The Triumphs and Travails of a Traveling Charity Leader

The charity I lead is based near Boston, but more and more my work calls for me to be elsewhere to meet with potential board members, foundation program officers, and leaders of nonprofit groups we might want to work with. I’ve learned the hard way that there is a direct relationship between how much I travel and the long-term health of our organization, Jewish Family & Life. Our periods of rapid growth coincided with years I earned privileged status in several frequent-flier clubs; our toughest times were preceded by periods of staying local.

Some of the logistics of travel have gotten easier with each trip. Among the helpful shortcuts I’ve found: signing up with Zoots, which picks up and delivers my dry cleaning to my home with convenient regularity. If only donations were as predictable.

Most recently, my travels have taken me to the West Coast. Three out of our first four foundation gifts were from California, and I’ve discovered that in the Golden State, there’s a greater openness than on the East Coast to new ideas and the kind of venture philanthropy that has been the core of the success of our nonprofit organization, which uses the Internet and print publications to promote Jewish values, ideals, and culture.

My weeklong trip to California last month was my longest yet as the chief executive officer of a charity, and it tested my abilities to balance the ever-growing demands on my time.

By the trip’s conclusion, I’d covered nearly 7,000 miles, racked up 47 items on my to-do list, made dozens of calls, sorted through about 500 e-mail messages, and responded to two crises, all between the official meetings I’d scheduled. During the time away from my wife and kids, I also missed six bedtimes, six morning rushes to schools, six dinners, and one school play.

Saturday

5 p.m.: Check in at Delta’s first-class line, a perk of so much long-distance travel that enabled me to cash in frequent-flier miles for an upgraded ticket. I quickly scan my carry-on to be sure I have everything: the five files my executive assistant begged me to go through on the flight, my Sony Vaio laptop, sleeping pills, eye mask.

Earlier this morning, I’d briefly considered canceling my trip after learning at synagogue of the loss of the seven Columbia astronauts. But my appearance at the board of a major foundation is too important to my charity to miss. As I board the flight, I touch my shirt pocket to feel for the picture of my kids.

6 p.m.: My Palm Pilot alerts me that it’s time for my airplane homework. I read the file with the background materials for my Monday-morning presentation to the foundation we hope will give us a $1-million grant over three years. I ignore my other files. My gut tells me that even though we have not yet received any grants from the foundation, we will land this one. After two years of discussions and planning, the stars seem to be aligned. After reading through our file of proposals and updates, I pop two Ambien sleeping pills and position my eye mask.

Midnight: Check into the hotel. Unpack. Set up the desk with laptop, files, cell-phone charger, Palm charger, peanut M&Ms. I flip channels between CNN and VH1. Fall asleep around 1:30 a.m.

Sunday

8:30 a.m: Since long flights traditionally wreak havoc on my back, I arrange for an in-room massage-therapy session (at my expense). As the masseuse kneads my muscles, my mind plots my schedule for the week: the 15 official meetings already set and the additional dozen or so I’m still hoping to arrange. I use a meditation technique I learned as a child called “white framing,” which involves putting a white frame around a mental picture of a hoped-for outcome. I picture energetic handshakes, smiles, and myself bringing back good news of two major gifts to our board.

Brunch: Back-to-back meetings with two potential board members: a young woman who has the ability to mobilize people to raise funds, and a seasoned company CEO with masterful strategic-planning skills who has been a donor to our nonprofit group. One of my highest priorities is to expand and diversify our board, to get more women, more national names, and more financial resources. We also need West Coast representation. She says she’s interested in continuing the conversation; he will get back to us within a week with an answer.

7 p.m.: Dinner with Bob Malina, one of my first board members six years ago and now an honorary board member. He has some powerful and unconventional ideas for the charity, such as an aggressive membership drive to recruit families with kids 5 to 13 years old. I make a note in my Palm Pilot to follow up with him next week. Dinner is an event that features Bob’s son, Joshua, who recently joined the cast of NBC’s The West Wing. Fun evening, but at the end I am approached by a major donor who yells at me about something that happened five years ago and is unrelated to my current work.

11:30 p.m.: Back at the hotel, I leave a message for my wife on our home answering machine, as is our deal. I delete about 70 e-mail messages, procrastinate writing my presentation for the foundation meeting the next morning because I am unsettled from the negative encounter with the donor. In addition to sleeping pills, I take Prilosec for heartburn before falling asleep around 2 a.m.

Monday

7 a.m.: “Good morning!” my assistant’s voice blares.

“I was going to sleep till 9,” I mutter.

“Well, you’re up now,” she continues with no hint of sympathy or remorse. We go through a list of messages, urgent tasks, and reminders.

“Are you ready for today?” she asks.

I tell her no, I’m planning to figure out my presentation before heading for the 11:30 meeting.

10:30 a.m.: I’m pacing in the hotel room, trying to break a mental block. This foundation is our organization’s top fund-raising prospect this quarter. I glance through the file one more time, ignore the computer (like Luke Skywalker turning off his targeting equipment), pick up a hotel pen, trust my instincts. The presentation flows, and in 10 minutes I’m done. I practice what I’m going to say based on the notes I’ve scribbled on the paper as I get dressed, deciding on the blue Jerry Garcia tie, even though it’s a bit funky.

11:30 a.m.: The foundation director greets me warmly, then apologizes that the foundation donor decided at the last minute not to come to the meeting. He’s not going to be listening to my presentation by phone, either. Bad sign. As the eight board members check their messages and snack before their meeting reconvenes, I move around the room, saying hello to the people I’ve met before, introducing myself to new ones I’d met only by phone.

11:40 a.m.: I have 15 minutes to make my case. “Two years ago when we began a conversation, there were five things you asked us to accomplish before approaching you,” I begin confidently. “I’m pleased to report that we’ve accomplished them all and are honored to present to you the opportunity to join a national funding partnership for Jskyway, the distance professional-development enterprise for Jewish educators.”

I get encouraging smiles, lots of eye contact, heads nodding at appropriate times. The questions come, and I can tell I aced it. I feel like the CEO my board wants me to be. As I leave, the director tells me the board will reconvene in the afternoon. “We may know later today,” he says. I feel great and decide to wear the suit for the rest of the day.

Lunch: Enjoy the beautiful LA weather at an outdoor event of a national meeting to promote Jewish day schools. Six hundred leaders and donors are here. Michael Steinhardt, the group’s chairman, gives a dynamite speech about the need for a “revolution in professional development” of Jewish educators. Bingo! I see him afterward, and we trade our traditional barbs. “At least your enthusiasm is cute,” he chides. Then he agrees to a 20-minute meeting with me in New York sometime in the next two months. Note in Palm: “Schedule meeting with Steinhardt.”

4 p.m.: My cell phone vibrates on my right hip. Like a Jedi knight, I unhook it with my thumb, spin it up effortlessly, catch a glimpse of the caller ID as I bring the phone up to my ear. “I’m here,” says Heather Smith, our vice president and project director for Jskyway.com. Heather’s a former IBM employee with an MBA, and we’re making a joint presentation the next day at a workshop on online teacher training. “Meet me quickly,” I tell her. I’m positioned strategically to see people leave the hotel where the foundation board is meeting. Two board members pass us without glancing our way, including the chair. Not good. A technology donor surprises me with a hug. He has an idea for a joint project with another nonprofit group. Heather and I promise a two-page memo within two weeks about an online high-school course on Israel.

Dinner: At the gala dinner for the education conference, I shake about two dozen hands and pass out business cards with our new logo. A nonprofit colleague asks me for an introduction to a donor I know well. Two years ago a friend and colleague introduced me to someone who ended up giving us $750,000, so I try to pass along the favor whenever I think there’s a fit. During the formal program, my Palm vibrates, beckoning me to check my e-mail. Spam on kosher Palm. I delete about a dozen messages, respond to five.

Tuesday

Breakfast: I meet with a representative of one of our major donors and come away with about five follow-up items.

10 a.m.: Heather and I make our presentations to a room of about 30 people at the education conference. We ask to go third on the panel, and the first two presentations are perfect setups. But my joy at the success of our presentation is severely tempered by the news I’d received just before. A nonprofit colleague I saw in the hallway told me the foundation that we’d seen the day before has decided not to give any grants this quarter.

Lunch: I run out to pick up my rental car, but the reservation has mistakenly been canceled. I just need a car with a Global Positioning System, I plead. The only one left is a Jaguar, and Hertz agrees to discount it because of the mix-up. I hope I’m not seen in it. I go to pick up Heather and am spotted by the director of a foundation that we have been courting for some time. I decide not to be defensive about the Jaguar and just wave hello, but I worry that he will think we waste money.

5 p.m.: Order flowers to be delivered to my wife on Thursday.

Dinner: At a Yemenite restaurant in LA with a lawyer (whom I’d love to join our board), several of his friends, and my wife’s sister. Good people, good conversation. But the loss of the foundation grant I’d come to California seeking weighs heavily, and I know that when the dinner’s over, I’ll be feeling down.

8:15 p.m.: Meet two Hollywood friends for a class on Jewish spiritual practice with Mordecai Finley. I’m weary, but my energy returns as I realize what he’s talking about. “There is no difference in happiness between rich and poor people,” he teaches. “The deciding factor is gratefulness. Those who are grateful in their outlook are happiest.” While we didn’t get the foundation grant, the negative impact of the news leaves my soul.

11 p.m.: I leave a message at home that I’m in and safe for the night.

Wednesday

8:30 a.m.: Heather and I meet with officials of an LA nonprofit group. I go into CEO “Mr. Vision” mode: no notes, no PowerPoint. As the meeting goes on, it’s clear we share many innovative ideas for reaching out to the next generation. The Palm is flying out of and back into my pocket as I add follow-up items. After we’re done, Heather and I jump into the Jag and zoom to LAX; Heather is off to Boston, me to San Francisco.

5 p.m.: Meet with a young entrepreneur, someone I’ve admired from afar. I’d like him to join our board eventually, but first we have to figure out a way for my charity and the nonprofit group he founded to work together. Note on Palm: Write strategic-cooperation memo.

6:45 p.m.: Dinner with friends who played a crucial role in designing the strategic plan for Jewish Family & Life. I’m happy to be eating vegetarian Vietnamese food with friends. My Palm snoozes.

10:30 p.m.: Check into the hotel, pick up a package with materials from my office for the next day. Work on my presentations, leave a message at home, watch CNN, fade around midnight.

Thursday

8:30 a.m.: Breakfast with a friend of a friend, who enthusiastically gives me five names of people in the Bay Area to talk with.

10 a.m.: Meet with a foundation program officer to sharpen our application. We’re hoping to get a $200,000 planning grant from the foundation when its board meets in mid-March. Make a note in my Palm that we need to quickly get two more small pieces of information.

11 a.m.: Meet with a staff member of another foundation. We’re aiming to get our application onto the September docket, but there is a lot of competition. I learn that it would help to have another foundation approach this grant maker about working together to pay for an aggressive marketing campaign of our programs. Note on Palm: Craft a one-pager on marketing partnership.

12:30 p.m.: Lunch with a friend involved with another nonprofit group; compare notes.

2:30 p.m.: This is the other big meeting I’ve been waiting for, my fourth with this potential donor. After our last meeting, I’d sent a two-page memo outlining my charity’s plan, and I am now hoping to close the deal.

“You must have been on the red-eye when you wrote that terrible memo,” the donor says when we sit down.

“Well, for part of it,” I confess.

“Let’s start over again,” he says. I remember my lesson in gratitude, and we begin outlining a more realistic program. When we’re done, we make a deal: I promise to produce the updated memo within a week, and he agrees to get back to me with an answer a week later. I note the deadline in my Palm.

4 p.m.: Meet with another foundation officer about getting our grant request to be considered at the April board meeting. We’re hoping to get a three-year challenge grant to help cover operating expenses.

6:30 p.m.: Meet with a major business and philanthropy leader at his home in Palo Alto to hear some of his ideas. He owns his own Gulfstream jet, and his thoughts and actions soar freely.

8:30 p.m.: Meet with a potential board member: a businesswoman on the West Coast who is a strategic thinker and has access to resources. This is our second meeting, and we click again instantly. She will, I hope, be coming for a visit to our Boston headquarters in a month. She is also interested in consulting for us on a big project. I make notes in my Palm to follow up and to send her a copy of our strategic plan.

10 p.m.: Leave for the airport, pick up instant ice packs for my back, return the rental car. The GPS tells me, “You have arrived.” As always, I answer, “Indeed.” It is as much a prayer as it is, I hope, a self-fulfilling prophecy.

Yosef I. Abramowitz is chief executive officer of Jewish Family & Life, a charity in Newton, Mass., that seeks to stimulate interest in Jewish culture among Jews. He can be reached at CEO@jflmedia.com.