Ends vs. Means

I’ve been spending time this month reframing how I think about my projects.
I kept catching myself shelving projects because they didn’t feel like The One. Good projects. Projects that I’d enjoy building and that I’d learn something from and that people would pay me to use.
Because “I don’t want to be a ____” – the blank representing any activity one can turn into an identity.
An example of this thought process in action:
“I don’t want my identity to be ‘coach.'” –> “Therefore I won’t offer coaching sessions.” (Not a problem I have. You can sign up for a coaching session here ;))
You know what one is balking from when they say “I don’t want to be a ‘coach'” — those airbrushed websites with studio portraits and a CTA at the bottom of every page. That’s not an identity that lights you on fire, so you shy away from associating with it at all.
But just because somebody finds your perspective interesting and your advice valuable, and you charge them to take advantage of your input, doesn’t mean you have to think of coaching as your identity.
Maybe it’s just a way to exchange value for money.
Or learn something by forcing yourself to articulate solutions to someone’s problems.
Or build credibility so people will take you seriously in areas you’re far more interested in.
Maybe it’s just a lucrative side hustle.
Nothing says being a coach locks you into the life trajectory of being a coach. And we don’t even assume that of other people — but it’s easy to put that pressure on ourselves.
If you catch yourself falling into that pattern (like I did), you need to sort the projects you’re thinking about into two categories: means and ends.
An end: a goal in and of itself. Example: I want to be a course creator.
A means: a step in a process moving one towards something else. Not a place one lingers, just a milemarker. I want to build courses, which will help me coalesce my thoughts, which will in turn help me become a better writer.
When you stop thinking about projects as ends and start thinking of them as means, it takes a lot of pressure off. There’s no need to choose the right one, or do something perfectly, or change your identity.
Offering your time in exchange for money doesn’t throw you into the category of “coaches.” It just gives you a new avenue to explore, learn, and make money.
Your “ends” feels important. It’s also much bigger than any one project. It’s the sweeping physical expression of all your values and deepest desires.
Expecting any one project to fill that category is going to lead to pretty much every idea you ever have going on the shelf. Nothing will ever be good enough. But when you think of your projects as means — only fulfilling one small step in the process of moving towards your ends — suddenly almost everything is back on the table.
As a means to explore, to learn skills that will translate towards your ends, to fund your other projects.
And who doesn’t love all of that?

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

How to Be a Rockstar Community Manager

The ultimate guide to making your customers feel appreciated, making your product feel loved, and building a vibrant community.

Are you as excited for this as I am?

If the answer is yes, then I did my job — I got your attention and I got you pumped.

In this case, I did it through sales (or maybe copywriting), but being able to grab people’s attention and draw them into your conversation is one of a community manager’s (not-so)-secret talents.

What good community management is all about: making people feel engaged and excited, supporting their needs (by answering their questions and providing guidance), and making them want — no, crave — your community experience.

I’ve been doing community management for Praxis for almost 2.5 years, and I’ve learned a lot of lessons along the way. Back when I was starting from scratch, this is the guide I wished existed.

In this post, I’m going to break down the most important elements of building an awesome community around your service, product, or ideas.

You ready?

Your #1 Job is to Build Engagement

This is pretty much the subtitle of your job description … but it can also be far harder than it sounds.

Unless your product or network has a built-in incentive for people to use your community (and count your blessings if it does!), getting engagement is tough. To a user, signing up and setting up feels like work (not to mention taking the time to check notifications to stay engaged). Regardless of the logical rationale, on an emotional level, the payoff doesn’t seem high enough to justify the upfront cost.

To get people engaged, you have to do two things:

  1. a) build in an up-front payoff (so people are excited to engage right away) and
  2. b) sell people on how awesome the experience is going to be once they’re in (so instead of this whole “join the community” thing feeling like work, it feels like something they want to rush through so they can get to the good stuff).

Once you’ve gotten your users into the habit of engaging, maintaining that engagement is far easier (the law of inertia is on your side). But how to ramp up that initial momentum?

Step 1: build a system that makes community engagement part of the process. The more integrated, the better. If you have a product, how can you integrate community into product onboarding? If you offer a service, how can you make your community a part of it?

If your community already is a feature, how can you make it more prominent? People do the things they assume they should. If you make your community a part of the assumptions about product/service usage, you’re going to get more traffic.

For example: at Praxis, engaging with the community is part of our product experience. It wasn’t always — there were phases in Praxis’s development when you could do the program but not engage with the community. But we realized the community was valuable, so we made it an inseparable part of the product experience).

CM Exercise: make a list of 10 reasons why your community is valuable in your customer’s onboarding process (think of these as your arguments for why it’s worth paying attention to), and then make a list of 10 ways you can integrate it into that onboarding experience.

Step 2: invite people personally to engage. People love feeling special. It’s easy to underestimate how much of an impact a small personal outreach can have.

As soon as someone joins your community/buys your product/enters your program, reach out to them immediately and get them pumped about getting plugged in and engaged.

Pro Tip: specific is ALWAYS better than vague. Use specific dates and times whenever you can. “Check it out when you get a chance” can mean either “two hours” or “two weeks.” “Can you do this before you log out?” or “Can you do this before tomorrow AM?” is much more specific (and gives you a concrete metric point for the conversation).

Step 3: set the tone right from the start. First impressions really matter — and so do the habits that are built through repetition. If you want your community to be engaged, you’ve got to get in there and engage first, and engage early.

When a community first launches, hit the ground running and with the energy you want to see your community have (no slow ramping-up phase. Are you in this or not?).

When a new member joins, get them integrated right away. If you’re in, you’re all in. Prompt them to take the plunge!

Step 4: provide a roadmap/offer entrance points. It’s hard to engage if you don’t know where to start. Make some curated suggestions for what people should take a look at when they’re getting started, or where they should jump in and interact.

“Post this in X channel!” “Share this with Y group!” “Check out these three posts with tips to get started!”

Step 4: follow up with people that don’t take the first bite. If someone doesn’t engage right away, give them another prompt. Assume they’re just wondering if you really mean it, and give them the extra nudge they need to be convinced.

Step 5: make it clear the community is the best place to be engaging. Don’t be shy about asking people to share questions or comments from 1-on-1 conversations in the group setting. If you want people to engage in the group, always be redirecting there.

Think of Yourself as a Content Curator

There are as many ways to be a community manager as there are communities, but as a generalization, content curation is a huge part of your role. You’re the knowledge bank for your community, the keeper of information, and the go-to when people have questions.

The “questions” part is key — it’s easy to limit your content curation to a reactionary activity (where you share things in response to peoples’ questions). Don’t limit yourself like that. Being proactive and starting conversations around content is important too.

There are two ways I curate content:

  1. Scheduled (making sure I have a fairly regular cadence for content, and a backlog of ideas to reference if I need them)
  2. Based on community needs (in response to things people are talking about or thinking about).

In general, I’d recommend using a mix of both. They balance each other out and keep your content pipeline strong.

Scheduled content— I try to follow a loose schedule for my posting — enough to make sure activity is consistent. Having standards throughout the week (such as #TipTuesday or #FeatureFriday) can be great, but if you do this, consistency is key. This rule applies to community management as much as it does to marketing — your customers need to know where and when to find you. I always keep a running document (Evernote is great for this, but Google Docs works too) where I keep ideas for content, so I always have a store to draw from.

Needs-based content — this is the fun part. As the person with your finger on the pulse of your community, you’ll notice trends — issues using the product, questions about the service, a slew of similar questions.

If your community is interested in something, it indicates that the iron for that topic is hot, and should be struck. Don’t just answer the question — turn it into the topic for a post. Write it out, curate relevant links, add additional points and notes.

Relevance is everything when building community engagement. The more relevant your content is to your community, the more direct value your users are getting. The more direct value they get, the higher the incentive for them to come back.

Pro tip: starting conversations only works if people actually engage and converse, and sometimes getting the initial bite is hard. The more specific you can be, the better. I love tagging people directly to get them involved in the conversation, or making a very direct ask (“I want to hear from each of you” or “don’t just read this post — take 30 seconds and respond to it before you leave this tab”). I see a huge difference in engagement when I phrase my CTAs with a direct ask or challenge. People love it.

Keeping Track of Your Members Makes You a Superhero

Good community managers make you feel seen and heard in the present. Great community managers make you feel known and remembered — by always being able to reference information about you.

It seems like a superhuman ability — being able to remember facts and details about all of your community members. Really, though, it just boils down to having great systems.

This is the fun part (if you’re not a numbers person, then yes, that sarcasm was for you). Operations and logistics and (shudder) spreadsheets.

Don’t worry. It’s not actually as bad as it sounds. Don’t think about this as admin work — think about it as outsourcing your brain and freeing up space to do the fun stuff (like having great conversations and engaging with cool people). The stronger your systems, the freer your mind.

Which means being organized is really, really important.

Depending on your organization, you may already have systems in place to track members/users. If you’re really lucky, you’ll have a CRM (and count your blessings if you do. A whole world of possibilities lies at your fingertips).

Spreadsheets are also your best friend. I’ve known community builders who kept a spreadsheet tracking every single member of their community, with cheat sheets and notes for each person. They logged location, occupation, skills, interests, conversation notes — everything they might want to remember. These same people built an incredible reputation as connection-makers — because they always knew what people were working on and what types of people it would be valuable for them to meet.

Start a spreadsheet and notes on each person in your community. If it’s easier, use a digital notes system, or a CRM — whatever works best. But log important notes on each person as you engage with them. It will make a huge difference in the quality of your interactions.

Systems for Outreach are Important Too

You want to make sure people in your community are getting regular (individual) touches, and those touches should be entirely systematized (so you don’t have to actively think about them). Trust me — I tried it the non-systematized way first. Your brain will be much freer if you outsource this to systems.

The frequency of touches will depend entirely on the nature of your community (and the things it’s built around), but touches are important — if you don’t have them, it’s easy for people to slip through the cracks.

If you have a product/service that operates on a standard timeline, you can organize your outreach around specific benchmarks in the customer journey. If your community is more loosely defined, you can schedule outreach by increments of time.

However you structure, build a digital system. I’d recommend:

  1. Digital reminders (for example, Google Calendar or a CRM task function)
  2. Context included in those reminders (or even pre-written messages you can customize and paste)
  3. A spreadsheet system to track everything (so you can log your outreach each time you make it, and reference at a glance every touch each individual has already gotten).

The same rule that applied to the first point (engagement) also applies to this: people want to feel seen and heard. Nothing will keep them coming back more than the sense of a personal connection, and the sense that they matter.

You aren’t just building community. You’re also doing internal marketing.

What’s new? What’s exciting? What should people be thinking about?

As the old adage says, “everything is sales” — and this is no exception. As a community manager, you’re constantly selling and marketing the benefits of being in this community to your members.

It’s less blatant than it sounds, but it’s really important to remember — especially if the community you’re managing is centered around a product. What cool features are you rolling out? What benefits do people get from being involved?

Obviously, you don’t want to sound like you’re marketing. But you also don’t want to be quiet about the cool new benefits, and run the risk of keeping your community members in the dark.

A few rules to keep in mind:

  • If you don’t talk about it, assume they don’t know about it. Somebody’s got to share — otherwise people aren’t going to know the things you’re rolling out even exist.
  • You’re guiding community conversation and internal brand narrative. What do you want people to know about/think about/be talking about? This doesn’t just have to apply to news — old content and features added into the conversation cycle count as internal marketing too.
  • Think of yourself, in part, as crafting experience. My friend James Walpole (who works in marketing at a cool ATL-based startup called BitPay) was the one who first turned me onto the idea of “experience crafting.” The concept sent me down a mental spiral of exploration — what makes a good experience or a good narrative? How are the experiences I have with other people’s brands and communities influenced by the way they’re framed? How can I be intentional about crafting the experience of people in my community? Think about these questions constantly as a Community Manager — because the better your members’ experience, the more excited they’re going to be to keep coming back.

The Master Community-Building Playbook

Want to put this in action? This is where I’d start:

  1. Build a weekly engagement cadence. Map out a rough posting schedule, so you have a system for keeping engagement up.
  2. Design workflows for a) new community members, b) unengaged community members, and c) standing community members that need extra touches.
  3. For each type of touch, draft a basic standard outreach (that you can customize for each individual situation). You don’t have to use it, but it will save time to have it.
  4. Start a spreadsheet, and slowly add to it each time you learn something new about a community member. Treat it as your outsourced memory, and your personal community CRM.

At the end of the day, good community is built by constant upkeep, consistent engagement, and great energy — which starts with you, but is built up around you through the excitement of your community members.

Photo by Priscilla Du Preez on Unsplash

The Best Books for Building a Startup Career

When I landed my first startup job, I felt like I knew nothing. Actually, some days I felt like I knew less than nothing.

I was nineteen years old, and my previous working experience consisted of tutoring homeschooled kids and picking apples for a living. I had no idea what a quarter was, let alone a KPI. I was excited and I was hungry and I had no clue what I was doing.

I realized (much later) that it wasn’t just me. One of the most frustrating things when you’re starting your career is all the stuff you don’t know. You’re young, and you’re excited, and you have all the time in the world — all advantages — but there are some pretty big disadvantages that come with the territory. The biggest two are a lack of experience and a lack of knowledge. The latter, in part, is a symptom of the former.

When you don’t have a lot of knowledge yet, one of the best ways you can compensate for it is by reading.

Here’s the thing — to be an effective player in the startup world, there’s a lot you have to be good at. Some of the most important:

  • understanding how startups work in the first place (pretty obvious, but as I quickly discovered, it’s a whole different world)
  • knowing how to articulate and sell ideas really, really well
  • being super adaptable, on the turn of a dime
  • understanding how to test ideas, learn from the results, and redirect course accordingly
  • being resilient, even when it seems like everything’s going wrong
  • thinking creatively about solving problems
  • thinking innovatively, and being able to come up with ideas no one’s ever tried before

Relying on experience as a source of knowledge limits you to a chronological progression of growth — one that’s constrained by how quickly you can accumulate experiences. It might take years to encounter enough problems and come up with enough solutions to really learn how to think innovatively and start to pitch ideas that have an impact.

When you don’t have experience, borrow someone else’s. The fastest way to level up is to read — a lot.

When you read, you get to immerse yourself in the thoughts and ideas of people far smarter than you. It’s the equivalent of landing a dinner with one of your professional heroes, and getting to ask them questions all night, and then getting lucky enough to have them accept your invite to go get drinks once dinner is over, at which point they’re answering questions you didn’t even know you had.

And even once you have leveled up, keep reading. If you rely solely on your own experiences and perspectives, your growth trajectory is limited by the linear and chronological pace of your own development. If you use books as a window into other people’s experiences, you blow your knowledge-acquisition potential wide open.

The following is a collection of some of the books that have been most impactful to me on my own journey as a professional, and the ones I’d most highly recommend to others trying to level up their startup game.

The Essential Classics:

Zero to One by Peter Thiel

This is the classic playbook of the startup world. The subtitle says it all: “notes on startups, or how to build the future.” Thiel boils down the lessons he learned through starting PayPal and Palantir into 12 chapters of pure wisdom. I reread it on the regular.

This book will help you understand how startups work, and it will give you a window into what it means to think innovatively — one of the most important skills to have if you want to really crush it in the startup space.

Thiel talks about:

  • What it means to go from zero to one. Zero to One means going from nothing to something (inventing something that has never existed before, like the Wright brothers building the first airplane). One to N means innovating on something that already exists (like Boeing releasing the 737 MAX). The best companies always want to start from zero, and create something entirely new.
  • How the paradigm around innovation and growth has changed over time, and what that means for business.
  • How all the most successful people know secrets, and build their companies around the secrets they’ve discovered about how the world works. There are lots of secrets left to be discovered in the world, and our job is to find them.
  • His philosophy around hiring and building great teams
  • The importance of coming up with ideas no one has ever thought of before (and what this looks like in practice)
  • The importance of thinking about the best businesses as monopolies.

Niche Down by Christopher Lochhead

This book starts with the idea of thinking innovatively/finding your monopoly and takes it one step further.

Niching Down means finding your niche — the smaller, the better — and then completely dominating it. That’s how all great companies are built. Lochhead explores great companies that have found their niches, and breaks down what makes each one so impressive.

It’s a phenomenal book that will help you understand markets, categories, customers, and the power of being really specific.

I’d recommend Niche Down as a starting point, but Lochhead has a lot of other content that’s valuable to explore. He’s the co-author of another book, Play Bigger, which talks about category creation (not competing against other products, but rather inventing an entirely new category of products), and he’s the host of two phenomenal podcasts.

He’s also a fun author and speaker. He calls himself a pirate of the startup world, and it’s an apt descriptor. He’s as colorful as he is smart (The Economist once called him “offputting to some,” and he was so proud of the title he put it on his website’s About page).

The Hard Thing About Hard Things by Ben Horowitz

This is a book for CEOs, not employees, but it’s an invaluable read no matter who you are. As an early employee, one of the most confusing things is the way executives think. It feels like there are lots of curtains and secrets, and a lot going on that you sense is there but never get to see.

This book is the distillation of everything Horowitz learned in his 8 years as CEO of Opsware — one of the fastest-growing companies in the country during the dot-com boom, which had its IPO after the bubble burst, had to lay off large numbers of its employees four times, and eventually sold to HP for $1.6b.

This book breaks down what’s going on in the head of a CEO, and what happens behind the scenes. It offers a window into the things you don’t usually get to see a an entry-level employee, but that are critical to understand in order to grow.

It’s also a great book to read if you’re ambitious and know you want to rise up quickly in a company. It gives you some toeholds as you start to understand what you need to be thinking about in order to grow.

It’s also a great book to remind you how gritty startups are, and how much grit you’re going to need if you’re going to make it big.

The Inner Game of Tennis by Timothy Gallwey

This is a tennis book, not a business book, so it may seem odd to see it on the list. But Inner Game of Tennis is one of the most important books to read to level up your game.

The author of this book is a professional tennis coach. Over the course of his career, he started to see patterns in the way people learned — and realized that the biggest differentiator between people’s success was what was going on in their heads. He started experimenting with the way he gave people directions, the way he coached, and the way he helped people understand the game — and over time, he pivoted his coaching from teaching tennis to teaching the mindsets that are pivotal for success.

Just like in sports, your level of success in your career is going to hinge on what goes on between your ears. The sharper your mental game, the sharper your game in the real world is going to be.

The Magic of Thinking Big by David Schwartz

I’m a big fan of books written in the first half of the 20th century, and while 1959 doesn’t quite hit that mark, this book still has that old-school feel. Take a look at this quote from the opening chapter:

“The most essential element — in fact, the essential element — in our space explorations today is belief that space can be mastered. Without firm, unwavering belief that man can travel in space, our scientists would not have the courage, interest, and enthusiasm to proceed.”

In a similar vein to The Inner Game of Tennis, this book is all about what’s going on in your head. Your inner game is just as important is your outer game in the startup world. You’re creating something out of nothing, and running up against hard challenges, and pushing yourself farther than you thought you could go.

How you think makes the biggest difference in how you perform. Your level of success hinges on what you believe. The first step to succeeding is believing you’re able to succeed.

This book is all about getting your head in the right space, and establishing elite thinking. It also talks extensively about learning how to observe the people around you, and how they think, and how to adopt the mindsets you see in other people’s thinking.

The War of Art by Steven Pressfield

To be successful, you’re going to have to create stuff — the more the better — and you’re going to have to ship that stuff out into the world. Creating stuff is hard. Shipping it is even harder.

In The War of Art, Steven Pressfield talks about why shipping is so difficult — because of a force called Resistance, which is always present and always equal in measure to the importance of the thing you’re trying to accomplish. When you sit down to watch Netflix, you don’t feel Resistance, because what you’re trying to do isn’t worth much. But if you try to get up and clean your room, you’re going to feel a little bit of Resistance, because that activity has value. And if you decide to scrap all of the above and go write an article, let along a blog post, the force of Resistance is going to recognize that as something that’s both valuable and hard, you’re going to feel a lot of adversity in getting started.

Pressfield also talks about how to combat and overcome resistance, to be a consistent creator — and why it’s so important to do so. This is a phenomenal book to re-read on the regular. It will reset your creative process every time you pick it up.

The Best Articles and Essays

How to Get Work Done: A Primer — this one was a post on the Praxis blog written by my friend and colleague Chuck Grimmett. It’s a masterful overview of how to think about working and efficiency.

How to be Successful by Paul Graham — a phenomenal essay on thinking about your success and career growth.

Breaking Smart by Venkatesh Rao — a brilliant essay “miniseries” built off of Marc Andreessen’s quote “software is eating the world.” It explores how technology is changing everything in the world around us and gives you an edge in thinking about the future of the tech/startup world.

The Ultimate Gide to Writing Online by David Perell — the best professionals are writers too, and the fastest way to accelerate your career is through writing. David breaks down writing as a tool not only for communication, but for learning. This essay is a great resource as you’re building your career.

7 Essays That Will Help You Succeed in Internet Business by Taylor Pearson — this collection of essays is a great set of resources on thinking about your career. While it’s written for “internet business,” it’s highly applicable to all things startup, and should be studied thoroughly.

Patrick Collison on doing things that don’t scale — this is a talk, not an essay, but it still deserves a space on the list. It’s a great piece on thinking about getting in the weeds as a strategic move, to help you a) make your customers happy, and b) obtain the information you need to build systems that do scale.

Six Principles for Making New Things by Paul Graham — the title really says it all. A great essay on thinking about innovation.

The Most Important Points:

Make up for your lack of experience with the work of those who are smarter than you. They were generous enough to give you a window into their thought processes. Take advantage of them.

Pursue resources that help you gain knowledge not only about how startups work, but how innovators think. The history of innovation is one of the most important things to understand. It tells the story of all the people who saw things that didn’t yet exist, which are now part of your day-to-day world.