I have always dreamed of winning a Pulitzer Prize. Laugh. Go ahead, it’s fine, because it’s never going to happen. The 2015 prizewinners will be announced tomorrow, and I will not be one of them. It may surprise you that I aspired to win the Pulitzer Prize in biography, not fiction or poetry. I wanted to take a fascinating, meaty subject, spend years in libraries poring over documents and letters, travel to where the subject lived, and write an inciteful, newly factual biography that changed the world’s perception of my subject. When I read biographies I always imagine the author’s process in detail. The research, the travel, the writing, the editing. For me, putting myself in the author’s shoes, seeing how they create the narrative web and introduce their research is part of the fun of reading a biography.

With a big birthday coming up later this year, I have been doing the expected reflection on my life and my accomplishments and lack thereof. Assessing the old bucket list. Crossing “Pulitzer Prize in Biography” right off there with a big bold black Sharpie. Last night I dreamt that the Dalai Lama and I were having a cup of tea together (meeting the Dalai Lama: also on the bucket list. It never happened, but I once attended a sunrise service that he led in Central Park). In the dream the Dalai Lama said to me, “Take two steps back.” That’s all: take two steps. Not one. Nothing more. I believe the cliché is to take “a step back and reflect on your life.” He didn’t say that, he just said to take two steps back. So now, as my coffee is perking this morning, I am wondering what he meant by two steps. By the second step, not just the first.

And I think I know.

Normally, in the whole bucket list assessment stage of life, people look at their lives thus far and make replacements. They take a step back and say to themselves, “I didn’t do X because Y happened, so I did Z and now I’m glad I did, I realize now I wouldn’t have been happy with X.” In my case, I had a lot of surgeries from my mid-teens until the end of my 30s. When I turned 40 I took one step back and determined that marriage and motherhood were apparently out of the picture for me, and settled down to accept that, even though motherhood had been an enormous dream for me, something I thought I could never live without doing. Fate intervened and I married the right guy at 41 and we now have a terrific teenage son. We knew each other and had gone on one date to a Grateful Dead concert in our teens. He was home from college for the summer, I was a rising high school senior. He went back to college, I moved on. A friend reintroduced us 24 years later. I remember sitting next to him on my couch that night so many years later feeling the immensity of our connection. It came over me: “Ah, so it’s going to be Ben Horowitz, the guy who lived around the corner and started an underground newspaper with his friends. After all these years, he turns out to be the one. Hmm. Cool.” They say that sometimes you just know, and I did. But I wish we had had those 24 years together. So does he.

I regret not listening to Hank Chapin, the literature professor who advised me to take education courses to become a licensed teacher as a “back-up” in case the whole poetry and academic thing didn’t work out. It didn’t. I ended up in bookselling and publishing. The bookselling years were among the best I’ve had. If I’d become the high school English teacher he envisioned, I would probably be retiring about now with a nice pension having spent wonderful summers on the beach in Cape Cod or traveling through Europe and Asia. I couldn’t admit it to anyone then, but I’ll tell you now why I didn’t become an English teacher: I was afraid I would have to teach literature I didn’t love. I didn’t think I could teach large sweeping novels by the likes of Dickens, for instance. I couldn’t get through Anna Karenina or Madame Bovary. What high school English teacher doesn’t revere those classics? I couldn’t tell my professor that I was a Lit. major fraud. Loved Huck Finn, hated The Old Man and the Sea. I slithered away, and took the wrong path.

I saw things in black and white, all or nothing. In our college years, before we get out in the “real world,” many of us naively think that we are going to spend our lives tending to our passions and nothing else. Boring adult jobs are for those who don’t know how to do it right. We know better. We won’t end up like the father in The Wonder Years who looks through his telescope in his backyard on clear summer nights and tells his son he doesn’t regret becoming a shipping manager instead of an astronomer. We would be astronomers! Into your starry eyes, baby! We would figure out a way to earn a living doing what we loved, changing the world on an inspired high every single minute. I wish I had had the maturity to realize that although I might have been compelled to teach A Tale of Two Cities, I would probably have also been able to teach Walden and the transcendentalists, and that would have made it worthwhile. It’s not all or nothing. I was too stupid to see that.

And that’s where I think the second of the Dalai Lama in my dream’s steps comes in. Step one could be to conclude that I didn’t become a high school English teacher but I did end up in a wonderful career in bookselling and publishing. Except that I didn’t. There were about ten or more years in there that were pretty horrific. And I have most certainly not taken a 25-year retirement package. Now, as managing editor of a small scholarly press I can say that I enjoy most aspects of what I do every day, and the inspired moments outweigh the drudgery of assessing author’s royalties and approving invoices. I am lucky to have a boss who encourages creativity and intellectual analysis. I haven’t written a groundbreaking book on a major biographical subject but my work did afford me the opportunity to contribute some new scholarship to the field of legal history in the book The Unsigned Essays of Supreme Court Justice Joseph Story. I’m delighted to have been able to identify and publish some writings of the great legal mind that were originally published anonymously. But I would have preferred to have written a Pulitzer Prize winning biography of Louisa May Alcott or Elizabeth Cady Stanton or Edgar Allen Poe.

It didn’t work out better in the end. I did something good, but it is not what I wanted and still want to do — and now won’t be able to do because there isn’t enough time left.

I have regrets, yes, I have a few. If the first step is to accept one’s failures, I think the Dalai Lama of my dream was telling me that the second step is to forgive myself. You have to do a lot of work and step back a lot further to get to that sweet spot of true forgiveness. You can’t rationalize anymore, you have to take responsibility for the wrongs. First you are angry with yourself, you don’t want to forgive yourself, you want to be mad. You want to wallow in the regret. You acknowledge that it’s bad, that you screwed up, and that you are going to die and will never have a chance to do those things you didn’t do. You have to own your mistakes, feel like crap about them, beat yourself up over them, and then you can let them go. Don’t just cross them off the list, erase them. Start a new batch of items on your bucket list that you can probably achieve and go to your grave not hating yourself for if you don’t accomplish them. I’m working on my new list now. I’ll let you know how it goes.

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