Something I’ve learned about myself over the years is that I’m not great at goodbyes.

It’s not that I find them difficult or onerous, but rather that I often fail to register them as being negative. Yes, we’re approaching the end of something, which is consequential. But I generally spend more time thinking what I’m moving toward rather than what I’m leaving behind, which can conflict with the moroseness one is supposed to feel at such moments.

I’ve gotten better at explaining this to people so that they don’t get the wrong impression. In my mind, this isn’t ‘goodbye’ in the sense that we won’t see each other anymore, but ‘goodbye’ in the sense of ‘see you later.’ We live in the future, we have astounding technologies that can move us around, help us communicate over vast distances, and allow us to share our lives across planetary hemispheres. Geographic distance doesn’t really intimidate me, but I know that for some, such distances represent a radical and possibly negative adjustment to how things have been. For some, changes represent little more than endings.

I can understand that sentiment. But change needn’t be a bad thing. A change in rhythm, in tenor, in daily habits, in what we’re exposed to, in the work we do, in our relationship status, in the keys we have in our pocket and the space we return to each night—it needn’t be daunting or debilitating. These changes are just as likely to be positive as negative. And the former is more likely, in fact, if we decide this newness is going to be positive regardless of what we find on the other side; if we decide to make the most of whatever comes next.

An established way of living and doing things is calming and comfortable. It’s predictable, and it allows one’s brain to chill the hell out for a time.

But shaking up that routine, those habits, creates a period of near-infinite opportunity. It’s an in-flux quantum superstate that can land absolutely anywhere. If you no longer go about your day on autopilot, if you no longer assume certain cycles and milestones, you can do anything, any time. You can fix problems view new habits. You can take up new hobbies, do your work differently, spend more time with friends and family, or more time with yourself. Or both.

Endings are the opening act for new beginnings, and part of why they can be so stressful is that we’re suddenly responsible for our future happiness in a way we haven’t been for maybe a good, long while. During a period of relative predictability, maintaining our rituals and holding down the fort keeps us engaged and occupied. Moving away from that routine, we instead must exert ourselves by filtering through our countless options and figure out not just what our new lives will look like, but who we will be, next. We have to figure out what priorities will shape our environments, and if we have what it takes to accomplish what we think we might be able to get done.

It’s frightening to think we might want something but cannot, under our own motive power, accomplish it. It’s terrifying to think we may end up someplace new, surrounded by new people, doing new work, and with everything sub-par to how it was before. It’s debilitating to worry that the choices we make might be the wrong ones, and that where we end up as a result will be no one’s fault but our own.

But approached intentionally, with enthusiasm and care, our conclusions can serve as reintroductions. For us toward the world, unveiling a brand new self, but also the world toward us, reigniting a flame of curiosity and passion, rediscovering what it feels like not to know, but to enjoy finding out.

This essay was originally published in my newsletter.



I think my favorite of all the business models I’ve come up with over the years was the one underpinning a project called Exiles.

Exiles was an email publication that I sent out every two weeks, and each issue contained five essays. These essays fluctuated in length, usually falling somewhere between 500 and 1,500 words, and generally had a more narrative tone than a lot of the other writing I was doing at the time.

I went through all my old blog posts recently, adding updated thoughts and messages to them, and the impact this project had on my writing back then was immense. On one side of the divide I was offering a lot of prescriptive advice and my work was formatted like most other blogs you might have read at the time. On the other side, post-Exiles, my work had a more narrative flavor. I began telling a lot more stories, pulling a lot more insight from my experiences on the road, and analogizing in a way that made the topics I was writing about a lot more interesting, comprehendible, and mentally sticky.

This project was also economically significant for me. I had no idea if the concept would work, because I’d never seen anything quite like it, but the pitch was that if subscribers paid $5 per month, they’d receive this twice-monthly missive, plus they’d get all the books I published for free. What I wanted to do was cut out all the middlemen and build my own patron-based model, where people could essentially sponsor my work for a low monthly fee, benefitting from the fruits of my labors (receiving the end results of my work in book form), but also seeing the interstitial evolutionary pieces. The thoughts and ideas that would eventually help shape those more substantial publications.

I started Exiles in August of 2011, and published the final issue at the end of October of 2014. Part of the rationale behind moving on was so that I could improve upon the model — it wasn’t by itself a successful enough sub-business to cover all my expenses, and I was anxious to spend the time I was putting into the project into some new ideas, some new potential models that I wouldn’t be able to properly invest myself in, otherwise.

I still think something like this might be feasible, and even desirable for some types of work and some types of people. An email I received in response to that final issue back in 2014, was from a reader telling me they’d initially subscribed to it not because they necessarily needed more to read, but because they were trying to figure out a way to give me money. The value they had derived from my blog and from my books, they said, was greater than what they paid for the books.

I’ve had that same feeling more than once about work produced by other people. I wonder if someday we’ll have micropayment capabilities built right into our browsers and apps which will allow us to, without muss or fuss, send a dollar to someone who wrote a particularly valuable blog post, or contribute directly to the artist every time we listen to music streamed on our smartphones.

Right now we have somewhat clunky options for this. I’ve been using things like Paypal and Venmo to allow listeners to contribute to my podcast, and have recently started a Patreon page to do the same, with a few added bonuses for those who do so. But these are all still indirect bridges between creators and consumers. Little by little they get better, and give us more capabilities in terms of supporting work we care about, but they still require clever business models, rather than being predicated on technologies that are so intuitive and widely available that we needn’t even think to use them; so that we can focus completely on the work.

Maybe someday that’ll change, and the distance between creator and consumer will be reduced.

In the meantime, we make do with the tools, the bridges, we have available. It requires a bit of intentional action to turn our love for things into the support they require to exist, but that these bridges exist at all is a step in the right direction.

This essay was originally published in my newsletter.



The following essay is an excerpt from my new book, Becoming Who We Need To Be.

Our instincts are informed by our knowledge and experiences. This means that they’re flawed, but it also means they’re trainable.

Which is to say that the more we learn, the more we know, the wider our range of personal experience, the more fine-tuned our intellectual reflexes, our instincts, will become.

If I showed you a poster, designed and illustrated to attract attendees for a conference in Seattle, chances are you would have some immediate, innate response to it. It will appeal to you, or not. It will make sense to you, or not. We all have aesthetic instincts, and while none of them are wrong, they’re also all different. Again, our tastes in these matters are informed by who we are, and all the things that make us unique. Our differing opinions don’t imply that one person’s taste is superior to another’s, just that they have senses of aesthetics that are defined by different things.

That said, if you were to show the same poster to someone who has a background in design and illustration, they might be able to point out structural and aesthetic strengths and weaknesses of the piece. It makes good use of the rule of thirds, perhaps, but the typography is too condensed for a poster, and the contrast not high enough; the words won’t be legible more than a few feet away. Further, while the graphics are beautiful, they don’t tell you much about the conference or where it’s being held, and the city skyline used in one of the graphic elements isn’t from Seattle, it’s from Portland.

Here we have a set of aesthetic instincts that have been sharpened by a completely different set of experiences and knowledge, and consequently, the designer sees things that the non-designer would have no reason to see. Someone who isn’t educated in aesthetics or visual hierarchy would have no reason to consider that the graphic elements might be unintentionally displaying visual cues from another city, nor to wonder if the pertinent information is visible from a distance, as one might hope it would be on a poster. They’d also have no reason to assume that part of why they find the work beautiful is because of the division of the space into thirds, which is a composition technique based on the Golden Ratio, which replicates proportions found in nature and which humans tend to find beautiful. This last piece of ratio-related information is something we’ve been aware of as a species since the early 16th century, and yet most people are unlikely to think about it when viewing a design or piece of art.

And so, while one’s taste is not directly comparable to another person’s in the sense of “better” or “worse,” you could absolutely ascribe a pragmatic value to the aesthetic instincts of a designer over that of a non-designer when it comes to, say, figuring out why a billboard isn’t quite right, or how best to compose a photograph, or how a room might be optimally furnished and painted. The collection of information a designer has, and their experiences with similar situations in the past, make it far more likely that their responses in such settings will be informed by actionable information rather than personal taste, the latter of which could be based on any number of things, many of them not relevant to the task at hand.

This isn’t to say that there’s no way a non-trained aesthete would ever come up with design-related ideas that surpass that of a professional designer. There are people who have the visual equivalent of perfect pitch in that they latently understand spatial problems, like those related to proportion and composition, or can mentally blend and contrast colors in the same way a musician might blend sound. It’s also possible that an untrained person with no particular knack for design simply has a “eureka” moment, understanding for whatever reason what needs to be done to make a room feel more comfortable, or a painting more impactful.

This will be the result of their knowledge and experiences, but they likely won’t know which combination of variables led to that particular idea. As a professional designer with over a decade of experience, I will sometimes construct or correct things based on knowledge of what tends to make for good composition and proportion, but in many cases I know what will work based on intuition, then circle back to figure out why it worked, afterward. The result will often be the same, because my instincts have been trained over the years, and my brain filled with knowledge on this particular subject, so my subconscious pulls up all that background and applies it without me having to consciously guide anything.

The same is true for auto mechanics who have spent years working on cars, and who suspect a particular component is causing problems in an unrelated area of the vehicle, even though they can’t quite say why they think that’s the case. This is also true of cops who have worked with people for a long time, and who have come to know when they’re being lied to, or when someone is holding information back, even though they wouldn’t be able to tell you if you asked how they know.

Training our instincts is like feeding our subconscious. It grants us more informed, helpful knee-jerk reactions, rather than blind and potentially damaging impulses.

I’ve spent the last six months learning how to cook, and though I’m still no chef, when you prepare all your meals for a decent amount of time, you begin to look at related things a little differently.

Going to the grocery store, for instance, is an entirely new experience for me now that I cook. I paid attention to different aisles back then, primarily those containing frozen foods and prepared meals. Today, I spend a lot more time in the aisles which didn’t hold any particular appeal for me before: those containing ingredients, things that aren’t food yet but which can be made into all kinds of things with the right knowledge and application. Flour and baking powder and salt and sugar and racks full of spices would not have been very valuable in the hands of the person I was six months ago. Today, though, these ingredients have unlimited potential.

As we learn more, we become more aware of the world around us. The grocery store is a far more complex place to me, now, because the percentage of the building that contains relevant products has increased tenfold. I now have reason to pay attention to all those bags full of whatever, because I understand how they fit together with all the other bags and boxes and sacks full of things.

The grocery store hasn’t changed, I’ve changed. And in turn, the way I experience my environment has changed.

The same is true of any field or body of knowledge. There’s a joke in the design world that if you really hate someone, teach them about typography. The rationale is that the world is so full of bad design, and particularly bad use of typography—on signage, t-shirts, billboards, the internet, everywhere—that you cannot help but see it everywhere you go. But you don’t notice how bad it is, or know what rules are being ignored, until you understand the fundamentals of typography. As you learn more about design, you come to feel more comfortable when surrounded by beautifully designed things and uncomfortable around things that need to be tweaked or corrected. Badly designed signage that you pass every day on the way to work can become torturous because you can see the flaws, almost viscerally feel the improper use of kerning, and that pain is a consequence of your typographic knowledge. Where once such signage may have simply blended into the background, now you know enough to see the flaws, and feel their dissonance.

Becoming more informed, more aware, has downsides. It means you’re more conscious of the bad stuff: not just the terrible typography, but also the violence taking place overseas, the way children are abused by their parents all around the world, the mistreatment of people because of their religion or skin color or cultural heritage. An awareness of these things can be valuable, but it can also be painful. Just as learning to cook opens up all those previously uninteresting aisles at the grocery store, their contents once blurred by ignorance but now crystal clear and relevant, learning about history and conflict and politics and humanism and disease and economics and international relations can be both uplifting and soul-crushing. It can fill your world with more colors and shapes than you ever knew existed before, but in seeing these new elements, you also see all the negatives, the horrors, the corruption and sadness and pain.

You can’t have one without the other. Increased awareness of anything increases your capacity to see and understand both bad and good.

Not many people would admit to keeping themselves ignorant for this reason, but many do. They don’t intend to blind themselves to the good, but they do want to overlook the bad. They want to keep such concerns from infecting their conception of the world, and from tinting a perspective they can control and have come to understand. Additional complexity could weaken what they’ve built and the worldview with which they’ve grown comfortable. The tradeoffs, in their minds, are simply not worth the risk.

For some, intellectual blinders are a handicap enforced upon them by others: authoritarian governments, overbearing parents, societies or organizations that preemptively label anything they don’t control as false or wrong.

For others, those blinders are self-applied. Which is a tragedy. If all you’ve ever known is the color blue, different shades and tints of blue, and you’ve never seen any other color from the spectrum, it’s understandable that you might be skeptical that there are other colors out there, especially if attaining them requires some effort; perhaps you have to leave blue behind for a time so that you can see red, so that you can see yellow. Some people, perhaps most, would never leave their familiar, comfortable blue world behind, because the costs of knowing other colors might seem too high, too risky. What if they can’t find blue again? What if perceiving new colors is a horrible experience? What if a multicolored world is more confusing and complicated than one that’s mono-hued?

Once you see the other colors, you can’t put your blue blinders back on. Not easily, anyway. The blues will still be there, but not with the same purity as before. You’ll perceive blues mixed with all the other colors, inextricably connected, because there’s nothing that isn’t connected to countless other things, and as such there’s no purity, no single-color perspectives in the real world.

Filtering is possible, but only at the expense of life’s many connections and realities. You can live your whole life in a blue-tinted bubble, but only if you’re willing to never see things as they really are. You’ll see greenish-blue and never realize that it’s actually yellow.

If we are going to pull off our blinders, we have to want to do so, and we have to be prepared for the consequences, both good and bad.

Is it possible to keep yourself, and potentially your society, sequestered from everything and everyone, and in doing so avoid much heartache and sadness, but also joy and fulfillment? Yes.

Is it advisable?

That’s for each of us to decide for ourselves.

If you’re interested in reading the full book, you can get it as a paperback, ebook, or audiobook, and from wherever you typically get your books.