On Friday, I had the tremendous honor of being awarded a Doctor of Letters degree from Simmons College, and giving the Commencement address at the Simmons graduate students’ ceremony.

Simmons is an inspiring place, and not only for its deep commitment to educating women. Being honored this way — especially along with Ruth Ellen Fitch, Madeleine M. Joullié, and Billie Jean King — made me very, very happy.

Thank you so much to Simmons College, President Drinan, and the Board of Trustees for this honor, which means the world to me. I’m just awed by it. Also, Professor Candy Schwartz and Dean Eileen Abels, a special thank you. And this honor is extra-special meaningful because my father-in-law, Marvin Geller, is here today, and his sister, Jeannie Geller Mason, was, as she called herself, a Simmons girl, class of 1940. Afterwards, Marvin will be happy to sing you the old “We are the girls of Simmons C” college song if you ask.

So, first, to the parents: I have been in your seat, and I know how proud – and maybe relieved – you are. So, congratulations to you. And to the students, it’s such an honor to be here with you to celebrate your being graduated from Simmons College, a school that takes seriously the privilege of helping its students not only to become educated experts, but to lead the next cohort in their disciplines and professions.

Now, as I say this, I know that some of you may be shaking your inner heads, because a commencement speaker is telling you about how bright your futures are, but maybe you have a little uncertainty about what will happen in your professions and with your career. That’s not only natural, it’s reasonable. But, some of you – I don’t know how many — may be feeling beyond that an uncertainty about your own abilities. You’re being officially certified with an advanced degree in your field, but you may not quite feel the sense of mastery you expected.

In other words, you feel the way I do now. And the way I did in 1979 when I got my doctorate in philosophy. I knew well enough the work of the guy I wrote my dissertation on, but I looked out at the field and knew just how little I knew about so much of it. And I looked at other graduates, and especially at the scholars and experts who had been teaching us, and I thought to myself, “They know so much more than I do.” I could fake it pretty well, but actually not all that well.

So, I want to reassure those of you who feel the way that I did and do, I want to reassure you that that feeling of not really knowing what you should, that feeling may stay with you forever. In fact, I hope it does — for your sake, for your profession, and for all of us.

But before explaining, I need to let you in on the secret: You do know enough. It’s like Gloria Steinem’s response, when she was forty, to people saying that she didn’t look forty. Steinem replied, “This is what forty looks like.” And this is what being a certified expert in your field feels like. Simmons knows what deserving your degree means, and its standards are quite high. So, congratulations. You truly earned this and deserve it.

But here’s why it’s good to get comfortable with always having a little lack of confidence. First, if you admit no self-doubt, you lose your impulse to learn. Second, you become a smug, know-it-all and no one likes you. Third, what’s even worse, is that you become a soldier in the army of ignorance. Your body language tells everyone else that their questions are a sign of weakness, which shuts down what should have been a space for learning.

The one skill I’ve truly mastered is asking stupid questions. And I don’t mean questions that I pretend are stupid but then, like Socrates, they show the folly of all those around me. No, they’re just dumb questions. Things I really should know by now. And quite often it turns out that I’m not the only one in the room with those questions. I’ve learned far more by being in over my head than by knowing what I’m talking about. And, as I’ll get to, we happen to be in the greatest time for being in over our heads in all of human history.

Let me give you just one quick example. In 1986 I became a marketing writer at a local tech startup called Interleaf that made text-and-graphic word processors. In 1986 that was a big deal, and what Interleaf was doing was waaaay over my head. So, I hung out with the engineers, and I asked the dumbest questions. What’s a font family? How can the spellchecker look up words as fast as you type them? When you fill a shape with say, purple, how does the purple know where to stop? Really basic. But because it was clear that I was a marketing guy who was genuinely interested in what the engineers were doing, they gave me a lot of time and an amazing education. Those were eight happy years being in over my head.

I’m still way over my head in the world of libraries, which are incredibly deep institutions. Compared to “normal” information technology, the data libraries deal with is amazingly profound and human. And librarians have been very generous in helping me learn just a small portion of what they know. Again, this is in part because they know my dumb questions are spurred by a genuine desire to understand what they’re doing, down to the details.

In fact, going down to the details is one very good way to make sure that you are continually over your head. We will never run out of details. The world’s just like that: there’s no natural end to how closely you can look at thing. And one thing I’ve learned is that everything is interesting if looked at at the appropriate level of detail.

Now, it used to be that you’d have to seek out places to plunge in over your head. But now, in the age of the Internets, all we have to do is stand still and the flood waters rise over our heads. We usually call this “information overload,” and we’re told to fear it. But I think that’s based on an old idea we need to get rid of.

Here’s what I mean. So, you know Flickr, the photo sharing site? If you go there and search for photos tagged “vista,” you’ll get two million photos, more vistas than you could look at if you made it your full time job.

If you go to Google and search for apple pie recipes, you’ll get over 1.3 million of them. Want to try them all out to find the best one. Not gonna happen.

If you go to Google Images and search for “cute cats,” you’ll get over seven million photos of the most adorable kittens ever, as well as some ads and porn, of course, because Internet.

So that’s two million vista photos. 1.3 million apple pie recipes. 7.6 million cute cat photos. We’re constantly warned about information overload, yet we never hear one word single word about the dangers of Vista Overload, Apple Pie Overload, or Cute Kitten overload. How have the media missed these overloads! It’s a scandal!

I think there’s actually a pretty clear reason why we pay no attention to these overloads. We only feel overloaded by that which we feel responsible for mastering. There’s no expectation that we’ll master vista photos, apple pie recipes, or photos of cute cats, so we feel no overload. But with information it’s different because we used to have so much less of it that back then mastery seemed possible. For example, in the old days if you watched the daily half hour broadcast news or spent twenty minutes with a newspaper, you had done your civic duty: you had kept up with The News. Now we can see before our eyes what an illusion that sense of mastery was. There’s too much happening on our diverse and too-interesting planet to master it, and we can see it all happening within our browsers.

The concept of Information Overload comes from that prior age, before we accepted what the Internet makes so clear: There is too, too much to know. As we accept that, the idea of mastery will lose its grip, We’ll stop feeling overloaded even though we’re confronted with exactly the same amount of information.

Now, I want to be careful because we’re here to congratulate you on having mastered your discipline. And grad school is a place where mastery still applies: in order to have a discipline — one that can talk with itself — institutions have to agree on a master-able set of ideas, knowledge, and skills that are required for your field. And that makes complete sense.

But, especially as the Internet becomes our dominant medium of ideas, knowledge, culture, and entertainment, we are all learning just how much there is that we don’t know and will never know.

And it’s not just the quantity of information that makes true mastery impossible in the Age of the Internet. It’s also what it’s doing to the domains we want to master — the topics and disciplines. In the Encyclopedia Britannica — remember that? — an article on a topic extends from the first word to the last, maybe with a few suggested “See also’s” at the end. The article’s job is to cover the topic in that one stretch of text. Wikipedia has different idea. At Wikipedia, the articles are often relatively short, but they typically have dozens or even hundreds of links. So rather than trying to get everything about, say, Shakespeare into a couple of thousand words, Wikipedia lets you click on links to other articles about what it mention — to Stratford-on-Avon, or iambic pentameter, or about the history of women in the theater. Shakespeare at Wikipedia, in other words, is a web of linked articles. Shakespeare on the Web is a web. And it seems to me that that webby structure actually is a more accurate reflection of the shape of knowledge: it’s an endless series of connected ideas and facts, limited by interest, not an article that starts here and ends there. In fact, I’d say that Shakespeare himself was a web, and so am I, and so are you.

But if topics and disciplines are webs, then they don’t have natural and clear edges. Where does the Shakespeare web end? Who decides if the article about, say, women in the theater is part of the Shakespeare web or not? These webs don’t have clearcut edges. But that means that we also can’t be nearly as clear about what it means to master Shakespeare. There’s always more. The very shape of the Web means we’re always in over our heads.

And just one more thing about these messy webs. They’re full of disagreement, contradiction, argument, differences in perspective. Just a few minutes on the Web reveals a fundamental truth: We don’t agree about anything. And we never will. My proof of that broad statement is all of human history. How do you master a field, even if you could define its edges, when the field doesn’t agree with itself?

So, the concept of mastery is tough in this Internet Age. But that’s just a more accurate reflection of the way it always was even if we couldn’t see it because we just didn’t have enough room to include every voice and every idea and every contradiction, and we didn’t have a way to link them so that you can go from one to another with the smallest possible motion of your hand: the shallow click of a mouse button.

The Internet has therefore revealed the truth of what the less confident among us already suspected: We’re all in over our heads. Forever. This isn’t a temporary swim in the deep end of the pool. Being in over our heads is the human condition.

The other side of this is that the world is far bigger, more complex, and more unfathomably interesting than our little brains can manage. If we can accept that, then we can happily be in over our heads forever…always a little worried that we really are supposed to know more than we do, but also, I hope, always willing to say that out loud. It’s the condition for learning from one another…

…And if the Internet has shown us how overwhelmed we are, it’s also teaching us how much we can learn from one another. In public. Acknowledging that we’re just humans, in a sea of endless possibility, within which we can flourish only in our shared and collaborative ignorance.

So, I know you’re prepared because I know the quality of the Simmons faculty, the vision of its leadership, and the dedication of its staff. I know the excellence of the education you’ve participated in. You’re ready to lead in your field. May that field always be about this high over your head — the depth at which learning occurs, curiosity is never satisfied, and we rely on one another’s knowledge, insight, and love.

Thank you.

Categories: education, experts, too big to know dw