The real work is never done, and has no clear beginning, and shows no result, no losing no winning. -Great Lakes Swimmers, The Real Work
Here I am continuing on in my exploration of Compulsion and Compensation, something I’ve been thinking and writing about for at least a year, and which I’m still puzzling over to get it out, to you! To go back to previous sections, click here. I hope you are enjoying reading, that your own thoughts are stimulated by my own, and that you will share with me if so! Let’s continue:
After long consideration, I see a big reason for my feelings of burnout and resentment were (and are!) centered around money; or more precisely money illiteracy, money emotional entanglement, and money addiction.
Jenny and I were married, and immediately as we were setting up our life together, had (good) jobs, paychecks and bills to pay. After doing apartment living for a few years, we bought a house and got a mortgage. Actually, I’m chagrined to report, we got two mortgages! In what I now recognize as a fit of optimism and irresponsibility in those early days of making real money we bought a “second” summer house up north . . . before we bought a “first” house to live in back home! It was a very cheap house in a part of the country to which I had romantic connections from cherished family vacations, and going to college there for a couple years. We enjoyed going there for a number of years, but then that “second home” became a burden that we had to work hard to rent out over a number of years, and then sell, for a loss. We had no money for a down payment on a “first” house; we each had college and grad school loans to pay off, and no equity; but for a while we had a double income and no kids, and the paycheck cash was flowing.
(From the beginning, and sporadically over the years, I’ve spent some amount of time exploring co-housing and life-sharing situations to avoid some of the costs of the “single family household” lifestyle, but never found a good fit for our family. But maybe it’s worth noting here that I was uncomfortable with the middle-class-nuclear-family-home-ownership path and lifestyle from the very beginning.)
The conundrum of how to buy a (much more expensive) home to live in somewhere near our jobs in Chicago was resolved for us when Jenny’s church employer offered us a loan of the down payment that we lacked to make that purchase. Thus, within a couple years, we now had two houses, a mortgage on each of those houses, and a secondary loan tied up with one of those mortgages.
We did what so many college educated middle class folks do: entered adult life with debt. . . and then took on more debt (even though it was “good house debt”). Jenny came into adulthood better educated than I was regarding personal finance, but I must say I think we were both pretty clueless. We have learned the hard way like lots of people, through experience . . . and we have not made any really big mistakes. . . and I must say we’ve had generous support from friends and family through the years in the form of gifts, loans, and advice. This is some of that “privilege” that gets talked about that people coming from backgrounds like ours benefit from. It is very real, and I see it functioning in our lives through the years to keep us solvent. We’ve never loaded up a credit card, and we’ve never missed a payment on anything. I think we’ve actually been quite “risk averse” and conservative compared to many others. But even so, by living in perpetual debt (like pretty much everyone else does, other than the uber-rich), a huge portion of our paychecks has gone to service our mortgages (and auto loans), enriched the banks, and driven up the GDP. We’ve done our part to drive the economy, I say with plenty of sour cynicism.
Once again, one would think with our privileges and incomes that we should have been happy, and we were in many ways. But, as I came to live in the felt experience of middle class living, I was increasingly bothered by the fact that we were “house poor,” meaning that we had sunk so much money and dedicated so much of our paychecks to the purchase of our house(s), that we could not afford to really do much of anything else other than live in it (them!). Furthermore, Jenny’s church had (generously) lent us the down payment, and so we were now even more tied to her work than we had been before! We were doubly, nay triply in debt!
We could have been much more disciplined than we were. But, we were newlyweds, and were both working 60+ hour weeks in creative, idealistic, caring jobs that we were so, so dedicated to . . . the extra money we made went to pay for things we couldn’t, or didn’t, want to do for ourselves, because we were so busy. Things like restaurants and prepared foods, and fancy meals when we could find the time to hang out together; and trips when we could find the time to get away from our busy jobs. And, we were paying off debt, always paying off debt. In fact, that same generous church of Jenny’s helped her with paying off her college debt, too. I remember we finally paid our college debt off the same year that Barack Obama did, his first year of being President of the United States.
Jenny worked for a church in a very wealthy suburb of Chicago, while I worked for an urban private school in Chicago proper. Her job was so much better paying, with so much better benefits, better health care coverage, so much better everything; that’s not to mention that her employers had financed our house purchase and helped her pay off her debts. My job was far less consequential to our lifestyle and cash flow. As I became increasingly uncomfortable with our financial situation, I realized two things: First, that if we wanted to honor our debt obligations, we’d both better keep working, forever! In other words, we were suddenly “locked in,” we were compelled to keep working. Secondly, if we wanted to make a change (which, more and more, I did); if we wanted to have a less-leveraged, more “home-based life,” we would have to reduce or ameliorate the debt, and I was the one who was going to have to give up my work to free myself up for the tasks necessary to do that. Although I was (overly) dedicated to my work, loved it and was enriched by it, I was being paid so poorly relative to my wife’s job, and pouring so much of my life into my work, that, in the middle-class landscape of my “debt-serviced” life, I was effectively losing money, and losing life, to keep working.
Slowly, painfully, I came to realize that I was giving more of myself to my job (which I thought of as my calling and was incredibly important to me) than I was to my spouse and our home life (and, upon long reflection, I wanted to change that). And there was another factor at play: because we did not have kids for the first ten years of our marriage, I was not receiving the major benefit that most Waldorf teachers receive: a free Waldorf education for their own kids, and more importantly, a community to which to belong.
This became a huge sticking point when I was working full-time in those years. I had some colleagues with up to four kids all enrolled in the school, all for free. Adding up the potential tuition savings that this amounted to, these colleagues were getting a humongous benefit, more than doubling their actual salary. This irked me, and eventually became a very poisonous lack of fairness that I couldn’t ignore. When teachers had their own kids in the school, they were part of the parent community as well as being teachers. I had no children, so I was “just a teacher.”
Can you see in my story as I relate it that I was all mixed up in my motivations and my expectations? I can! No wonder I suffered from unrequited love! I was deeply devoted to my work as a teacher at a wonderful, idealistic school; and also, over time from my debt-strapped middle class perspective, I was laying expectations on that school to reciprocate by giving back to me gifts that I would feel were commensurate with my own giving. Yet, the school, by our compensation agreement, owed me none of that. All they owed me was the paycheck I’d been promised. I received much more than this, of course, as I’ve related in previous posts. But, year by year, it came to feel like not enough.
What was the real rub? Was it the fact that although I think my colleagues respected me and liked me, they didn’t really have much interest in what I did, as long as I did it? Or, was it the fact that I came home every day having worked at least as hard as my spouse and made less than half the money she did? Or, was it the fact that some of my colleagues were compensated so much better than I was, simply by having more kids? Or, was it something else, something deeper?
After all, no one was forcing me to work for this school. I could have gone back to public school teaching and received much better money and much better benefits any time. Yet, I stayed. I must have been receiving some benefit after all, at least for quite a while, something that kept me coming back, despite the fact that I was giving of myself in an unsustainable way, pushing myself habitually beyond my limits, and eventually causing myself harm.
Reflecting on my experience, I now see that part of my confusion had to do with money. Money is a proxy, and a powerful, symbolic and homogenized proxy at that. I will once again mention Charles Eisenstein’s book Sacred Economics if you would like to go deeply into the origin and symbolic meaning of money. I won’t do that here. But allow me describe in the simplest terms I can manage one facet of money that seems crystal clear to me by now: If I work a job and I come home with a paycheck, I may feel a sense of “accomplishing something”. I’ve “made some money” (a really interesting phrase if one starts to dwell on it). But the truth is that absolutely nothing has been accomplished other than the potentiality that I, and everyone else, ascribes to the dollars in that paycheck. All I've really accomplished is an increase to the numbers in my bank account, and that is nothing at all, in reality. But what those bank account numbers represent is quite powerful. They represent the (almost entirely) unmitigated power to acquire something (goods or services) that I want in the future. In other words money is a vehicle for each of us to compel each other to give me what I want, when I want it. With money, I can simply buy what I want, whenever I want it, if I have enough of it. Because the vast majority of us are entirely tied into the debt money system, and that system compels us to work jobs for money, we have an incredibly complex economic system that will provide us whatever we want, whenever we click “buy” on Amazon, or sign for a credit card transaction. With money, I can compel goods and services to come to me, without any relationship to the people I am compelling. So we see that money by its very nature breeds situations of compulsion. In fact, this is what money (as we currently conceive of it, and currently use it) is best at. This means that in some deep way, there is a near-complete disconnect between money and truly good work. Good work should always have some rich relationship to the world, to other people and to the benefit that work is creating. In fact, good work as I understand it is good relationship, period. Money, being a homogeneous “medium of exchange,” is relation-less compulsion, pure and simple. Witness how scary it becomes for people when money suddenly loses its value, for example during an economic downturn. What is so scary? It is precisely that we won’t be able to compel the world to give us what we think we need (or what we think we deserve) whenever we want it.
In the case of our lives, Jenny’s church was able to provide us with much more money; and so, because we lived in typical middle class debt and “needed” that money, we found ourselves more and more compelled to continue doing what we were doing, year after year, with little possibility of changing course without serious consequences. We both felt deeply called to our respective work, and loved it, and we were loathe to give it up. But forces we had fallen into quite innocently started conscripting our choices, and (for me) poisoning the really good work we had to do. Money became an intrusion and a goad that made my work into a doppelganger of what I wanted it to be.
I’ll end this section here and continue on in the next installment. Have you had experiences or reflections like (or contrasting with) mine? I’d love to know. Please be welcome to make comments as you feel moved!


“…there is a near-complete disconnect between money and truly good work. Good work should always have some rich relationship to the world, to other people and to the benefit that work is creating.”
👍🏻👍🏻