Examining Your Luck Tree

In my younger and more vulnerable years my father gave me some advice that I’ve been turning over in my mind ever since. “Whenever you feel like criticizing anyone,” he told me, “just remember that all the people in this world haven’t had the advantages that you’ve had.” — Nick Carraway, in F. Scott Fitzgerald’s The Great Gatsby.

At one point during a recent Democratic presidential debate Michael Bloomberg was asked how he got his billions of dollars and whether he or anyone deserved to have that much money. In response he said two things, basically back-to-back, that got my mind going.

First he said, “I’ve been very lucky.” Then he said, “I worked very hard for it.”

I don’t know or, frankly, care enough about Michael Bloomberg to determine how much work he did vs. how much good luck he had. I know he created a product that produced billions in revenue for him. I also know he was in a position to do that because he got a $10 million cash buyout when the investment bank he worked for got bought out. I know he got to the investment bank because he got a Harvard M.B.A and, as far as I know, he didn’t come from money so he, presumably, worked hard and did well enough in school to get that degree and get the job at the investment bank. I also know that since he made his fortune he has, no doubt, expanded it greatly via passive investments, connections, and legal and financial advantages to which only the wealthy and powerful are privy. All of which is to say: his life and fortune is, I am pretty certain, a product of work and luck. Some of it is public record. Some of it is not.

But how much work and how much luck?

We have something of a national ethos in this country which holds that wealth and power come only to those who worked for it and poverty and despair come only to those who did something to deserve it. We also tend to possess the cognitive bias known as the Just World Fallacy, in which we believe that a person’s actions will always bring morally fair and fitting consequences, for good or for bad. That all noble actions will eventually be rewarded and all evil actions will eventually be punished. It’s manifestly not true, but a shocking number of people believe it.

In light of this I suspect that if you put that direct question — how much work and how much luck? — to Michael Bloomberg, he’d talk up the work part and discount the luck part. I also suspect that he and a great many others would be quick to assume that the misfortune of others — be it poverty, or bad health, or disadvantage of any kind — is largely their fault. That it was because they didn’t work hard enough. Or that they were lazy. Or that they made bad choices or they possess character flaws.

In the abstract people might claim they don’t believe this, but we have set up a political and economic system which has that as its basic assumption. A system which stigmatizes and punishes poverty and misfortune no matter what caused it and which rewards wealth and power, regardless of how it is attained. A system which, if you oppose it or its basic assumptions, you are deemed a “radical.”

I was thinking about this the other morning and wondering how to change it. I quickly concluded that, on a macro level, that will only happen by virtue of major political change and that’s beyond any power I have.

I do, however, have an idea about how, on a personal level, people might begin to question the assumptions underlying our system. About how to get them to take a harder look at what part of their lot in life was authored by them and what part was authored by fate and circumstance: I’d ask them to trace their luck tree.


That’s kind of a dumb name, but we can work on that later. The idea I’m getting at, though, is a cousin to straight genealogy in which, rather than determining who begat whom, one looks at what breaks they got. And the breaks their ancestors got, for that matter. Breaks for both good and for bad. It’s an exercise in which one thinks critically and as objectively as possible about their life’s circumstances and the circumstances of their family and community and determines what, exactly, got them where they are and/or what kept them from attaining more.

It certainly wouldn’t be easy, as honest and sometimes critical self-examination is not something most people are really good at or eager to undertake. And I don’t know the best form for such a thing would take — maybe it’s less a tree and more of a narrative — but I can see some benefits to the exercise.

An obvious one is basic self-awareness, which is something most of us lack to greater or lesser degrees. Another is that, considering someone else’s luck tree might actually instill some empathy. Or, at the very least, it may force people to abandon their reflexive dismissal of history and society’s role in people’s present circumstances.

For example, in the abstract, it’s quite easy and common for white people to say that everyone has an equal opportunity in today’s society so we have no need to grapple with America’s history of slavery and racism. It’d be much harder, however, for someone to look at someone’s specific history — the names and places and jobs and things a given person had — and see how, in very concrete terms, that history worked great injustice and created massive inequality long after Emancipation and the end of de jure segregation and discrimination. And how, because just like in a white person’s case, what a black person’s ancestors went through impacts their very specific lot in life, it still does so to this day. People way smarter than me have written books and spoken at length on this stuff, but the people who need to read those books the most probably aren’t doing so. Maybe they need an example or three.

The key, here, is that we must first engage in self-examination and that examination must be as objective as possible. That’s certainly no given.

I’ve dabbled in a little genealogy recently, and one thing I’ve found is that people who are really into that stuff tend to fudge things a bit in ways that make their family look better if given the chance. If, say, a great-great-great grandpa was in the Civil War, he was ALWAYS at Gettysburg and if grandpa fought in World War II he stormed the beaches at Normandy, even if they can’t find the documents to prove it. If it’s unclear whether the father of their 12th great-grandfather was Lord Baron von Royalpants or, alternatively, he was the bastard son of the shit-shoveler, they tend to go with the former.

That’s an understandable impulse, but it’s one that, when doing a luck tree, we want to avoid. And we should realize that the distorting impulse in the case of a luck tree might, actually, be to reverse things to make one’s circumstances seem more challenging than they actually were.

Say your grandpa was the son of a plumber and never finished high school but he landed a great job in 1947 that led him to a comfortable upper middle class life. In that case it might be tempting to ascribe all of that to his hard work and moxie and to cast his rise in life as one of overcoming considerable obstacles. Which, to be fair, he may very well have.

It might be tempting, however, to leave out the part where the guy who gave him that job was his girlfriend’s dad — who would become your great-grandpa — who, oh by the way, later left grandma and grandpa $250,000 that they used to buy that big house on the coast of Maine that your dad flipped for $1.3 million in 2005 which, in turn, funded your gap-year of world travel and a college education which left you debt-free and allowed you to afford to live in a trendy neighborhood in a major coastal city while working for a non-profit.

One way to tell that story would be to say “I came from blue collar roots and hard-working self-made businessmen and now I’m giving back to the world by writing grant applications to save the rainforests.” That’s not inaccurate! Another way to tell it, however, is of your grandpa getting a job he wouldn’t have gotten but for who his sweetheart was, your dad not getting rich if not for an inheritance and some fortuitous real estate flipping and you not being in a position to save the rainforests if not for the fact that you are standing on the shoulders of considerable good luck and privilege.

Which is still OK! Your grandpa probably did work hard and I am sure you care a lot about the rainforests and are doing everything you can to make the world a better place! This is not about making value judgments or engaging in character assessments. In this I am not throwing shade at you or your family. This is simply about trying to figure out what, exactly, built your life.

Figuring it out so that you might better appreciate what it is about our society that makes some people better off than others and some people worse off than others outside of the distorting ways we tend to view these things in the political sphere and without the distorting filters of the Just World Fallacy. To create self-awareness of your own circumstances while simultaneously helping foster empathy for others whose circumstances aren’t as pleasant. All of which, in turn, might help build support for specific policies and, eventually, a society which promotes equality and opportunity in real, rather than merely rhetorical ways.

First, though, let’s do someone’s luck tree. Let’s do mine.

As I said, last year I wrote a big post about my adventures in genealogy. I won’t recap all the details, but it’s certainly going to inform all of this. Here are the broad strokes that get us from, well, as far back as I can reasonably find until the more recent fate-rendering events of my personal history:

  • I’m white and all of my ancestors came from Europe. Most of them from the British Isles. Most of them came here before the United States was a country. While they largely did so because they found themselves on the wrong side of land disputes or because they chose the wrong side in a war, thus rendering their circumstances in the New World less-than-super prosperous, all that is already a pretty big leg up on a great many people. They weren’t slaves or indentured servants. Nor were they, as far as I can tell and as far as geography suggests, slaveowners, though they obviously lived in a country whose economy was largely premised on slavery. While they had to deal with some English/Scottish/Irish politics and some class bias, they were not subject to racial discrimination or persecution. It was a pretty fortunate place to start, relatively speaking;
  • The only non-British folks were my paternal grandmother’s family. They were Jewish immigrants from Romania in the late 19th century. Their story tracks that of many Jewish immigrants: persecution at home which they fled, large barriers of discrimination, segregation and antisemitism once they got to the United States but then, later, a good degree of assimilation and the assumption of a place that was, more or less, a part of the middle class, albeit a still-segregated part of the middle class due to still-extant antisemitism. They ended up doing OK for themselves. Some better than others

So that’s the background. Now the more recent bits of luck and fate. I thought about trying to quantify this and put little plusses and little minuses near each factoid, but that seemed daunting. As you read it, though, read each fact as either a plus or a minus. It should be pretty obvious which is which.

As I’ve written before, in 1910 my maternal great-great grandmother killed my great-great grandfather with an axe. It — please forgive me — struck a considerable blow to my mother’s family. While that was over 100 years ago, their children were separated and sent off to live with relatives that, in some cases, did not care for them properly. As I described in the second half of that story, the trauma of the event and its consequences and the mental illness which fueled it all continues to persist, directly or indirectly, in very tangible ways many generations later. My mother was really the first person to emerge from that into what one can call normal circumstances, but even then it was without any higher education and with no familial safety net of any kind. Whatever one can say of that, there is no wealth or opportunity that has flowed to me through my mother’s family.

My dad’s mother married outside of the Jewish faith twice, once — with his biological father, who was descended from all those British people  — into unfortunate circumstances of alcoholism and abuse. The second time, when she married the man who would adopt my dad and give him what would become my last name, things were better. That guy came from a somewhat sketchy past, but by his 40s he opened a taxi cab company and became a modestly successful businessman. He died in the 1960s and no money or business interests flowed to my dad, but he did provide my dad with a stable, middle class 1940s-50s upbringing that informed his sensibilities and would later come to inform mine.

Despite that middle class upbringing, my dad was not college material and when he was 17 he joined the Navy. This is where, arguably, the greatest bit of good luck — sheer dumb luck — that ever affected my life happened.

Having grown up around a taxi garage, my dad was a decent mechanic. In the Navy he wanted to become an aircraft mechanic. The two-letter abbreviation for that particular Navy training program (AD) was one letter and two typewriter keys off from a different school: aerography (AG). The guy typing up my dad’s form made a typo and he was mistakenly sent to learn to be an aerographer’s mate, which in the Navy was basically being a weatherman. The process of getting him to the correct school would take a couple of weeks but in those couple of weeks he decided he kind of liked learning about the weather so he stayed.

Back then, being a naval aerographer’s mate was a pretty direct ticket to getting a job in the U.S. Weather Bureau, which became the National Weather Service. My dad got out of the Navy in 1965 and would spend the next 40 years there. He got a solid federal government job with a pension and, in his case, a path to management. It was also a field office-based job, which meant moving a good bit. That stable employment, those benefits, the promise of a good pension and exposure to places that were not Detroit, which is where both sides of my family had called home for generations, were massively formative in my life.

Moving meant that I spent the second half of my childhood in West Virginia. That exposed me to a very different culture than I or my parents knew in Michigan and, perhaps ironically given what people think of when they think of West Virginia, gave me greater opportunities than I might’ve otherwise had.

In the small, poor towns I grew up in, a federal employee is towards the top of the professional class, which gave me an odd, minor sort of status only people from small towns might appreciate. It got my dad in the newspaper, for example, and allowed us to live in neighborhoods next to doctors and stuff. That would not have been possible in bigger cities. It also allowed me to get an interesting job when I was a teenager that, in addition to being a unique experience, was pretty good college application fodder. Finally, while schools in places like West Virginia face a lot of challenges as far as resources go, being a fairly bright (but by no means exceptional) kid at such a school created something akin to a big fish/small pond dynamic that might not have existed had I gone to some suburban school near a major city. I stood out there more than I might’ve elsewhere which was good for both my transcripts and, frankly, my self-confidence. It’s also worth noting that as a straight white guy I didn’t — then or now — have to contend with discrimination, bigotry or the stress and pressure one experiences growing up in the face of those things.

I was the first person in my direct family line to ever go to college. That was a big deal, obviously. I left West Virginia to do it, going to Ohio State. While a federal job was a good job, it was not a lucrative job, and the only way I was able to afford out-of-state tuition was via both my parents and me taking out loans. Of course part of what allowed my parents to do was (a) the job security of that federal job; and (b) the pension, which guaranteed their retirement, putting less pressure on them to save and thus making going into debt less risky. Also, given America’s history with discrimination, it’s likely the case that my being white made it easier to get loans on better terms than others might have.

For reasons I am not sure about even to this day, I was placed in Ohio State’s Honors Program from the outset. I did not, however, fit the objective criteria for it (SAT scores, high school GPA) and I never did figure out why they did that. It may have been because I was from Appalachia? Maybe I benefitted from a typo like my dad? I really do not know and never have inquired. The significance, though, was that I was placed in more challenging classes with way better professor/student ratios and way more hands-on attention to my academic path than I would’ve otherwise gotten at a massive school like Ohio State. I was also placed in classes with high-achieving peers who became my friends and in many ways my role models. That attention and those peers were critical to me given that I had no college-educated role models growing up and, frankly, did not know how to be a college student. Without that it would’ve been very easy to imagine a situation in which I just coasted through college with no particular plan. In reality, I ended up being a high-achiever who got good grades and was mentored on a path that would lead to a lucrative career and, eventually, the writing career I now have.

That career: the law. Good grades in college and good mentoring put me in a position to get into a top-25 law school. Again, paying for it was a daunting task, and again I went into debt to do it. That debt lasted for a very long time and prevented me from taking advantage of some opportunities I might’ve been able to take. At the same time, it was not crushing in the same way it can be for more recent college graduates who started school later than I did when college expenses truly began to spiral. I’ve gotten by. I got in under the wire.

Law school was in Washington D.C.. Because of the location — and because I was married just before law school and my then-wife worked — I was able to take an unpaid internship at the U.S. Justice Department one summer. My law school grades were not exceptional, but the school’s ranking and that internship allowed me to get a summer associate job at a good law firm back in Ohio.

I question whether I’d get that kind of work if I had stayed in Ohio for law school. In this particular legal market — Columbus, Ohio — going to a local law school usually helps you get a job and going non-local like I did makes it harder, but the firm that hired me was sort of status-seeking and liked to hire people from “better” law schools like the big New York and Washington law firms do. That was, in my view, a crappy strategy — everyone who went on to become partner from my hiring class came from Ohio, not one of the “better” schools, and all of us good school people washed out or moved on — but that was the firm’s thinking in 1997-98. Either way, that whole dynamic led to a permanent job offer nearly a year before I graduated. It was a well-paying job. I would stay in well-paying jobs with excellent health insurance and stuff for the next decade.

The law job allowed me to become a homeowner at age 26. While one does not get rich buying and flipping starter homes in Ohio like they might in hotter real estate markets, home ownership has obvious financial benefits. Tax breaks and at least modest wealth accumulation most notable among them. I was also making juuuuust under the income threshold that allowed me to take advantage of a government subsidized first time homeowner’s assistance plan that prevented me from having to make as large a down payment or pay PMI taxes. Which program it was escapes me at the moment but I am not sure exists any longer.

When I had children a few years later, the modest wealth accumulation of home ownership (i.e. the equity in my starter home) allowed me to put a down payment on a larger home in a suburb with high property taxes and very well-funded and well-equipped schools. My kids, if they one day go through this exercise, will need to cite that as part of their good fortune.

I once wrote 7,000+ words about my journey from being a lawyer to being a professional writer so I won’t recap that again. In many ways the actual transition into my job at NBC was luck, as people I did not know at all and with whom I never spoke or networked with seemingly pulled my name out of thin air to offer me the part time freelancer job that I would later parlay into a full time job. But there was more to it. Off the top of my head:

  • The lawyer work honed my writing ability and critical analysis, which obviously helped my baseball writing;
  • NBC hired me while I was writing an independent blog which is what got me noticed in the first place. I was able to maintain that independent blog, in large part, because a lawyer has more control over his schedule and has more moment-by-moment autonomy than people do in a lot of other kinds of jobs. I couldn’t blog about Barry Bonds or whatever if I was on an assembly line or waiting tables. Or, for that matter, if I was in a cubicle at a data processing company or something and everyone could see my monitor and paid attention to what websites I visited. Writing that independent blog killed my legal career in a lot of ways but it definitely helped me write more and write more often, which led to my writing career;
  • My little blog likely would’ve remained obscure, but (a) a guy named Darren Viola who moderated a fairly well-connected baseball message board; and (b) and Rob Neyer, who worked for ESPN at the time, somehow saw my writing and linked it out many times, leading to a bigger audience which, in turn, at least put me in a position to be on the radar of those NBC people who pulled my name out of thin air. They don’t link it unless it’s good, so that’s on me. But a lot of people write good things that don’t get seen at all, so that’s good fortune.

I’ve been in that job for over ten years now. It still doesn’t pay me close to what I made as a lawyer 15 years ago, but it’s a good gig and it’s been good for me in countless ways. Working at a big recognizable media company has opened some doors and lines of communication with people I might not have met. It has given me experiences I might not have had. It even, indirectly anyway, put me in a position to meet the woman who wouId become my second wife. It’s pretty much shaped the last decade of my life. I’d like to stay in this job until I die, but even if I do not, it’ll likely help dictate what the next thing in life is for me.

I’ve been fortunate.

I’ve lacked some things some other people have — I don’t come from money or education and I never had any family connections that could do anything for me, really — but I’ve been lucky in a lot of ways too. I’m a white man in a patriarchal society that has been defined by systematic racism. While my extended family history is fairly harrowing, I was brought up in a stable, two-parent house with steady paychecks, everyone experienced good physical health and if we got sick we had access to quality healthcare. I got a strong education that led me to not one but two good careers and, again, good benefits and healthcare. I am not wealthy — that career change/pay cut, a divorce and the costs of raising kids means I haven’t saved much. I carry more debt than I should. I work in a field that is not, exactly, the healthiest it has ever been and thus a career or economic setback could mean big trouble for me. But I’m more fortunate than a lot of people are.

Which brings me back to where I started. The appreciation — perhaps shared by Michael Bloomberg, perhaps not — that where I am is a function of a lot of my own work, sure, but it’s also a function of some privilege, some good fortune and, in a couple of cases pure, dumb luck. I did not come into this world with what I have now, but nor did I obtain all that I have now by virtue of my own efforts. There are many people who are worse off than me who have worked far harder than I have but who have not had the same fortune I’ve had. There are people who are better off than me who have not worked as hard and had better fortune. The reverse of both of those is true as well. We live in a world where neither equality of opportunity nor equality of circumstances exists. The central question of our time — of any time — is what we do with that information. What we do about that inequality.

First we decide, apparently, whether we wish to address it at all.

I say “apparently,” because while it just seems intuitive to me that we must do so in the name of basic humanity and justice, there are a shocking number of people who think the answer to that is “no.” They say that inequality is not an issue because they either refuse to acknowledge it in the first place. Or because they believe that inequality is predestined. Or because it is unavoidable or unable to be remedied. Because it is just. Maybe because of some combination of all of those things.

If, however, the answer to that is “yes,” we have no choice but to address it. And we cannot effectively address it, either on an individual level or on a societal level, unless we examine its nature. To determine what it is that causes some people to flourish and some to suffer irrespective of their own efforts. To see what part of it is attributable to race. Gender. Sexual orientation and identity. Ethnicity. Religion. Geography. Educational opportunities. Economic opportunities. Health or sickness. To assess where we fall short as a society in delivering the goods and heading off the ills which can reasonably be delivered or headed off by acts of said society.

People are loathe to do that I think. Maybe for cynical reasons but, more understandably, because it’s difficult to grapple with such big issues and questions. Maybe those of us who find that grappling daunting should start smaller. Maybe we should first try to understand, on a personal level, how fate, circumstance, privilege and luck has benefitted us or harmed us and what part our own efforts, honestly, played in where we are today.

I feel like, the better we understand that, the more we’ll realize that not everything is on our own hands. And that far more is in everyone’s hands.

Craig Calcaterra

Craig is the author of the daily baseball (and other things) newsletter, Cup of Coffee. He writes about other things at Craigcalcaterra.com. He lives in New Albany, Ohio with his wife, two kids, and many cats.