The Children of Israel finally reach the Promised Land. In an effort to plan and strategize their entry into the land, Moshe sends 12 spies to check out the situation. But tragically, 10 return with an evil report and manage to convince the entire nation—against the protestations of the two good spies, Yehoshua and Calev—that they should not attempt to enter Canaan. As a result, Hashem sentences the nation to 40 years of wandering in the desert, until that generation is gone and their children, who did not rebel, are ready to enter the Promised Land.

Why were the Children of Israel unwilling to enter the Promised Land? Because it was too risky. Sure, it was a land flowing with milk and honey, but there were also giants there. Who knows what might happen in the new, strange country? And so, the safer position was to stay put.

Thank God for Yehoshua and Calev! Without them, who knows where we would be today? On Pesach, we say, “Had we not been redeemed from Egypt, then we, our children, and our children’s children would still be slaves to Pharaoh in Egypt.” Without Yehoshua and Calev, we would probably still be wandering in the desert today!

I know what you’re thinking: That’s ridiculous. Eventually we’d have entered the Promised Land. We wouldn’t still be wandering in the desert thousands of years later! But, when you think about it, it’s really not so far-fetched. Even today, in the 21st century, there are many nomadic peoples still wandering in the desert. Just look at Afghanistan: Every time it looks as though order will prevail, warlords return the people to tribal life. Some people just can’t enter their “promised land.” Why not?

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Today’s daf continues the analysis of retroactive, conditional designation. A fellow purchases a flask of wine that he wants to consume immediately. He knows it wasn’t manufactured for idolatrous libation purposes, because it was made by Samaritans who are Torah observant. And yet, due to their laxity in certain mitzvos, he can’t be sure they tithed the grapes precisely prior to crushing them. So, he’ll need to separate the tithes himself. When you buy Jaffa Oranges you separate a small portion and designate it as sanctified produce, discarding it respectfully. But when all you have is a bottle of wine, how do you separate terumah and maaser (priestly gifts)? You can’t simply pour it out onto the ground; it must be handled with care. But the fellow has no other container to utilize as a tithe receptacle. What should he do?

תַנְיָא הַלּוֹקֵחַ יַיִן מִבֵּין הַכּוּתִים אוֹמֵר שְׁנֵי לוּגִּין שֶׁאֲנִי עָתִיד לְהַפְרִישׁ הֲרֵי הֵן תְּרוּמָה עֲשָׂרָה מַעֲשֵׂר רִאשׁוֹן תִּשְׁעָה מַעֲשֵׂר שֵׁנִי

וּמֵיחֵל וְשׁוֹתֶה מִיָּד דִּבְרֵי רַבִּי מֵאִיר רַבִּי יְהוּדָה וְרַבִּי יוֹסֵי וְרַבִּי שִׁמְעוֹן אוֹסְרִין

אָמְרוּ לוֹ לְרַבִּי מֵאִיר אִי אַתָּה מוֹדֶה שֶׁמָּא יִבָּקַע הַנּוֹד וְנִמְצָא זֶה שׁוֹתֶה טְבָלִים לְמַפְרֵעַ אָמַר לָהֶם לִכְשֶׁיִּבָּקַע

If one purchases wine (say, 100 lug) from a Samaritan (and wants to drink it straight away), he should say, “Two lug that I intend to separate in the future belong to terumah; 10 are the levite first tithe; nine are the second tithe. (In other words, he promises to leave over the tithed amount in the flask to discard respectfully after he has finished consuming his portion.) He then deconsecrates it and may drink immediately, according to Rabbi Meir. Rabbi Yehuda, Rabbi Yossi and Rabbi Shimon prohibit this method. They said to Rabbi Meir: Aren’t you concerned that, perhaps, the wine flask will burst (and he will be unable to tithe as promised), meaning that whatever he has already drunk is retroactively untithed (unkosher) wine? He responded: Let’s worry about that when it bursts.

Why are some people unable to enter their promised land? Because they are trapped in their desert mentality. They are stuck in a state of inertia. They may have dreams and aspirations, but they think, “What if the wine flask bursts? What if something goes wrong and it doesn’t work out as hoped and planned? And so, they don’t take the chance. They stay mired in mediocrity while the world passes them by.

Rather than assuming the worst, they should be thinking like Rabbi Meir, the optimist. He didn’t ask, “What if the flask bursts?” He asked, “What if the flask doesn’t burst?” A Rabbi Meir doesn’t ask, “What if something goes wrong and it doesn’t work out?” No, the question is, “What if something goes right and it does work out?” If you take that risk on fulfilling your dreams, the worst that might happen is that it doesn’t work out. But if you stay put and don’t take that chance on your dreams, then you’re pretty much guaranteed that it won’t work out.

Maybe you’re thinking of starting a business or setting out on a fresh career path. Right now, your professional life is stable and predictable. You could stay the course. After all, it’s safe. But you know that Hashem has planted a dream in your mind. A vision of greatness. But it’s risky. What if it doesn’t work? Can you afford to take the risk? If the little voice inside you is saying to go for it, then listen. Daven for success. And Hashem will lead you into the promised land.

Perhaps, it’s a young man you’re seeing but not sure about. How do you know he’s the one? Let’s ask a different question: What makes you think he isn’t the one? Sometimes we need to trust where Heaven has led us in life. If Hashem has presented you with an individual who seems to have what it would take to be a good life-partner, then take that leap of faith. Daven for a healthy marriage. And Hashem will lead you both into your promised land.

Might there be issues when you set out to fulfill your dreams? Maybe, says Rabbi Meir. Nothing in life is guaranteed. But worry about the problems when they present themselves. There’s no use worrying ahead of time—you can’t change what hasn’t happened yet!

Stop being concerned about what could go wrong if you try. Start thinking about what could go right if you try! May you take that leap into your promised land and know that with the Almighty’s help, it will all work out!

Rabbi Dr. Daniel Friedman is the author of The Transformative Daf series and the founder of the Center for Torah Values.