I Never Promised You a Goodie Bag Page 11

  To me, Bennett was like a brother. But to other women he was catnip, and he had a series of lovely girlfriends. One year it was Stacey, and they were obviously very serious. They were always cuddling on the couch and would make their own plans most nights. Once Bennett and Stacey were having a predinner drink at the house, and he asked me if I wanted to come to dinner with them. I had no plans, but the last thing I wanted was to be the third wheel on Bennett’s date, so I put on my trusty bike pants and headed out for a run.

  The driveway leading down from the house was steep, and I was gone not two minutes when I wiped out on the pavement and came limping back up in tears. My hands were bleeding, my knee was bleeding, and Bennett was all over me with ice and bandages. He refused to go to dinner without me, so I got cleaned up and went along with them, hands wrapped in gauze and all.

  That summer Bennett and I were both paired up with other people—he with Stacey, and I had met Rich, a man who looked good on paper. He was handsome and successful, he came from a wonderful family, and we had a lot in common; he seemed to be everything I thought I wanted. Except we fought a lot, and I felt like he was competing with me all the time.

  One weekend in the Hamptons, Bennett and his girlfriend and Rich and I went out to a restaurant together. I excused myself to go to the bathroom, and on my way there I ran right into Jimmy, whom I hadn’t seen or spoken to in two years. My heart flew into my mouth, and I could barely speak. He seemed just as flustered, and quickly explained that he was there to pick up a pint of ice cream for him and his fiancée. His fiancée. I’m not sure which exploded first, my heart or my brain. We said our good-byes, and I staggered into the bathroom to bawl my eyes out.

  Seeing Jimmy happy and engaged to be married jolted me into realizing the degree to which I wasn’t where I wanted to be in my life. Maybe we weren’t the right people for each other, but still I was shocked at how emotional I felt to see him marching on with his life while I was still spinning, and running, and seeking. I was planning everyone else’s adult milestones, and meanwhile all of mine were still out there in my uncertain future. Jimmy had moved on, and here I was with a man that I didn’t really want to be with—that, truth be told, I didn’t even like all that much. I thought, What am I doing?

  I don’t remember much about dinner after that. When we got back to the house that evening, Rich and I got into an enormous fight. I was done—I was tired of forcing the relationship, and I wanted out.

  It was a long, cold night in the Hamptons after that, and on our way back to Manhattan the next day, Rich continued to berate me. He couldn’t grasp why I was such a wreck over an old boyfriend. He was so confident in his own status as a brilliant catch that he simply wouldn’t accept that I wasn’t happy with him. It wasn’t that he loved me—I knew he didn’t—it was that his competitive juices were flowing. Finally, exhausted by the screaming, I told him to pull over, and I got out of the car.

  I figured Rich would drive around the block and come back for me after we’d both cooled off a bit, but no. Rich never came back, and I was stranded on the side of Montauk Highway. I only made one call. I called Bennett. He was just about to head back to Manhattan with his girlfriend. And of course he answered my call. I blubbered one long stream of gibberish until they finally figured out my general coordinates. Then he picked me up, without saying a word. That was the thing about Bennett, he just showed up for me, every time. And that meant everything.

  Chapter Ten

  The Scary Mask

  My work was my life during those years. It was all-consuming, and that’s just the way I wanted it. My goals were to make the clients happy, get more and bigger clients, and make my company a success. This was very tangible, and easy to measure. Business was a daily challenge for me; someone was going to win a job, and someone was going to lose, and who likes to lose? That took all of my emotional energy and focus. And while I was certainly more secure in my abilities than I’d ever been before, still I wouldn’t allow myself to relax long enough to examine what exactly I was building, and why.

  I had six women working for me—all as young or younger than I was—and I had absolutely no idea how to be a great manager to them. My only concept of that relationship was that I needed to be in charge—a benevolent dictatorship was probably an accurate description. I couldn’t be friendly and also expect my staff to respect me, so I put on a mask of all-business.

  When I walked into my office in the morning, a tense silence fell over the room. I never said good morning, or asked anyone about their weekend. I wasn’t being unfriendly on purpose, but as I walked through the door I’d already be in the middle of a thought about who I had to call or what event we had that week, and I’d fire off follow-up questions from the day before. If the office got too chatty, I’d look up from my desk, and everyone closed their mouths and went back to their jobs. I’d forget to say, “Good work,” or “Nicely done.” It never occurred to me that people needed to be encouraged. I wasn’t motivated by praise—if I did a good job, we’d get more clients.

  I liked to think that my staff knew I was on their side, and realized that if they ever needed me, I was there for them. If a client ever treated them rudely, then that client was either fired or put on notice. But when it came to the kind of casual office exchanges that most people didn’t even have to think about, I was hopeless. I remember someone actually telling me they heard that I made Anna Wintour look like a pussycat, and I actually laughed. I thought it was a compliment, sort of. Looking back on it now, I think I was terrified that if I showed one tiny hint of vulnerability, the floodgates would open and I wouldn’t be able to keep everything in check.

  There were still so many days that I woke up after nightmares and bad sleep. I’d walk into the office with a leaden cloud over my head. Later, after I’d scared the bejesus out of everyone, I would sit in my office and think to myself, Why can’t I be normal? It hurt my feelings when the women in my office would head out to drinks after work without a thought of inviting me. I didn’t want to be the way I was, but I couldn’t help myself. And I didn’t blame my employees for not realizing there was a human being under all my armor. I’m sure they would have been shocked to know what an insecure mess I was inside.

  The only upside to this alternate persona I put on for the world is that it seemed to give me insight into my clients and their own private moments when they thought no one else was watching. Didn’t everyone wear some sort of mask? There was the A-list socialite who secretly worried that no one would come to her party. One stunningly beautiful bride seemed so sure of herself but lost it when she was faced with performing her first dance; she never liked to be the center of attention. Inside, I found out, she was just as self-conscious as anyone. One particularly shy bride, a “plain Jane” type, showed a totally different side of herself when she went for the vampiest, skintight wedding dress. She was the youngest of five kids, and nothing ever fit quite right during all those years of hand-me-downs. She didn’t want to look like anyone else in her family on her wedding day. From all these women I learned that I wasn’t the only person in the world with something to prove. It occurred to me I could never judge anyone again. I had to have an open heart and mind when I met people. Maybe the outgoing woman I was speaking to had her own secret story. If anyone judged me based on first sight or my tough exterior, they would have gotten it completely wrong.

  This was a profound insight for me. I’d always believed that what made me truly good at my job was my perfectionism. Now I was discovering that my far greater skill was that I could sense the hidden aspirations that drove my clients to want to write a fresh new story on their special days. My mission wasn’t to be perfect. It was to surround myself with people who were celebrating, and to know that I had helped them make their joy tangible. I hadn’t yet figured out how that could be better reflected in my office itself, but it was a first step.

  When I first got into the business and was chasing aft
er corporate clients, it was all about being fabulous and impressing the clients with how hot, cutting-edge, and stylish I could make their events. But now I was evolving in my sense of what was really important, and slowly I began to focus much more on the emotional content of my events, the meaning behind the celebrations. And while I immersed myself in my clients’ emotional milestones, something inside me was clicking into place as well.

  One client in particular brought home for me how much I had changed since my attack. Michael was a highly successful Internet entrepreneur at the very height of the boom. He was good-looking, wore $3,000 handmade suits, a gold Rolex, and custom-fitted shoes, and had a cultivated swagger, but inside lurked the insecure science geek he’d been in high school. He was head over heels in love with his drop-dead-gorgeous girlfriend Alana—a girl who wouldn’t even have glanced his way ten years before—and wanted to throw a surprise party for her thirtieth birthday. He gave me carte blanche to make it memorable—he actually told me that he wanted me to design a night that would impress even me. He’d been to a million standard-issue over-the-top parties, and he wanted this night to be unique. What touched me more than anything was that he wasn’t just some rich businessman with a trophy girlfriend. He loved her. And he felt like the luckiest man on the face of the planet that she loved him back.

  I don’t think I have ever had a more nervous client. He was anxious about everything. He was desperate to make his girlfriend happy, and afraid no one would come. And if people did come, he was worried that the evening wouldn’t be fun—then all his guests would find out that he really was just a big nerd. I calmed his nerves and assured him the event would be everything he wanted and more, and then I came up with an elaborate plan that would have knocked my own socks off.

  My idea was a scavenger hunt that would take Alana to five different locations, leading up to a big reveal at the end of the night. First came the ruse: I had my client tell Alana that his birthday gift to her was a night out with her best friend. That night, a big black limo arrived to pick up Alana, and inside was her best friend, who was holding the first clue in a sealed envelope. The answer to that clue took Alana and her friend to the first location, where they met two more of her friends, holding a second clue. At each new location they were ushered to a special table or a private room and given meticulously chosen cocktails and appetizers, and Alana continued to gather more girlfriends—all of whom were in on the surprise.

  Finally, the last clue led Alana and all her friends to the Rainbow Room, where I met her, pretending to be the hostess, and led her to a private room. The planning of the whole evening had been so elaborate, and my client’s excitement and anxiety level had been so high, that I felt my own heart beating faster as we approached the pocket doors that led into a private room. As I pushed them open, Alana was met with a shout of Surprise! from everyone she loved most in the world—her boyfriend, her family, and a slew of out-of-town guests. As I stood back to let the cheers wash over Alana, I felt the residual glow myself.

  My client was beaming. Here was this highly successful man who had people catering to him every day of his life, but underneath it all he just wanted the woman he loved to be happy. It was a bittersweet moment for me. This time I hadn’t planned the perfect night for a client—I’d planned the perfect night for me. But it wasn’t me in that doorway, meeting the embrace of everyone I loved most in the world—it was someone else. It was always someone else. I felt like a young kid at a friend’s party, watching her opening up birthday presents, unable to hold back my jealousy that she got the gift I had always wanted. At one time, I’d believed that standing on the sidelines of other people’s events was all I could expect from life. That by osmosis these events would bring me the emotional satisfaction they did for my clients. And for a long time, they did. But somewhere inside, I was starting to hope for more.

  Around this time I was able to buy out the original investor in my company, and now Save the Date® was one hundred percent mine. It felt like a divorce, and I had been awarded sole custody—and along with it came all the financial and emotional responsibilities of being a single parent. It was a huge step for me, and the process was wrenching and stressful, but it also felt like a fresh start.

  On a whim, I decided to apply for the Entrepreneur of the Year® Award sponsored by Ernst & Young. It was a lengthy process, including essays, followed by a series of interviews. Not for a second did I think I had a chance to win, but it was a vote of confidence in myself to try. Why not? I didn’t care that I would lose.

  When I was named a finalist in the under-forty category, I laughed out loud. The other finalists were men and a good ten years older than I was, and their companies were technology start-ups with hundreds of employees. Meanwhile, I was twenty-nine, I had six employees who were women my age or younger, and I was a party planner. Give me a break—there was no way I was winning that award. I figured they’d only included me for diversity reasons.

  The awards dinner was held in a massive banquet hall at the Marriott Marquis. There were at least 1,500 people there, and while the other finalists had multiple tables, I just barely managed to fill one table with my staff and my parents. There was a ridiculously massive screen in front of the banquet hall so they could air documentaries about each of the finalists. In mine, I seem to recall that they interviewed a number of my clients, but the worst part for me was when I was the talking head up on that movie-theater-size screen. The documentary described how I had shifted the paradigm of my business and turned the whole structure on its head. I should have been feeling on top of the world, but instead I felt like such a fraud, competing with a crowd of MBAs and captains of industry with my measly little event-planning business.

  When they announced the winner—Jennifer Gilbert of Save the Date®—I was so shocked that I just sat there, frozen. Finally Nikki, the staff member who’d been with me the longest, said, “Jen, get up!”

  My spotlit walk up to the podium was an out-of-body experience. Standing at the podium was surreal, and looking out at those 1,500 faces was so unexpected that I hadn’t even prepared a written thank-you speech. The only thing that settled my nerves was to look at the table where I’d left my staff and my parents. I saw six young women full of shock and joy for me, and I was struck for the first time with a startling fact: I had never thanked them. All those years of wearing my scary mask, I hadn’t been able to show them the gratitude I felt in my heart every day. Finally, I found my words. I think I started by saying that it was the first time in my life I’d ever been speechless. And that most of all I needed to thank my employees—the people who showed up every day for me and with me, and who had made my company and that award possible. It was as if someone had turned on the lights. These women were my constant well of reinforcement. That office and my job fed me all those years when I felt small and unimportant and needed external validation.

  That night marked a major turning point for me, and the beginning of a process that would change the entire way I looked at my company as a business owner. There were multiple steps along the way, and the next came soon after the awards dinner. Nikki, who’d been the one to nudge me up to the stage, was a tall, gorgeous South African woman, and no shrinking violet. She was my first real employee, and she was the one all the newer employees looked to for advice and guidance. When she came knocking on my door one afternoon and asked if she could speak to me privately, my heart did a little jump. I felt nervous—Oh my God, was she leaving? I could sense that she had something serious to say. But my way of dealing with nervousness was to shut down emotionally. My face got stern, and I said, “What’s wrong?”

  Nikki sort of laughed, but I could tell she was taken aback. She said, “You know, Jen, after all these years you still scare me.”

  Me? Scary? I knew I could be intimidating to the younger women in the office, but I’d known Nikki for years at this point. Hadn’t she been able to see past my scary mask? And if not, then I re
ally did have a problem. I quickly apologized to her for freaking her out, and then she sat down and told me a story. She said she wanted to thank me, because she’d just experienced a stressful situation in her personal life, and she’d gotten through it by hearing my voice in her head. She said that when she was nearly convinced that the situation was doomed, she heard me saying, “You don’t ask, you don’t get, so go get it.” And then she found herself a yes—and she wanted to thank me for that.

  For the first time in all my years of working, I burst into tears in the office. I was so moved that I had been a role model for someone else. Me—the inner basket case who for so long had felt like she was barely holding it together. This was an epiphany for me. It gave me a glimpse of the whole, integrated person that I wanted to be: a person who carried her beliefs, her kindness, her love, and her passion into every area of her life.

  After the trial, I’d realized that I couldn’t go it alone in my personal life anymore. Now I’d reached that point in my business life as well. I made a vow that I would never walk into my office again if I couldn’t smile and offer a salutation of some sort. If it meant that I needed to get a cup of coffee at the corner deli and walk around the block a few times until I could shake my mood, then that’s what I would do. I didn’t want to be scary Jen anymore. I didn’t want my people to be frightened of me, waiting to see what kind of day they were going to have based on my mood that morning, and I never again wanted to sit in my office feeling like a freak because I found it so challenging to say a simple hello. I cared about my employees as people—their home lives, their happiness in and out of the office, and their personal growth—and it was time to start showing them.