When I was nineteen I went to Yale.

Before you get too impressed, I should clarify. When I say “went to Yale,” I mean, I took a bus to New Haven, walked to the Yale campus, located the freshman women’s dorm — where my girlfriend, who unlike me was an actual matriculated student there — and moved in. For the next few months I could be observed skulking about the campus with my cello, scoping out empty rooms where I could practice for an hour or two. (My mother dubbed me “the Yale ghoul.”)

This arrangement worked out quite well, until the dean sat down with me for a friendly chat, during which he pointed out the unavoidable facts of my circumstances — namely that I was a) not a freshman, b) not a woman, and c) not enrolled at Yale — and suggested I might consider seeking residence elsewhere.

Which I promptly did. I found an apartment eight or ten blocks away, out behind a little hair salon in a distinctly dicey neighborhood. I moved in on a Friday. That weekend there were two stabbings and a shooting right across the street.

Ah, youth.

They say “youth is wasted on the young,” but I’m not sure that anyone but the young could survive it. It still amazes me that I did so, and relatively intact, given that there were so many choices made and actions taken in my twenties and thirties that in retrospect seem … how shall I say this gently? Monumentally unwise.

This is a perspective that Ellis Boyd “Red” Redding (played by Morgan Freeman) faces during a parole hearing in that most wonderful film Shawshank Redemption:

“I look back on the way I was then: a young, stupid kid who committed that terrible crime. I want to talk to him. I want to try to talk some sense to him, tell him the way things are. But I can’t. That kid’s long gone, and this old man is all that’s left.”

I’ve often wondered what that conversation would have looked like, what words Red would have used to “talk some sense to him, tell him the way things are.”

What would I say, if I had the chance to talk to my nineteen-year-old self? I think I would say five things:

1) Listen more to your gut, and trust what you hear there.

In my youth, I had a hard time distinguishing between gut sense and passion. Passion is a wonderful thing. But making life decisions by following your passions is a little like picking your drunkest friend to put behind the wheel of your car.

I was typically too driven by a sense of urgency to stop, get quiet, and explore what the core of my being was saying. I was in too much of a hurry to do the next thing.

When Tom Hanks was asked what he would say to his twenty-year-old self, he replied, “Floss.” Then he thought for a moment and said, “Calm down. You’ll get there.” I love that. Calm down, quiet down, and listen to your bone marrow.

The second thing I’d tell my younger self:

2) Listen less to your head, and don’t be so quick to trust what you think you know.

One resource that was never in short supply, when I was young, was certainty. It amazes me how often I was absolutely sure I was right, and how often that turned out not to be true. (As Eve says about Adam, in Twain’s The Diaries of Adam and Eve, “He knows a great many things … but they are not so.”)

And the third thing:

3) Take more time with important decisions, and listen to the advice, or at least the perspective, of the people who love you the most and have known you the longest. If what they say makes you uncomfortable, listen harder.

“Question authority” is a popular thing to tell the young. This is a message I would not have needed to hear; I already questioned authority, probably more than was wise. Arbitrary or self-important authority, I would still question. But sometimes the people who know more actually do know more.

I would also say this:

4) Write more!

It was at age nineteen that something I wrote was published for the first time. (This was an article in the magazine East West Journal.) But somehow it didn’t occur to me then that I was “a writer,” or even that being a writer was something you could actually do. It would be decades before I saw this as a possible career path.

In the meantime I did all sorts of other things. I drove a taxi in Boston, taught kids to play the recorder in Philadelphia. Played cello recitals and did Shiatsu massage therapy. Started businesses. And I edited other people’s stuff. That last one, I did a lot. What I didn’t realize was its actual purpose: it was training me to write my own stuff.

If I could talk to my younger self, I would tell him that writing deepens and improves who you are.

Or maybe that’s not quite accurate. Perhaps it’s that the practice of writing clarifies and brings to the conscious surface some of the stuff inside that would otherwise have remained inchoate, unarticulated, unused. As Joan Didion wrote, “I write to find out what I think.”

Which leads directly to the fifth thing I’d say to my younger self:

5) Read great writing.

If writing deepens who you are, reading great writing deepens what you write.

Back in 2003, at the suggestion of my best friend (and now wife) Ana, I read Steinbeck’s East of Eden. The experience was exactly the way my father described my big brother Adrian’s first encounter with chocolate at the age of two: “His look of puzzled curiosity gave way to an expression of shock and then sublime transfiguration, a look that said, ‘Why didn’t anyone TELL me about this before?!’”

I’d read tons of nonfiction over the years, but very little of anything I’d call great writing. Now I became fully engaged in the joy of reading.

In the years since, I’ve gobbled and slurped up hundreds and hundreds of great books. (My absolute #1 favorite of them all: Kate Atkinson’s Behind the Scenes at the Museum, nearly due for a fourth read.)

Those five things: that’s what I’d say to my nineteen-year-old self, if I could.

And perhaps I still can.

Because I disagree with Red when he says, “That kid is long gone, and this old man is all that’s left.” I think that kid is still alive and well, inside the old man disguise.

I think youth never goes away; it just settles into your interior crevices and speaks more in whispers than in shouts. But it’s there, your younger self, eager as ever to take big bites out of the world.

So what would you tell your nineteen-year-old self?

Once you’ve identified what that message is, then go ahead and deliver it. Your nineteen-year-old self is in there, listening.