had spent decades preparing for leadership and still needed courage when the moment came to lead.


As we approach a new year, there is something particularly meaningful about this message. We should look back and learn from the year that has passed. We should ask what worked, what did not, what we would repeat and what we would change. The past is an extraordinary teacher, but it is not a map of the future. None of us knows exactly what the coming year will bring. We take the lessons with us, but eventually we must turn around and face forward.


Perhaps that is the challenge Moshe was giving Yehoshua, and the challenge for each of us as well. Learn everything you can from those who came before you. Learn from your own successes and mistakes. Prepare yourself carefully. But don't wait until you know exactly what lies ahead before you begin moving. Leadership Skills include learning from the past to lead the future, but at some point, preparation has done its job and courage has to take over.


So as you consider the next step in your own life, ask yourself: Have I genuinely not prepared enough, or have I prepared enough and am simply waiting to feel completely ready?


Sometimes the next stage of our lives begins when we accept that we may never feel completely ready, and move forward anyway.


In this week’s parsha, Ki Seitzei, the Torah gives us a surprisingly practical instruction: if you build a house with a flat roof, you must build a fence around it. The purpose is obvious. If people are going to use the roof, there is a risk that someone could fall. The Torah does not tell us to wait until someone gets hurt and then work out what went wrong. It tells us to identify the danger in advance and do something about it before the accident ever happens.


There is a powerful lesson here about leadership, responsibility and life. We often judge leaders by how well they respond to crises. We admire the person who remains calm when everything goes wrong, who solves the problem, rallies the team and somehow gets everyone through it. But perhaps the best leaders are the ones whose crises never happen. They notice risks early. They ask uncomfortable questions before there is a problem. They put policies, systems, safeguards and relationships in place long before they are desperately needed.


The same principle applies well beyond leadership. One of the most important questions we can regularly ask ourselves is: What steps do I need to take today to create the future I want tomorrow? There is a well-known saying: The best time to plant a tree was many years ago. The second-best time is today. Whatever the precise wording, the message is important. Many of the things we will value most in the future cannot simply be produced when we suddenly need them. They have to be built gradually.


If I want financial security later in life, I cannot begin thinking about retirement the day I retire. I need to save and invest years earlier. Even relatively small amounts become meaningful when they are repeated consistently. Investing around $28 a day is more than $10,000 over a year, even before allowing for any investment growth. Over decades, the combination of consistency and compounding can become enormously significant. But the same principle applies to things far more valuable than money.


If I want to be healthy and strong when I am older, the work starts now. Strength, mobility, fitness and healthy habits are built over years. If I want a strong marriage decades from now, I cannot neglect the relationship for twenty years and assume it will somehow remain strong. Trust, communication and friendship are accumulated through thousands of small interactions. If I want my children to grow into confident and capable adults, that process does not begin when they leave school. It begins when they are young, in the encouragement we give them, the responsibilities we allow them to carry, the way we respond when they make mistakes and the confidence we show in their ability to handle life.


The same is true with friendships, learning and leadership. If I want meaningful relationships later in life, I have to invest in people now. If I want wisdom, knowledge or expertise, I have to keep learning. If I want a strong organisation in ten years, I have to develop its people, culture, systems and financial sustainability today. We sometimes hear about an “overnight success”, only to discover that the person had been quietly working for ten or twenty years before anybody noticed. Most meaningful outcomes are not sudden. They accumulate.


The Torah’s fence around the roof represents more than physical safety. It represents the responsibility to think ahead. We know that life brings predictable challenges. Children grow up. Parents grow older. Bodies change. Careers evolve. Organisations expand. Expenses increase. Relationships need attention. Eventually, all of us grow older. Much of this is not a surprise. The question is whether we prepare for it.


There will always be unexpected events that no amount of planning could have prevented. Leadership does not mean controlling everything that happens. But many crises give us warning signs long before they become crises. A relationship gradually deteriorates. An employee becomes disengaged. Expenses consistently exceed income. Our health slowly declines. A child begins struggling. An organisation becomes too dependent on one person. Often the warning signs were there. The fence simply was not built.


Good leadership means occasionally stepping away from whatever feels urgent today and looking further ahead. Where could someone fall? What could become a problem? What will I wish I had started five years from now? What investment of time, energy, money or attention today could make life significantly better in the future?


And perhaps most importantly: What do I want to have in forty years that I need to start building now? The answer may be financial security, health, strong children and grandchildren, a meaningful marriage, enduring friendships, knowledge, or a strong community or organisation that continues long after we are gone.


Whatever it is, the lesson of the maakeh is simple. Do not wait for the fall before building the fence. We already know that the future is coming. The question is whether we are preparing for it.


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About the author: Elimelech Levy is a Rabbi, educator, and coach based in Sydney, Australia. He is the director of Chabad Youth NSW, where he develops programs that support Jewish identity, confidence, and community connection for young people and families.


Alongside his communal work, Elimelech holds an MBA from Macquarie University and is a member of the International Coaching Federation. His coaching focuses on helping individuals gain clarity, set meaningful goals, and take consistent action.


He is also the founder of the Knei Lecha Chover initiative, a global peer coaching network for rabbis, and is involved in property development projects that reflect his broader interest in building sustainable communities.


Every one of us likes to imagine that our lives will be defined by a few big moments. Choosing a career. Getting married. Buying a home. Starting a business. We think these major decisions determine our future. Yet Parshas Re'eh begins with a very different perspective: "See, I place before you today a blessing and a curse." Not once in a lifetime. Today. Every day presents another choice. Another opportunity to move slightly closer to the person we hope to become, or slightly further away. The reality is that our future is rarely determined by one dramatic decision. It is usually built through thousands of ordinary choices that seem almost insignificant at the time.


This creates one of life's greatest contradictions. Most of us have a clear picture of the person we would like to be. We want to be healthy, yet we regularly choose convenience over exercise and comfort over discipline. We say family comes first, yet work consumes our attention, and when we finally spend time together we are distracted, impatient or exhausted. We want deeper relationships, but we spend more time looking at our phones than looking people in the eyes. We want financial security, yet we buy things we don't really need. We want peace of mind, yet we fill every quiet moment with noise. There is often a surprising gap between what we say matters most and what our daily choices suggest actually matters. That gap is worth paying attention to.


Why does it happen? Sometimes we are trying to live up to an image of who we think we should be. Society applauds certain goals. Friends admire certain lifestyles. Social media rewards appearances. We slowly begin chasing a version of success that was never truly ours. Other times our long-term goals simply lose the battle against immediate comfort. The healthy body we hope to have one day cannot compete with the pleasure of dessert tonight. The peaceful relationship we want next year struggles against the temptation to win today's argument. The meaningful future we dream about is quietly exchanged for whatever feels easiest in the present.


Behavioural psychologists call this present bias. The rewards we can experience immediately often feel far more powerful than benefits that will only appear months or years from now. The Torah recognised this long before modern psychology. Re'eh reminds us that blessing and curse are placed before us "today". Not because today's decision is everything, but because today's decision is the only one we actually control. Our habits become our character, and our character shapes our future.


The blessing and the curse are not simply rewards and punishments waiting at the end of the journey. They begin with the choices themselves. Every decision either brings us a little closer to the person Hashem created us to be, or a little further away. In that sense, the blessing is found not only in the destination, but in the direction we choose each day.


If we want to understand what we truly value, perhaps we should spend less time listening to what we say and more time observing what we repeatedly choose. That can be confronting, but it can also be liberating. Because if our lives have been built one choice at a time, they can also be rebuilt one choice at a time. You do not need to reinvent yourself overnight. You simply need to make today's choice slightly more consistent with the person you genuinely want to become. The next healthy meal. The next conversation with your spouse. The next hour spent fully present with your children. The next decision to be generous rather than selfish, patient rather than reactive, grateful rather than resentful.


There is another important lesson here. We often judge ourselves by our intentions, while the world experiences us through our actions. We tell ourselves, "I meant to call my parents. I meant to spend more time with the children. I meant to exercise. I meant to learn more. I meant to give more." Good intentions are important, but they do not build a life. Choices do. If our actions consistently fail to reflect our deepest values, then perhaps it is time to stop asking, "What do I want?" and start asking, "What am I choosing?" The answer to that question is often far more honest.


No single choice will transform your life, but thousands of them will. Perhaps that is why the Torah begins with the word Re'eh, "See." Before we can change our choices, we first have to see them honestly. Not the story we tell ourselves. Not the image we present to others. But the life our everyday decisions are quietly creating.


Because in the end, your future is not built by what you intend. It is built by what you choose. And today's choices are already writing tomorrow's story.


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About the author: Elimelech Levy is a Rabbi, educator, and coach based in Sydney, Australia. He is the director of Chabad Youth NSW, where he develops programs that support Jewish identity, confidence, and community connection for young people and families.


Alongside his communal work, Elimelech holds an MBA from Macquarie University and is a member of the International Coaching Federation. His coaching focuses on helping individuals gain clarity, set meaningful goals, and take consistent action.


He is also the founder of the Knei Lecha Chover initiative, a global peer coaching network for rabbis, and is involved in property development projects that reflect his broader interest in building sustainable communities.


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