What I’m Reading: The Infinite Game by Simon Sinek

Sinek’s most recent book brings an application to James P. Carse’s ideas on life as a series of games, both finite and infinite. We are accustomed to the former; they have clear sets of rules, consistent strategies, and clear winners and losers. The infinite game, on the other hand, is not played to win, but to keep playing, with no clear winners and inconsistent, if any, rules at all. Using these ideas, Sinek argues that the prevailing structure and strategies of today’s businesses are playing the wrong game, favoring finite and arbitrary metrics over the values and developmental incentive of a game that is endless.

What I’m Becoming Obsessed With: Documentaries

One of the biggest challenges I face is attempting to limit media consumption as a distraction. While I don’t think I’ll ever be able to break up with Netflix entirely, I’m always looking for things that can make that time more valuable without sacrificing entertainment or creativity. So when I stumbled onto The Imagineering Story and Free Solo on Disney+, I quickly became hungry for more.

What I’m Challenging Myself With: More Writing

As the new year approaches, I’m starting to think about what I am beginning to think of new challenges or “resolutions” for myself. Of all of the projects and practices I have developed this last year, writing has been the most rewarding and creatively challenging. Motivation, however, has been missing, and not for lack of inspiration. It seems then that I need some accountability. Therefore, I am going to challenge myself to put out at least one new post or article a week in addition to the weekly roundups. A small and straightforward start. Who knows what more might come after this small step?

What I Want to Try: The Notecard Method

A significant flaw of mine has always been my inability to capture and process ideas or inspiration. In my recent exploration of the works of the author, Ryan Holiday, I discovered his way of doing just this. The basic idea is that when you are struck by an idea or by something intriguing, you write it on an index card and file it away, categorized by project, concept, or use. Then, when you return to that project or idea, you can return to the cards for inspiration and organize them into a structure and story. I have absolutely no idea if this will work for me, but of all of the systems I’ve come across, this seems the most promising. Perhaps an update on this method in the future.

The Quote I’m Pondering: “The pretense of knowledge is our most dangerous vice because it prevents us from getting any better.” – Ryan Holiday

What I’m Reading: Ego Is the Enemy by Ryan Holiday

Holiday’s book fell into my lap via a recommendation during the freelancer’s workshop I’ve spent the last month or so working on. This book will force you to make some hard confrontations with yourself. Approach with ease, Holiday’s insights and methods can be brutal and overwhelming at times. That all said every time I put the book down, I walk away considering myself and how I can better rid ego from my interactions. If you are interested in the ideas of stoicism and enjoy books like The War of Art, I can’t recommend this book enough.

What I’m Re-discovering: Bouldering

I’ve never been any good at it, but something about the act of climbing rocks and solving “problems” is an endless source of enjoyment. Not to mention the extreme sense of accomplishment that comes with discovering a level of fitness or flexibility you never knew you had. This love of mine started about two and a half years ago, just at the end of my freshman year. For lots of reasons not worth going over I took about a year off. But now coming back to it, I find myself obsessed all over again. In some ways, I’m better at it now, in other ways worse.

A Quote I Love: “Most people are just too self-absorbed, well-meaning, and lazy to bother orchestrating Machiavellian plans to slight or insult us. It’s more often a boring, complicated story of wrong assumptions, miscommunication, bad administration, and cover-ups—people trying, and mostly failing, to do the right thing, hurting each other not because that’s their intention but because it’s impossible to avoid.” – Tim Kreider

I’ve recently fallen in love with Kreider’s work. I’ve just finished his collection of essays We Learn Nothing. He has quickly become my favorite writer (a reckoning I’m still considering the implications of).

The quote speaks for itself, but there’s something beautiful in the way Kreider reminds us that people genuinely aren’t out to get us.

What I’m Reading: Stumbling on Happiness – Daniel Gilbert

It took me a long time to come around to reading this book. Eventually, so many people I respect and look up to recommend it that I had to give it a shot. I’m glad I did. One you forgive the self-help-y title, this book is a fascinating dive into the psychology of happiness. A lot of Gilbert’s arguments have wormed their way into how I think about my everyday life. I’m interested to see how they play out in the long term,

What I’m Struggling With: Health vs. Habits

I’ve been on a roll lately. I’ve been healthy, mindful, and have spent a lot of time on my intellectual and artistic pursuits. But this week, for the first time in a long time, I got sick. The things I’d been doing every day for the last six months ground to a halt. Priority one for me was to try and maintain as much of my day to day life as I could. But the hardest part is putting your health against your habits. It’s hard not to feel guilty when you need to take a step back. At some point, we need to remind ourselves that we are playing the long game. A break when we need can be even more important than the work we put in.

The Quote I’m Thinking About: “In an infinite sea of possible beliefs, evidence is the only life preserver we’ve got.” – Mark Manson

I love two things about this quote. The first is the acknowledgment that the conflicts we deal with are wholly based on belief, not facts. This perspective is something that often gets overlooked and forgotten in the shoot-from-the-hip arguments on social media. Secondly, that those facts are not tools for our discussions, but something substantial to hold onto in the rush of those beliefs. Too often, we jump to using facts and data as our weapon of choice. But today’s conflicts are that of belief, and no armor is more equipped to dull facts than belief. The importance of evidence lies not in its lethal potential, but in how we use it to tell a story. When told in the right way, a story can encapsulate any belief, turning that evidence into a movement and an epidemic of change.

What I’m Reading: Everything is F*cked by Mark Manson

In true Manson fashion, this book is filled with wit and dripping with personality. In his latest book, Manson takes on our preconceptions about hope. Giving it to us straight, Manson forces the reader to challenge their approach to hope, drawing on the ideas of philosophers like Plato and Kant along the way. Though these are not necessarily “new” ideas, Manson’s skill as a writer has you turning them over long after you’ve put the book down.

What I’m Reminding Myself: Who Are You Serving?

Who is the story for? What is the culture we are trying to change or influence? These are questions we need to be asking ourselves constantly, in every decision we make. When we lose sight of the audience our story falls apart. When it’s for no one it’s for everyone (and vice versa). It becomes a land grab of selfish and misguided ideas. The walls fall and integrity goes missing. So then, we must reinforce. We must approach with intent. In everything we build we return to our integrity to ask: ”Who are you serving?”

The Quote I’m Thinking About: “The Goal is to see what happens, so there’s No way to fail” – Derek Sivers

If we approach life as a series of experiments then there can be no failure. Only learning.

What I’m (Re) Reading: The Tipping Point – Malcolm Gladwell

I read this book 3 years ago when I was first exploring Gladwell’s work. At the time I wasn’t all that interested in the implications of the book but found it to be a good read. Now, I don’t typically re-read books. I can’t say there’s any specific reasoning, I just never find myself inclined to. But the more I dive into my recent obsessions with marketing, storytelling, and social science the more I keep coming around to Gladwell’s book. I want to see if my perspective on the book and its ideas have changed. Maybe I’ll find something new, maybe I’ll hate it, or maybe it will just be a reminder of a good read. In any case, I’m excited to find out.

What I’m Pondering: Mismatched Results

It’s really easy to derive progress from measurement. Data tells a story. Often a very clear story. But sometimes the data doesn’t reflect how you feel. When we follow the diet and exercise we expect the numbers on the scale to go down. We feel lighter. We feel more confident. But what happens when that number doesn’t go down? Or worse the number goes up? What do you do when your faith and feeling aren’t aligned with the numbers? We could change the system. Experiment for success. Or maybe redefine our goals. Perhaps we decide the feeling is more important than the scale. Or is it that we need to measure differently? Every answer is a path. But what is the path for you?

The Quote I’m Considering:

“If more information was the answer then we’d all be billionaires with perfect abs” – Derek Sivers

This is a trap I get caught in a lot. I trick myself into believing that if I just do more research or read another book then everything will change, the world will become clear. But change can only occur through motion. Learning is one of my favorite things, but what good is all of that knowledge if we don’t use it.

What I’m Reading: Freakonomics – Steven D. Levitt and Stephen J. Dubner

This book has been on the back burner for a while now, but I’m really glad I got around to reading it. Unlike most of my reading list, Freakonomics doesn’t focus on a central theme. Rather, Levitt and Dubner take us through some interesting questions and show us how conventional wisdom may be easily broken if we only look at the right data. The book is filled with great studies and anecdotes, It’s got me thinking a lot on how similar situations may be dealt with in our lives.

What I’m up struggling with: Free Time

It’s been a while since I’ve had so much time to myself. I’ve mostly been working back to back to back for about 8 months now. I’m now confronted with (entierly on purpose) by a ton of free time. It’s really great to be able to relax but I constantly find myself going a little bit insane. I think this time will serve as a great creative resource but also as a nice mental reset.

What I can’t get out of my head: This TED Talk

I watched this about a week ago and I haven’t been able to stop thinking about it. Though Shirky directs most of his examples towards internet culture (that is his specialty after all) it also applies almost directly to everything we do as artists, especially in the theater. I think it’s easy to rail against the institution as collaborators but Shirky draws some interesting conclusions on the application of both.

The quote I’m thinking about: “You must respect the body you are trying to heal”

What if that body is an institution, a system, an industry?

What I Overcame: The Fear of Posting

I’ve been turning over how this blog was going to take shape for weeks now. Admittedly these weekly posts have started to feel safe. The thing I feared was putting the ideas down and lacking any authority to carry them. Yesterday’s post on initiative was ironically the thing that broke me down. It came in a burst of inspiration and for a moment felt confident about posting it. If it hadn’t happened then and there it might not have gone up at all. Hopefully, overcoming that has opened to door to exploring more of what this blog and my writing can be.

What I Didn’t Know I Needed: To Get Away

Yesterday I had a bit of extra time in my day. Usually, I spend my free time in a room somewhere, writing, reading or watching something. but I wasn’t feeling inspired to do any of these things. On my way back from my errands I happened to be walking by the Boston Public Garden and couldn’t remember the last time I had walked through them. I ended up sitting under a tree in the gardens just watching the tourists and families around me. I left an hour and a half later completely revitalized. It had been so long since I had taken that kind of time to be still and sit and listen and observe. I’m making a pact with myself to do this every so often, as often as I can. it sounds cliche but I think we often forget how important it is to stop and take it all in. And hey things are cliche for a reason.

The Leap I Took: The Freelancers Workshop

It’s no secret that I’m a fan of Seth Godin. I mean that’s his quote at the bottom of the post. Outside of his books and talks, one of the things I’ve kept an eye on for a while is Godin’s training courses through his company Akimbo. He and his team have created various programs focused on different areas of business and marketing. They happen every few months throughout the year. This past week I decided to sign up for the Freelancer’s Workshop and it’s already opened my eyes to so much. The program hasn’t even officially started yet and I’ve gotten the chance to talk and learn from dozens of different people providing all kinds of art and service. I can’t wait to see what the rest of the program brings.

The Quote I’m Pondering: “Sometimes the best thing to do is to break it for the people you don’t care about and make it work for the people that you do.”

It can’t be for everyone.

What I Accomplished: 100 Days of Morning Pages

This week I hit a 100-day streak of Morning Pages. If you haven’t heard of the morning pages they are the daily practice introduced by Julia Cameron in her book The Artists Way. The idea is that first thing every morning you sit down and stream-of-consciousness write 3 pages. It doesn’t matter what they are or what comes from them. It could be absolute nonsense. The goal is to clear your head and start the day off in the right headspace. It’s a practice I highly recommend to everyone. I can point to it as one of the most important parts of my daily routine.

What I’m Reminding Myself: Your Art Can’t be for Everyone

And it shouldn’t be. I think it’s easy to get lost in wanting your art to affect people. But the issue is that we think too globally. “People” is too vague. We need to be clear about who our art and who are change is for. It can’t be everyone. When we talk about “great art” we have to remember the context of that statement: it’s great art to someone. There’s no such thing as bad art, just wrong art for you. So before we go trying to mass market out ideas and stories lets start by considering who we want to change.

What I’m Pondering: The Fundamental concepts

Maybe it’s just me but the more I read the more I’ve started to wonder if there exists a single set of fundamental topics or ideas that every other area of learning or passion can be broken down into in one way or another. I don’t think I have a clear answer yet. Now to be clear I don’t mean topics like science or math. Those to me are a different kind of fundamental. I’m looking for the things that we can point to as a source for the way we talk about business, marketing, art, philosophy, belief, sociology, etc. The conceptual fundamental.

What I’m Reading: Purple Cow – Seth Godin

I’ve been burning through Godin’s books these past few months (he’s written 23!) and with each one, I gain some new insight into how marketing (storytelling) is one of the most influential things we have at our disposal. Purple Cow is Godin’s dive into the product side of marketing. He argues (quite convincingly) that today’s society has no tolerance for the mild. The days of mediocre products backed by stellar marketing have passed. The products themselves (and our ideas) must now be as remarkable as the marketing that drives them. These are our purple cows.

What I’m Reading: Talking to Strangers by Malcolm Gladwell

Gladwell’s most recent book has been dominating my free time. I mentioned last week how huge a fan I am of his work. I’m willing to say that this is his most intriguing book yet. His exploration of human interaction and the assumptions we make about others is perhaps his most urgent dive yet. True to fashion, Gladwell strings his readers through story after story showing us how our assumptions and our biases about others play against us.

What I’m Pondering: Thresholds

This week I’ve noticed myself crossing a lot of thresholds, or at the very least become aware that they are behind me. It has me thinking a lot about how we look at change. The changes don’t come day by day. They stack up until suddenly we notice how far we’ve come. We cross a threshold. The thing about instituting change is that the results aren’t linear, and they never will be. But the consistency compounds and sooner or later you’ll find yourself in a completely new place. The important thing then is to balance how we treat the small and putting faith in their ability to collect and push us forward.

What I’m finding passion in: Writing

Through this blog and my daily journaling, i’ve discovered how much I love to write. Or maybe re-discovered. To be clear I don’t mean the act of having written. That distinction hangs on the idea of completion or publishing. What I enjoy is the process. Sitting down and putting words on a page. It’s taught me a lot about the traps of perfectionism and the value of focusing on the act of creating rather than the end product.

The thing I’m reading: Thinking in Bets by Annie Duke

An exploration of making decisions when you don’t have all the information. What I appreciate is that this book not only covers all of the information groundwork but it also provides applicable knowledge of how to become a better decision-maker. A former world champion poker player, Duke takes the reader through all of the psychology on decision making and guides the reader on her approach to refining that talent. I especially love the insistence on becoming comfortable with uncertainty. I highly recommend it as a follow up to Thinking Fast and Slow by Daniel Kahneman or Blink by Malcolm Gladwell.

The Thing I’m Reflecting on: Transient Change

This summer was the first time I got a taste of what it was going to be like after college. By the end of it, I was more than ready to jump headfirst into that life. But of course, I am now back in Boston, finishing up my last year of college. I’ve come to realize that every “change” in my life thus far has been highly transient. Sure I spent a lot of summers away as a kid. I even moved across the entire country for college. But there was always some end in sight. Some calendar or time marker that I could use as a baseline. But the coming change of graduation is unlike any other. It’s the first change without any sign of “normalcy” on the other end. I think that’s the real scary thing about graduating. It’s the fact that there’s no longer that promise of a “return.” You can’t see the end of the slope anymore.

The Thing I’m Fearing: A Habit Relapse

I spent a lot, and I mean a lot of my time in New York working on personal growth. This blog is sure a sign of that as any. I built incredibly good habits, destroyed bad ones, and have come out the other side mentally, and physically, healthier than ever before. So, I have to admit being back in the place where those bad habits originated is a little worrisome. I guess acknowledging that is the first step.