New Age Skills for Cynical Bastards.

Some thoughts on how to practice self-care, self-compassion and radical empathy without becoming an intolerable hippie douchebag

[My main personal website is offline until this winter, when I’ll be converting the entire thing to WordPress for the first time; and in the meanwhile, I’ve made a commitment to write a new personal journal entry once a week this entire summer. See them all at, which is a forwarding address this year to]

It’s no secret that collecting rare books is a big hobby of mine (one I partly monetize at eBay), and I make it a practice to hit a bunch of used bookstores whenever I visit a new city; but visiting such stores is always a push-pull experience for me, because of the following facts:

  • Every used bookstore in the United States is owned by a white male in his sixties.
  • Every used bookstore owner in the United States is a pissy, mean-spirited curmudgeon.
  • Every used bookstore owner in the United States institutes a series of cartoonishly backwards policies that no other kind of retail store could possibly get away with — refusing credit cards, open for only 15 hours a week, merchandise shelved ten feet above customers’ heads and no ladder available — because these mean-spirited curmudgeonly owners don’t actually want customers at all, nominally making their spaces “open to the public” so to prove that they’re somehow productive members of society, but in reality only wanting to be shut away with their thousand-square-foot library so they can read in solitude for 16 hours a day and otherwise be left the fuck alone.
  • And in fact, in perhaps one out of every ten used bookstores I visit (for example, the Chicago store in the above image, whose name I’m deliberately omitting so that this doesn’t show up in Google searches on the store’s name), it becomes painfully, heartbreakingly clear that the curmudgeonly owner has literally lost his very sanity, no longer even bothering with the pretense of being a “business owner” with “merchandise” for “sale” to “patrons,” instead exiling themselves to a nightmarish hoarder prison of their own creation, with aisles consisting of endless eight-foot-tall vertical stacks of books that no customer would ever possibly be able to navigate in order to actually purchase one, crammed so tight together that eventually they’re fated to topple on the curmudgeonly owner on a random Monday night, his crushed, rotting corpse not discovered until a month later, when a handful of his loyal visitors finally notice that the store’s been closed even longer than it usually is.

So in other words, visiting a used bookstore is like getting a glimpse of one of my own possible future fates, and the prospect deeply terrifies me all the way down to the core of my being. Because let’s face it, I’m a mean-spirited white male curmudgeon too; in fact, that was this very journal’s main attraction for many years, that I ran around being all pissy and cynical about everything and everyone I was ever in contact with, and I sold quite a few books of slam poetry and essays back in my twenties based entirely off this shtick. And so in one of those Sliding Doors-type situations where I’m looking forward at the possible forks my life could take from this point on, one of those forks involves me becoming a bitter spinster with no friends but 50,000 books, locked in my weird little intellectual prison that I open to the public from 1 to 5 pm, Wednesdays through Saturdays, chasing away anyone who might want to actually buy something so that I can instead let the tomes keep piling and piling up, until my fittingly poetic death when they all come tumbling down on me and no one’s around to hear my pitiful cries for help.

But, see, I don’t want this to be my eventual fate, which is why at the age of 48 I’m starting to take big steps to change the kind of person I am; for if I’ve learned anything during the process of becoming middle-aged, it’s that the pissy, cynical behavior you can get away with in your twenties — indeed, that some people find funny or even attractive at that age — is only possible because you’re still young enough for it all to be a ruse, an act you’re putting on to mask the inherent optimism and excitement over the future that most people in their twenties can’t help having. By the time you’re in your forties, however, that cynicism has gotten baked into your blood — all those breakups, all those lost jobs, all those failed dreams, all those dead relatives — so being pissy and mean at that point carries this harsh, unpleasant edge to it, one that threatens at that point to spiral into an unstoppable whirlpool that eventually ends in a punctured lung on the dusty floor of The Dog-Eared Page (NO CREDIT CARDS ACCEPTED / WE DO NOT BUY BOOKS).

It was a realization I was already starting to come to in my early forties, earlier this decade; but attending DevBootcamp in 2015, and being around a bunch of twentysomethings on a daily basis again, really cemented for me how much I want to work on my social skills here in middle-age, in a way I never bothered with or even cared about in my youth, where socializing was easy because I was still going to four open mics a week, had the stamina to get wasted at them and stay out until three in the morning, and had the overclocked sex drive that kept me mixing it up with others on a regular basis. And it just so happened that part of the DBC curriculum at the time (which is no longer the case, now that they’ve been bought by mainstream corporation Kaplan) was that we were required to participate in a series of “New Age” activities as part of our time there — mandatory yoga twice a week, mandatory “emotional intelligence” workshops three times a week — and were strongly encouraged to participate in yet more New Agey activities voluntarily — there were various meditation groups you could join, and they hired an on-site therapist for free weekly sessions if you wanted to take advantage of it.

To be honest, I probably would’ve never incorporated such New Age activities into my life if they hadn’t been forced on me; but once they were, I found myself really responding well to them (especially talking regularly with their therapist, which I’ve continued doing in her private practice in the two years since graduating DBC), and I credit these activities with pushing me a long way towards being a much more sociable and even-keeled person than I used to be even in my late thirties, and for saving me from my fate as a pissy used bookstore owner who shuts himself off from the world because he doesn’t have the skills to deal with other human beings. But that said, it’s important to note right away that I wanted to be able to do this without drinking too much of the New Age Kool-Aid; because like most others, I tend to roll my eyes a lot at the hippies who go around unthinkingly spouting New Age homilies like some kind of conservative Christian spitting out Bible verses at anti-abortion rallies, and also like many others I suspect that a lot of New Age people use these New Age activities as a way of justifying being a fuckup, and as an excuse to not actually work at the hard job of getting better at these things they’re constantly fucking up (which for the remainder of this essay we’ll call “Stuart Smalley Syndrome,” after the Saturday Night Live character who was the living embodiment of one of these blinders-wearing New Age fuckups).

Is it possible to get positive results from New Age activities without becoming Stuart Smalley? That’s essentially the question I’ve been trying to answer for the last two years, and I thought I’d finally sit down this weekend and share my particular observations, specifically when it comes to the three New Age activities that have had the biggest impact on my day-to-day life since starting to practice them, starting with…

Radical empathy

One of the most interesting things I’ve discovered in the last couple of years is that I’m actually a highly empathetic person — much more empathetic than the average human being — and that a big part of why I became such a pissy cynical asshole in my twenties and thirties was because I lacked the skills to keep my empathy at a healthy level (instead, the pain of every single person around me became my own personal pain, like a psychic in a science-fiction movie who can’t turn off the constant voices in his head), and so I reacted the only way I knew how, which was to reject 100 percent of my empathetic skills and turn it off altogether. Oh, and I suppose I should take a moment and explain exactly what empathy is, for those who don’t know; unlike “sympathy,” which is when you feel sorry for someone who’s going through a rough time in their life, “empathy” is when you literally take on and similarly feel the pain that that person is going through, the proverbial “putting yourself in someone else’s shoes” in order to better understand where they’re coming from. (The “radical” part of “radical empathy,” then, simply means to practice it in situations that are particularly difficult to do so — to be empathetic to a deeply religious person, for example, when you’re an atheist.) When done in healthy moderation, it’s one of the most powerful tools we have for making powerful connections with other people, and for understanding your “antagonist’s” viewpoint (“antagonist” here being someone like a feuding romantic partner, a co-worker you don’t get along with, someone who believes in an opposing political view from yours, etc); but if you’re the kind of person who was born with a natural high level of empathy, then never learned how to moderate it or keep it in check, it can ironically lead to a highly dysfunctional relationship with most other people in your life. (For example, if you’re the type of person who tends to jump straight into deeply intimate and highly intense romantic relationships right after meeting a person for the first time, or who has a habit of telling profoundly personal secrets to acquaintances at dinner parties, you’re likely the kind of person I’m talking about.)

That’s what a lot of my time with my therapist over the last two years has been about, learning and then practicing the exercises a highly empathetic person can do in order to have a better handle over their empathetic skills. (This isn’t some industry secret, by the way; you can do a simple Google search on the subject to discover many of the exercises I’ve been doing with the aid of a professional. In particular I recommend starting with the concentric circle exercise, in which you draw out the relationships you have in your life as a series of widening and narrowing circles in a bullseye pattern, from most intimate to least intimate. If you’re anything like me, it can be an eye-opening experience, and can help you understand how to better categorize the various people in your life and what level of intimacy you should be having with them.) So that’s really the first big difference between New Age practicality and New Age homilies — that you can go a long way towards having a sophisticated sense of empathy for your fellow humans without necessarily having to “just love all your brothers and sisters on Spaceship Earth, maaaaaaannnnnnn.” The reality is much more complicated than that, one that leaves a lot of wiggle room for thoughts like, “I really can’t stand this person, but I can at least acknowledge that the things they believe in are important to them, and that it’s possible for me to respect that without agreeing with them.”


Admittedly, this has been the hardest New Age skill for me to get on board with, even though it’s one of the most important, because this is the textbook definition of something us non-New Agers hold in suspicion about New Age people. When coming to it from the outside, and especially when listening to New Age people talk about it, the definition seems to be, “The act of forgiving yourself when you screw up;” but that right there is literally the source of the humor in all the Stuart Smalley skits on SNL, that he’s a guy who’s constantly screwing up, in ways that would be super-easy to correct if he would simply take a moment to be cognizant of the problem and be committed to the small steps of avoiding it in the future, but instead he pours an insane amount of time and energy into the act of “forgiving himself” for screwing up in the first place, thus fating himself to keep repeating the screw-up over and over for the rest of his life. This is one of the biggest accusations that non-New Age people have about New Age thought, unfortunately corroborated by many of the most hardcore New Age people out there; that the entire thing is basically one big scam designed to absolve lazy people from any sense of personal responsibility or accountability, a “get out of jail free” card that gives people permission to be the most horrible monsters they possibly can, with no repercussions as long as they “forgive themselves” afterwards.

So after two years of practicing this skill myself, I’ve come up with what I consider a much better and more precise definition of what self-compassion should be about — not “forgiving yourself when you screw up” but “forgiving yourself when your output for the day was at 80 percent, when you had been trying for 100 percent.” When defining it like this, it helps me remember a number of very important things about my life…

  • That as a highly ambitious, highly productive person, I tend to over-estimate how much I can get done in a single day to begin with, and that an 80-percent day for me is like a 100-percent day for many others;
  • That the 20 percent I don’t get done usually boils down to me being a human being and therefore suffering from very typical human problems — because I wasn’t feeling in tip-top health that day, because I didn’t get a good night’s sleep, because I got stuck in traffic longer than I was expecting, because I meant to watch one episode of that new Netflix series and watched four instead.
  • And thus, the reason to “forgive myself” is not because I failed at something major because of a big screw-up, but because I was slightly off my overly ambitious goal, because of being a human being who lives in a world of other human beings.

That’s the biggest overlap between what I’m talking about and what the stereotypical definition of “screwing up” is; because to be clear, there’s a big difference between not feeling at the peak of your game and therefore only reading four chapters of a textbook instead of five, and deliberately blowing off an entire day in order to get high and go to the park and therefore not doing any reading at all. That latter case is very definitely an example of screwing up, and I feel that there’s room in New Age thought for acknowledging that kind of screw-up, being critical of yourself for doing it, vowing not to do it again, then monitoring your behavior so that you don’t repeat it in the future. The problem, though, especially for ambitious perfectionists like me, is that we can easily make ourselves feel just as bad and guilty for slightly missing our ambitious goals as we do when deliberately screwing up in a catastrophic way; and that’s where self-compassion becomes a powerful tool in one’s arsenal, when you’re able to look at that situation and say to yourself, “Okay, yes, I’m a human being, just like the other seven billion human beings on this planet, and therefore sometimes I try my hardest and I still don’t accomplish everything I wanted to. That’s what human beings do, they try and sometimes fail; so instead of becoming obsessively focused on that and letting it affect my future behavior, I’m simply going to accept that today was an 80 percent day and then start all over again tomorrow morning.”

To tell the truth, the absolute number-one thing that’s helped me develop my self-compassion skills, way more effective than any other thing I’ve ever tried, has been to simply pretend that that behavior has just been committed by a good friend or a romantic partner, then to imagine what I would say to that person when they were feeling down about the behavior. It’s amazing, I think, how easy it is for us to forgive or at least wave away the small indiscretions committed by the people around us, yet how difficult it is for most of us to do that forgiveness when it comes to our behavior; to be able to look at a situation and understand it for what it is, to be able to say, “Sheesh, the world isn’t going to end just because you were feeling blah and decided on a random Tuesday to knock off work at 2:30 pm instead of 5 pm. There is really no reason at all to beat yourself up over something as impermanent and inconsequential as that.” If you can tell your boyfriend that without hesitating, why can’t you say it to yourself? That to me is what self-compassion is mostly about, the simple act of acknowledging that you’re an imperfect human and therefore will act imperfectly on almost a daily basis, but that it all balances out because the seven billion people around you are also regularly acting imperfectly.


And finally we come to one of the most sneaky parts of all about living a healthily socialized life, so hard to comprehend because it seems so counter-intuitive — that if you really want to be productive, if you really want to be churning along at your full ability, the key is to actually step back and not push yourself harder than your system can handle, and that this is doubly true when you get behind on something and are feeling the pressure to get better and faster. And in this we can start with something that author Ryan Holiday mentions in his 2014 Stoicism primer The Obstacle is the Way, which I only recently read but has had a profound influence on the way I now look at the world and my place in it. (But more on Stoicism, and the fascinating ways this ancient Western philosophy overlaps with the then-concurrent Eastern philosophy Buddhism, in a future journal entry later this summer.)

One of the things Holiday talks about in his book is about how when you’re trying to learn how to do something new, as long as you’re sincerely doing something productive every single day when it comes to that subject, seven days a week and 52 weeks a year, then it’s quite literally pointless to create artificial deadlines for yourself, because by definition you are absolutely guaranteed to eventually learn that thing you’ve decided that you want to learn, even if you don’t know ahead of time how exactly long that’s going to take. I’ve found myself thinking about that a lot this year when it comes to my coding work; because for those who don’t know, after two years now of doing just general education about general learning about this particular language and that particular protocol, here in 2017 is when I’ve decided to sit down and start building some actual real-world, working examples of the things I’ve been learning, projects that are actually live on the web and that potential employers can check out as a way of understanding what my skills are and why they should hire me.

I just recently got done with my first major project of this type, which is that I completely overhauled the website for the arts organization I own, the Chicago Center for Literature and Photography; this involved not just the part you can see as the end-user, how it looks and feels and what the buttons are and how they work (known in industry talk as “front-end development”), but also involved ditching the “back-end” software that’s been making it work for the last ten years, the now-outdated MovableType, and basically building the entire database back up again from scratch in the currently hot and trendy “content management system” known as WordPress. And so this involved me doing not just all the designing and user-testing and wireframing and HTML/CSS coding and user-interface creation that comes with the front-end jobs I’m out trying to get these days, but also involved me learning WordPress from scratch, learning the programming language PHP from scratch, learning how to set up a commercial web server host space, learning how to change all the DNS settings of a domain name to get it to point to the right place, and a half-dozen other subjects that are even nerdier and more obscure than these (non-coders, you may now roll your eyes here).

I’ll be the first to admit it — as a 48-year-old from a non-tech background, it takes me sometimes a painfully long amount of time to learn some of these things, with forward progression that comes only in fits and starts and sometimes sputters out altogether for days at a time. (For one good example, it took me two entire weeks of daily work to finally figure out how to add arrows to the sides of the colored boxes containing the tags of that particular blog entry, a process I detailed at my coding blog for those who are curious; just to have one of my UX mentors point out that people are going to mistake them for a breadcrumb trail when in fact they’re not, and that the best thing to do from a user-experience standpoint is to get rid of them altogether. Siiiiiiigggggghhhhhhh.) To keep myself motivated during this process, I had set up a series of artificial deadlines for myself during the five months it ended up taking to complete the project — old database migrated by March 16th, basic blog entry template finished by April 10th, etc — but whenever I’d get close to one of these arbitrary deadlines and found myself still hitting my head against the wall about something I couldn’t figure out, I found myself applying a tremendous amount of pressure to just keep working harder and harder, longer and longer, which was doing nothing but getting me more and more frustrated and outputting less and less. Or even worse, getting so frustrated that I would just burn out on the entire idea of coding, and spend entire week-long stretches not doing any work at all.

Once I took Holiday’s Stoic advice, however, and just started coding with no specific daily goals and no particular arbitrary deadlines — just sitting down in the morning and saying, “It doesn’t really matter how much I get done today, as long as I do something” — then ironically things started going better than they had at any other point in the entire project; because with the pressure off to perform up to the level of some nebulous outside Other I had been comparing myself to (“a professional coder would have this done by March 16th, so therefore I must as well”), then suddenly I could just appreciate the learning for its own sake, which gave me the freedom to try things out, test and revise, iterate quickly, and finally get something working in two or three days that would’ve formerly taken me a week. And meanwhile, with every detail that I converted from “this is never going to work” to actually working, my confidence was building more and more; and with this sense of ease I was able to work in an even more dedicated way than when I was trying to force myself to sit down and do eight hours of work a day, making the progression of this particular project not a straight diagonal line upward but more like a bell curve.

The obvious parts of self-care, the stuff the hippies are always crowing about, are certainly important but are also patently self-evident — getting enough sleep, eating well, exercising regularly, practicing mindfulness, having regular mental downtime, etc etc. But to me, the crucial part of self-care is the hardest part to identify, and certainly doesn’t fit into an easy New Age homily, which is the ability to acknowledge and understand our limitations, to own them and get comfortable with their existence, then to choose to keep moving forward despite them (or in a perfect world, while flipping them from liabilities to assets). It’s not just the crude “tending of the meatsack” aspects of self-care that are important, but also the act of getting deeply inside your own head, understanding your weaknesses, and choosing not to spend your life futilely flinging those weaknesses against the obstacles they’ll never be able to overcome. And that’s hard, because acknowledging your weaknesses is a tough and humbling process, one that most people don’t want to go through. And that’s difficult to encapsulate on a hemp totebag, which is why you rarely hear this crucial part of the process being discussed whenever New Agers want to extol the virtues of aromatherapy to you.

Okay, I think that’s enough for today. Next week, some observations and opinions about the three trips to New Orleans I’ve made in the last year, why NOLA is such a fascinating and unique destination that delights and infuriates in equal measure, and why regular visits to this “ehhhhhhhh, fuck it” town is so good for me as an uptight Northern Yankee German Protestant, despite how crazy it sometimes drives me. See you again then!