“I Tend to Focus on Everything That Could Go Wrong and Underestimate the Upside of a Decision.”

Interview: Sarah Hurwitz

From 2009 to 2017, Sarah Hurwitz served as a White House speechwriter, first as a senior speechwriter for President Barack Obama and then as head speechwriter for First Lady Michelle Obama. She's the author of a new book, Here All Along: Finding Meaning, Spirituality, and a Deeper Connection to Life—in Judaism (After Finally Choosing to Look There).

I do love a long subtitle!

I was interested to hear what Sarah had to say about happiness.

Gretchen: What’s something you know now about happiness that you didn’t know when you were 18 years old?

Sarah: I’ve always been risk averse—I tend to focus on everything that could go wrong and way underestimate the upside of any decision. But as I grew older, I realized that I was totally miscalculating risk. 

For example, when I left the White House, I had this crazy idea that I wanted to write a book about Judaism. I had grown up without much Jewish background and had started learning about Judaism while I was in the White House. I was blown away by what I found and wanted to share it with others. But my risk-hating brain was terrified of this idea: Who was I to write a book like this? I’m not a rabbi—I’m not qualified! And what if it turns out terribly? And what if no one reads it?

But by framing things this way, I was only thinking about the risk of writing this book…and I wasn’t considering the risk of not writing it. I really wanted to write this book—Judaism has so many insights that I wanted to share about how to be a good person, lead a meaningful life, and find spiritual connection. And when I finally considered the risks of not writing it, I realized they were pretty serious: deep regret, frustration, misalignment with my truest self. 

So I took the plunge and wrote the book. And while it was tremendously challenging, I felt a great deal of joy and purpose in doing it, and I never had a single moment of regret. Again and again in my life, when I’ve recalculated risk that way—taking into account the risk of not taking risks—I’ve made decisions that have led me to happiness.

You’ve spent a lot of time studying and writing about Judaism. What has surprised or intrigued you—or your readers—most?

People often think of ancient religions like Judaism as conservative and reactionary…but it turns out that Judaism offers plenty of wisdom that’s both quite radical and wildly countercultural. Just consider the foundational Jewish idea that we’re all created in the image of God, which Judaism understands to mean that we’re each of infinite worth and we’re all totally equal to each other. You don’t have to believe in any kind of God to see the power of that idea. And if you don’t think it’s radical and countercultural, ask yourself why you didn’t stop to help that person on the street who asked you for money. If that person had been a celebrity or CEO, I’m guessing you probably would have stopped. In other words, if we really internalized and acted upon this in-the-image idea, our world would look very different.

Another example is Shabbat (the Jewish sabbath), which involves taking a day of rest each week. Jews who observe Shabbat often refrain from working; spending money; using their phones, computers, and TV; and much more. And they spend time in prayer, and with their families and communities, being fully present with loved ones. In a way, Shabbat can be understood as a weekly protest against the consumerism, materialism, and workaholism of the modern world – all those voices that say, “You’re not enough, you don’t have enough—you need to work more, spend more, improve yourself, and do a better job of curating your life for others’ consumption on social media.”

Those who observe Shabbat are, at least for one day, choosing to tune out those voices and focus on the things that really matter. I think it’s awesome.

Is there a common misperception or incorrect assumption about Judaism that you’d like to correct?

I used to assume that Judaism says that God is essentially a man in the sky who rewards and punishes us as we deserve, and if you don’t buy that, then you’re an atheist. But actually, Jewish theology is incredibly diverse and offers all kinds of sophisticated thinking about God—some of which really resonates with me. There are Jewish thinkers who have argued that God is everything and we are all interconnected, all one.  Or that God is the process by which all living things become their highest, truest forms—the process by which we become more ethical, authentic people. Or that God is what arises in moments of deep connection between two people—that when we encounter another person in their fullest humanity, we’re encountering God. And there are plenty of other Jewish God conceptions as well.

It turns out that Judaism is a vast, deep, millennia-old tradition that encourages questioning, debating, and thinking for ourselves (and maybe you’ve heard the old joke: two Jews, three opinions). This approach is one of the many things that I love about Judaism.

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Gretchen Rubin is the author of Outer Order, Inner Calm, her most recent New York Times bestseller about how getting control of our stuff makes us feel more in control of our lives and frees our minds (and our shelves) for what we truly value. She has also written four other bestsellers: The Four Tendencies, Better Than Before, The Happiness Project, and Happier at Home. She writes about happiness and habit-formation at gretchenrubin.com. Follow her here on LinkedIn by clicking the yellow FOLLOW button, on Twitter, on Facebook, on Instagram, and listen to her popular podcast, Happier with Gretchen Rubin.