I always liked Esquire‘s What I’ve Learned feature.  So, in response to a 16-year-old’s question  on one of the discussion pages I frequent, “what, I guess, life lesson or advice would you give to a regular 16-yr.-old, or your own younger self?” I put together this list.  I’m only 35, but here’s a collection of things that come to mind; either what I’ve learned, or what I wish I’d done differently.

Find a good woman (man, whatever floats your boat.) It likely won’t be the first one you run across. It very possibly won’t be the tenth one you run across either.

Have as few things as you can. Clutter keeps you down. Do you really need that? Then again, keep your dad’s watch.

Your parents (most probably) aren’t nearly as bad as you think they are. They were once your age too. Cut them some slack, humor them a bit. You won’t have that much time to hang out with them later.

As the man said, sex. Lots of it. And use a goddamm rubber.

You think you know everything. You don’t. Figuring out how little you know is actually a pretty humbling experience and the first step to knowing something.

Keep a cool head at all times.

Heinlein was right:  specialization is for insects.

If you ever get the feeling that some of your friends might be bums, they probably (but again, not necessarily) are.

Practice drawing people. If nothing else, it’ll give you something to smirk at when you flip through old notebooks.

Doubt everything anyone tells you. The more they claim to be an authority, the more you should doubt them. This doesn’t mean you should always ignore others, just do your own fact checking. Then doubt what you found while fact checking.

Clothes do, at least to some extent, make the man. Make sure you know how to shave, and when you want to have a decent haircut. Own at least one decent suit, tie, shirt and pair of dress suits. At worst, you’re not overdressed — everyone else is underdressed. Find a good tailor; sometimes, he/she is the wrinkled grandma sitting at the back of the Chinese laundry (mine was in college.)

Always be a gentleman.

Be curious.

Always take the moral high road. Then again, sometimes you have to pop the son of a bitch in the face.

More Heinlein, TANSTAAFL. Then again, sometimes there is.

Chivalry is not dead.

Learn to listen (my biggest weakness, look at me, I’m preaching to a 16-year-old.) Learn to express yourself.

Don’t give up the piano lessons.

You’re probably better than you think you are. Still, you’re probably nowhere near as good as you think you are.

Roman emperors in victory parades had a slave who stood behind them in their chariot, holding a laurel wreath over their heads, and continually whispering “thou art mortal, thou art mortal” in their ear.

Don’t be defensive towards people who’re easily offended.

Never underestimate the importance and value of reading absolutely insane amounts of books and learning seemingly random, inane facts.

Learn at least 2 foreign languages. Do it soon, it gets harder the longer you wait.

While you’re at it, go backpacking across the country. Then go backpacking abroad if you can. You most likely won’t feel like sleeping in gritty hostels when you’re over 25.

Buy a decent entry-level DSLR. Use it. A lot.

Back up your photos. Often. Back up everything else often as well. It will crash.

Buy a small, lightweight laptop and keep a journal.

Keep in touch with people, always.

Accept criticism graciously. If it’s negative, ignore it. If it’s constructive, consider it.

Make it a habit to smile at people. You get a lot more out of them.

It’s only money, there’ll be more of it.

Learn to care for your belongings.

Make it a habit to make lists of things to do, then do them.

Learn to cook. It’s not that hard, it impresses women (men, whatever), and if worse comes to worse, it’s an excuse to have a martini.

Don’t watch TV, it’s mostly crap.

Get as much education as you can as early as you can. Even if it’s not your thing, it will come in useful. And if it doesn’t, you can impress people with the diploma.

Many people are easily impressed by charlatans. Don’t be, and don’t become a charlatan.

Always read the fine print. Remember that the other guy’s out to make a living.

Then again, some people are just good at heart.

Think before you talk. What looks and sounds good on first glance may be ill-considered.

Organized religion is a crock. That shouldn’t stop you from learning about it, reading its literature and admiring its art. Then again, do whatever works for you.

Learn how to do some useful things that might be distasteful to you (shoot a gun, iron shirts, whatever.)

Ask yourself how the other guy sees things. That doesn’t mean he’s always right, but understanding his point of view can sure make things easier.

Learn a few hands-on trades (plumbing, car repair, painting, electrical work) — when the poli sci degree is useless, you can build things.

The law isn’t always right.

Don’t overpay for things. Let other people do that.

Appreciate beauty.

There are no absolutes, ever.

Yes, that last one was meant to be a joke.

But some things and ideas are just non-negotiable.

Learn to negotiate.

Cussing is a sign of a weak vocabulary. Then again, it can be mighty satisfying.

Nobody ever died of a hard day’s work.

Nobody ever lay on their death bed wishing they’d spent more time at the office either.

Don’t procrastinate. If there’s something you’d rather be doing and you can get away with it, go and do it and don’t apologize.

Don’t be afraid to do look ridiculous. If someone’s scoffing at you and you’re not hurting anyone, the other guy is probably (but not necessarily) not worth your time.

The guy you hate may become your best friend.

Learn to be wary of the slippery slope.

If you have five really close friends that you stay in touch with, you’re lucky. If you have ten, you’re exceptional. Did I mention stay in touch?

Develop a work ethic.

Learn to prioritize.

Be good to others, karma (usually) comes around. And if it doesn’t, you get to be smug about it.

Don’t be smug.

If all else fails, RTFM. Oh, and learn to read maps. I usually get there faster than my friends with a GPS.

Go to the dentist.

Experiment, but stay the hell away from anything harder than pot or booze.

Know your limits (you do have them.)

Get enough sleep and exercise, eat well and all that jazz, and keep doing it. Lack of sleep leads to the dark side.

Murphy was an optimist.

Don’t believe everything you read online, including long lists made by people who should have gone to bed but stayed up writing to-do lists out of some perverted sense of get-shit-done-itis.

Get off reddit, it’s a nice day outside.

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