To be present. I’ve learned to train my mind to focus on what I’m doing in the moment—because if I don’t, it tends to wander. I’ll find myself composing emails while I’m reading a bedtime story or thinking through an unrelated problem when I should be listening to a presentation. Without focus, I end up running harder and not getting nearly as far. Plus, staying present forces me to be more disciplined about how I choose to spend my time in the first place. If you’re going to give something 100 percent of your attention, it had better be worth it.

To keep myself focused, I try to develop healthy habits like turning off notifications and resisting the urge to compulsively check my email. I also take a moment before meetings to think about how I want to approach it and what I’d like to learn. I think the key is to see your mind as a separate entity from yourself that can be trained, just like you train your body.

Don’t do it—unless you have to. Everything about starting a company is hard. When I co-founded CenterRun with Schrep and Basil, there were so many obstacles. Even worse were the doubts about whether anyone will see the value in it or want to join us. And the second one, Clearwell, was just as tough. I remember telling my wife, “If I hadn’t already done this once, I’d think it was impossible.” So starting a company should be less a choice and more something you do because you’re compelled to—because there’s something that you believe has to exist, and starting a company is the only way you can make it happen.

Once you’ve decided to go for it, though, I’d say, “Don’t overthink it.” Some things are must-haves, like co-founders with whom you share values, and an unmet need that can give you a foothold in the market. But beyond those basics, you have to get comfortable with uncertainty. The future is complex and impossible to predict, and you just have to let things play out and see what happens.

Going to bed 30 minutes earlier. A while back, I listened to a podcast about sleep and the things you can do to improve it—like sensory deprivation, going to bed at the same time every night and keeping the room cold. For me, the one that worked was going to bed at 10:30 p.m. instead of 11 and getting seven hours of sleep instead of six and a half.

The better I sleep, the sharper and more engaged I feel and the more I enjoy my day. It helps me make the most of that golden time in the morning, when it’s easier to think clearly about difficult things. For me, sleep is a performance-enhancing drug.

On a personal level, I wish I knew more about how to engage with each person I care about at each stage of their life. We’re all constantly changing, and so are the people we love. With kids, for example, you engage with a 5-year-old much differently than a 15-year-old, and feeling out those transformations can be a challenge.

In the context of work, I wish I always knew the correct level of knowledge I should gather and analyze before I make a decision. When you go too deep, everything looks hard. After we sold CenterRun, for example, I knew the data center space so well that I overestimated the difficulties of other opportunities, like open-source virtualization, and I think that held me back from dreaming as much as I should have. But there are also times when you don’t go deep enough and miss things that should be obvious. The necessary depth depends on the issue, and it’s a difficult thing to get it right, but I’m always working on it. No matter your role, I think exercising good judgment and making good decisions is the most important thing you can do.

I just finished Being Mortal, by Atul Gawande, which is essentially about dying and how to think about it in the same way we think about health and life. Now I’m rereading Sapiens, by Yuval Noah Harari, because there’s so much good stuff in that book that I couldn’t take it all in the first time around—from how humans have moved up the food chain as every other animal moved down, to how humanity and our four primary sources of protein literally outweigh everything else on the planet. I’m also starting How to Change Your Mind, by Michael Pollan, which examines psychedelic drugs and how they came to be associated with the counterculture. I like books that challenge conventional wisdom. You often find it’s only been conventional for a short period of time.

I also like to do what I call “communal reading.” Right now, my nine-year-old and I are working our way through the Harry Potter books together, and my wife and I are both reading Small Great Things, by Jodi Picoult. My wife picked that one out, which is part of the fun—not only do we get to talk about it as we go, but I’m reading something I wouldn’t otherwise choose.

I’ve been wrong about plenty of specific decisions—the future is so hard to predict; I don’t know how anyone could possibly be right all the time. What comes to mind for me is a more fundamental change in the way I think. I used to see things in pretty black-and-white, binary terms. “This will work,” or “That won’t.” Now, I think more in terms of probability. “How likely is a version of a future in which this product will be significant, or that things will break a certain way?”

Thinking probabilistically reinforces a sense of humility that I believe is part of being a VC, because none of us knows the future. When you recognize that fundamental uncertainty, it eliminates absolutist thinking.

For an entrepreneur, I think it’s the shortest unit of time from which you can get meaningful data that could lead you to change course. In an enterprise business where deals could take six months to close, we judged ourselves in 90-day increments. A consumer business might be monthly or weekly.

Personally, I find it most helpful to think in terms of weeks, because that’s the unit within which I try to balance my time. When it comes to work, I’m balancing meetings and email with taking time to read and explore—being proactive rather than just reactive. But I’m also balancing work with personal time, whether it’s talking with my 15-year-old on the way to school or calling my mother. If you haven’t had a meaningful conversation with someone you care about in more than a week, that should give you pause.