So I’ve been signing my name the same way for a long time. All lower case letters, a la e.e. cummings. But for various reasons I’m thinking I need something new. For one thing Jerry York says all lower case letters is an affectation. “Look, if you were in high school and going through a phase or something, fair enough, I could see it. But Steve you’re 52 fucking years old, right? Time to grow up and start using capital letters.”

Normally I wouldn’t listen to anything Jerry York says but I’m in this period of deep reckoning, questioning everything about my life. This options stuff has struck a nerve deep inside me. Who am I? Where am I going? Why am I doing what I’m doing? Is this what I want to do? I’m spending lots of time on reflection and introspection. I’m reinventing myself. And to do that, I need a new signature.

I’ve been working on this since January, sometimes putting in grueling five-hour days, just signing and signing, using fountain pens, Bic pens, Mont Blanc pens, different color inks, different shades and grades of paper — anything that could free up my creativity and help me harness my immense intellect to this task. I’ve covered the walls of my office with signatures, even covering up all the photos of myself, so I could just have all these hundreds of signatures around me and let them speak to me and tell me which one should win.

I’ve also asked Jon Ive and his team to come up with some ideas. They’re pissed cause they’re supposed to be working on new iMacs but look, first things first. So they’re giving me lists of ten at a time, which I take to the Tassajara room and non-think about for several hours until I can choose an emergent design, which I tell them is shit but they should use as the starting point for the next round. Lately they’ve been dragging their heels.

Last week, to light a fire under Jon and his guys, I brought in this Japanese design firm, Kuso Sukatoro Associates. So far everything they’ve done is shit. What do I want? Something strong and bold, egotistical and arrogant and self-centered but also modest and humble. Minimalist. Less loopy than the current signature. I hate that “b” in jobs. It looks fat. Same for the lower case “s” in steve. And I don’t like the slash over the j. Should be a dot. I don’t know. I’ve tried a million things. I’m just racking my brains here. Back in March I was a hundred percent sure that I should go with just initials, and I worked up a zillion different models, like, SPJ, and SJ, before realizing I’d gone down another blind alley and that in fact I wanted to go with full words after all, and it was back to the drawing board.

Groan. I guess I’m obsessive. But at this point in my life I’m keenly aware of being judged by history. That’s a very cool thing but also a huge burden, to think that every little thing I do is going to be judged and measured and remembered for centuries to come. It’s something that all great artists must come to grip with after they’ve attained success. You become very self-conscious. It can be very daunting and even stifle your work. You have to find a way to be as free and daring and crazy as you were back in the early days when nobody knew who you were.

Anyhoo, like everything I do, I’m bringing huge amounts of effort and creativity to this signature project. I’m sure we’ll come up with something really beautiful and perfect and it will just be the coolest and most amazing signature that anyone has ever had in the history of the world. But for now I’m in that part of the project where you just struggle and search and you’re filled with self-doubt. Well, must go. Our Pilates instructor just arrived for the Sunday workout.