Nearly 600 Montrealers are visiting Israel on a mega-mission this May. The delegation’s size and quality reflect the central role Montreal’s Federation CJA plays in the community’s life.

Just as the eastern European kehillah kept the Jewish People together for centuries with independent, enveloping, communal institutions, the federation serves as the central address for Montreal Jewry (and most Canadian communities), helping the needy, educating the young and protecting the community, while standing with and for Israel. The organizers have done an extraordinary job of planning an impressive itinerary. The people of Israel are ready to host them. Still, the best advice I can give to my friends on the delegation is: “Get lost!”

I say, “Get lost” in two meanings of the phrase, but not a third. No, I am not being ungracious and saying, New York-style, “Get outta here.” But I am suggesting that each visitor – on this mission and all others – carve out some private time, break away from the group, turn off the Waze or Google Maps, and wander.

“Get lost” in the Old City of Jerusalem’s alleyways, and see how ancient and modern harmonize together in the Jewish People’s eternal capital. “Get lost” around Machane Yehuda and absorb the sights, sounds and smells of the pluralistic modern Jewish market. “Get lost” on Tel Aviv’s beaches and boulevards, noting that Israel is not just an historic tourist site, but a living, breathing, experiment in creating a modern Jewish democracy. “Get lost” in the desert outside Be’er Sheva or the forests by the Golan, seeing what our forefathers and foremothers saw.

“Getting lost” in this way helps people own their experiences. As much as we honour and cherish our tour guides, once we become our own tour guides we internalize the experience better. In that spirit, skipping one of the hotel breakfasts or fancy dinners and buying food in a supermarket or a makolet, a corner store, navigating the unfamiliar, interacting with non-English speakers, can prove very rewarding. And, of course, every good, happy “getting lost” story ends with salvation, finding your destination, often with waves of self-satisfaction and empowerment.

There is another dimension to “getting lost.” Every visitor to Israel is a pilgrim who should be ready to get lost in some aspect of the Israeli or Jewish experience. It could be the history or the nature or the politics or the spirituality or the demographics. There is so much to learn.

Unfortunately, so many of us have been fed such a boring, thin, pathetic diet of Jewish and Zionist ideas and attitudes that a trip to Israel should serve as a shock to the system, like overdosing on sweets after Yom Kippur. We must go beyond the juvenile Judaism of cutesy stories and shticky rituals that slights the Torah’s profundity, the Talmud’s depth, Maimonides’ genius, Theodor Herzl’s vision.

We also need to go beyond the Israel-can-do-no-wrong advocacy models that overlook the complexity of history, the multi-dimensionality of democracy and the ongoing challenges of making this modern country the fulfilment of the Zionist dream in a messy world.

Of course, this kind of “getting lost” truly helps us find ourselves, find our way – partially by charting new paths. So one last piece of advice – the same advice I give to March of the Living groups. When you return and people ask, “How was the trip?” don’t answer with the usual “great,” “awesome,” “fantastic.” Challenge yourself – and others – by saying, “I don’t know yet, we’ll see.”

Don’t judge this trip by how much fun you had. Judge it – six months, 12 months, two years from now – by how much it changes you, what ideas and values you internalize, how you use it to move forward. Let this trip be a “reset” in your life – an opportunity to stretch and grow, becoming a more giving, more committed – and thus more connected and satisfied Jew, Zionist, and human being.