Dear 16-year old self,

At 47, I have no pretensions of being a wise man. Because as Hunter S. Thompson, that godfather of gonzo journalism, whom I worship, wrote so eloquently: “To give advice to a man who asks what to do with his life implies something very close to egomania. To presume to point a man to the right and ultimate goal—to point with a trembling finger in the right direction—is something only a fool would take upon himself."

That said, I couldn’t help but think of what my friend Dr. Rajat Chauhan keeps articulating in so many different ways. The other day, for instance, he tweeted, “Failure is inevitable. It’s about having the persistence to beat the pulp out of failure."

It got my attention and I asked him to make a signed poster out of it that I may frame and keep in my room.

That is why I know what you feel right now. With the kind of scores you have managed in Class XII, you will never make it to medical school. I know you want to go there real bad. So, it’s okay to cry. And feel those tears running down your face. I want you to hurt. Not just hurt, but hurt real bad. I want you to embrace failure, make it your best friend, and learn from it.

That said, there are three instances I want you to particularly fail in as you grow up—love, friendships and work.

I understand I may sound ridiculous to you right now. But let’s face it.

That object of your affection whose hand you hold right now exists only in fairy tales. Even as she consoles you and tells you the both of you can carve a life out in some pretty corner of the world, don’t forget you are only 16, much like she is. Don’t hate me for saying this. What you are experiencing right now is puppy love. I am not suggesting here you ought not to experience it. Everybody ought to. But it won’t last. You know why?

Because right now you are in love with the idea of love. I wish I could explain that as eloquently as John Steinbeck, one of my favourite writers, did in a letter to his son:  “There are several kinds of love. One is a selfish, mean, grasping, egoistical thing, which uses love for self-importance. This is the ugly and crippling kind. The other is an outpouring of everything good in you—of kindness and consideration and respect—not only the social respect of manners but the greater respect which is recognition of another person as unique and valuable. The first kind can make you sick and small and weak but the second can release in you strength, and courage and goodness and even wisdom you didn’t know you had.”

It is a rare set of individuals who find the second kind of love when they are as young as you are.

So, I want you to go out there and get your heart broken a few times, until you find that somebody who can extract goodness out of you—of your own free will. Trust me, the road to finding this kind of love is a painful one. It is inevitable the one whose hand you are clinging to now will move on as will you. It is also inevitable you will find true love. But brace yourself for heartbreak on the way to it.

Because, as David Whyte writes in Consolations, “Heartbreak is how we mature; yet we use the word heartbreak as if it only occurs when things have gone wrong: an unrequited love, a shattered dream… But heartbreak may be the very essence of being human, of being on the journey from here to there, and of coming to care deeply for what we find along the way…. There is almost no path a human being can follow that does not lead to heartbreak.”

And when you do find love, respect it and cling to it.

Much the same can be said of friendships. It is a myth that deep and meaningful relationships are forged in your formative years. The fact is, over time, you outgrow them. The friends you have in your teens are very different from the ones you have in your 20s, 30s and 40s. As you search for meaning, with every decade, you will morph into a different animal and will seek bonds that fit the animal you are then.

By way of example, I can think of this gentleman I met the other day, now in his 60s. There was nostalgia and tears in his eyes as he reminisced about his friend from 40 years ago who sought him out for counsel every other day. Time changed things between them. His friend has gone on to larger things and doesn’t need his counsel any more. His attention has turned instead to others with a larger perspective whom he looks upon with awe and seeks out.

I understand the tears and the nostalgia. But they are rooted in the past. You swear now by friends who roar to Metallica and Guns N’ Roses. But trust me . When you discover the pleasures of Paul Simon, the serenity of Beethoven and the comfort good single malts offers over Old Monk rum, you will wonder how you air-guitared at alcohol-soaked, pot-filled concerts all night long.

And while I am at that, another word of advice from a now world-weary man—never, never touch a cigarette a friend offers. It may seem cool and you may look like a wimp if you decline. But the real wimps are the ones who smoke. I know. I’m still paying the price for having indulged in it.

When it comes to work, there is this tussle you will be engaged in. Allow me to assure you once again, like most people, you are destined to fail if you don’t give yourself the room to think through and introspect. Who do you want to be? What is your calling? What are your priorities?

But the exigencies, such as money, that life imposes will push you towards a path often trod by most people. Like I did when looking for a job. Entrepreneurship wasn’t my calling. It was an accident. That it turned out to be a lucky accident and eventually my calling is an altogether different matter. It is entirely possible, though, that you may not get as lucky. That is why I want you to dwell on this passage from The Road to Character by David Brooks.

“I’ve been thinking about the difference between the résumé virtues and the eulogy virtues. The résumé virtues are the ones you list on your résumé, the skills that you bring to the job market and that contribute to external success. The eulogy virtues are deeper. They’re the virtues that get talked about at your funeral, the ones that exist at the core of your being—whether you are kind, brave, honest or faithful; what kind of relationships you formed.

“Most of us would say that the eulogy virtues are more important than the résumé virtues, but I confess that for long stretches of my life I’ve spent more time thinking about the latter than the former. Our education system is certainly oriented around the résumé virtues more than the eulogy ones. Public conversation is, too—the self-help tips in magazines, the non-fiction bestsellers. Most of us have clearer strategies for how to achieve career success than we do for how to develop a profound character."

My final submission to you is, the earlier you can think of a eulogy to yourself, distanced from the exigencies of life I spoke of earlier, the better off you will be for it.

Much love,

Your 47-year-old future self