I try to be a realistic optimist: I’m very clinical about where we are today, but extremely optimistic about what we’re going to get done in the future

BEN SILBERMANN helps millions of people collect things they love as co- founder and CEO of Pinterest. Ben grew up in Iowa, where he spent a lot of time collecting bugs, so this makes sense. Prior to Pinterest, which launched in March 2010, Ben worked at Google in the online advertising group. He graduated from Yale in 2003 with a degree in political science. He lives in Palo Alto, California, with his wife and son.

What is an unusual habit, or an absurd thing, that you love?

Have you ever seen the blog Wait But Why? [written by Tim Urban] They have a chart of the weeks of your life.

I have a wall chart of boxes representing every year of my life: ten years across and nine rows down. Then things are plotted on it, like average life expectancy in the U.S. I always thought it was kind of cool, because it puts time into a visual format, and I’m a visual person. Even at the company, every week I show employees the current week within the year visually, just to remind them that every week matters. I didn’t think my own chart was weird, but in January, I showed it to my team, thinking they’d find it really inspiring and motivating. But people respond to mortality in very different ways. It was the worst meeting I’ve ever run.

I don’t think they knew what I was trying to convey. Some people see that as, “Hey, every year is really exciting and valuable,” and some people react with, “Oh wow, I’m gonna die.” It didn’t go over well, so I don’t share that chart anymore.

Experiment failed.

How has a failure, or apparent failure, set you up for later success?

I’ll say the following, and it’s not exactly an answer to your question, but it does shape the way I think. Both of my parents, both of my sisters, and a lot of my friends are doctors. One thing that always struck me was how it takes a minimum of 12 years to become a doctor, and then you’re a low-level doctor. One thing that is different about where I live now [Silicon Valley] is that people tend to measure everything in very short time frames, like one or two years. A lot of professions assume that you’re going to take eight to ten years just to achieve the minimum level of competence necessary to start to practice.

That’s been a good grounding force when doing projects, because a lot of things go wrong here and there, but if you just assume that anything worthwhile is going to take five to ten years, they don’t feel as severe.

For instance, I left Google in 2008 to start a company, and the first two or three things didn’t work out. Pinterest launched in 2010. It didn’t really start growing quickly for another year or two, and it really took off around 2012. That’s a four-year period where things weren’t going awesome. But, I thought: “That’s not that long. That’s like med school before you go into residency.”

What is the book (or books) you’ve given most as a gift, and why? Or what are one to three books that have greatly influenced your life?

The Better Angels of Our Nature by Steven Pinker. Most news is about things that are going wrong. It can be discouraging and makes people feel powerless. This book takes a long view and shows the long-term decline in violence that has occurred.

Salt, Fat, Acid, Heat: Mastering the Elements of Good Cooking by Samin Nosrat. I enjoy cooking, and this book taught me a lot of the basics of flavor and cooking technique. It helped me feel more confident going off-recipe.

What is one of the best or most worthwhile investments you’ve ever made?
I had never been to the gym until around two years ago. This was partially laziness and partially intimidation.

I don’t think there was a single breakthrough moment. I just had this realization: “Am I going be the kind of guy who doesn’t exercise ever? Or not? And if the answer is ‘not,’ then why not right now?” That was the reasoning, but I didn’t have a medical crisis or anything. It’s one of the things that I always felt I was putting off. Then I went to the gym and realized I had no idea what to do. That’s why I got a trainer and invested in them for a year. I just went to the gym and asked, “Do you have any trainers?” I didn’t put a lot of thought into the person, but the benefit was that, once it was scheduled and I was paying for it, it became harder to not go than to go.

It was a sunk cost, and there was a person who I’d have to text and say, “I’m not going to show up,” which is a different type of accountability. That helped me to get over the initial hump of starting an exercise routine. If regular exercise could be bottled, it would be a miracle drug. Basically, everything in your life gets better if you find time to exercise regularly.

I feel like a lot of people in Silicon Valley serialize their lives. They think, “First I’ll do college. Then I’ll do a startup. Then I’ll make money. Then I’ll do X.” There’s some truth in that [approach], but most of the most important stuff has to be parallel-processed, like your relationships and your health, because you can’t make up the time by doing more of it later. You can’t neglect your wife for four years and then say, “Okay, now it’s my wife years.” Relationships don’t work that way, and neither does your health or your fitness. . . . Figuring out a system, so that the stuff you need to do all the time happens, even while you might be placing disproportionate focus on one thing, is pretty important. Otherwise, you’ll be setting yourself up to be lonely and unhealthy in your future.

What purchase of $100 or less has most positively impacted your life in the last six months (or in recent memory)?
It’s not very original, but I like Apple AirPods headphones a lot. They’re wireless and they stay charged. I really like them a lot more than I expected.

What are bad recommendations that you hear in your profession or area of expertise?
I think this idea that you learn the most from failures is wrong. It’s a good thing to say so that people feel better, but whenever you want to learn how to do something well, you start by studying people who are really good. You don’t study all the failed sprinters to learn how to run fast; you study the person who’s really fast. There are a lot of reasons things can go wrong, but your job is to make things work.

I’m not saying it’s either/or. Obviously, when something goes wrong, you should make the most of it and think about what you could have done better. Because of the way people process failure, those lessons will have a longer emotional carry. Most people have a pretty heavy emotional aversion to failing.

I think it’s great to make people feel safe to take risks, but it’s become distorted into believing that you should take all of your lessons from things that don’t work, versus studying the people who are doing really well.

[This overfocus on failure] seeps into everything. I have to tell my managers: You need to spend time with your best performers, not just with all of your problems.

In the last five years, what have you become better at saying no to? What new realizations and/or approaches helped?
I’m still not very good at it, but I know time really is zero-sum, and it’s the one thing that no one’s making more of.

I don’t have special go-to language. I try to tell people the truth, and people are surprisingly understanding. I might say something like “I really wish that I could, but I’m really trying to focus on [XYZ project] right now, and I hope you understand. I genuinely hope that we’ll connect in the future.” Maybe they’re just not telling me [they’re upset], but people are more understanding than I imagine. In my head, I have this image of them doing something like slamming their computer down with “That asshole!” but I think people kind of get it.

When you feel overwhelmed or unfocused, what do you do?

One, I usually go for a walk, and two, I try to write down everything that’s going on, so I can get it out of my head and look at it. Sometimes your brain gets caught in little loops, and it’s not making any progress. For me, it’s helpful to write everything down and visually reflect on what’s important.

It isn’t super structured. I might write down, “Here’s what’s on my mind . . .” and put it on paper. Then I try to step back and ask, “Okay, what’s going on here, and which stuff matters?” There’s something to be learned from the way that companies set goals on different time resolutions: what matters this week, this month, this year, in ten years. . . . I think people usually end up losing it when they let short-term things crowd out what they want to take care of in the medium or long term.

Over the longer term, what really matters to you? If you answer that, you can reverse-engineer toward that end.

In the last five years, what new belief, behavior, or habit has most improved your life?
It sounds kind of cheesy, but I started to keep a gratitude journal. If you [have a habit of writing] things down that you’re grateful for, then some part of your brain is constantly looking for those things, and you feel happier. It’s absurd in its simplicity.

I find the time during the day and write down one thing. Sometimes I miss a day; I’m not perfect about it. I always tell my team that I try to be a realistic optimist: I’m very clinical about where we are today, but I’m extremely optimistic about what we’re going to get done in the future. I feel that optimism is important to communicate to the team, instead of solely focusing on problems. Someone once told me, “If you only engage with people about problems, pretty soon, you’ll become the problem for them,” and I agree with that. I now try to make space and time for saying, “This is what’s going really well . . .” whereas, when I first managed people, the approach was more, “What do we need to fix today?”

I use a little notebook I got at Office Depot or somewhere. It’s not super cool, and it’s more about the habit. But I do want to get that culty Japanese journal that all the designers use, a Hobonichi Techo. It’s the kind of thing you see in Japan: a notebook turned into a high art. Maybe next year. . . .

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