Ask yourself, ‘Would you say yes if this were next Tuesday?’ It’s so easy to commit to things that are weeks or months out, when your schedule still looks uncluttered

ESTHER DYSON is the founder of HICCup and chairman of EDventure Holdings. Esther is an active angel investor, best-selling author, board member, and advisor concentrating on emerging markets and technologies, new space, and health. She sits on the boards of 23andMe and Voxiva (txt4baby), and is an investor in Crohnology, Eligible API, Keas, Omada Health, Sleepio, StartUp Health, and Valkee, among others. From October 2008 to March 2009, Esther lived in Star City outside Moscow, Russia, training as a backup cosmonaut.

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 Biology of Desire: Why Addiction Is Not a Disease by Marc Lewis. Addiction is short-term desire. Purpose is long-term desire.

Scarcity: Why Having Too Little Means So Much by Sendhil Mullainathan and Eldar Shafir. An explanation of scarcity for rich intellectuals, showing how poor people do stupid things for lack of money, while rich people do stupid things for lack of time.

From Bacteria to Bach and Back: The Evolution of Minds by Daniel C. Dennett. How consciousness arises, and how much it depends on a sense of past, present, and future (plus a lot of other interesting insights).

How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?
Many over the years! Most recently, one of the five communities my ten-year nonprofit project Way to Wellville was working with just wasn’t engaged—like someone who hires a personal trainer but just never makes it to the gym. We politely cut ties and selected a different community. Not only has that worked out, but it has made it clear to everyone—the communities, potential funders, and partners, et al.—that we hold ourselves and others accountable. With this move, we honored those communities who are willing to take risks and work hard to make a difference.

If you could have a gigantic billboard anywhere with anything on it, what would it say and why?
“Always make new mistakes!” I actually get royalties of about $50 per year from Quotable Quotes for this one.

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

Well, I don’t think it’s absurd—space travel. I hope to retire on Mars, but not too soon! I have trained as a backup space tourist, for six months in Star City, Russia.

In the last five years, what new belief, behavior, or habit has most improved your life?
I started using Audible and now I’m reading books regularly again. (Or perhaps the 30-year period when I was not reading books should go into the “failure” question.) It’s great. Even as I work in the weeds with Wellville, I’m reading intellectual books about poverty, neuroscience, nutrition, complex systems, addiction, and the like. The two strands—highly abstract and intimately, personally concrete with real humans—complement one another.

What advice would you give to a smart, driven college student about to enter the “real world”?
Always take jobs for which you are not qualified; that way you will inevitably learn something. And do not drop out of college unless you truly have a better alternative. Some notable individuals have succeeded in spite of doing so, but it’s a serious obstacle to overcome for most people.

In the last five years, what have you become better at saying no to?

I have become slightly better at avoiding conferences that are fun but not terribly useful.

My tip: Ask yourself, “Would you say yes if this were next Tuesday?” It’s so easy to commit to things that are weeks or months out, when your schedule still looks uncluttered.

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

[When I’m] overwhelmed: Ask, “What is the worst thing that could happen?” Fear of the unknown is generally far worse than fear of something specific. If it’s not the death of yourself or those you are responsible for, there’s probably some reasonable set of options you should consider calmly and thoughtfully.

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