Always Ask for a Small Coffee in a Medium Cup and 21 Other Pieces of Advice for My Sons

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Dear Boys,

Despite your brilliance and good judgment, you appear to have very little interest in my advice, either because you are too old for it (or you think you are, Declan) or you are too young for it (but not for long, Grey and Rye!). I, meanwhile, have a surplus of advice building up in me. I am like a lactating cow that needs to be pumped, or a pregnant sea turtle maybe. I need to get this advice out of me, and put it somewhere for safekeeping.

Be forewarned, not all of this is actually good advice … I am still learning and figuring things out. I am only 48, after all.

With no further ado, the first installment of my partially baked, unsolicited advice follows:

Begin Conversations With People on Airplanes When You Hear “We’ve Begun Our Descent”

If they prove to be fascinating, you will broaden your world; if they prove insufferable, it’s only 15 minutes. Uber rides and chairlifts provide similar opportunities — exposure to people you would not otherwise meet in controlled time periods.

Collect Words the Way Other People Collect Stray Cats, Tropical Birds, or Pokemon Cards

Words are pixels, they are units of thought; just as you can render more precise images with more pixels, you can communicate ideas more powerfully — and maybe even think more efficiently — with more words. This is why vocabulary is among the metrics most highly correlated with success. But don’t be pedantic — use big words sparingly, only when they are the perfect fit.

Develop Tastes and Habits

If you drink green tea without sugar 30 times, it will taste acrid and mouth-puckering the first 29 times, and on the thirtieth it will taste pretty good. This is true of everything … there is no activity or habit you can’t develop a taste for. So you may as well develop a taste for things (and people) that are good for you.

Habits Are for Lazy People

And you are lazy. We all are. Habits are shortcuts to getting a whole lot of things done without spending too much of your finite supply of willpower. So use ’em.

Embrace Your “Funny-Looking” Features

People don’t look bad in photos because they “aren’t photogenic” — they look bad in photos because they think they are better-looking than they are. Don’t be one of these people. Embrace and own the degree to which you are funny-looking. It gives you personality, and it will cause you to be pleasantly surprised by your reflection in the mirror now and then.

Use People’s Names Whenever Possible

When you forget someone’s name, ask them again and blame your dad for passing on bad-memory-for-names genes. Names are a door handle to a person; that small effort opens them up.

“Beer Before Liquor” Is a Myth

When it comes to hangovers, the problem isn’t mixing types of alcohol — its simply about how much you drink. That’s always been my hunch, and I just looked it up and it appears to be true. It’s extremely difficult to do accurate research with a sample size of one (though I am still working on it), and this results in a lot of inaccurate conventional wisdom.

Wear the Same Shirt Every Weekday

Find a shirt you like, and buy 8 of them. It will simplify your morning, and communicates to the world that you are focused.

Wear Funny Shirts on the Weekends

You know this about me, I like silly shirts. Shirts that express joy, and perhaps an element of self-parody. Seventies Givenchy. Mr. Bubble. The technicolored dream coat. Moods are contagious, and a mood can be sparked by a shirt. Humans, broadly speaking, take themselves far too seriously, and you, in your silly shirt, are an antidote.

Figure Out What Your Strengths Are and Build on Them

Become empowered with the knowledge that there is no such thing as a normal or even optimal brain type. I believe I have low level ADD — you may too. Attention deficit disorder is a misnomer — its a brain type that is inclined towards creativity, and selective deep focus, and I happen to love it. Neurodiversity is not an accident … there are a range of different brain types each of which confer advantages and disadvantages and contribute to society in complimentary ways.

Worth Is Relative

If peanut-butter could only be found in the placenta of a rare tropical bird, it would cost $1,000 per ounce. Sure, caviar tastes good, but so does peanut-butter. People are irrationally attracted to that which is scarce, because scarce things function as status symbols. If you understand the elements of human behavior that are irrational and predictable, you are freed from them and can benefit from the insight.

Respect Science

It’s not an ideology. It’s a system for limiting our crazy human inclinations toward bias and misperception, borne out of humility. Every time you get into a commercial airplane, you are betting your life on the scientific method. If a collection of science skeptics build an airplane and offer you a ride, don’t get in.

When Microwaving, Choose Random Numbers

Hit 66 seconds, 99 seconds, or 2:22 rather than even numbers. Why? Because 60 seconds is no more likely to be an appropriate amount of time to heat a cup of tea than 55 or 66 seconds. They are all arbitrary time periods. And you save a couple seconds. More important than the time savings is the ability to think for yourself.

Mentors — Even Highly Successful Ones — Are More Accessible Than You Think They Are

Seek them out. Identify the people who have climbed the mountains you want to climb before and cold-call them. They are accessible because mentoring is a form of therapy; we can’t give advice to our younger selves (this is quite frustrating), so instead we give advice to younger people and it feels good.

Always Give Money to Street Musicians, Even Bad Ones

Well, maybe not really bad ones, but the streets need more music.

When You Are Young, Poverty = Freedom, But When You’re Older, If You Have Kids, Money = Freedom

It makes it possible to do things you used to take for granted like sleep, read the newspaper, and see a little bit of the world. I am not saying money should drive your career decisions — quite the contrary, it’s not what matters in life. But it’s good to understand that your relationship to it will change.

Small Negotiations Are Practice for Big Ones

Engage in small daily negotiations as a form of learning. Almost everything is negotiable … I had heard this, but didn’t believe it was true until I met your mom. You have succeeded when the person with whom you are negotiating feels pleasantly surprised by their capacity for generosity. You win not when you get the best price, but when you do so while building a strong relationship.

When You Are at Starbucks, Ask for a Small Coffee in a Medium Cup

They will over-pour, and you will end up with just enough room for milk. And save 50 cents. This is a little hack; the world is full of them.

Always Tell the Truth

Not because it’s written on a stone tablet, but because it’s a better practice. I used to occasionally find myself bending the truth, but I decided to stop about 20 years ago for four reasons: humans have highly evolved abilities to detect dishonesty, even when they don’t understand how; sharing vulnerability and imperfection connects you to people; the truth is generally good for people even if it’s hard to say; and as it turns out, it’s less work — if you always tell the truth it’s easier to remember what you have said.

Lead With Your Weaknesses

Make fun of yourself. Not compulsively — this reads as insecurity — but in an honest, playful, friendly way. This makes people comfortable, creates trust, and counter-intuitively, it comes across as confidence.

Community, Broadly Defined to Include All Relationships With Other People, Is Everything

It’s not 60 percent of happiness, it’s 99 percent. Everything you think is important — success, building things, writing novels, gaining status — is important only insofar as it nourishes your current and future possible relationships.

Failure Is a Data Point

Whether it’s a failed jump shot, a failed relationship, a bankrupt company, or a scoop of ice cream falling off the cone, failure is data. Aspire to love data the way a father loves his sometimes obstreperous three boys: because of, not in spite of, imperfections.

If At All Possible, Have Kids

Children are extraordinary and infuriating, and among the most powerful human experiences available to us. Kids are a front-row seat to the most extraordinary of spectacles: the unfurling of a human life. Mommy and I are so lucky to have you boys … we are grateful every day. Having your own kids is also a good way to rediscover humility when you think you’ve figured it all out. And humility opens us up to powerful new experiences and relationships. Don’t have them too soon, or too late, and don’t underestimate the challenge, but for gosh sake have em, if you can.

Rufus Griscom is the father of Declan, 11, Grey, 8, and Rye, 5. He is also the co-founder of Heleo.com, 6 months, Babble.com, 8, and Nerve.com, 18.