It’s late August. Summer storms arrive as if from nowhere, soaking the sun-warmed pavement. Parents are transitioning from the childcare scramble to the school drop-off scramble. Sand particles cling to the bottoms of canvas bags as you shop supermarkets stocked with snack-packs and pumpkin products.

The High Holidays are on their way. Do you know where your rabbi is?

Rabbi Miriam Terlinchamp is in the car. She’s driving through Cincinnati to her study group, where she’ll read Scripture with Evangelical pastors, a Buddhist, a Baptist, a professor of theology and an Imam. She did chevruta study with a Jewish colleague on Tuesday, as she does every week. She also tries to finish a book a week, though with two small children at home, it’s a challenge. And, of course, all her work doubles in August. In August she stays up late most nights, behind the closed doors of her home office, preparing.

Rabbi Robert Haas is also going to church. Two types of church – one is Methodist. The other is a comedy club. Once he decides on his sermon themes, he weaves them into standup, fine-tuning ideas throughout the summer at the clubs throughout Savannah. It makes the jokes sharp, he says. It helps drive home his message. This year his topic is hate. “I have a lot of comedy about that,” he says. “How ridiculous it is.” As the leader of the third oldest synagogue in America, the Reform Congregation Mickve Israel, he’ll practice delivering his Rosh Hashanah and Yom Kippur sermons – all five – as a guest clergy at local churches. This way, when the time comes for him to stand in front of his own congregation, he’ll be ready.

Rabbi Suzie Jacobson is in a coffee shop with a trusted colleague, who pauses, leafing through a draft of Jacobson’s Kol Nidre sermon. “This joke,” he says. “Is it funny?” Shira Stutman, the senior rabbi at 6th and I synagogue in Washington, DC, wrote part of her sermon today in the pediatric exam room as her 14-year-old waited for an appointment.

And Rabbi Naftali Citron of the Upper West Side’s Carlebach Shul still isn’t sure what he’s going to talk about. He’s been texting congregants, asking what they might want to hear. Answers have been vague so far, he says. When we talked in early August, he’d just come from a shiva where he ran into Rabbi Avi Weiss, the prominent Orthodox rabbi and the founder of Yeshivat Chovevei Torah. “He asked me what I’m thinking of for this year,” Citron said. He didn’t tell Rabbi Weiss that he had no idea, or that he’d been texting congregants. “Weiss has a thought,” Citron lamented. “He has a theme.”

The last days of summer mark the busiest, most stressful season for rabbis. Besides the normal duties of leading a congregation -– the weekly, daily, or thrice-daily services, the board meetings, the disgruntled congregants, lifecycle events, budget talks, and social-justice work – they are tasked with planning a spiritual bonanza, a month-long ritual experience: the High Holidays. A rabbi at a solo pulpit might, during that period, deliver sermons during the following services: Selichot, Erev Rosh Hashanah, Rosh Hashanah, Taschlich, Rosh Hashanah second day, Shabbat Shuva (the Shabbat between Rosh Hashanah and Yom Kippur), Kol Nidre (opening service of Yom Kippur night), Yom Kippur day, any of the eight days of Sukkot, Shemini Atzeret, and Simchat Torah, not to mention meals, study sessions, and alternative prayer experiences. Three days after Simchat Torah comes Shabbat, and with it — the first chapter of the Book of Genesis. And the cycle starts over again.

Rabbi Wesley Gardenswartz of Temple Emanuel in Newton, Massachusetts is done with his sermons – all five of them. He finished them in March, the earliest by far of the twelve rabbis and one spiritual leader I spoke to for this article. “If they weren’t [done], I’d have a heart attack,” he laughs. And not for nothing – on Yom Kippur, he’ll give the same sermon five different times to accommodate the 1,300 families who belong to his synagogue. If you plan to give a sermon five times, you can’t start thinking it over in June. You can’t start at all, he says, because you never stop. “Sermons are my great passion in life,” Gardenswartz says, with the kind of reverence people usually use to describe caloric desserts. “I wake up in the morning thinking about sermons, I go to bed thinking about sermons, everything I read and see, I’m thinking, ‘Is there a sermon here?’” There almost always is.

What Makes This Night – and Day – and Night – and Day – Different From Any Other?

Rabbi Joseph Dweck is the senior rabbi at the Spanish & Portuguese Sephardic community in London. He presides over three member synagogues and three affiliate synagogues, a beit din, and a kashrut authority. The massive size of his workload doesn’t decrease the gravity of his work. “Any opportunity that I get to speak to members of my community – that is a golden opportunity,” he says.

Across the world in the hills of Berkeley, California, Rabbi Yoel Kahn agrees. “I spend eleven months of the year obsessing about what I’m going to say at the high holidays,” he tells me. Because it doesn’t matter if your congregation has a healthy group for Shacharis three times a day or can barely make it to a the post-services kiddush luncheon – on Rosh Hashanah and Yom Kippur, all rabbis stand equal before their God. It’s the opportunity to reach the greatest number of people at once, and at the time when they’re feeling the most connected. Kahn sums it up “People are giving you a lot of trust — you better have something.”

Kahn usually avoids the subject of Israel, he tells me. His congregants are sensitive, and what’s more, he says, they should be. “They’ve come to their sacred space,” he says. “They want to feel safe, and they don’t want to hear my political analysis. So the question for me is always, ‘What is the Jewish value-added that I have to bring?’”

Kahn is a Reform, male rabbi on the West Coast, but his argument is identical to that of Rosh Kehillah Mijal Bitton, a young Orthodox woman who co-founded Manhattan’s Downtown Minyan, a semi-traditional Orthodox prayer community which she says in some ways resembles a start-up. “I want to make a space where people from different political persuasions can sit comfortably and not feel under attack,” she says, pointing out that people in her community are perfectly well-informed and aren’t looking to prayer spaces to provide a forum for political discussions. Like most of the leaders I spoke to, Bitton, who is also a social scientist and Resident Fellow at the Shalom Hartman Institute, says that she can speak about topics like the moral responsibility towards immigrants without touching on specific policies. “I’m not saying that the Torah doesn’t have opinions on politics,” she laughs. “But I’m very careful of what I can say the Torah claims – it’s not a monolithic book that tells you which candidates to vote for.”

Robert Haas, down in Savannah, puts the political preaching question simply: “You’re here to serve the congregation, not alienate fifty percent of them,” he says.

This issue of politics and the pulpit, long simmering, only heats up at the High Holidays. For Rabbi David Wolpe, the celebrated leader of Los Angeles’ Temple Sinai, a Conservative synagogue with a whopping membership hovers around 1,800 families, it’s an issue of major significance. On the phone, Wolpe’s voice rises with emotion as he speaks about a topic on which he has written controversially in the past: “I think it’s an improper arrogation of rabbinic authority for political opinion,” he says. “To – to stand up there,” he stutters, with obvious passion, “where no one can argue with you, and to deliver those political opinions, and to invest those political opinions with that authority and sanctity is, to me, not right. You can argue about which issues are political and which are moral, but I find that rabbis tend to err on the side of ‘everything is moral and nothing is political.’ So I encourage other rabbis to not take political positions.”

“Of course,” says Wolpe. “I just gave a sermon about Israel. I talked about the question of settlements and the Nation State Law and all the normal stuff.”

Yoel Kahn, too, is preparing to speak about Israel, despite knowing that the topic makes many of his congregants want to march out the door. He says that as he writes, he thinks of the prophets. “The prophets were not popular,” he says, smiling ruefully. “This is a time for speaking truth, but how can we speak truth without rachamim?” he asks, invoking the biblical Hebrew word for mercy. “The High Holidays are a season for rachamim.”

And Rabbi Wolpe rests in knowledge that he picked up from decades of sermonizing. “I know going in that there’s nothing I can say that won’t upset some of my members,” he says, cheerfully. “It’s liberating, because I get to say what I believe. And to people who are upset I say: I will invite speakers who represent your points of view.” No one, he says, will leave synagogue unrepresented.

All the “Normal Stuff”

Take, for example, the situation of Rabbi Sam Spector. The 29-year-old Seattle native has lived in Southern California for 8 years and planned to center his sermon on the mass school shooting in Parkland, Florida. On July 1, Spector completed his first day at Congregation Kol Ami, the biggest Jewish community in the state of Utah. Suffice it to say, Spector has since changed his topic.

And not because he doesn’t believe in preaching politics -– he does — but only when people are ready to listen. “When I’m walking in and trying to be family with someone, saying ‘Let me tell you why your values are wrong’ – that’s no way to start a family,” he says. In that sense, he agrees with Wolpe and Bitton – hearing politics from a rabbi, he argues, has a greater gravity than from anyone else. “They hear it not as me, Rabbi Sam Spector, interpreting the Torah, but as the spokesperson for Judaism.” To congregants, he says, a sermon, especially on the High Holidays, can sound like the rabbi is saying, “Your Judaism is wrong and flawed.”

“And that’s not the case,” he says. “I’m saying – this is my Torah. What is your Torah?”

Two years ago on Rosh Hashanah, Rabbi Miriam Terlinchamp asked herself, “What’s your Torah?” and the answer, which she shared with her synagogue in Cincinnati – was an angry Torah. A Torah of justice. As she had increasingly attended events after the riots nearby in Ferguson, Missouri‎, she was sometimes asked to give invocations. “One day, right before the High Holidays,” she remembers, “A leader said, ‘Can you just tell us why you’re here?’”

And what she felt was a call. “I found this voice,” she says. She recalls telling her congregation what she says boiled down to: “Yo. We are privileged. We have messed this up. We need to be shouting from the rooftops: Black Lives Matter!”

Responses were painful. “I remember the first sermon, people were walking out and crying,” she says. But the synagogue changed. A year later, 100 percent of members had paid dues, up from forty. Donations had increased. “Last year, I couldn’t yell at them [any more],” she laughs. “I was like, ‘You did it!’”

This year, Terlinchamp will find a new voice. She plans to talk about changes — why do we wait till things are horrible to fix them? Why do we wait until our marriages are broken or our jobs are unbearable? For rabbis like Terlinchamp, the personal is political. But how personal should a rabbi be? Rabbi Shira Stutman, leader of the unaffiliated Washington, D.C. community 6th and I, uses something she calls “strategic vulnerability.” If you don’t share some of your heart, people can’t trust your story, she theorizes. This can go very right, and dreadfully wrong. Last year, Stutman remembers grimly, she gave a High Holiday sermon about saying goodbye, and, quoting a segment from NPR’s “This American Life,” she began to cry. Some congregants liked it, but Stutman was disappointed with herself. “I was so upset with myself,” she says. “What happens when you start to cry is that people start to feel like they have to take care of you.”

Sermons Are For The Self

So: There’s no crying in sermonizing. Still, almost all rabbis said, the sermon-writing process can be deeply personally rewarding.

“Sometimes, I write sermons for myself,” Sam Spector says. “That might sound bad, but before I was a rabbi, I was a Jew.” Rabbi Richard Hirsh agrees that sermons should, on some level, serve the rabbi, who is in dialogue with congregants at all times.

“A sermon works best when it is reciprocal,” says Hirsh, a longtime Reconstructionist rabbi who now serves M’kor Shalom, a Reform congregation in Cherry Hill, New Jersey. Hirsh, as well as Kahn and Wolpe, don’t write their Yom Kippur sermons until Rosh Hashanah is over. “I need to experience Rosh Hashanah and see how it goes for me personally and what’s going on with people first,” he says. “But waiting that long to write a sermon – my colleagues call it ‘rabbinic chicken.’”

Stutman agrees that a sermon cannot be given unless it feels deeply personally resonant. “It has to be something I’m personally grappling with and other people are grappling with as well,” she says.

A few years ago, Sam Spector’s serious relationship ended just before the holidays. The loss inspired him to speak on the topic of imposter syndrome — the terror that you do not really deserve to be where you are. “I didn’t reference myself,” he says, “I talked about it because that was what I needed to hear, and it turned out it was something a lot of my congregants needed – congregants whose lives seemed perfect but they had drug-addicted children, or houses that were in foreclosure.”

Mijal Bitton agreed. “If it doesn’t matter to me, I won’t speak about it,” she says. At times, she runs her ideas past congregants to ensure that her ideas matter to them as well. Just like a startup, she says, her spiritual organization should always respond to the community.

A Family Affair

The holiest season of the year is the most hectic season for a rabbinic family. Stutman’s husband is the head of a school, so early autumn slams their family twice as hard. “By the end of the holiday season, my children and my husband feel deprived,” she said.

Terlinchamp, who calls herself a “solo artist” (she’s her synagogue’s only rabbi) finishes everything by the morning of the eve of Rosh Hashanah, so she can take her children out of school to go apple picking.

For Gardenswartz, the Newton rabbi who calls sermons “one of the most joyful parts of being a rabbi,” preaching is also a family affair – his wife and three adult children are his best editors, he says. Suzie Jacobson and Yoel Kahn’s spouses are professional writers and editors whom they treat as exceptionally precious, though dangerous secret weapons. Jacobson says she works on a deadline to finish her sermon in time for her wife to “inevitably tear it apart.”

And Richard Hirsh throws himself to the mercy of his wife. “Sometimes I think I’ve got a great sermon and I think it’s 75 percent done and she’ll say, ‘I can’t follow this.’” Both his wife and son read his drafts and will often ask him, “Is this really valuable for the sermon? Or are you just trying to show off how clever you are?”

“That said,” he told me, sobering. “I am somewhat notorious for alliteration. They are very good at saying to me, ‘Okay. Two, maybe three runs of alliteration are okay. More than that and you’re just showing off.”

“Of course, the most important part is the opening joke,” Yoel Kahn told me, sounding like he was only half-joking. And Hirsh agrees –- outside, perhaps, of the Kol Nidre sermon, entertainment value is expected in sermons. “It’s a technique,” he said. Hirsh knows what story he’ll use this year to open his Rosh Hashanah sermon, but he only told me after I promised I wouldn’t use it.

Citron, the Carlebach rabbi, loves telling Reb Nachman of Breslov stories, and Talmudic quotes, but he also believes that sermons should have an element of self-help “that you can’t just get from Barnes and Noble.”

I Don’t Know How He Or She Does It

Naftali Citron, the sole rabbi at a 300-family Orthodox synagogue, seems to have the most speaking commitments of anyone I interviewed (between Sukkot and Simchat Torah, he estimates he will speak fifteen times.) That doesn’t mean he’ll be coming up with 15 topics. “As innovative as we want to be, we have to educate people about those themes,” he says. “What do they say in advertising? Advertising is re-advertising.”

And in spite of the number of speeches he gives, he doesn’t like to sit and write. “On a good year I’ll have two or three pieces of paper with some kind of sloppy notes,” he says. To hear Citron tell it, you would imagine that his sermons are a bumbling ordeal. But I have seen him hold a room of 300 people at rapt attention past two in the morning. “I don’t script it,” he says. When you speak that much, it’s not sermonizing, he says. “I’m teaching.”

Wolpe, who is considered one of the greatest sermonizers today, also speaks off only loose notes, often improvising.

Gardenswartz, the enthusiast, says, “I write down every word, and sweat over every comma.” After his sermons are edited, he reads them out loud (five times for Shabbat, ten times for the high holidays) committing them to memory in the process. (His sermons are notoriously flawless.)

Bitton’s minyan does not have women service leaders, but she delivers the weekly sermon and will give the Kol Nidre sermon at the Yom Kippur service. She, too, finds she does best when she doesn’t read her words straight off a page. Refining the art of sermon delivery is thrilling to her. “I’ve learned a lot from how some Evangelical preachers teach and speak,” she says.

And how long are these speeches anyway? “No more than 22 minutes,” says Gardenswartz. Kahn does 18-20. Stutman believes anything said in 25 could be said in 15. “I usually go for 20 but end up with 25,” says Jacobson, adding that people stop paying attention when you hit 20. “25 minutes and you’re holding people hostage,” Spector agrees. Dweck’s answer is the most extreme: “Seven to ten,” he says, crisply. “At times, it will go up to 15.”

And Citron’s is the most true to life: “They’re pretty consistent at about 10-25 minutes,” he says, adding, “I don’t suddenly do a 40-minute one on the High Holidays. I do a bit more like 15-20.” He pauses. “25, but I don’t acknowledge it.”

Milkshake, Milkshake, Milkshake

Rabbi by rabbi, the process varies. But not by much. Wolpe, Stutman, and Bitton keep files of sermon ideas throughout the year. Gardenswartz’s wife sends him anything she reads that she thinks might spark an idea. Haas, fresh from a trip to Iceland, laments, “I had a wonderful time! But I didn’t pick up anything I thought could be a sermon.” And Jacobson, who three years into her rabbinate is the most junior leader I spoke to, begins with a long period of studying traditional Jewish texts, followed by listening to podcasts and TedTalks.

And then?

“I go to Denny’s,” says Spector. “I order milkshake after milkshakes. I put on a bunch of weight during the High Holidays because I’m just sitting there writing and ordering milkshakes.” Wolpe paces his home, talking into a recorder. Haas works in a “hip” coffee shop.

True to Berkeley stereotypes, Kahn goes to a Zen retreat when he can, while Terlinchamp, Dweck, and Hirsh prefer to work from home.

“At home I’m writing primarily as a Jew and in the office I feel like I’m writing primarily as a rabbi,” says Hirsh. “And I think my best sermons are when I’m sharing something that’s important to me as a Jew.”

Hirsh is in the 37th year of his rabbinate, but this will be his first year leading High Holidays in M’kor Shalom. Suddenly, the way his sermons are received matters more than ever.

Miriam Terlinchamp can’t eat during the High Holidays – not just on Yom Kippur, but Rosh Hashanah as well. “If I don’t feel nervous, whatever I wrote is probably not worth saying,” she says. Jacobson says that as a younger, female rabbi, it’s hard not to be nervous. “Who am I to stand up in front of all these people and give this message?” she finds herself wondering. “Who am I to speak on the holiest day of the year?”

Joseph Dweck’s congregation is so large, at first I don’t believe him when he claims he doesn’t get nervous on the High Holidays. Then he says, “We recently celebrated the 100th anniversary of the Balfour Declaration and we held a service where Lord Rothschild and Lord Balfour were in attendance.”

That, he says, made him nervous.

A Circle Game

And eventually, it’s over. Though even “over” isn’t easy to define – “The hardest thing about the holidays is you think it’s over and then it’s Sukkot,” Miriam Terlinchamp tells me. “Every single year, I’m like, ‘What the hell is this?’” And taking care of a congregation throughout the season is hard as it is. “People don’t stop getting sick and dying for the High Holidays,” one rabbi told me.

Together, the leaders I spoke to serve over 10,000 Jewish families. Each of them spoke fluently about their process, their values, their challenges, and their joys when it comes to giving High Holiday sermons. I concluded my conversation with every one of them by asking them what they do to relax when the holidays end. Some of them were silent. Some laughed out loud. Several said, distantly, “That’s a good question.” Two half-heartedly mentioned massages. Several expressed the hopes of using the time to see their families.

But for now, the work lies ahead.

The season of mercy arrives later for rabbis than it does for the rest of us. “Things don’t really slow down until after Thanksgiving,” said Kahn. “The slowest time of the year is December.” The High Holidays dominate most days of the Hebrew month of Elul. The next month, Cheshvan, is the only month on the Jewish calendar that has no holidays.

“I don’t know who figured out the Jewish calendar,” says Rabbi Hirsh, “But whoever did that, on behalf of all rabbis, I thank them.”

Jenny Singer is the deputy lifestyle editor for the Forward. You can reach her at Singer@forward.com or on Twitter @jeanvaljenny