How to 'Stay Hungry, Stay Foolish:" Fixing Steve Jobs Commencement Advice

With just about every Apple product I’ve bought, from my first Mac—a 512, I go way back almost to the beginning—to the iPad2 I got last week, just opening the box filled me with optimism. In my hands was this great new thing that was really going to change my life; happiness, organization, efficiency, and, yes, even a little coolness were just around the corner. Sometimes, like with my iPad, even before turning it on I’d marvel at the sleek contours and fully expect that I too would soon feel myself to be a sleek hipster riding the crest of the future.

But, it was not to be. While these devices have changed how we all live in so many ways, my feelings always adapted to the new functions and experiences so that soon I pretty much felt like the same me I’d always been. Of course, there’s always some residual hope that maybe all that happiness would come with the next upgrade.

Same thing with loss. We adapt. Shock, sadness, grief all dissolve in time, like a drop of oil in soapy water. That doesn’t mean those feelings aren’t meaningful and painful, they surely are. It’s just that they won’t last. Since saddened by Steve Jobs’ tragically early death, I’ve been watching public grief and thinking about what will last, what do we get to keep after we emotionally adapt to the loss of a creative visionary, what remains after the flickering touch-screen memorial candles go out and the make-shift memorials in front of Apple Stores are cleared to make room for more commerce.

What will last is what works, and what of his works is more than just the “insanely great” things he built. He didn’t just leave stuff, he left inspiration. And of a particular kind. Steve Jobs inspired people to make things work. And in that spirit of making it work and thinking about what will last, I’m going to take his now iconic 2005 Stanford commencement address and, well, fix the psychology. I’m going to do to it what he did with so many prototypes: make it work (links to full speech at end).

He memorably closed his speech by advising graduates to follow the advice Stewart Brand offered when Brand finished the final edition of The Whole Earth Catalog: “Stay Hungry. Stay Foolish.” Great advice. Psychologically sound, and with inter-generational poetry.

But how to do it? How to stay hungry, stay foolish? Framed by his brush with death, he advised his listeners to make the most of our time on the planet. He counseled eager graduates to look in the mirror each morning and ask themselves whether or not they were living the life they wanted:

“When I was 17, I read a quote that went something like: “If you live each day as if it was your last, someday you’ll most certainly be right.” It made an impression on me, and since then, for the past 33 years, I have looked in the mirror every morning and asked myself: “If today were the last day of my life, would I want to do what I am about to do today?” And whenever the answer has been “No” for too many days in a row, I know I need to change something.”

However moved and inspired I was—and am—by his comments, when I put on my geek hat and read this as a procedure to follow rather than just inspiration, I find that it might just not be the best way to achieve the goal. We need to fix the algorithm and really ask whether anyone would really be able to “Stay Hungry. Stay Foolish” by checking in with themselves each morning during water rituals. And the answer is, probably not. In fact, he got the psychology wrong in two important ways, ways that are easy to fix and, once fixed, can help make his inspiration last beyond the immediate moments of either techno-optimism or sadness and grief.

The first problem is doing an existential audit in the morning before what is being audited actually happens. We’ve learned that people are terrible predictors of their own happiness. Trying to say in advance whether or not one would want to do what one is about to do is an activity that will inevitably yield profoundly unreliable information. It’s biased by what psychologist Daniel Gilbert has called the “impact bias,”  i.e., our human tendency to predict (imagine?) that future emotional experiences will be more intense and last longer than they really will.

What this means on the positive side of the emotional ledger is that we expect experiences—like that new iPad2 or that new job or that ice cream—will make life feel better than it really will. You may be looking forward to knocking it out of the park at an afternoon meeting, but the prediction will feel better and last longer than the actual experience.

And we do this with negative feelings as well, often to our detriment. In fact, sometimes the most satisfying, richest experiences are those that have significant “start-up costs.” Perhaps you avoid completing some mundane task because you expect doing it will feel much worse than the experience of actually doing it will prove to be. Then you get stuck in a loop of procrastination. Or, you choose not to engage with some potentially meaningful experience, preferring the quick-and-easy instead, because you predict getting started will be much more difficult than the actual experience proves itself to be.

Luckily, there’s a fix. A much better strategy for staying hungry, staying foolish would be to evaluate your day at the end, to ask Steve Jobs’ question in the past tense: “If today were the last day of my life, would I be grateful to have done what I did today?” Of course, memory is not perfect. But it is more accurate than imagination.

Second, isolated introspection is an over-valued and highly unreliable road towards self-knowledge. You really don’t want to look in the mirror as a way to conduct your existential audit. Learning how many days of not being grateful are too many is pretty much impossible when it is just you and your reflection. Psychoanalysts (Eisold) and cognitive scientists (nicely reviewed in recent books by DiSalvo and Herbert) have described how our minds use various strategies, biases, and heuristics to make our way in the world. And these processes make the mirror one of the last places where you should look for self-knowledge.

For example, we overestimate the importance and power of recent experiences. You might have had a pretty great day.  But if it ends with a frustrating, annoying experience, the recency of that experience might lead you to think the entire day was sort of a wash. Another bias is that we overestimate the value of those experiences that are most perceptually salient. We act as though the loudest is the truest. So, even if you had a pretty great day, a loud argument with a loved one might cause you to undervalue an interesting day spent in the flow of good work.

Again, there’s a fix. Don’t do it alone. Any existential audit that has a chance of being appropriately accurate needs a partner. Self-knowledge happens in dialogue, not isolated introspection. Sometimes, because of language, that other person does not need to be there in the flesh. They can even be present as the author of a book, or an imagined reader for those who like to write. Sometimes it can even be in an interior dialogue with an imagined other. But sooner or later, you’ll need intimate dialogue with an actual other person if you want to know yourself.

Todd Esig - Forbes