But this very dark season should also force us to accept the possibility that it’s really not that kind of story: as we’ve noted many times before, Game of Thrones is no fairy tale. Fairy tales are often about children being threatened, and defeating the monsters, and finding their way home, and growing up to live happily ever after. We all still long, understandably, for that comforting formula, in nearly every story we encounter.

More mature works, however—and Game of Thrones is one of them—recognize that our fears change as we grow older: they recognize that “growing up” is not a solution, but an expansion of problems. They realize that home is a responsibility, not a safe haven. They acknowledge that there’s no such thing as “happily ever after.”

They recognize—as this long, dark season has done—the sad, uncomfortable truth about what the end of childhood really means. It means we stop being quite so afraid of monsters, and we start being afraid of becoming monsters.

One of the drawbacks of being an illustrator, for me, is the difficulty of enjoying my own work. It’s so much easier to spot the flaws and experience the burn of missed opportunity than simply enjoying a job well done. I spend so many hours in front of an image in process, that I can become somewhat numb to what the picture does exactly: the feeling, mood, whatever, if that makes any sense. But I think that’s a pretty common experience amongst illustrators, and part of the whole craft is to have the discipline to work through those difficulties.
It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.
- this isn’t right
- what?
- you have this woman hanging out with the kids and you’re getting closer to her and they’re spending time with her and she’s leaving?
- yeah
- ..
- so?
- how are the girls gonna feel when the rug is pulled out?
- they’re going to be sad. so am i. we’re enjoying her company while she’s here and then we’re all going to miss her. you know, janet, sometimes people are supposed to be sad. it’s ok, it’s the flip side, and it’s actually good
- yeah you want your kids to be sad?
- no. well, yes. if it’s cos they love somebody

- this isn’t right
- what?
- you have this woman hanging out with the kids and you’re getting closer to her and they’re spending time with her and she’s leaving?
- yeah
- ..
- so?
- how are the girls gonna feel when the rug is pulled out?
- they’re going to be sad. so am i. we’re enjoying her company while she’s here and then we’re all going to miss her. you know, janet, sometimes people are supposed to be sad. it’s ok, it’s the flip side, and it’s actually good
- yeah you want your kids to be sad?
- no. well, yes. if it’s cos they love somebody

I’d love to be able to say I’m immune to all this, but I’m as Intsa-guilty as anyone. I recently lost my phone, and it only struck me how much I missed it when I went into town on a sunny Saturday with friends. The city was looking especially beautiful, and our day culminated in cocktails in a particularly cool, hard-to-get-into rooftop bar. And because I didn’t have a phone I couldn’t Instagram a single bit of it.

This is probably the point where I should say that I had a far better time because I wasn’t trying to capture everything in a photograph, because I was actually living the moment. But the sorry truth is, I couldn’t enjoy it because it felt like a missed opportunity to record a fabulous day. As much as I’d like to deny it, today, for those of us who spend our days nearly permanently tethered to the digital realm, if it doesn’t pop up on Instagram, it might as well have not happened at all.

I wish I could say I felt elated, that I experienced the thrill of victory, or started hatching elaborate plans to spend my returns from the deal. But in those moments right after the deal closed, I was just too tired. I just wanted to take a nap and then get back to work and normalcy. Intellectually, I know this is a life-changing event. The financial rewards are great, and if I ever want to start another company, every piece of that process will be easier. But it’s going to take awhile for all that to sink in. For now I’m just glad to be done talking to lawyers three times a day and excited to return to solving business problems.

One thing that did cut through the exhaustion was a task I’d been anticipating for more than six years: writing the Facebook post in which I announce to friends, former friends, frenemies, ex-girlfriends, college roommates, future wives, and family members that I was not in fact an obscure failure but a new, minor footnote in the annals of Silicon Valley startup successes.

Writing it was easy. I’d had six years to plot it in my head. I kept it simple and tried to strike the right mix between “Aw yeah!” and “Aw shucks!” No one likes a sore winner. I pushed it live and watched as over 400 comments rolled in. Meanwhile my phone buzzed across my desk as it received text messages from people I’d not heard from in years. The middle school crush. The Sunday school teacher. The startup friends from Chicago. At last!

I’m unsure sometimes if the AI moniker isn’t misleading people as to what is really happening. We (human beings) aren’t creating an artificial intelligence. We are learning about our own intelligence and then trying to put instructions to a machine so it can process them and simulate our intelligence. Beating Kasparov wasn’t the result of powering up a machine and letting it learn on its own: on its own it would just sit there with a light on indicating power is passing through the on/off switch. People spent perhaps thousands of hours studying how chess experts approached the game and developed algorithms from it. I think of what they did as not so much artificial intelligence as collective intelligence in which the computer was just a medium.
Expressing ideas helps to form them. Indeed, helps is far too weak a word. Most of what ends up in my essays I only thought of when I sat down to write them. That’s why I write them… Just as inviting people over forces you to clean up your apartment, writing something that other people will read forces you to think well. So it does matter to have an audience. The things I’ve written just for myself are no good. They tend to peter out. When I run into difficulties, I find I conclude with a few vague questions and then drift off to get a cup of tea.
It’s tempting to judge what you read:
I agree with these statements, and I disagree with those.
However, a great thinker who has spent decades on an unusual line of thought cannot induce their context into your head in a few pages. It’s almost certainly the case that you don’t fully understand their statements.
Instead, you can say:
I have now learned that there exists a worldview in which all of these statements are consistent.
And if it feels worthwhile, you can make a genuine effort to understand that entire worldview. You don’t have to adopt it. Just make it available to yourself, so you can make connections to it when it’s needed.