Simon Sinek is an interesting guy. The author of a number of books (several of which I own), a sought after motivational speaker, a business culture consultant, and a professor of strategic communications. I’m not sure how he earned his influence — it’s unclear by looking through his biographical materials — but he’s undoubtedly deeply insightful about human nature, and a compelling speaker.

It’s important to note, however, when taking this sort of advice from someone like him, that he’s been very successful in his career.

The sentiment he expresses in the tweet above is, as an axiom, correct. But I think it’s worth observing that people who “give to get” usually come not from a place of malice, but a place of “not enough.” Insufficiency means it’s hard to bear the loss of the gift, unless one of comparable or greater value is received in return.

I used to think this way. Deep down, I had this hope that someone more well-off, more “lucky” than I had been, would come along, feel moved, and give free stuff to me, even though I couldn’t have dreamed of being similarly generous with others. I was the victim, you see. The guy down on his luck because of the hand fate had dealt me. It wasn’t my fault I couldn’t get ahead. My circumstances just weren’t favorable. Maybe it was just God’s will. And so, it wasn’t my fault that I couldn’t help myself, let alone others.

I’ve never been destitute, and I don’t think my experience was uncommon, but growing up, my family was on the poor side of lower middle class. Our family of 7 shared the rented upstairs of a two bedroom, one bath duplex in Connecticut from 1981 to 1989. I ate reduced or free lunch from the cafeteria for most of the time I was in public school. It was cheaper than food from home, and more convenient. When my youngest sister was born, cramming five kids into that tiny space became too much, and my parents moved us back to a tiny nowhere town near Binghamton, New York, where they bought a three bedroom, one bath home for less than $60K. It was the first home they’d ever owned, and it had taken 12 years of saving up (and my dad working a lot of late nights) to get to that point. (Later, my youngest sibling would be born into that also too-small house, but not until I’d already gone off to college, which I paid for with too many student loans.)

My parents didn’t buy me anything that wasn’t an absolute necessity unless it was my birthday or Christmas. I’m the oldest, but I rarely got new clothes, and when I did, they were usually from a clearance bin. Most of my apparel was of the hand-me-down variety, and it usually arrived in large black trash bags, the collected cast-offs from my more well-to-do older cousins. I got made fun of a lot in school because of my clothes, or the fact that I wore whatever generic sneakers my mom could grab for cheap from K-Mart instead of Nikes or Reeboks. It was the age of Air Jordans and Reebok pumps, after all. None of this Spaulding crap. So I started picking up jobs as early as I could. Babysitting at 14 turned into mowing the parish cemetery at 15 and then working at the local hardware store at 16. I quit football after my freshman year so I could work. The wages were garbage, but I worked as much as they’d let me, and it felt good to go the mall and buy my own clothes, my own shoes, and my own video games. I could even go to the movies, or go out to eat at the Chinese buffet. I had to go alone most of the time, but at least I got to go. My dad, seeing the effort I was putting in, was willing to give me a small loan the first summer I worked at the hardware store, and I bought myself a new computer. That was a euphoric day.

Our family never owned a new car. (In fact, my dad just got his first new car last year, and he’ll be 70 this summer.) We didn’t go hungry, but we did a lot of filling up on bread and butter when the main course ran out — something I now realize, as a probable celiac, contributed significantly to my frequent bouts with depression. We almost never went out to eat as a family unless it was a very special occasion. Maybe once every couple of years, unless we were on a road trip somewhere, and then we’d hit the dollar menu at Burger King. I recall having to negotiate paying the price difference with my mom when my adolescent appetite demanded a Whopper instead of a cheeseburger. We had an old oil-burning furnace, and in the brutal upstate winters, my mom kept the heat at 62. I’d frequently come down in the morning to see my younger siblings all huddled around various air registers with blankets, trying to capture as much warm air as they could. We never had air conditioning or a dishwasher. And we never went on actual vacations, though we’d sometimes visit out of state family or friends.

The constant refrain when I wanted something was, “We don’t have money for that.” More to the point, I was informed that my dad worked hard for the little he got, and my mom didn’t want me to make him feel bad, so she discouraged us from asking for anything at all.

My folks are also very risk-averse by nature, so my nascent ambition was treated like a dangerous wild animal. I felt like I was always getting lectured about how I wasn’t thinking through whatever crazy idea I had — you know, like getting a cheap car so I could drive myself to work instead of having to ask my reluctant mom for rides — and how much it was going to cost me. There was a religious undertone to all of it, too. “Blessed are the poor” wasn’t said explicitly, but it hung heavy in the air. It was part of the fabric of my understanding that rich people were materialistic, and that as Catholics, we were supposed to eschew such things, and even moreso, to resign ourselves to the suffering and difficulty in our lives. I came away from childhood feeling guilty for wanting more than what I had. It took years before I could accept that people would pay me well, give me benefits, AND paid days off. I felt guilty about that, too, almost like I was stealing something when an employer simply treated me fairly. Later, as I became more successful, I started feeling like I needed to excuse myself and apologize for my prosperity. As though I was somehow not authentic if I had more than others in my family. It didn’t matter that I’d worked for it. It only mattered that I had what others didn’t. I still struggle with that to this day.

All of this led me to a “hoard what’s mine and keep it secret” mentality. When I was young, every time I got something good, there was this feeling that I just had no idea if or when I’d be so fortunate again, so I’d better drink it to the dregs and keep it to myself. One of my biggest, longest lasting disputes with one of my brothers was over a stupid blueberry pie I bought at a Church picnic. I had left it in the fridge, and he ate more than half of it without even asking me. We argued about it for years afterward. The fact that I still remember something so inconsequential tells you how deeply rooted this mentality was for me.

When you always expect to be broke, your mentality tends to be busted.

Despite a personality hardwired to share good things with others, the circumstances of my life had conditioned me against generosity. I’m much better than I used to be, but it’s still a tendency I have to fight. It was my wife Jamie, who, it seems worth mentioning, was not raised in a religious home, who started to pull me out of my “Gollum mindset.” She taught me to stop looking at every good thing I had as though it was my “precious” that I had to keep secret and safe.

Her family has their own deep issues, to be sure. But her dad, who had lived in abject poverty in China, had seized an opportunity to come to America at 14 even though he had to leave his parents behind, and he had made something of himself. He owned property and businesses. Sure, it was the slums, but he made a good living. He had grown up poor and hungry, even facing possible starvation for a time when the Japanese invaded China in the late 1930s, and the first business he purchased in America was a grocery store. His thought on the matter was simple and utilitarian: “People always need to eat, and I’m never going hungry again.” And while he wasn’t a philanthropist towards most outsiders, he made damn sure none of his friends or family ever had to feel bad for asking for what they needed. When they’d go out to eat at the various Chinese places around town, he had a constant refrain: “You want more food, ask. I’ll get you more.”

Now, don’t get me wrong, I don’t want to make him out to be some kind of hero. He’s done some incredibly selfish and destructive things to my wife, and to us as a family, that completely violate this way of thinking. But despite those contrary episodes, the philosophy my wife learned from him as a child stuck with her. If there’s one thing Jamie won’t tolerate, it’s her children fighting over things like food. In our house, it’s not “the quick and the hungry.” It’s, “we make sure there’s enough to go around.”

One of the things about being poor that I don’t hear people don’t talk about a lot is how it can actually make you more selfish than the allegedly selfish rich. When you’ve only got a little, it’s easy to think, “This is MINE!” and be stingy with it; when you’ve got a lot, you know you have the freedom to give some of it away.

I remember one time, early in our marriage, Jamie and I went out to breakfast with good friends, and she elbowed me and told me to get the check. We’d only just stopped getting supplemental government food boxes, and I was not enthusiastic about the suggestion. The way I felt in that moment, you’d have thought she suggested I go get a root canal without anesthetic. I didn’t know how to give. It caused me acute emotional distress. I couldn’t stop counting the cost. I couldn’t stop thinking, “Whatever I spend on this is that much I don’t have to spend on something else I need.” It was always like that: tit for tat.

I’m embarrassed now at how selfish I was. I thought life was a zero sum game. I didn’t realize there really is enough for everyone.

And the truth is, my attitude seemed justified by our circumstances. Despite some brief periods of modest prosperity, for most of the first decade of our marriage, we were barely scraping by. I often struggled to find good jobs, and had stretches where I wasn’t working at all, or only doing temp gigs. Jamie was more successful than I was early on, but we kept having kids every two years like good Catholics do, and she’d have to stop working to take care of babies or risk leaving them in the care of others. This situation made me upset every time we found out we were expecting again, which took a toll on our relationship. We frequently couldn’t cover all our bills, and were constantly floating late payments. We didn’t go on dates. We didn’t do much of anything but stay home.

During one particularly rough patch, when my wife was pregnant with our fifth child, I was working 50-60 hours a week in a state with no mandatory overtime pay and no benefits. It wasn’t enough to cover food, utilities, rent, and all of our other expenses. We couldn’t afford living room furniture, so we sat on an old air mattress that kept deflating on the hard tile floor. The front two tires on our van wound up blowing out because the rubber had worn paper thin. The generosity of a stranger who was reading my blog at the time and offered to loan me a couple thousand dollars is the only reason we got out of that situation. We broke our lease, moved across country into my parents’ cramped 1-bedroom basement apartment with all five of those kids, and stayed there for a year until I had saved up enough, with the help of a loan from one of my brothers, to put down on a house. The son my wife was pregnant with at the time is named Jude because a novena to St. Jude I was praying was answered. The petition I was praying for was that our food stamps would be renewed. My pregnant wife and small kids needed nutritious food, not borderline spoiled garbage from the “manager’s special” section of the ghetto grocer. My son Ivan was so excited the first time we were able to buy fresh fruit again that summer. I gave him a bag of oranges, and you’d have thought it was Christmas.

Generosity was the furthest thing from my mind in those days. In fact, it was something I couldn’t understand when others showed it to me. A bunch of folks helped us out with money during that period of time. And I was just so puzzled by their willingness to do so.

Now, it’s undeniable that the lean times are hard, but if you have the right attitude, they can also form you. Dwayne “The Rock” Johnson, now the most bankable star in Hollywood and worth about half a billion dollars, named his film company after an event that reminds him of where he came from:

Johnson was born into professional wrestling. His Black Canadian father, Rocky Johnson, was a successful wrestler, as was his Samoan maternal grandfather, Peter Maivia. This was wrestling before the large national audiences and big paydays. It wasn’t an easy life. Dwayne was born 49 years ago in Hayward, near San Francisco, but the family frequently moved wherever a sustained period of wrestling work could be found. There are two particular moments in Johnson’s life that he often refers to as low points from which he derives motivation. The second occurred much later, when—in the final indignity of his failed football career—he was cut from the Canadian Football League at the age of 22. As he was being driven back to live with his parents, he searched through his pockets to find all the money he had in the world: a five, a one, and some change. (Johnson would memorialize the moment in the name of his film company, Seven Bucks Productions.)

The first event came when he was 14. The family had been based in Hawaii for some time, but his father was off wrestling in Tennessee. One day, he and his mother came home to their Hawaii apartment to find a padlock and an eviction notice. His mother was distraught. “That was a defining moment,” he says. “I remember at 14 thinking, I will never, ever have my parents go through this again.”

I’ve heard Johnson speak, repeatedly, about keeping the mentality from those days of his back being against the wall — because when your back is against the wall, the only place to go is forward.

But you have to get to the point where you realize that to move forward. And, in my opinion, you also have to experience enough success to know that you can get out of it, or you’re never going to be telling anyone your motivational story. Only the people who have overcome those challenges inspire us. If Dwayne Johnson were just some guy rotting away in prison because of a life of theft and violence — one possible outcome, based on some of the episodes from his past — nobody would be showing up to hear his wisdom.

When you believe in abundance, and that there’s more out there for the taking if you just go out and get it, suddenly the stuff you have isn’t such a big deal anymore. Suddenly, you don’t feel like you need to cling to it for dear life.

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I’m sad I didn’t learn how to be generous until my late 20s. Sadder that I didn’t become comfortable with it until my late 30s. I had to experience the possibility of prosperity before I was really willing to “share the wealth.” I had to have my white-knuckle grip on what’s mine pried open.

When Christ says in the Gospels that the poor are blessed, I find the message confusing. I don’t think poverty is a blessing in any meaningful way, except as a contrast against what you actually want out of life, and a motivation to never get lazy. But the actual experience of poverty makes most people miserable. It frequently makes them selfish, or entitled. There are people I know who are so convinced that they are victims of fate that they could never get out of their circumstances, and so, consequently, they believe it is the moral obligation of others to give them handouts. So while yes, being poor makes people more dependent on God — you’ll rarely pray harder than when you’re about to be evicted or don’t have enough to eat — I’m just not sure that’s the best way to experience religion.

One of the most important things I had to learn was to do for myself, and that meant not expecting God to do it for me. I believe I’ve written about this before, but the notion that we “can do nothing without God” needlessly debilitates people, sometimes keeping them from recognizing their own ability to help themselves. Praying for a raise isn’t the same thing as asking your boss for one. Novenas for a good job aren’t the same thing as building the skillset you need to land the position. And resigning yourself to poverty because you don’t want to be overly attached to money or material possessions means you’ll always be mired in mediocrity. If you don’t have the ambition you need to properly provide for yourself and the ones you love, how is that a virtue? How is the mentality that you’re blessed because you’re poor not just an excuse not to do your best?

Again, it’s very often a busted mentality.

When Sinek says, “Let us not give to get. Let us give for the joy of giving,” it’s good advice, but I hear the words of a man of means. Of someone who knows what abundance feels like, and how it is a treasure best shared. And he’s right. But his insight comes from a place a lot of people have never experienced.

We shouldn’t judge too harshly those who can’t imagine what it feels like to be able to give without sweating the cost. Those who have rarely known anything but want. We can’t expect them to find joy in increasing their own lack, when this is something they rightly associate with suffering. They have not learned there is another way.

It must be acknowledged, though, that there is another group of people: the truly, inexplicably generous. Those who, while not affluent at all, would offer the same advice Sinek does. Poor folk who give freely and without reserve. People who will give you the coat off their back on an icy day, or the last bowl of soup in the pot even though they don’t know where the next meal will come from.

They exist, and they are mysterious. Almost inexplicable, humanly speaking.

These people are truly next level. They’re the ones I really admire. They’re the truly blessed poor. The ones whose wisdom we could all stand to benefit from, if we can only understand how it works.

I’m not there yet. I’m still more in the Dwayne Johnson mindset, remembering what it feels like for my back to be against the wall, and never being willing to wind up there again. I don’t yet believe that if I did find myself back in that place, I could continue to practice the nascent generosity that I have learned, after an arduous process of unlearning what I thought I knew.

But I have hope that I might remember that I should, and find a way to try.

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