Where did you grow up and what was your childhood like? Did you have any particular experiences/stories that shaped your adult life?

I grew up in Shaker Heights, Ohio, a Cleveland suburb. I had a pretty standard American white upper-middle-class upbringing, although I’d say that my parents pushed their kids unusually hard for achievement.

Our school system was 55% Black, 45% white, so most of us kids didn’t think much about race. I mean, the Black and white kids usually sat at separate lunch tables and stuff, but there wasn’t much racial tension. (My parents had moved to Shaker especially because of the schools’ famously successful integration.)

The downside, though, is that I was totally unprepared for the real world. I had no idea how little American society had progressed in racial terms: That if you were Black, you still couldn’t get a cab, walk through a store without being tailed by an employee, get certain jobs, buy houses in certain neighborhoods, and so on. It took years for the full reality to sink in, for me to understand how isolated and unusual that school system was.

What is something you wish you would’ve realized earlier in your life?

My parents, my mom especially, strove to protect us from the ugliness of the world. The bad news of the world rarely filtered through to dinnertime conversation, and if it did, its impact was minimized. Wars, corruption, mental illness, racism—all kinds of nastiness were kept out of our childhood bubble, and even our teenage bubble. The whole idea was to give us a happy childhood.

I’m torn about that approach. It did provide an untroubled childhood, but also left me completely shell-shocked when I graduated from college, moved to NYC, and realized that the world I’d been taught to envision was something of fiction.

With my own kids, I’ve tried to present the reality of the world and its problems (age-appropriate, of course), but always with a thoughtful, analytical tone, with an emphasis on what solutions people are working on. I try to instill hope as well as accuracy about the world.

What are bad recommendations you hear in your profession or area of expertise?

I’m always amazed at how tricks, tips, and techniques are passed along from author to author without ever being analyzed or even tested. Lots of life hacks sound super cool, but actually don’t work at all. (Like the old saw about drying out a wet phone in a bag of uncooked rice. “We did a study, and rice was slower to work than just leaving the phone out on the counter,” electronics-drying expert Craig Beinecke told USA Today.)

My coauthor Joe Schorr and I used to get really annoyed when people would cherry-pick tips and tricks from our 600-page book “Macworld Mac Secrets” and post them as their own. So in one year’s edition of that book, we actually published a bogus tip—one that actually didn’t work—just to trace the theft online. It was like tagging a pigeon and then setting it free.

It was super fun to see our phony tip show up first (without attribution) on a blog, and then in a computer magazine who’d found it on that blog, and, ultimately, a competitive Mac book, whose author got it from that magazine. None of them had ever tested it!

Tell me about one of the darker periods you’ve experienced in life. How you came out of it and what you learned from it?

Oh god—my divorce. I actually call it the Dark Times. Full-on depression, panic, insomnia. Would my kids be OK? Would I be OK? What would I be when it was over? The most devastating sense of destruction and hopelessness I’ve ever known.

Of course, studies have shown that the biggest disruptors of your psyche are big life changes: births, deaths; starting a job, ending a job; entering a relationship, ending a relationship; moving; big health changes.

What I find fascinating about the research is that ANY kind of change is stressful, whether it’s good or bad. You might think that winning a lot of money is much easier to accept than losing a lot of money, but that’s really not true; both are intensely stressful, and a lot of lottery winners flame out as a result.

In all cases of life change, you’re facing down big elements of the unknown about your future. And the fear of the unknown triggers a fear response in the brain.

What is one thing that you do that you feel has been the biggest contributor to your success so far?

Weirdly, I think it’s having been the last of three children.

I’m seven years behind my brother, five years behind my sister. As a result, I was generally the kid who got the least attention—and also the kid subject to the fewest rules.

So I wound up becoming sort of a showoff, a comedian. My armchair-therapist analysis is that the seed of my work as a TV host, author, and public speaker was that childhood effort to get noticed within the family!

What is your morning routine? 

I’m a severe night owl, possibly because much of my career was tied to the goings-on in Silicon Valley, which was three hours behind time on the East Coast, where I live. I usually hit the hay at 2 am and get up at 10 am or even later, unless there’s some reason to get up earlier, like a meeting or a shoot.

I usually grab the laptop and scan the Inbox for brush fires while I’m still propped on the pillows. Then come the usual morning ablutions, and then breakfast.

What habit or behavior that you have pursued for a few years has most improved your life?

I’ve always been really non-athletic—lousy at team sports, the last kid picked for kickball, slow on the running track.

But starting about ten years ago, I started dipping my toe into fitness: lifting some weights and using the treadmill. (This summer, I’ve been exercising daily, without exception—we’ll see how long I can keep that up.)

The astonishing thing is what exercise does for my mood. I feel great afterward, for hours, like everything’s going my way, and everything’s gonna be OK. Let’s face it: The emotion known as happiness is a chemical process in your brain, and exercise is a simple lever you can pull to get those chemicals flowing!

What are your strategies for being productive and using your time most efficiently?

I am a gigantic, hopeless efficiency nut. I cannot STAND hardware, software, or interfaces that require an unnecessary number of steps.

So my laptop is almost hilariously tricked out with shortcut software. I use a macro app to open apps, to format text, to adjust zoom levels, and so on (by pressing keystrokes). I use a typing-expander app, currently stocked with something like 500 abbreviations that auto-expand into longer words. (I type “t” for “the,” “hv” for “however,” “bs” for “because,” and on and on).

I use a password manager, so that I never have to remember (or type in) my web passwords. I have edited the keyboard shortcuts in every Mac app so that, for example, Command-F always triggers the Find command, no matter what the app. I’ve set up a backup that works continuously and automatically without my participation. I’ve replaced the laces on my sneakers with magnetic closures. (My wife Nicki thinks that part is going too far.)

I guess that the overall strategy boils down to this: Take the time now to set up and program these shortcuts, automation, and time-savers. You’ll lose an hour or two of time today, but you’ll gain it back thousands of times over for the rest of your life.

What book(s) have influenced your life the most? Why?

This will sound weird, and maybe a little self-serving…but the most influential book was “DOS for Dummies” by Dan Gookin.

It was unlike any that computer book had come before. It was funny, which was revolutionary in itself. But more importantly, the tone took an us-versus-them stance, where “them” was people who are already good at using computers. Never before had an author taken potshots at experts—the very people the reader is ostensibly aspiring to become!

Of course, he wasn’t actually denigrating those people or their expertise, but rather the jargon, the smugness, the resentment of newbies by people who’ve worked hard to master a topic.

The big bookstore chains refused to stock “DOS for Dummies” because the title, they feared, would insult customers. But the book became a huge bestseller anyway—by starting in independent bookstores—and from there, the whole “for Dummies” series was born.

Today, there are “Dummies” books for 2500 topics. “DOS for Dummies” was the first one; my own book, “Macs for Dummies,” was the second. I did my best to adopt Dan Gookin’s irreverent, us-versus-them tone, which never would have occurred to me otherwise. The book did great—I wound up writing eight “for Dummies” titles in all.

Do you have any quotes you live by or think of often?

Yeah. I love this Wayne Gretzky quote: “You miss 100 percent of the shots you never take.”

Obviously, it’s got both a literal meaning (hockey goals) and a metaphorical one (trying things out of your comfort zone).

For me, as a freelancer, someone who’s tried his hand at writing books, giving talks, hosting TV shows, reporting news, conducting Broadway shows, creating a podcast, teaching a grad-school course, and so on, that quote comes in handy in two cases. First, I think of it when I’m considering trying something new. “No, I’ve never done a podcast, and there are already millions of them. But hey—you miss 100 percent of the shots you never take.”

Second, when I try something that fails commercially, I think of that line again. Yeah, OK, not everything is going to be a hit. But you’ll never get a hit unless you take the shots—so no need to beat myself up.