2020 Reading List

The following is the list of books I read in 2020. Some of these were re-reads, and a handful I read more than once.

I’ve only added books to the list that I actually finished. I started many more books this year. Some weren’t interesting. Others only had a small section that was relevant.

My rule for “finished” = 85%. If I’ve gotten through 85% of a book, I’ve absorbed the core ideas and I consider it read.

Honestly, though, I rarely leave a book at 85%. If I’ve read that far, I find it interesting, so I’m likely to read it all. Almost every book on the following list was read cover to cover.

List Key:

  • Bold = personal development books (career, mindset, or skill-specific)
  • Italics = fiction
  • * = recommended
  • ** = highly recommended

2020 Reading List:

(In chronological order)

  1. Turning Pro — Steven Pressfield
  2. Dumbing Us Down — John Taylor Gatto
  3. The Four Agreements — Don Miguel Ruiz**
  4. Ego is the Enemy — Ryan Holiday
  5. All the Pretty Horses — Cormac McCarthy
  6. How Fiction Works — James Wood
  7. This Won’t Scale — Drift Marketing Team
  8. The Call of the Wild — Jack London
  9. The Pine Barrens — John McPhee
  10. The Game of Life and How to Play — Florence Scovel Shinn**
  11. The Story of Land and Sea — Katy Simpson Smith
  12. Plainsong — Kent Haruf
  13. The Score Takes Care of Itself — Bill Walsh
  14. The Act of Creation — Arthur Koestler**
  15. On the Road — Jack Kerouac
  16. In My Stead — Robert Day
  17. Economics in One Lesson — Henry Hazlitt
  18. Relentless — Tim Grover*
  19. To Sell Is Human — Daniel H Pink
  20. Winesburg, Ohio — Sherwood Anderson
  21. Writing to Learn — William Zinsser
  22. Hemingway on Writing — Larry W. Phillips and Ernest Hemingway*
  23. Zen and the Art of Writing — Ray Bradbury
  24. 21 Stories — Graham Greene
  25. Becoming a Writer — Dorothea Brande**
  26. Their Eyes Were Watching God — Zora Neale Hurston**
  27. Mastery — George Leonard**
  28. Zen and the Art of Archery — Eugen Herrigel*
  29. Mothering Sunday — Graham Swift
  30. Johnny Got His Gun — Dalton Trumbo
  31. Gentlemen Prefer Blondes — Anita Loos
  32. Prodigal Summer — Barbara Kingsolver**
  33. Tobacco Road — Erskine Caldwell
  34. Thinking as a Science — Henry Hazlitt**
  35. How Will You Measure Your Life? — Clayton Christensen
  36. A Moveable Feast — Ernest Hemingway*
  37. Mastery — Robert Greene
  38. Ogilvy on Advertising — David Ogilvy
  39. Think and Grow Rich — Napoleon Hill**
  40. What to Say When You Talk to Yourself — Shad Helmstetter**
  41. Book of Sketches — Jack Kerouac
  42. Steal Like an Artist — Austin Kleon
  43. Evensong — Kent Haruf
  44. Benediction — Kent Haruf
  45. Wilderness — Scott Stillman
  46. In a Narrow Grave — Larry McMurtry
  47. Oranges — John McPhee***
  48. Good to Great — Jim Collins
  49. The Bean Trees — Barbara Kingsolver*
  50. The Personal MBA — Josh Kaufman*
  51. The Great Gatsby — F. Scott Fitzgerald**
  52. The Old Man and The Sea — Ernest Hemingway
  53. Let My People Go Surfing — Yvon Chouinard*
  54. The Love Artist — Jane Alison*
  55. Anthem — Ayn Rand
  56. Meander, Spiral, Explode — Jane Alison
  57. The Magic Path of Intuition — Florence Scovel Schinn**
  58. My Life and Work — Henry Ford**
  59. Black Water — Joyce Carol Oates
  60. A Short View of Great Questions — Orlando J Smith
  61. Letter to My Daughter — Maya Angelou
  62. Garden of Eden — Ernest Hemingway*
  63. The Boron Letters — Gary Halbert**
  64. Your Word is Your Wand — Florence Scovel Shinn

How I chose these books:

My book choices (generally) come from three places:

  1. Recommendations
  2. References from another book
  3. Questions I’m exploring

I got some great recommendations this year from colleagues and friends. That’s where many of the personal development books came from.

I also like going down rabbit holes in my reading. If an author has insights I appreciate, the chances are high I’ll also like their book recommendations.

Most of the books I choose, though, come from areas I’m curious about — which is why there are some underlying themes in the above list.

The questions that drove this year’s reading:

  1. How do people learn? How can I better learn and facilitate other people’s learning? –> The best books for answers: Mastery by George Leonard, Zen and the Art of Archery by Eugen Herrigel, Thinking as a Science by Henry Hazlitt, Writing to Learn by William Zinser, Mastery by Robert Greene
  2. How can I improve my mindset (and therefore my success, my self-actualization, and my creativity)? –> The best books for answers: Think and Grow Rich by Napoleon Hill, What to Say When You Talk to Yourself by Shad Helmstetter, Ego is the Enemy by Ryan Holiday, The Four Agreements by Don Miguel Ruiz, The Game of Life and How to Play by Florence Scovel Shinn (most of these were books I’d read before, and will re-read many times in the future)
  3. How can I improve my business acumen? –> The best books for answers: Personal MBA by Josh Kaufman, The Boron Letters by Gary Halbert, Ogilvy on Advertising by David Ogilvy, Let My People Go Surfing by Yvon Chouinard
  4. How do I get better at listening to my own intuition? –> The best book for answers was hands-down The Magic Path of Intuition by Florence Scovel Shinn
  5. What makes a really great novel? –> The best books for answers: How Fiction Works by James Wood, Becoming a Writer by Dorothea Brand, and Meander, Spiral, Explode by Jane Alison
  6. What are the best books from each place I traveled?

Travel-related books:

I read a number of books this year that were from and about the places I was traveling. I spent most of 2020 in Colorado, Texas, and Florida, and I tried to read at least a couple books tied to each place.

Colorado: Plainsong by Kent Haruf, Evensong by Kent Haruf, Benediction by Kent Haruf (a trilogy), Wilderness by Scott Stillman

Texas: All the Pretty Horses by Cormac McCarthy, In a Narrow Grave: Essays on Texas by Larry McMurtry. Definitely not enough Texas books. I’m going back in 2021, and I’m planning to add more to the list then.

Florida: Their Eyes Were Watching God by Zora Neale Hurston, Oranges by John McPhee

Top fiction recs:

At the start of the year I went down the rabbit hole reading American authors from the 20th century (especially authors I hadn’t read before). A lot of this year’s fiction fell under that umbrella, although my interests definitely meandered.

I read 24 novels this year, but these were my favorites:

  1. Their Eyes Were Watching God by Zora Neale Hurston (re-read — it’s one of my all-time favorites)
  2. Prodigal Summer by Barbara Kingsolver
  3. The Garden of Eden by Ernest Hemingway
  4. The Love-Artist by Jane Alison (re-read — another favorite)
  5. The Great Gatsby by F. Scott Fizgerald (another re-read, another favorite)
  6. All the Pretty Horses by Cormac McCarthy

H/t to Chuck Grimmett’s “Reading” page, which inspired me to put this together. Spending the last couple days of 2020 auditing this year’s reading list has been a fun exercise — I intend to make this a habit.

Be So Good Your Worst Customers Love You

This has been (one of) my motto(s) in 2020: build customer experiences so amazing even your customers who aren’t a good fit end up loving you.
I had a call once with a customer who was struggling to use my company’s product. This was an on-the-brink, about-to-cut-ties kind of call — but as we were talking through options, he adamantly said: “You guys have been f***ing amazing.”
That’s stuck with me ever since. The product didn’t work, but the people did — for him, relentlessly, to the point that he had an amazing experience even though he had to drop the product.
When you’re wholly focused on giving your customers an awesome experience, you’re increasing the likelihood of their success using your product.
But even if it doesn’t pan out, the indicator of whether or not you did your job right is whether or not they enjoyed working with you.
Think Comcast vs. Chick-fil-A. Everybody hates working with Comcast (at least, everyone I’ve ever met does). And Comcast doesn’t care about whether or not you succeed using their product — or at least, they don’t make you feel like it. Nothing about their company is designed to make a customer happy.
People use Comcast because they have to, not because they want to. They need internet, it’s the available option. They bite the bullet.
But everybody loves Chick-fil-A. Customers love the experience as much as the food — the friendliness, the quick service, the customer-centric mentality. Everything about the way it’s set up — from the quick drive-through times to the chronically happy employees — makes the experience better.
People don’t go to Chick-fil-A because they have to. They go because they want to.
There’s a distinction here, because it’s easy to get misled down an ego-driven road of seeking customer approval. Wanting to be the coolest customer service rep ever is a false compass. Pandering to your customers to buy you their favor is not an effective strategy.
Being respected for being good at what you do is more important than being liked. Respect implies you’re doing a good job. Being liked implies people enjoyed the experience of interacting with you.
The ideal is to hit both.
Be the point of contact for a customer who really listens, and understands what they need. Be the person who goes out of their way to find possible options to make things work. Be the person who empathizes with their needs, and frames every interaction around what’s best for them (not around company policy, the product’s intended purpose, or anything else they don’t care about). Be the person who’s quick to respond and always makes them feel like they’re your first priority. And be the person who’s pleasant to interact with, always.
A product isn’t going to be the best fit for anyone, and some people will still end up cutting ties. But if they do, make sure they know you went to bat for them and that, in seeking a solution, every possible stone was turned. And that their best interest was always the compass.
That’s the stuff that builds a powerful brand.

2019 in Review

In 2018, I recapped my year with a blog post full of memories.

This year, I’m recapping my year with a more tangible exploration of growth: the things I accomplished, the ways I changed, the lessons I learned, my favorite memories, and the biggest things I’m carrying with me into 2020.

The Things I Accomplished:

Curriculum building: 2018 was the year I learned how to coach, and 2019 was the year I learned how to build curricula. When I came on full-time with Praxis in December of 2017, I was the team’s first-ever full-time bootcamp advisor. I spent most of my days on coaching calls and in contact with our participants. It was mentally exhausting, but I got countless reps in with coaching. This year, I dug deep into translating the things I’d learned coaching into a revitalized version of our curriculum — some areas two or three times over.
In February, I rebuilt our placement module, which at the time felt like a huge project to tackle in one month. My muscles have grown since then– in December I rebuilt our entire bootcamp.
I’ve fallen completely in love with the curriculum building process, and I’ve also learned a lot about content curation, the information simplifying process, and what students best engage with — all topics I’ll be writing about in the coming months.
Coaching coaches: we made a number of coaching hires in 2019 — which means I went from coaching participants to coaching our own advising team. When I was first getting started, I spent a morning mapping out our entire coaching process onto a whiteboard. Writing everything down was exciting as hell and I learned a that I knew a lot about coaching I’d never articulated for. It made me a better coach and a better leader and much better at articulating things I’d never forced myself to explain before.
Switched from location-dependent back to remote: this one wasn’t my doing — it was a change embraced by the whole Praxis team. But it’s a shift allows me to take action on the dream I’ve always had for my 20s — traveling widely, and living wide and deep not just in one place, but many. I don’t know exactly where this change will take me, but my plan is to drift for a while until I find a place I feel compelled to spend more time. I always wanted to live in the south and live by the ocean, and I got to do both of these things in 2019. I left Charleston to spend five weeks in Traverse City, Michigan this fall, where I got to run the dune trails and swim in Lake Michigan and watch the northern woods turn to fall and see the start of the November gales blow in off the lake. I’ve spent November and December back in Pennsylvania, enjoying quality time with family and getting laser-focused with work and study and growth.
Doubled my efficiency and output: this is an approximation, not a direct measure. I got very focused early this year on leveling up the way I work — offloading everything I could, streamlining what I couldn’t, and trying not to get too far in the weeds on anything — and it paid dividends. I haven’t sat down and measured exactly how much more I’m able to do than I was before, but I do know that the little things don’t distract me as much as they used to, the big things don’t take as much time, and the amount of weight I carry in the work that I do has increased dramatically from where it was at the start of the year. As someone who wants to push the boundaries of productivity as far as they’ll go without breaking the energy bank, this was a big win for the year.

The things I learned and the ways I changed:

Online content creation: Content creation is always something I’ve been semi-consistent with, but I got much more intentional in 2019. I re-did the 30-day blogging challenge in May to reset my focus, and this fall I signed up for David Perell’s Write of Passage course. I’ve been a big fan of David’s writing process for some time, and learning the ins and outs helped me sharpen the way I create my own content. I’m much sharper and faster at synthesizing ideas than I was at the start of 2019, and that’s exciting to me. I feel like I’ve built a framework that will dramatically improve the amount of weight I’m able to carry in 2020.
Turning 23: this sounds like a strange thing to put on the list, but it really does feel like a milestone. Growing up, people always ask you if your new age feels different from your old one, and I always thought that was a strange question — but 23 actually feels different from 22. Part of it is coincidental — smaller changes I’d been accumulating over time finally catalyzed into a larger metamorphic shift — but part of it comes with the age, too. At 22 you’re still college-aged, still at the point in life where not going to college and working instead makes you distinct. At 23 you’re past that “young and earning your stripes” phase — the tone with which you interact with the world is different.
The personal stuff: I lost both of my grandmothers in quick succession this fall — their funerals were two months and a day apart. One was an expected death; the other wasn’t. It was a strange experience, and it changed me. Being close to death and the end of life sharpens how you look at the rest of the world. The other stuff stops mattering as much. Losing the eldest generation makes everyone else in the generational cycle take a step forward, and it changes your sense of place in the world. When all the times you’ll spend with a person are finally over, you start reflecting on all the memories you’ve made, and your knowledge of the person, and categorize it. You look back on all of it, and try to articulate how it defined you. It changes the way you interact with the world — or at least, it did with me. Blood and family is strong. It’s a pivotal part of how you interact with the world. And going through shifts and reflections on that front sharpens you. You become aware of all the little connections — living next to the harbor in Charleston this summer, just like my grandmother lived right by the harbor in Long Island years ago. I went to Sarasota this spring, the place my grandparents met in the 1950. I learned to sail a sunfish, just like my grandma used to do. One made me kind, the other made me bold.

Biggest Lessons:

The way things evolve over time is hard to predict. People I never thought I’d be cool enough to be friends with have become close friends over the past year. People I grew distant from are now people I get to work with on a regular basis. Things aren’t nearly as black and white as they first seem. I’ve gotten much better this year at trusting the process and letting things evolve.
Changes at startups are like the weather in Kansas, where they say “if you don’t like the weather, wait five minutes and you’ll get something else.” Things change fast. Don’t be married to how things look in the present — keep focused on the end goal.
The subconsious creative process is much easier to dictate than I originally thought. I had an epiphany about this in June: I was hosting a Praxis workshop, and had put off pulling together a topic because I was distracted by other projects. I went to sleep one night thinking about it, and woke up the next morning with the topic on my lips: documentation. The concept was clear, and it took me a minute to realize what I was thinking about. I went into the office and wrote that down on my whiteboard and left it, then came back in the next day and dumped an entire framework onto the whiteboard — which became both one of my favorite workshops I ran in 2019 and one of my favorite frameworks for talking about documentation. In the months since, I’ve gotten much better at consciously prompting the subconscious, percolating elements of the creative process — and letting it be something that runs quitely in the background of everything else I’m doing, as opposed to something I have to carve large blocks of time for.
As a subset of the above point: I learned that the content I’m consuming synthesizes much better than I realize. This epiphany came to me in two parts: the first, in a live writing workshop hosted by David Perell and Will Mannon. Our prompt was to write an essay in about an hour using materials stored in our digital notes. I went out on a limb and compiled a bunch of notes I hadn’t thought critically about before, and wound up writing one of my favorite essays of this year, which you can find here. A few weeks later, my friend Nick told me one of the biggest ways I’ve changed this year is that I’ve gotten much better at synthesizing ideas — which reaffirmed that this ability has changed in a visible way, too. I just hadn’t yet become aware of it. This makes me incredibly excited for 2020 and beyond — now that I’ve learned how to consciously explore this process, I’m very excited to see what ideas I’m able to synthesize.
A lot of the limits you think you’re running into in life are limits you’re placing on yourself. I spent a large portion of 2019 feeling like I was running into the same brick walls, only to realize (in a rather anticlimactic epiphany) that really the brick walls were of my own devising. Don’t rule out the possibility that you’re running into walls because you’re placing artificial limits on how fast you can grow.
The things that make you cry are the best things in life. Heartaches, jokes, the times so good you don’t know what else to do, the projects you take on that are so hard they reduce you to tears. I’ve gotten much better this year at embracing the hard stuff — which has in turn accelerated my own growth.

Goals for 2020:

Publicly announcing goals has never been a comfortable thing to me. I think of myself as ambitious and intuitive, not goal-oriented — I have a plan for where I’m going, but something better might come along two months from now that makes me scrap the whole thing and start over.
But I also like the public accountability of goal-setting, and the collective nature of communicating your goals to the people interesting enough to want to follow you.
So in that spirit, my biggest goals for 2020:
Get better at seeing places to improve: I’ve gotten much better at synthesizing observations into plans for improvement. The professionals I respect most are very good at this, and I want to do better at consistently streamlining. I love the metaphor of aerodynamic when thinking about how I work, and I want to systematize and habituate that process — reach a level of unconscious competence with it.
Get better at synthesizing ideas: two meanings for this: 1, combining the ideas I’m collecting and micro-epiphanies I’m having into more tangible, substantial things (blog posts, curriculum content, etc.), and 2, getting better at seeing what isn’t yet, but could be.
Increase my own equity: over the past few years, my focus has been primarily directed towards building things in conjunction with other people. This is a strategic decision — your impact and your learning are both accelerated and amplified by the reach of working with other people — and when thinking about growth, I’ve always been biased towards leverage. But this limits your personal worth. Your reach is tied to things that belong to someone else, not your own. In 2020 I want to be intentional about building my own equity. The specifics of what this will look like are undetermined (and I like it that way — I don’t want to be so set on an arbitrary goal that I limit myself to possibilities) — but having more equity as an independent entity is very important to me.
Curate a world-class education experience: If I doubled my output in 2019 (a trend I fully expect to see continue), I want to focus this year on improving the quality and richness of the work I’m producing. I’ve always been fascinated by alternative education, and have become more and more convinced that the path to success in our digital world is being completely re-defined. How we educate ourselves — not only how we access information, but how we think about problems and solutions and questions in the first place — will make a huge difference in our ability to capitalize on the opportunities suddenly available to us. Right now, this gets me fired up more than just about anything else. What we’re doing at Praxis is a big piece of this puzzle, and I’m excited to
Build some killer side projects: I was one of 6 Write of Passage alums invited to work closely with both David Perell and Tiago Forte in 2020 to work on a project build of my choosing. I’m still defining the details of what this will look like — I’ll share more in the coming months. But I want to use this energy I’ve built to intentionally build some really killer projects — most likely around some ideas I’ve been chewing on for a while. More on this coming 😉
Deepen my friendships: Christopher Lochhead summed this up well in the Praxis workshop he led in November — he talked about how the personal stuff in life is really what makes it worth living. I have friends scattered all across the country, and part of the incentive for traveling more often is to get to see them, spend time with them, have real and deep conversations with them. Friendships in life are strengthened by the time you spend together and the growth you get to experience alongside each other, and I intend to intentionally cultivate both.
And lastly, embody my favorite quote from Joan Didion, “to remember what it was to be me; that is the point.” 
Meaning: document the hell out of everything.

List of Favorites:

The highlight reel from 2019.
Favorite weekends:
  1. Hanging out with friends in St. Petersburg, Florida. Best part of the weekend: getting a behind-the-scenes tour of the Tampa Bay Rays training camp and Tropicana Field.
  2. Spending a weekend at my friend’s farm on the Kiawah River, where I learned to sail a sunfish, watched the sun set on the river, and watched a meteor shower on the back porch late at night talking philosophy and life.
  3. Canoeing on a still, secluded lake in Michigan while the leaves were turning colors — so much blue on the water and the orange on the trees — and having a campfire on the beach lake that night (and reading Hemingway’s Up in Michigan late at night)
  4. Spending my birthday weekend in Pittsburgh catching up with lots of old friends
  5. Spending a weekend going to the mountains and the ocean all in the same day, just because I could
Speaking at FEEcon: I got to speak at a couple conferences last year (including on a panel with Ryan Craig, author of A New U), but my favorite was FEEcon. I’ve always been a big fan of the work FEE does, and it was pretty cool to get to be on their speaker lineup.
Travels: this one’s a tough tie between Florida (which fascinated me — I expected boring commercialized retirement communities, but northern Florida has a wild feel akin to the west, but mixed with the tropics and the jungle, with a Spanish flair. Fascinating), and Traverse City Michigan.
Outdoors activity: sunset beach runs in Charleston and trail runs at the Sleeping Bear Dunes
Favorite books read:
  • A Farewell to Arms by Ernest Hemingway
  • The Inner Game of Tennis by Timothy Gallwey
  • The Hard Thing About Hard Things
  • The Act of Creation by Arthur Koestler

Layered Stories: How to Add Richness to Your Writing

Humans are fascinated by complexity. Complexity creates richness.

It’s a fine balance — too simple and we get bored, too complex and we become confused. But as a general rule of thumb, the more complex something is, the more interesting it is to us, and the longer it can hold our attention.

Adding layers of complexity to your writing (both fiction and nonfiction) keeps your reader engaged in a way a simple story can’t.

You want to start with something simple, and then build. The word “layer” is key — layers of complexity is what will breathe richness into your writing.

Simplicity makes it easy to slip in; complexity keeps us captivated. The best writing has both.

The core plot/thesis of your piece is the framework upon which everything else will be built. You want this framework to be simple enough to follow easily — too complex, and there won’t be room for anything else.

But on top of (and underneath) the main plot and thesis, add layers of complexity. Subplots, additional stories, new threads. Weave them like a tapestry. The more complex, the more interesting your piece will be.

Moving as a Study in Persevering

I moved today — for the fifth time in fifteen months. Not far — just across the Ravenel Bridge, from Downtown Charleston to Mt. Pleasant — but the distance almost doesn’t matter. If you’re moving, it’s unsettling and a bother.

Also, again — the fifth time in fifteen months. I reused boxes today I used in that first move 15 months ago. I’m getting rather good at this.

Tonight’s blog post is less a set of cohesive thoughts, nor an endeavor to create a lucid narrative, or draw a conclusion. Instead, it’s a collection of reflections that I’ve been chewing on today as I pick up my life and carry it, one cardboard box at a time (and a second set of hands for my bed, table, and chairs) out of my old house, down the stairs, into my car, back out of my car, through a parking lot, up four floors in an elevator, and down a set of halls.

Moving is a good time for reflection. Two reasons for that:
a) physical labor tends to elicit thoughts like this, and
b) it’s the closing of a chapter and a start of a new one.

Even if the era wasn’t distinctly defined on other fronts, each place I’ve lived has felt like a chapter, and each move, a close.
The parameters you set around the way you experience life on the daily shift each time you move to a new location, and those parameters shape the way you perceive the things you’re doing as you’re living.

The closing of a chapter always prompts me to reflect on the one closing — what went well, what went badly, what we learned, how we changed, and what we could work on doing better. In addition, the opening of a new chapter always fills me with excitement — so much you can do with this new space being opened,

The handling of my belongings makes me happy. Handling each piece I’ve intentionally acquired, each piece with a back story, each piece that brings joy into my life. I take pleasure in handling each.

The adversity, too. Moving is hard. It’s uncomfortable. It’s a lot of work. In this context, it was 95 degrees and humid as hell. You can look at this as something uncomfortable and miserable, and fight it the whole way — or you can look at it as a challenge designed to make you smarter, and lean into it and embrase it.

Always Seek to Become More Interesting

Always seek to become more interesting. Becoming more interesting requires learning. It requires obtaining new experiences, and new information, and new knowledge.

Interestingness is a good indicator of value.

The more interesting you are, the more interesting the content you’re able to create. The greater your well of information that you can draw from, the better your creative capacity, and the higher-value ideas you’ll have.

The more interesting you are, the more interested other people will be in you — in talking to you, in learning from you, in collaborating with you, in working with you.

The more interesting you are, the higher your own quality of life will be — because you’ll be more interesting to yourself.

Always seek to become more interesting. Go out into the world and consume content, have interesting experiences,