A few months before my daughter was born, I started jotting down notes for her. Nothing formal, little more than anecdotes, stories or examples - the good, the bad and the ugly. They were initially strewn all over the place; some were captured in To Do apps, others in stray text files or scribbled in a Moleskine notebook. Part lessons learned, and part personal and familial history. Something in the spirit of Mark Oliver Everett's "Things the Grandchildren Should Know," I thought of it very loosely as a "User Manual" for life, the one that I was never handed.
Eventually I consolidated the various fragments down and discovered that I had something close to 18,000 words of advice for my unborn daughter. I never got around to finishing the project, let alone publishing it. First, because how does one “finish” a user manual for life? Second, because it would be years before she could even read, let alone digest the advice I had to give. But the main reason it sat incomplete was simple: because I assumed that I had plenty of time to finish it.
Best case, this is still true.
In the months before the end of his life, Ulysses S. Grant was diagnosed with cancer of the throat. The condition was not curable. In spite of the cancer's accelerating progress, the impact of which made it difficult for him to eat or swallow and made him feel as if he was perpetually choking, he wrote furiously. He viewed the memoirs as his final task, the commercial means by which to provide for his family once he was gone, and labored at them on that basis.
He died five days after they were completed.
Enduring the excruciating pain that came to define his life, he devoted what time he had left to documenting his experiences. The speed at which he produced pages, sometimes approaching fifty per day, was proof of the will that defined the man. The final work, in the end, was worthy of that effort. Grant’s memoirs were a masterpiece. Well received by contemporaries, no less an authority than Mark Twain compared them favorably to Caesar's Commentaries. They have stood the test of time and are appropriately regarded as one of the true masterpieces of American non-fiction.
I bring all of this up not for the sake of comparison, of course. My health, unlike Grant's, is fine for the moment. Nor have I any hope of this project being commercially viable, let alone providing for my wife and daughter. This is a labor of love, literally. And I hope that it goes without saying that I have no intention of implying any equivalence between Grant's observations and what follows. He was the Union General who accepted the surrender of Robert E. Lee, thus closing the chapter on the darkest period in the history of the United States, as well as the President arguably most responsible for Reconstruction, and his memoirs were a vital, definitive account of American history. I am a software industry analyst who works for a small firm few have heard of and these are random thoughts I scribbled into a notebook in the frenzied weeks ahead of my child's birth.
Also, I would strongly prefer not to die five days after I publish this.
Grant's memoirs nevertheless have come to mind often for me in this period of unprecedented uncertainty, because of the mathematics of the outbreak that is gaining speed as I write these words. COVID-19 is not a death sentence for my particular demographic, but neither am I obviously in the clear. The virus has killed people far younger and healthier than I am, and because there's more that we don't know about than that we do, the uncertainty means that only the foolish take it lightly. The virus is dangerous, but what makes the outlook even less promising are the limitations of our healthcare system’s ability to scale. Doctors in Italy have had to make decisions they will carry the rest of their lives, forced by a lack of equipment to choose who shall rise and who shall not. It is not certain that that is our fate here in the United States generally or Maine specifically. Neither is it clear that it will not be.
In such times, the operative phrase is memento mori.
In doing just that, I came back both to the scattered words of advice I had written down for my daughter as well as to Grant’s famous efforts to beat the clock. If I were to contract the serious form of this disease, there is no guarantee that I would have the window that Grant did. This suggests that the labor of love needs to be completed before a potential infection, as there may be no after.
The below then is at best imperfect. It’s not even as perfect as I can make it, but as they say in the industry I have found an unexpected home in, “perfect is the enemy of good.”
By way of introduction, let me quote Umberto Eco wildly out of context: “these features cannot be organized into a system; many of them contradict each other.” The following features are, however, strategies that have worked for me.
Some I was born with. Others I learned on my own, often through hard lessons. More frequently the points below are what I might have learned from family, friends, coaches or mentors if I had been willing to listen. If I hadn’t, in the typical manner of the young, been convinced that I already knew everything and that what I might not I could figure out. What follows are lessons that I’ve collected over my years on this earth from people who have accomplished more than I will, that are smarter than I am or that are just fundamentally better people. It is, in short, what I wish I had known when I was younger, and what I would go back to tell my younger self if such a thing were possible. There may be lessons or history in here that could be of use for you, Eleanor, if you decide to be open to them.
No guarantee there, of course - I was young once. But it’s worth a shot. You can’t quite read yet as I write these words, my little bear, but this is for you, for when you’re ready.
This is the way.
“Far and away the best prize that life has to offer is the chance to work hard at work worth doing." - Theodore Roosevelt
Growing up dirt poor in South Boston, my grandfather on my Mom’s side - named Theodore after Teddy Roosevelt - had guidance counselors who were so convinced that they could get him into Harvard and that his intelligence deserved it that they made the long trip out to visit his parents in their home to sell them on the idea.
It was not to be.
His status as the eldest son meant he had to pass on higher education to go to work to provide for his mother and his brothers and sisters. He was never bitter or resentful about this opportunity denied him, this turn in his life. He went to work in the shipyard and did his job. He taught his daughter, your grandmother, to do the same. She, in turn, married a man with the same philosophy.
Your mother, incidentally, fits this description to a T. No one works harder.
Anyway, when my grandfather passed away, we waited an appropriate period and celebrated his life. Many people talked about him and his impact on their lives. My Mom, as is typical, gave the best talk. It was a simple, powerful and poignant list of what she had learned from her Dad. We were there to celebrate, but everyone wept terribly as she spoke, myself included. I asked her later for a copy of what she’d written. It included this line:
“His knee jerk response to any challenge or setback was to simply put his shoulder to the wheel and try harder; as a result he accomplished just about everything he set his mind to.”
It is what is expected of you. You do your job, you do it to the best of your ability, you do it without complaint, and you don’t expect a gold star for that. We will never celebrate Father’s Day, as one example, because my job is to be your father and we do not believe in holidays for doing your job.
Your job will not always be what you want to do. Some of your jobs will be unpleasant. Some will be actively miserable. This is not relevant. You do your job anyway because that is what we do. Whatever your job is, you will work like a dray horse. Many things in life will be out of your control. Your effort level is not one of those things.
I don't ask you to always be the best. I simply ask that you always do your best.
‘"It is not the strongest of the species that survives, nor the most intelligent that survives. It is the one that is the most adaptable to change." - Charles Darwin
I apologize in advance, but you’re going to hear a great many things in your life related in some way to baseball. Things that really have no business being related to baseball.
This is one of those things.
When you listen to the Red Sox games, and you’ll be doing that a lot (sorry), you’re going to hear baseball talked about as a game of adjustments. A player has success, the league adjusts to him. The player then adjusts to the league’s adjustments. Which then adjusts back. This process continues until a player’s ability to adapt is sapped by old age and he retires, or the player is retired prematurely by the league.
Your life will be the same. The only thing you can predict with certainty about it is that it will be beyond your ability to predict it. Your way of life may become obsolete. Your relationship may end. You may get injured or sick. You may have your car impounded twenty-two hundred miles from home in the middle of nowhere.
Whatever life holds for you, your job is to deal with it. To display adaptability. In nature, if you don't adapt, you die. The consequences will hopefully be less dire if you fail to do so, but material nonetheless.
You may want to focus on how unfair it is, say, that you have to seek a new profession when yours becomes obsolete. That is pointless. If you need to bitch and moan, make it quick. Your grandfather had to reinvent himself four or five times in his time in finance, but then again this was the same man who taught himself to play tennis with his off hand after breaking a wrist and made it to the state semi-finals that way.
As Arthur Ashe put it, “Start where you are. Use what you have. Do what you can."
Show adaptability, in other words.
"I don’t like bullies; I don’t care where they’re from." - Captain America
Because I’m a poor and unimaginative storyteller at heart, your bedtime stories as a child cribbed liberally from a wide variety of sources. Everything from Jules Verne to Marvel Movies to Scooby-Doo made appearances in the various adventures of Puppy, Kitty and Noble Raccoon. One of your particularly favorite lines, however, was Captain America talking about bullies.
I can't tell you how many times you made me play that clip for you; I half-expected to get an email from YouTube asking if my excessive viewing was a cry for help.
Initially, the intent was to use Captain America as a mechanism for both introducing you to the idea of bullies and steering you away from that path. What became obvious when you began repeating this mantra to yourself at night when talking to your stuffed animals, however, was that you took it seriously. So seriously that the stuffed animals who were “bullying” your other stuffed friends were roughly treated and put forcefully into "body breaks."
Which was good, first because you were literally a head taller than all of your preschool friends and could easily have taken advantage of that. But more because we intended to raise a kind little girl. One who not only didn’t bully her friends but helped them stand up to bullies. One who didn’t laugh at their mistakes. One who gave them a hand up when they fell. And one who thought as much about others as she thought about herself.
All of which you’ve done, so keep it up.
”Don’t worry about the level of individual prominence you have achieved; worry about the individuals you have helped become better people. This is my final recommendation: Think about the metric by which your life will be judged, and make a resolution to live every day so that in the end, your life will be judged a success.” - Clayton Christensen
There’s a saying in business that if you can’t measure it, you can’t manage it. This may or may not be true; W. Edwards Deming, the source most often credited for the quote, certainly believed the opposite. For our purposes, it doesn’t matter. What is true is that measurement is important. And that to measure, you need to understand what you intend to measure with.
When I speak to college students today about their post-college careers, most of the advice I provide has little to do with their career path or salaries or possibilities. It’s to understand, or work towards an understanding of, what makes them happy.
With some distance this is obvious, of course. You’re much more likely to be successful doing something that makes you happy than something that makes you miserable. But it’s surprising how easy it is to lose this when you’re in the middle of making these decisions. Life can come at you fast, and it’s easy to focus on what you think you should do at the expense of what you want to do.
If money makes you happy, so be it. If it’s having fun, likewise. If helping other people is what drives you, so much the better. As your father, it is not my place to assign you a motivation, but rather try to make sure you understand what your motivation is, and more importantly, the tradeoffs involved. If you focus on making money, you may sacrifice time with friends and family, for example. If you choose a path that allows you to do what you love, you may have to adjust your material expectations downwards to accommodate.
Understanding what makes you happy, and how you might measure success, guarantees neither. But it can’t help but inform your decision-making process so that you have a better chance of getting there.
Or at worst, being happier along the way.
Over the course of my career, I've spent about five nights on the bench seats at the O'Hare airport. I've had to sleep at the office maybe half a dozen times. I've almost been laid off twice and actually been laid off once.
All of which in the professional world means I've had things pretty easy. My friends who went into investment banking out of college slept at the office ten times a month in their first few years. As for airports to be stranded in, O'Hare's not the best, but it's far from the worst. And one layoff is a streak of luck these days.
Still, none of the above was fun, exactly. When you’re at work at two in the morning and people are screaming at you, or when you get a call in the middle of a meeting with a client in Dallas to inform you that you no longer have a job, life could be better.
What can be useful at such times is to have a fixed point on the horizon. Something to hang on to, something to look forward to, where mundane or major. Vacation. Seeing a good friend. A date (not until you’re old enough). A new record from your favorite band out Saturday. A trip to the islands next weekend. Snow, maybe, next month. Whatever.
You might not be able to successfully visualize laying on the beach or sitting in the bleachers at Fenway when it’s the middle of the night and everything’s on fire around you, but every second you're looking forward to something is a second that you're not dealing with the crisis of the day.
“If you have one true friend you have more than your share.” - Thomas Fuller
A lot of people you’ll meet use the term friend casually, and apply it indiscriminately to everyone in their social circle. I have no problems with this approach, and there are certainly merits to assuming friendship and good intentions, but it is not an approach that works for me.
If I use the term friend with intent, it is rare, purposeful and has a very specific meaning. If I call someone a friend, I expect them to be there when I need them.
You will be friendly with many people throughout your life. People you grow up with. People you go to school with. People you work with. Many of them - most of them if you’re lucky - will be reasonable, good people. Some will be fun. Some will be interesting. Some will simply be the least bad alternative.
Unless you’re exceptionally lucky, however, you will have a much smaller number of actual friends. In my experience, the difference between a friend and an acquaintance is simple and comes down to convenience. Acquaintances are there for you when it’s convenient for them. Friends are there when it’s not.
When you’re young, this might mean remaining friends with someone unpopular or uncool at school. As you get older, it could be being there for someone who’s lost a job, gotten divorced, had surgery or been sick. It may mean, though hopefully not until later in life, being a friend to someone who’s dying.
There is nothing easy about visiting a friend with a terminal illness, which is why acquaintances don’t do it. Your job as a friend is to be there when your friend needs you, no exceptions. If they’re sick, you visit them. You do what you can for them or their family. What you don’t do is say, “it’s too hard, I can’t.”
In most cases, the stakes will be lower. If your friend is moving, for example, you show up five minutes before they ask you to, throw some hustle at it and you stay until they’re done. If your friend had a relationship end but isn’t up to talking, you sit with them in silence so that they don’t have to be alone. If they lose their job and can’t afford the rent, you take them in. If they get too drunk and end up throwing up in a toilet, you sit with them and hold their hair.
If all of this seems like a lot of responsibility, that’s because it is. It’s why most people don’t have many true friends. When you find someone that you care about enough to be there for, and that you know will be there for you, cherish that person and that relationship. Be prepared to sacrifice for it though, because if you’re only there for someone when it’s convenient for you, you can only expect the same in return.
One of the things that businesses strive for - mostly because it’s fantastically lucrative financially - is a monopoly. By virtue of honestly earned success, illegal market manipulation or, more frequently, some combination of the two, competition is eliminated. Absent competition, companies wield immense power, and can essentially dictate terms to customers, suppliers and partners.
They get their way in all things, in other words.
The funny thing is, over the long term, this is bad for the monopolist. With competition, companies are forced to evolve, to innovate - to compete. In a world with no challengers, these normal market incentives are depressed or eliminated entirely. Which leads to stagnation, laziness and decline.
What’s true for companies is also true for people. There’s a reason the very wealthy say appallingly dumb things. It’s the same reason that wildly successful writers eventually churn out poor material: there’s no one in a position to tell them “what were you thinking?” People who get their way and operate unchecked are universally poorer for it.
It’s important to know your mind and to know what you want. It’s unhealthy, however, to always get that. Look for balance, people to challenge you, press you and encourage you to try things you don’t like - or think you don’t like.
Companies who always get their way inevitably behave in ways that negatively impact the market around them and, counterintuitively, the company itself. People who get their way are just as unfortunate. Don’t be that person.
“I am certain that there is too much certainty in the world.” - Michael Crichton
If you’re reading this, you’ve been told a great many things by this point. About yourself, about life, about the world around you. Many cultures would encourage you not only to accept what you were told as the gospel truth but would punish you for questioning it.
You are fortunate to not live in one of these cultures. Accepting something you have been told without question requires faith, and faith is - in my opinion, at least - dangerous. The fact is that a sizable percentage of what you are told will not be correct. Some will deliberately lie to you for their benefit. More often, people will pass along untruths because they believe them to be true.
With the exception of the Red Sox, I hope that you will take very little on faith. That you will instead question everything. Why are you being told this? What are the facts behind it, so far as they’re available? How might those facts have been selectively chosen to put one position in a better light?
Always ask yourself the question: is this true? Or is this simply the way things have always been done?
Nor does it end there. Even if you’ve taken the time to consider the available evidence and make a rational choice, new evidence may emerge. You must be intellectually flexible enough to willing to change your mind, even if that idea is unpopular. As Keynes said, “When the facts change, I change my mind. What do you do, sir?”
Because of everything you know to be right and true, only some is.
“Self-sacrifice? But it is precisely the self that cannot and must not be sacrificed.” ― Ayn Rand
If you grow up to admire Ayn Rand, I’ll be disappointed and I will think of myself as having partially failed my job as your father in some unknown but critical way. Many of the most important relationships in your life will be defined by sacrifice. One of the ways that you know someone is important to you will be your willingness to put their needs in front of your own.
Or even their life in front of your own.
Your family understands this. One of your great-grandfathers took care of his wife, without complaint, every day of her life following an Alzheimer’s diagnosis. Another great-grandmother did the same for her husband following a stroke. Your grandparents on both sides made uncountable sacrifices so that their kids, your Mummy and I, could have an opportunity at a better life, just as their parents did before them. Each generation made these sacrifices because they understood that’s what love means.
Understanding this means being selective in your relationships, of course. Surround yourself with people who understand this and are willing to equally make sacrifices on your behalf, not people who want to take advantage of you.
“The diseases which destroy a man are no less natural than the instincts which preserve him.” - George Santayana
The funny thing about most of the major mistakes I’ve made in my life, personal or professional, is that I knew, on some level, that they were mistakes beforehand. Even in some cases where a particular decision looked fine on paper, part of me just felt wrong.
It could be argued that this is confirmation bias, that I’m selectively remembering only the cases that confirm this perspective. But I don’t believe that: there is a perfectly logical explanation for this phenomenon. People take in an enormous amount of information, but when it comes to making decisions and conscious thought, you’ll probably consciously recall only a fraction of the relevant details. Your instincts, however, are operating on all of the information. Trust them.
There have been many times something didn’t feel right, but as I couldn't articulate why, I overruled my instincts. In every case, I regretted it - which is bad. Worse is the fact that I knew, on some level, that it was wrong and did it anyway. Even if it isn't great at showing its work, your brain is looking out for you. The trick is listening to it and not letting anything else - internal or external - distract you from its counsel.
If something just feels wrong - even if you can't say why - steer clear. The odds are strong that your brain has put things together that you haven’t been able to process yet.
"All of life is peaks and valleys. Don't let the peaks get too high and the valleys too low." - John Wooden
When I was in my twenties, I had an unhappy couple of months. In order, a girlfriend of over five years unexpectedly and abruptly broke up with me, then I was laid off from a job that I liked and finally, the apartment in South Boston I was living in was sold out from under me. So I went from having a good job and living together with a girlfriend in a nice apartment to single, unemployed and homeless in a span of time measured in weeks.
I didn’t get over any of those experiences instantly, but neither did any of them sink me.
First, because the majority of people in this world had a much harder life than me. At the same age that I was at the time, my father had been shipped halfway around the world to be shot at, had been emergency airlifted to see his brother because the latter was badly wounded and nearly killed in a rocket attack, and had had cancer twice. By comparison, my life just wasn’t that bad. My issues were in the grand scheme of things mundane, painful as they might have been at the time.
Second, because while I had lost someone important in my life, good friends remained. My best friend, your Uncle Andrew, was there when I was unexpectedly single. My friend Leigh, who spoke at our wedding, gave me a place to stay when I had no place to live. My parents supported me financially, to bridge me to my next job. And so on. The point is that I was never on my own; there was always someone there for me.
Last, because I was fortunate enough to have a choice. As Sean Connery once put it, “I spent a lot of my life being miserable. Then one day I thought, I’m here for the day, I can enjoy the day or not. I decided I might as well enjoy it.”
I was never a PollyAnna: I didn’t get up and think everything was sunshine and roses, I simply tried - and try to this day - to even out the bad and the good.
This approach is, admittedly, not for everyone. It may not be for you. And even if it is for you, it will irritate some of the people in your life who want you to ride the roller coaster with them, who want you to be more emotional than this approach allows for. But I’ve avoided bottoming out even during trying circumstances by trying to remain even-keeled. Emotional volatility is common. That doesn’t make it inevitable, or preferable.
When good things happen, appreciate them, celebrate them or cheer them, but don’t get carried away. (Unless the Red Sox win the World Series - in that case, go nuts).
Conversely, when bad things happen, learn from them and move on. Don’t bottom out; always remember that “this too shall pass” isn’t just a phrase that originated with Persian Sufi poets.
There will be times, of course, when you won’t be able to keep yourself on that even path when you’ll stray. This is unavoidable. As soon as you’re in a position to do so, simply nudge yourself back on course.
This approach is a lot more manageable than most people think. You may not always be able to control a situation, but you can control how you view it.
One of the things you’ll discover as you get older is that different people and, just as importantly, different cultures have very different expectations concerning time. In Argentina, for example, showing up on time for a dinner party is equivalent to arriving an hour early in the United States - which you should, as an aside, never do.
Examples like that notwithstanding, however, we aim to be early in our family. Part of the family attributes this to the time that your great-great-grandfather spent on General Patton’s staff during the Second World War, but wherever it came from it's part of this family, and thus who you are.
If you’re traveling - particularly if airports are involved - it reduces stress and gives you a cushion in case of unexpected delays. If you’re meeting a friend or colleague, it’s common courtesy. Some people will interpret your tardiness as a sign that you believe your time is more important than theirs. It’s not, so don’t inadvertently give them this impression.
You don’t have to be quite as extreme as your grandfather, who had us at my cousin Sarah’s wedding a full three hours early. But you’re an O’Grady, so for you on time is late.
“You think that you're too cool for school, but I have a newsflash for you Walter Cronkite...you aren't.” - Derek Zoolander
They’re fewer and farther between in Maine than in some other places you’ll visit, but sooner or later you’re going to meet people who think they’re better than other people because they make more money. Live in a nicer neighborhood. Have a particular job. Are smarter. A better athlete. More attractive. Whatever.
These people are called assholes. Unless your mother and I utterly fail you as parents, you will not be one of them.
If you pick any region of the world, in any time period, the odds are very good that you will find that people stratify into classes. These may be dictated by economics, religion or some other combination of factors, but history says there will be haves and have nots, there will be upper and lower classes and - if things get too out of control - there will be revolution.
That’s as may be. On an individual level, there’s basically zero you can do about the intrinsic human tendency to form multi-layer, complex social constructs to operate within. What you can do, however, is not buy into them personally.
In practical terms, this means that you are not better than someone else because of the job you have, the money you make, the house you live in, the car you drive or what you believe. You are a descendent of a family that donated large swaths of the land Philips Exeter sits on, a Governor of New Hampshire, a US Senator from Maine, a doctor who helped found the hospital you were born in, and the brother of one of your ancestors signed the Constitution of the United States. But you are also a descendent of shipbuilders, fishermen, factory workers, several Protestant ministers, janitors, soldiers, something called a “rigger,” and a laborer great-great-grandfather that helped dig the Panama canal and shot a rather large crocodile while he was there.
As an O’Grady, what someone does for a living is a lot less important to us than how hard they work at it, so if you ever act like you’re better than someone, I’ll be disappointed.
I can’t express this any better than Randall Munroe did, so I won't try.
By the time you read this, I hope that you’ll know where that quote comes from. Or you can just Google it. Even if you don’t, however, the lesson is an important one.
The word deserve is a morass, one that most of us struggle with in some fashion. Some more than others. You might meet people, for example, that believe they deserve certain things in life - typically very expensive things - simply because. Others might believe they deserve something because their job is hard or because their day was long.
Either way, as Admiral Ackbar would say, it’s a trap. The idea that you deserve something is a particularly pernicious mechanism for self-justification, often employed to rationalize the purchase of things we can’t afford or the consumption of things that aren’t good for us.
Some of this is inevitable. A lot of it is harmless. But entitlement is a very bad habit to get into. Be wary, then, any time you find yourself thinking, “I deserve this.”
Along the way, you’re going to meet people who regularly lose their car keys, their phone, their wallet or items of similar import. Depending on which of those it is, the consequences range from inconvenient to potentially disastrous.
The simplest way to address this is via a routine. Place a bowl or a box near your front door. When you get home, empty your pockets of wallet, keys and so on into the bowl. It takes essentially no time to make this routine, assuming it’s placed within reach of the door, and you'll always know exactly where everything you need is.
Sounds simple, but it works: I honestly couldn't tell you when the last time I couldn't find my wallet was, and in all likelihood, it was because you “helpfully” moved it somewhere. Even better, routine can be extended into many other areas of your life. You might have a pre-travel ritual. One for writing, or painting, or athletics. More than likely you’ll have a lot of them.
Variety, as they say, is the spice of life. The more areas of your life that you can put on autopilot via routine, however, the more time you have for that spice.
This was a habit I picked up from my friend Alex King, who you will sadly never have the opportunity to meet. Here’s how he put it:
“I wanted to pass on another nugget I’ve learned about how to approach and define problems: working backwards. I’ve found this to be useful in both technical and business situations and I use it all the time.
Basically, start with the end result you want, and figure out how to get there from here. If you can’t define the desired outcome, then step one is getting to that point.”
In this case, he’s talking about it as a business or technical approach, and it’s very useful in that context. But the truth is that it works just as well in your personal life. Understanding what you want and need out of a relationship, for example, makes it much easier to work towards that.
Or consider this for your career. Many adults find themselves lost, adrift and unhappy with their job. I was one of these people.
When I graduated from college, I had no idea what I wanted to do, so I simply took the best job that was available to me, which was in consulting. After doing this for some years, it became clear that it was unfulfilling and required a willingness to travel that I did not possess.
While paying the bills with consulting, then, I worked backwards from what I knew I didn’t want, which was full-time travel. This led me to apply for industry analyst jobs, which leveraged my existing work skills as well as my liberal arts background but importantly asked significantly less travel of me.
Step one to determining your path, then, is to decide what, precisely, you want - or, as in my case, don’t want. By understanding that at a fundamental level, it’s possible to create a plan to get where you want to go. But the last part is the key.
Whenever you find yourself struggling or without direction, it’s worth taking a step back to make sure you understand what direction you want to head in.
Another of my friend Alex’s favorite sayings, this is important given the fact that you're going to make mistakes. I love you and think you’re the world’s greatest human, but at some point, you’re going to be a young person and when you’re a young person you will be, at some point, an idiot.
With that said, there are three important things to remember about the mistakes you will make.
First, try very hard to make sure that none of them are catastrophic. Do not ever drink and drive, for example. Most mistakes are recoverable, at least to some degree. Avoid the ones that aren’t.
Second, forgive yourself for the mistakes that you do make. Beating yourself up relentlessly for past errors is a waste of time. If you’ve learned your lesson, doing this is pointless and likely to lead to more mistakes in the future. Let these mistakes inform your path moving forward, but otherwise just let them go. Move on.
Last, of course, make better mistakes tomorrow. Learn from what you did wrong today and try and make new and improved mistakes going forward.
“If you can’t fly then run, if you can’t run then walk, if you can’t walk then crawl, but whatever you do you have to keep moving forward.” - Martin Luther King Jr
Life is, in some respects, like driving in the snow. If you stop, it’s easy to get bogged down and stuck. If you’re in motion, as the second law of motion states, you’ll tend to want to stay in motion.
There will be periods in your life when you feel lost or adrift. In the best-case scenario, as discussed above, you work backwards from what you want. Should you not know that, however, the best thing you can do is simply pick a direction and head that way. You’ll have to overcome the initial inertia, the tendency to want to stay at rest because stagnation tends to perpetuate itself. But by setting yourself in motion, you can avoid stagnation while opening up paths you could not have foreseen otherwise.
So just keep moving. Even if your progress is minute and barely measurable, it’s still progress.
“My older brother was trying to get a report on birds written that he'd had three months to write, which was due the next day. We were out at our family cabin, and he was at the kitchen table close to tears, surrounded by binder paper and pencils and unopened books on birds, immobilized by the hugeness of the task ahead. Then my father sat down beside him, put his arm around my brother's shoulder, and said, "Bird by bird, buddy. Just take it bird by bird." - Anne Lamott
You may have days where it’s tough to get out bed. Something bad happened in your personal life. Maybe it’s a pile of work that seems insurmountable. You’re paralyzed by choices, none of which are good.
Whatever the cause of this inertia, the solution is to do one thing. Seriously, that’s it. If that one thing is the only thing you accomplish in a day, well, it got you out of bed. And one thing is better than zero.
But more likely, after you do this one thing, you’ll be able to do one more thing, and another after that. The basis of this trick, of course, is simple. Big things can seem impossible. A small thing is always achievable. Focus on the possible, then, and let the impossible take care of itself.
One of the things you may discover at some point is that there are some things that once said, cannot be taken back. You can apologize, you can attempt to make amends, you may even ask for and be granted forgiveness. Time will always from that point forward be divided between before and after those words, however. You cannot go back to the world before, that’s gone.
The goal is to never say something like this - the question is how. The solution, in my case, has been to not get to the point where something like that comes out of your mouth. If you feel yourself losing control, walk away. Remove yourself from any conversation in which you may say something you don’t mean because some damage cannot be repaired.
You’re a frighteningly bright and animated kid, but what your adult personality will ultimately be isn’t clear. We have clues, here and there, but whether you’re introverted or extroverted, bold or cautious, rule follower or rule breaker are things we’re looking forward to finding out.
What’s important, however, is that you come to understand these things, because they’ll help you optimize your life.
It was apparent to me very early along, for example, that while I was friendly with a great many kids, I was genuinely close to a much smaller number. As I got older and learned about concepts like Dunbar Numbers, this made sense: I was a better friend and happier myself when I invested more of my time and attention with a smaller number of people. Translated, this meant a fewer number of closer friends. If I tried to be tight with a larger number of people, I was stretched too thin.
This is what works for me, and I’ve oriented my life around this fact. What works for you may be the same. It may be different. In either case, the key is knowing what you need and optimizing your life accordingly, lest you find yourself with social habits that don’t match your personality.
One of my Mom’s favorite phrases when your Uncle Kick and I were growing up was “You act like the world owes you a living.” This meant nothing to me at the time because I was too young and dumb to think it through.
It was just something Mom said from time to time.
Today, I get it. The context was always that we were being lazy and not helping out, that we wanted something that we hadn’t earned or both. That we felt like we were entitled, in other words, just for showing up. All these years later, I understand what she meant: we behaved, on occasion, like entitled little brats.
My Mom considered it her job, therefore, to disabuse of us this misguided notion, swiftly and with extreme prejudice. In fact, the world owed us nothing and if we didn't swim we'd sink.
If your mother and I are very fortunate, you won't have this problem. If you do, well, now you know what I'm going to tell you.
"As we grow older and realize more clearly the limitations of human happiness, we come to see that the only real and abiding pleasure in life is to give pleasure to other people."- P.G. Wodehouse
Their admirable efforts to dramatically limit the wealth passed on to their children notwithstanding, it seems probable that Mark Zuckerberg or Warren Buffet’s progeny will be granted financial resources that you will not. And while I hope like hell this is no longer the case by the time you enter the workforce, as I write this, women can expect to earn considerably less than men for the same job.
In spite of that, however, you are born into some measure of privilege. Your parents are both educated. Your parents both work. Your parents are both involved and active in your life. You have a stable home and enough to eat. Your parents have medical coverage. You were born a fan of the only baseball team to win four World Series championships this century. And so on.
This all means that you have responsibilities - noblesse oblige.
Specifically, you are obligated to help those less fortunate than yourself. How, and in what form, is up to you. Whether you donate experience, money, time, or all of the above and who you choose to help are all questions that you have to answer for yourself.
But there are billions of people born less fortunate than you, and for that reason you are indebted to them.
One summer when I was in high school, I was fortunate to attend a summer camp which included a trip on horseback over the continental divide. On the bus up to the ranch where we were to link up with the guides, a couple of us were talking about horses.
My own experience with them was, in general, not good. In almost every case, I get along very well with animals. Horses, not so much. I had very little exposure to them, and what I had was not positive. My seatmate had no more experience with them than I did, but for whatever the reason was intent on not getting stuck with "a shitty horse.”
The guides asked each of us about our level of experience with horses. My seatmate claimed that he rode regularly, and enjoyed a spirited ride. They gave him an impressive but temperamental mount named Jupiter. I told the rancher that I’d basically never been on a horse but that they tended not to like me. They gave me a mare named Sunday, who was one of the better horses of the lot but also had a patient, sweet disposition.
Twenty minutes into our trek, Jupiter bolted off the trail, bucking my seatmate off in the process. He broke his collarbone in the fall and they took him out in an ambulance. His trip was over. Sunday, meanwhile, carried me over the divide letting me steer when I wanted to and simply following the horse in front of her otherwise. I was sad to say goodbye to her. I gave her an extra piece of apple, she licked my hand.
Pretending to be something you are not is a bad idea, one that can get you hurt. Even if there’s short term downside, being honest upfront is worth it. Ask your Mom about our first date sometime.
My first job out of college was as a consultant. The first project I was staffed on, I worked with a man named Angelo. Like many of the other men and women on that particular engagement, he was nearing retirement and counting the days despite a difficult personal life which involved being the sole caregiver for his elderly mother. On top of this, he was quirky. If you’ve seen Office Space by the time you read this, Milton would give you a pretty fair idea of what Angelo was like.
The easy thing would be to dismiss him as dead weight. He had less than no interest in learning how to use even something as basic as Microsoft Office, little use for tools we were creating like an incident and procedures database and most of the applications he was charged with were closer to retirement than he was.
Angelo had a truly unique skill, however: he could read the hex dump from a DOS/VSE mainframe as if it were English. He could look at a seemingly random pattern of characters spread over dozens of pages, in other words, and tell you that you had a bad loop on line 42.
This kind of thing has happened a lot in the years since I started working with Angelo. People’s skills and abilities are not always obvious, and you never know when someone you’re tempted to write off will bail you out.
So don’t write them off. It really does take all kinds.
Generally speaking, being curious is regarded as a positive character trait. Same with being brave. Or funny.
Any of these, however, can become a weakness. Curiosity can make it difficult to respect people’s boundaries. The brave can take silly, unwarranted risks. And in certain contexts, humor can be seen as a lack of sincerity, gravity or respect.
This is not to say that you shouldn’t be curious, brave or funny. If you’re any or all of those, it will speak well of you. It is worth remembering, however, that whatever your strengths turn out to be, in a different context, on a different day, they can quickly become liabilities.
You may or may not be able to change this, but understanding that your strengths may not always be strengths can at least help mitigate the damage.
You will be told otherwise, and society may at times make you feel that this is not the case. But one of the saddest things you will see in this life are people who trap themselves in terrible, destructive relationships because the alternative - being on their own - terrifies them. Even in circumstances where this doesn’t lead to verbal or physical abuse, it’s a recipe for an unhappy life.
My hope for you is that you will be independent and content on your own. If you choose to share your life with someone, let it be on your terms and for the right reasons, not because you can’t stand on your own two feet.
“I'm always learning something. Learning never ends.” - Raymond Carver
“Is not life 100 times too short for us to bore ourselves?” - Friedrich Nietzsche
When my brother and I were little kids, we were sitting around our grandparents' house on the Cape one sunny summer day doing absolutely nothing, waiting for something to entertain us. One of us made the mistake of telling our grandmother that we were bored. She wasted absolutely no time lighting us up, all but physically kicking us out of the house with the reminder that there was a great big wide world out there to explore, and consequently that there was no reason that we should be bored. Ever.
She was right. There are so very many things to learn. In or out of the classroom, you should be learning everything you possibly can on every subject, because you never know when it will be useful.
I never had any interest in knitting, for example, because that “wasn’t what guys did.” A friend of mine fell for her now-husband, however, because he knit her a hat. I wish I’d spent more time learning to ski, meanwhile, because the first time I went with your Mom I fell on the first run and later ended up skiing backward down a hill almost giving myself a concussion in the process (which reminds me: wear a helmet).
Besides the utility of a wide range of knowledge and experience, learning will make your life more interesting. The more you know about anything, the more interesting it becomes.
Never, ever let me hear you say that you’re bored.
Dating back at least to the days of the Pharaohs, the golden rule is a basic, bedrock social principle across a wide range of cultures and religions. It can also get you into serious, serious trouble.
The reason they call it the Golden Rule is that it seems completely foolproof: treat people like you yourself would wish to be treated. What could be more reliable?
But there’s a reason that it’s the “Golden Rule” and not the Diamond Rule or Platinum Rule. What they usually fail to mention about the Golden Rule is that different people generally want to be treated differently. What is a kindness to you may be cruelty to another.
Many years ago, long before I met your mother, I was dating a girl from Williams and decided to do her the kindness of not inviting her to a family wedding. For one, my experience at that point was that they were lengthy tedious affairs, and for another family - particularly extended family - can be problematic. Unfortunately for me, but predictably in hindsight, the reaction I got was the opposite of the one I had expected. Instead of being elated at being spared the drama of a family wedding, my decision was received as a terrible signal, a sign that I either didn’t take our relationship seriously, that I was embarrassed by her, or worse, both.
Instead of being happy, as I’d hoped, she was crushed. Which everyone I’ve relayed this story to said, “Of course she was.” But if you’re strictly operating according to the Golden Rule, you can miss the potential for damage.
There’s not much you can do about this, unfortunately, except to be mindful of the rule’s limitations. In general, it’s a fine strategy, but always remember that you may need to make adjustments based on differing expectations.
“Terror made me cruel.” - Emily Bronte
For at least a decade now, our country has been grappling with an irrational, damaging and entirely disproportionate fear of terrorism. Even though the average person is more likely to win the lottery or be hit by a meteorite than be killed in a terrorist act, the majority of US citizens are sadly subservient to this fear, and willing to trade their liberty for an imagined, but impossible in fact, security. Which means that they deserve, as Benjamin Franklin said, neither.
You might think this kind of bizarre over-reaction to horrifying but statistically very rare events would be unprecedented. Perhaps an unfortunate byproduct of the information age, in which, as John D MacDonald might put it, “everyone knows everything too fast and too often and too many times.”
Unfortunately, this has happened before. Many times. Not content with one Red Scare, we manufactured a second. Before Communism, anarchists were the boogeyman. The list goes on, because people in the aggregate are, counter-intuitively, easily frightened, and when they’re frightened, they’re stupid. As I write this, China and its citizens are the new targets thanks to that country's unfortunate status as the origin point for the pandemic which has brought the world to its knees.
This is a serious problem. As Franklin Roosevelt noted, fear is most certainly something to be afraid of. Fear makes us cruel. It short-circuits rational thought. Fear leads to the internment of Japanese-Americans. Calls to ban Muslim travel. And, as the history of the Jewish people attests, even more horrific crimes.
What you must always remember is that after the initial shock wears off, being terrified is a choice that you make. You can live your life in fear, and accept the poor decisions that result from that, or you can be like the people of London. During the blitz during the Second World War, the city saw an average of 160 people killed per day, every day, for better than eight months. Their reaction? Keep calm and carry on.
Refusing to be terrorized will not always be the popular choice. It will always, however, be the correct one.
Remember how I told you too many things would be compared to baseball? Let’s talk some more about baseball.
In the first half of the 2015 Red Sox season, David Ortiz - playing at age 39, and who I made sure you see play in his final game - put up a batting line of .231/.326/.435. Hopefully, by the time you read this, you’ll understand what that means, but just in case you’re fuzzy on the whole good/bad thing, that’s bad. Your Mom and I attended a Q&A event that spring with one of my heroes, Peter Gammons, and he reluctantly acknowledged that it was possible Papi was done.
But as Ortiz was fond of saying, it’s not how you start, it’s how you finish.
Which is what they call foreshadowing. In the second half, Big Papi surged to life, closing out with a .325/.401/.701 line - which on the good/bad scale is somewhere up near transcendent. He ended 2015 with an OPS+ mark of 140, which in English means that despite his miserable start, he finished the season having hit 40% better than the average major leaguer that year - a mark that placed him eighth in the American League.
You may have occasions where you stumble out of the gate. On a team, at work or in a class. You have two choices at that point. You can get discouraged, and let the poor start infect your attitude moving forward.
Or you can remember that it’s not how you start, but how you finish.
It took me far too long to learn this lesson, but with any luck, you’ll be better than I am. Like everyone else, I have strengths and weaknesses. But with notable exceptions, I was far too accepting of the latter.
Particularly in this day and age, there are very few things you can’t learn to some reasonable level of competency. I used to grill so infrequently, for example, that I had no idea what I was doing (Uncle Ferd’s father once asked me while I was grilling if I wanted to give up and order pizzas because my efforts were such a disaster), and to not kill people with undercooked meat I defaulted to overcooking everything. As it turns out, however, you can look up things like how long to cook a given piece of meat, and how to check to see if it’s done. Just because you’re bad at grilling doesn’t mean that you have to be.
Talent plays a role, of course, and there will be some things you may never be an expert at, or even proficient in. Conversely, there may be other areas that you could learn but choose not to, as is your prerogative.
With any luck, however, you will treat the areas you’re deficient in as little more than problems to be solved. Because thanks to YouTube, that’s usually all they are.
There are few things more exhausting in life than a miserable person.
Before I continue, let me be clear: I'm referring here to a very specific type of willful, privileged kind of misery.
There are masses of people who live their lives in what Thoreau called "quiet desperation," whether because of mental health issues, poverty, domestic issues, the color of their skin, their sexual orientation and so on. This is not the type I'm talking about. Misery is not an option or their choice, it's their default, inescapable reality. They deserve support and understanding, not scorn.
But you will encounter people who are little more than animated, ambulatory storm clouds. Everything’s terrible and nothing is ever their fault. Pick a subject: job, sports, relationships, politics - especially politics - and the response will be the same. If someone casually throws around "hate" every other sentence, you've met one of these types.
Everyone grumbles, of course. Under certain circumstances, it can even be useful, as commiseration has a way of creating bonds and bringing people together. But when misery becomes your default outlook on life and everything in it, you’ve created not just a problem for yourself, but you become an active drag on the people around you.
Setting aside the normal day to day gripes, which aren't the problem, ask yourself this the next time you're tempted to complain: what have I done to fix this?
In our house, we have a rule: no bitching about something you haven't tried to fix. If you've made the effort to address an issue and been unsuccessful, ok. Bitching still isn't encouraged, but it may be tolerated. If you haven't attempted to resolve the situation, however, we don’t want to hear about it.
This has two positive impacts. First, less complaining, which is less negativity. Win. Second, more things fixed.
Beats the hell out of the alternative.
“The cost of a thing is the amount of what I will call life which is required to be exchanged for it, immediately or in the long run.” - Henry David Thoreau
One of the things you learn to pay attention to as you get older is time. When you’re young, time can feel limitless even if you intellectually understand that it’s not. And as with any other limitless resource, it doesn’t appear to hold a particularly high value.
As the years go by, though, time assumes a more prominent role. Gone are the days when you couldn’t wait for time to roll on by to get to summer. Over time, this indifference is replaced by a recognition that time is, in fact, short and therefore precious.
This realization makes you think carefully about time. It can make you, for example, take a huge pay cut to work at a job that doesn’t have you on the road five days a week, every week, all year. It can lead you to say yes to spending inordinate amounts of time with friends because you never know what life may bring them, or you. It can also be something you decide to commit to a hobby, even though it’s costly from an hours perspective, simply because it makes you happy.
Whatever its impact on your life specifically, the sooner you appreciate time the better because it’s only going to get shorter.
“In my whole life, I have known no wise people who didn't read all the time — none, zero.” - Charlie Munger
“If you don't have time to read, you don't have the time (or the tools) to write. Simple as that.” ― Stephen King
Speaking to the New York Times in 2008 regarding Amazon's Kindle reader, Steve Jobs said: "It doesn’t matter how good or bad the product is, the fact is that people don’t read anymore.” Besides broad generalizations about the number of readers on average, it's unclear what Jobs meant precisely but his assessment of the market seems flawed given both some estimates of Kindle revenue and the fact that Apple itself felt compelled to introduce a book product.
Whatever Jobs believed or what the reality is, however, the fact is that reading is an essential part of education. Besides their ability to teach, entertain or to inspire, books have the unique ability to package up an individual's thoughts or take a snapshot of the world at a particular place and time.
The more you read, the better that you will be able to write. The better you can write, the better you'll be able to think, not to mention to communicate.
As you get older, too, you'll find new things to extract from what you read. The joy of deciphering references or themes that eluded you the first time around has no equivalent.
You've loved books as long as you've been able to hold them; there can't be many kids who can't yet read who stay up late with a flashlight paging through books.
For your sake, I hope this continues.
Life is short. Depending on when you read this, that phrase may have effectively no meaning. That’s fine. If you can tentatively accept it as true, however, it’ll make some of your more important decisions easier. You may have a career that will make you miserable because of the hours, the content, or both. And there’s nothing wrong with that for a few years; paying your dues is a necessary part of the process in a great many industries. But if you are still unhappy years later, remember what you’ve been told: life is short. Do you want to spend it doing work you hate, or would you prefer to work on something that you enjoy?
That question is easier to answer than execute. It’s hard to get paid to do what you love. Paul Graham believes – and I happen to agree – that there are two primary approaches to this:
The organic route: as you become more eminent, gradually to increase the parts of your job that you like at the expense of those you don’t.
The two-job route: to work at things you don’t like to get money to work on things you do.
Which one of those works for you will – assuming that the idea of doing something you love appeals to you – depend on your passion and your priorities. Being a starving artist sounds romantic until you’re actually starving.
Eventually, however, you will get to a point in your life where you’ll look back on what you’ve accomplished and reflect. If you’ve been punching the clock for ten years, that’s not going to be a fun conversation to have with yourself, so my advice is to work on things that matter. Whatever those might be for you.
There's a famous saying in the technology industry, "as soon as you create the system you create the game that plays the system." The idea is that for any given system that's created from performance reviews to dolphin feeding, a game is implicitly created. Those who understand this concept broadly, and more specifically can identify and understand the mechanics of the game are likely to have an edge over those who do not.
This is, as stated, broadly understood in the tech sector at least. What is less apparent to people is that their life is, in some sense, a system. And like all systems, it can be gamed.
The trick is understanding the incentives, the rewards involved. Motivating to write a book, for example, can be a challenge given the effort involved. If you are careful to tease out and precisely articulate the incentives involved, however, your task is greatly simplified.
When I wrote my first book, as an example, I kept my perception of the effort level required down by targeting a much lower word count than is typical, while at the same time focusing on the professional benefits, be that recognition, financial compensation or reducing the need for repetitive conversations.
If I'd begun with just an abstract desire to write a book, I would likely never have completed it.
Whatever you want to accomplish, then, be sure to deeply understand the incentives and keep your focus on them. Incentives will determine, ultimately, what you can commit to and sustain. They'll determine what you want to do, and how well you do it.
And to a degree, they'll determine how you live your life and what you orient it around. So pay attention.
Maybe it’s the high dive. Maybe you’ve listened to me talk about it, and you’ve gotten yourself to the Grand Canyon to get up at four in the morning and hike down to Havasu Falls. Maybe you’ve driven up to the Tubbs while at Williams and are jumping into the swimming hole. Or maybe it’s something else entirely.
And just to be clear, the following assumes that you know a given jump is safe. That there are no rocks, the water is deep enough and so on. If you don’t know that for a fact, do not proceed until you do.
Assuming you know intellectually it’s safe, the trick is to jump before your brain figures out what’s going on. Given time, it will come up with a million reasons you shouldn’t dive off the high dive. Don’t give it that time.
Jump first, think later. You were able to do this at the age of three with a high chair, so if you’re reading this I’m pretty sure you still can.
Another of my Mom's favorite phrases when I was younger and acting like it, "the world doesn't revolve around you" is a lesson that can be hard to learn. Many never do. The lesson can be particularly hard for only children such as yourself to learn because they've never had to compete with siblings for time, attention or things like toys.
But it's critically important because people who waltz through life assuming they are the only ones that matter, and that others' needs are secondary, are tedious at best and dangerous at worst.
It's one thing, as John Barth put it, for people to be "the hero of [their] own life story." It's quite another to believe that the hero is the only character in the story that matters and that everyone else is essentially a secondary player of no meaningful importance.
It's sad that it needs to be said at all, but never forget that other people matter.
The first time you have a bad guest or travel with someone difficult you will understand why this is important. But because the world does not revolve around you, it’s important to not act that way and minimize your impact on the people you’re with.
If you’re staying with friends, do the dishes, make your bed and leave their refrigerator with more in it than when you arrived. If you are traveling, pay for more than your share of the food, be flexible about plans and be on time.
If you’re not considerate of other people’s space and experience, you can’t expect them to be considerate of yours. You don't want to be around people like that, so don't be a person like that.
"People everywhere brag and whimper about the woes of their early years, but nothing can compare with the Irish version...the English and the terrible things they did to us for eight hundred long years." - Frank McCourt
“Once the storm is over you won't remember how you made it through, how you managed to survive. You won't even be sure, in fact, whether the storm is really over. But one thing is certain. When you come out of the storm you won't be the same person who walked in. That's what this storm's all about.” - Haruki Murakami
You know your family history is not all roses if its motto is “wounded, not conquered.”
As a parent, I want you to always be happy, and for your life to be unmarked by disappointment, hardship or misfortune. As an adult, I recognize that what I want in this respect is not relevant. Your parents’ best efforts aside, you will have your share of unhappiness - and with any luck, no more than your share.
Many wounds heal. There are some wounds, however, that will never be healed, not fully. Your job is to endure these as best you are able, and to never let them break you. You may not think yourself capable of surviving, at times, but you can and you will. You will be different, changed because of them, but you will survive.
Just as my coaches trained us to understand that there’s a difference between being hurt and being injured, there’s a difference between being wounded and being conquered. It may not always be easy to remember, but we expect you to.
And really, what’s the alternative?
The above notwithstanding, try not to make a habit of enduring. It will, unfortunately, be necessary for you to grin and bear it, at times. But there is a real danger to making a habit of this, to defaulting to a reactive position of mere survival as opposed to proactively attacking a problem.
Endure what you must, but never be content with mere endurance.
The last in a trilogy of my Mom's favorite sayings, this was invoked when my brother or I was whining. Whenever we complained that a chore was too hard, that a test was unfair - or later that a speeding ticket was targeted at me specifically, she would remind us both that we had no reason to expect otherwise.
It was infuriating as a kid, but it was what we needed to hear. Even as incredibly privileged white male kids of moderate means, we had no reasonable expectation that the world would be easy or fair, and we were playing the game of life on the easiest setting there was.
As a young girl, I wish I could tell you that the world will be easy and fair when you grow up. But I can't. Your experience will likely be easier and fairer than what your mother experienced, let alone the world our respective mothers grew up in.
The world you will be raised in will almost certainly be less fair to you than it will be to the boys you grow up with, however, a fact that fills me with sadness, disgust and rage. But my job as your father is to prepare you for the world as it is, not the world as I'd like it to be.
The next time I ask you whoever told you that life would be easy or fair, then, you'll know why.
“[I]t should be noted that the main reason for the Romans becoming masters of the world was that, having fought successively against all peoples, they always gave up their own practices as soon as they found better ones.” Montesquieu C., Considerations on the Causes of the Greatness of the Romans and Their Decline
As you move through life, you are likely to be variously pulled between two opposite poles: idealism and pragmatism. The former prioritizes closely held principles, while the latter focuses on results.
While allowing that both have important roles to play, for better or for worse your father is a pragmatist first, everything else second.
Perhaps the best example of this in practice is politics. Do you prioritize someone fully aligned with your own principles, or do you vote strategically for a candidate you identify with less but who is more likely to win? That choice I will leave to you, though I will note that the history in this country - just as with the Romans - proves fairly conclusively that pragmatism and compromise will win out over idealism more often than not.
Which is why you will have heard the phrase "whatever works" thousands of times by the time you read this.
“I like to listen. I have learned a great deal from listening carefully. Most people never listen.” - Ernest Hemingway
The Socratic Paradox, which may or may not be correctly attributed to the man, has him saying “I know that I know nothing.” When you’re young, you are not going to know this. You will, unfortunately, be convinced that the reverse is true. I promise not to hold this against you because everyone goes through this phase. Some never get beyond it.
But to the extent that you’re able, listen. Even if you think you know everything, listen.
You're going to have to learn a lot of lessons the hard way - by experiencing them - because you won't be able to listen. The fewer of these you experience, the easier your life will be. So you might want to listen.
When your Mummy and I were first dating, we had a place that we would go to in Portland together called The Front Room. It was on the corner of the block we lived on, and when the bartender Bob would see us through the window, he'd have two chairs set up for us and two beers cracked and waiting before we even got in the door.
This was accomplished in large part because we got to know the staff there, but also because we tipped well.
The United States operates differently with tipping than most of the world, and many argue for tips to be replaced by a higher, livable wage. It's possible that by the time you're old enough to read this and for it to be relevant to you, the service industry's historical reliance on tips as a fundamental component of income will have been retired.
But that seems less than likely, and even if it does come to pass the point behind tipping remains: to recognize and reward special, above and beyond service. Tipping need not involve money at all, in fact. When your mother was in the hospital before you were born, Grammie brought a steady supply of baked goods for the nurses on our ward. As a result, your Mom was the most popular patient on the floor. The hospital takes care of all of its patients, of course, but when you make the people taking care of you happy your experience is likely to benefit.
And even if it doesn't, you're improving the lives, be that marginally or materially, of the people serving you beer or taking care of your family.
This advice may be difficult to follow in an era that offers escalating rewards to self-promoters and it actively won't work under poor coaches or unprofessional managers, but for what it's worth the best teams I have been on had two common characteristics.
While the first suggestion is unnecessary on good teams, which recognize that who's responsible is much less important than addressing the problem, the gesture is always appreciated because it's an immediate signal that the blame game is off the table.
The second, meanwhile, is a useful characteristic in that it keeps the focus on the team rather than individual contributors.
The problem with the above approach is obvious; it leaves you exposed in a political, every person for themselves environment.
To which I'd reply that you may have to adjust this approach depending on the context you find yourself in. But honestly, the better plan is to find a better context.
“Always remember there was nothing worth sharing
Like the love that let us share our name.” - Scott Avett
This is the simplest, most profound, most important and yet most boring thing you need to know.
You are the 7th generation of O’Grady (that I can trace). You are the sixth of your line to bear Gilman as a middle name, and the sixteenth generation when surnames are included.
It doesn’t matter who you turn out to be or don’t, your mother and I will always love you. If you cure cancer or become President, we’ll be proud. If life leads you astray, we will still bore people talking about our daughter. You will always be special to us, no matter what path you follow. Our job is to be your parents, which is to say love you without condition, to always put your needs in front of our own and to do our best to raise you to be a strong, independent woman.
But know that whatever else happens, you will always be my little girl.
As your father, I am certain there will come a time when I will regret saying this, but my sincere hope is that you make your own choices in life rather than simply accepting everything we say at face value. Many of the world’s problems are the result of people blindly accepting what they are told rather than evaluating it critically.
There is, however, one exception: you will be a Red Sox fan like your parents, and their parents before them, and their parents before them.
Every other Boston team is optional. If you root for basketball or hockey teams, I recommend the Boston flavors, but this is not required. Your mother, I should note, would also recommend New England’s football team. And if you fall in love with a non-Boston team in any other sport but baseball, I will raise no objection.
When it comes to baseball, however, there is but one true faith: yours and my Boston Red Sox. You’ve been listening to them since you were in the womb, and some of your earliest days were spent on my lap watching the games, so I hope that this will all come naturally. But if it doesn’t, it’s a small ask.
If, by some sad misfortune, I’m no longer here to hand this to you, let me quote Cormac McCarthy, because he said what I would better than I ever could.
You have my whole heart. You always did. You're the best [kid]. You always were. If I'm not here you can still talk to me. You can talk to me and I'll talk to you. You'll see.
You have to make it like talk that you imagine. And you’ll hear me. You have to practice. Just don’t give up. Okay?
You have to carry the fire.
This is the way.