Here, she talks about her first big failure, the importance of turning off your phone, and how she manages her schedule as her own boss.
Tiffany is wearing the Giulia top, the Chester pant, and the Claressa earrings. Her hat is her own.
BOTH OF MY PARENTS REALLY LOVED WHAT THEY DID and were their own bosses. And that’s what they communicated to us: Love what you do, and don’t work for anyone else. My father was a doctor, and my mother is a psychologist. They ran their own practices, so they made their own hours. And my immigrant grandparents came over and worked for themselves. I feel like that’s in our DNA.
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I WAS SUPPOSED TO BE A BRAIN SURGEON. My father gave me the book The Making of a Woman Surgeon four separate times. I’m fascinated by the brain—I’ve made a lot of films about psychology and neuroscience—but I just didn’t want to be a doctor. My father was really disappointed about it. We had a lot of fights about me being a filmmaker. He finally came around when I was doing really well with the Webby Awards and at Sundance. He was very proud of me eventually, but we had a lot of arguments when I was in college.
I HAD A REALLY BIG FAILURE EARLY ON IN MY CAREER. I had just graduated from UC Berkeley, and I had won a big award for my films. People were saying that I was this rising star. Then I started making this feature documentary that was very ambitious, and I totally failed and ran out of money. I was so embarrassed, and I felt like I had let everyone down. I went through a deep depression in my early 20s. It was horrible. I didn’t want to get out of bed. I now think it was the most important lesson of my life, because I tried something really big when I was really young and fell flat on my face. And I can taste that feeling today. When any of my friends is going through a depression, I know what it feels like, and I have great empathy for them.
MY BIG FAILURE ALSO TAUGHT ME that sometimes things work and sometimes they don’t. Growing up, I’d always been told, “Never quit. The Shlains are not quitters. We’re immigrants, we’re survivors.” Because of that, I felt like I couldn’t move on and walk away. But I finally learned that it’s just as important to know when to stop something as to start something. You need to know when to walk away from a project.
Tiffany is wearing the Rowling top, the Logan skirt, and the Bezel earrings. The hat is her own.
EVENTUALLY, I REBUILT MY CONFIDENCE by taking baby steps. I applied for a job that I was way overqualified for, and the interviewer said so. And I was like, “Please let me do this job. I just need to do what you want me to do.” And then I put one foot after the other, and I gained my confidence back.
WHEN I STARTED THE WEBBY AWARDS, I was working for The Web Magazine. I was 26, and they said, “We have no budget, but we have a brand. Can you make these awards into something?” And I was like, “Yes. I know how to do things with no budget. I’m an independent filmmaker.” And then the Webby Awards became really big. I ended up spinning it out into its own company, and it was like a rocket for 10 years of my life. But then I wanted to go back to filmmaking, and combined that with everything I’d learned about making social change on the web. I made a film for Planned Parenthood that got into Sundance. And then I sold the Webbys and started a film studio to make more films. It’s all interlinked.
I’VE HAD A LOT OF GREAT MENTORS. One big one is Geralyn Dreyfus, who is my executive producer on my feature documentary, Connected. She really believed in me, and organized a bunch of meetings where I would speak to all these investors about my film. She put those together and then followed up with people afterwards. She taught me a lot.
Tiffany is wearing the Amber dress and the Bezel earrings. Her hat is her own.
I GOT THE IDEA FOR A TECH SHABBAT after I found out my father was diagnosed with terminal brain cancer and given nine months to live. That same week, I found out I was pregnant with my daughter. That was an incredibly intense time, to have my father dying and our child growing inside of me. Whenever I’d see my dad, I’d turn off my phone. And then he died, and my daughter was born. They never got to meet. But that time made me realize that I wanted to be more present. And then I participated in this National Day of Unplugging. Most people were just doing it ceremonially for that day, once a year. But in my family, we never stopped. We were like, “This is what we need in our lives. This is the modern version of Shabbat for us.”
IN THE RELIGIOUS CONTEXT, SHABBAT IS A TRADITION that is thousands of years old. I’m taking it out of a religious context, because I’m a cultural Jew, but I’m not religious. I want to introduce people to a very old idea with a modern twist for bringing some balance back into our lives. Now that everyone’s emailing, texting, and blurring the lines between work and leisure, there are no boundaries. I think we need to bring some boundaries back.
IN MY FAMILY, WE’VE DONE A TECH SHABBAT FOR TEN YEARS NOW, and our kids love it. People are always shocked when I tell them, probably because I’m the founder of the Webby Awards and my husband is a professor of robotics; we lead tech-heavy lives. That’s when I realized I had to write this book. People find it hard to imagine that one day a week, we block out devices and are present with each other instead of staring down at our screens. But as a working mother, it’s been unbelievably helpful to have this time with my family. We sleep well, we laugh more, we’re fully engaged with each other. It also frames the whole week. I feel like I have discovered the secret formula that makes every weekend feel very special and profoundly relaxing, like a vacation. It’s a very inspiring and insightful time. It also makes me feel less guilty when I have to travel for work or miss something like all working parents do sometimes.
Tiffany is wearing the Giulia top, the Chester pant, and the Claressa earrings. Her hat is her own.
MY TRICK FOR GETTING THINGS DONE is that I get up very early in the morning, usually at 5:00am. Lately it’s been even earlier, with my book coming out and other projects I’m working on. I’m embarrassed to tell you when I’ve been getting up. But I go to bed really early, like 8:30pm. When I first wake up, I don’t look at my phone for a while. That’s been a huge help. I used to look at the New York Times app first thing in the morning and get so stressed out. Now, to set the tone for my day, I write in my five-minute journal—it’s just three things that I’m grateful for, and three things that would make today amazing—and I drink my coffee and start working on writing. Morning is my best writing time. And then the world starts waking up—my husband gets up, my kids get up, my cat gets up—and I dive into the rest of the day.
ON AN AVERAGE WEEK, I GO TO MY FILM STUDIO in San Francisco two days a week, and I work from home the other three days. On Wednesdays, this amazing woman Teresa comes over and helps me with managing life stuff. We go through school forms, insurance things, and other life maintenance. All week, I’m putting things in a pile for Wednesday, because I know that Teresa and I will take care of it. And then the music teacher comes over on Wednesday afternoons. I play ukulele, and my kids play guitar. On Fridays, we always have a big Shabbat meal with friends and family. We set the table beautifully, and I make fresh challah. All the screens are off. Saturday is a very inward day. We hang out with family or go for a bike ride. We don’t make a lot of plans. And then Saturday night we’re all psyched to go back online. My husband and I usually go out on a date. And the kids are psyched to go back online and watch videos or whatever. I’ve found creating these boundaries in the week to be very liberating.
I KNOW IT’S A LUXURY TO BE ABLE TO TURN OFF YOUR PHONE. A lot of people have to work two jobs, and they can’t do it. I would just say that whatever time you do get off, turn off the screens, because it will slow down time and make you feel more relaxed. People have forgotten how much stress they feel from their phones. There are a lot of great things about it, but every time you pick it up, it’s a grab bag of stuff that you often can’t control. It’s important to take moments to connect, look around, and be human.
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