The Write to Roam

My Community Newsletter Playbook

On June 18, 2023

Someone recently asked me for the playbook we use to write our community newsletter over at Hampton. He was hoping for a one-pager he could give his team, so they could write something similar for their industry.

That was a big compliment.

It was also a little daunting because the last thing I wrote about content strategy was, like… Fifty pages. After cutting.

So I’m going to try and write something shorter and more actionable here. We’ll focus only on the real stuff I do each week to produce our email, and we’ll cover:

Developing A Template
The Importance Of Your Drop File
Writing The Bones Each Week
Editing + Style
The Final Step

None of this is Hampton-specific. It should all transfer.

1. Developing A Template

When I talk about a newsletter template, I’m talking about the overall structure for the email – the major sections, and what goes in each.

Having a template for your newsletter is important because…

It makes the email easier to write each week
It helps you think about the purpose of each segment you include
Over time, it sets expectations with readers, and helps them skim and find what they’re looking for faster

The easiest way to start is to copy the format of a newsletter you already like, and iterate from there as you see what works and what doesn’t with your audience.

Each week, when I sit down to write, the very first thing I do is duplicate the last week’s email. I remove the old content, and the rest of my job is just filling in the structure with new content.

This saves a ton of time and energy. In fact, steps 1-3 are all about saving time and energy so you can spend it on step 4 (styling), where it’s most valuable.

So have a template.

The important thing to know is that your template evolves over time, and will take a while to solidify.

I’d estimate it took us about 2-3 months of weekly emails to settle on a pretty good structure at Hampton. And even then, it’s still evolving (currently in the middle of a visual refresh, though structurally, it’ll remain mostly the same).

Ours currently looks something like this:

Brief Intro
Recap Of Popular Slack Posts
New Members From This Week
Upcoming Events
A Post From The Blog

Every one of these is designed to do something specific (like get people excited about the Slack group, drive event RSVPs, or get eyes on the member interviews we publish on our blog).

And each of those, really boils down to the same single thing – helping members connect with one another.

That’s the essence of a community email. It’s about creating points of connection between your readers.

There are a hundred little tactics (for example, we intentionally include a lot of names in each issue – names, names, names!), but if you just write with the intention of creating connections between your readers, you’ll find your way.

2. The Importance Of Your Drop File

Okay, so you’ve got a template. Now how do you fill it in each week?

Answer: Your drop file.

The drop file is a simple Google or Word doc that you keep handy all week long. As you stumble across things that could be cool for your newsletter, you drop them in the drop file, and forget about them until it’s time to write.

I keep mine right in my bookmarks bar.

The structure of the drop file is simple. It’s a running list. Just bullet-items for each idea you come across, and maybe a few quick thoughts or follow-up links to help you write later.

You can find ideas anywhere. But over time, you’ll narrow the list of sources down to a few that deliver great options every week.

At Hampton, most of our content starts with our Slack channels. We’ve got hundreds of members in there, and our weekly active users have hovered between 85-89% from day one. So every week, there are a bunch of great conversations going on.

When I come across one I want to remember, it gets added to the drop file.

Then, whenever I sit down to write newsletters or do content planning, I open the file to jump-start the process.

3. Writing The Bones Each Week

With your template and an active drop file, the process of writing the newsletter is actually pretty simple.

It’s usually a process of…

Looking at your template – what needs to be filled in?
Looking at your drop file – what fits where in the template?
Match one to the other.
Rinse and repeat to fill in the major sections of the newsletter

On the first pass, I don’t write much. I’m just slotting story ideas in to make sure I like how they all fit.

Sometimes, a story or link might be a good match for more than one section of the newsletter, and it’s not immediately clear where it should go. But a little plugging and playing usually helps sort things out as I see the broader email take shape.

As things start to click, I’ll add more detail to each section, writing segments the way readers will eventually see them.

4. Editing + Style

Ultimately, your voice is the most important part of your style, and that’s different for everyone.

But here are a few editorial best-practices we used at The Hustle, which I’ve carried to Hampton, and which (I feel) make the newsletter easier and more pleasant to read…

Use simple language
Short paragraphs (no more than 2-3 lines in a Google doc)
An image at least every 200-300 words to break up text
Use bullets and bolding to make it skim-able

Axios really pioneered this style in recent years. You can learn more from them in their book, Smart Brevity.

5. The Final Step

Finally, testing. You want to a send test-version of the email to yourself.

When you get out of the editing window, and review in your inbox, you’ll pretty much always catch at least one thing you missed.

At minimum, you should read the newsletter on your phone, and click each link to be sure it’s headed to the right destination.

It can also be a good idea to read it in dark mode if it’s very design-centric. A surprising number of readers leave dark mode on all the time, and it can throw off certain design elements or make certain text hard to read.

On Growing Captera’s Blog To 1M+ Visits Per Month

By Ethan

On May 13, 2023

In Case Study

Recently, I had the opportunity to sit down and chat with J.P. Medved, who helped build Captera’s blog to 1m+ visits per month.

He was nice enough to take a look at the early work we’d done in our first month publishing on the Hampton blog, and offer some notes. Here are some of the things we talked about…

Traffic: First, he was impressed by the amount of traffic we’d gotten so far. Our first 30-days (post-launch) saw ~39k visits. Much more than a new blog would typically get without a lucky viral hit. But we attribute that to two things:

Famous Founder: One of our founders runs a well-known podcast and has a pretty big social following. He currently drives most our traffic by sharing our articles to his audience.
Media Background: About half our team has spent years growing big newsletters (The Hustle, Trends, and Motley Fool). So we’re not starting from scratch on the storytelling side.

We’ve also gotten a little lucky. For example, our first-ever company Twitter thread popped, driving ~260k+ impressions and hundreds of visits back to our site.

So the traffic is looking good, but there were definitely some things that needed improvement…

SEO URLs: His first piece of constructive feedback was that our URLs are not very SEO-friendly. As soon as he said it, it seemed obvious. But we hadn’t thought of SEO at all when picking them.

I’m still not quite sure what it takes to choose a URL that is SEO-friendly, but it’s good to have something specific to focus on. I’ll learn that, create a playbook for how we pick URLs, then update all the old ones sooner rather than later.

Calls To Action: By the time he saw our site, we had two main C2A’s – one that was a pop-up, and another sitting at the bottom of the page. We need more. He gave me a few good tips which I’m going to incorporate into our content…

In-Line C2A’s: I’m going to add email collection boxes directly to our content. I haven’t checked yet, but I think HubSpot makes this easy.
Pop-Ups: We have one, but it only triggers if you either scroll half way down the page, or try to leave. The exit-intent is good, but I wish I could control it by time spent on-page. HubSpot seems like it should be able to do this, but if it is, the settings aren’t very easy to find.

Publishing: By the time Captera hit 1m+ visits per month, they had a writing team of 10 full-time writers producing 2-3 pieces per week. I have heard of other publications doing more with less, but it’s nice to know that we should factor this into our expectations.

Currently, I’m the only one working on content. BUT we get help, since our members write the first draft of most our pieces. So really, my job is more editor/curator than anything else, and while our current system couldn’t scale to 20-30 articles per week, I think it allows us to punch above our weight class while we let the business grow big enough to support a larger content team.

Consistency Was Key: JP gave me some tips on how writers selected and scheduled content too. Each quarter, they planned which articles they’d publish based on…

Keyword Research
Conversations going on in the community
News

They made a point to have each writer focus on one topic, and they published on the same days/times each week (unless there was a major holiday that would decrease readership).

Writers were focused on a mix of SEO and social pieces, where the SEO pieces were quite targeted, and the social pieces were designed to cause a stir in the community and get shared a lot.

They also had a quote for updating articles each quarter, since Google loves when articles are kept up to date.

Distribution: A major part of their strategy was sharing the articles in LinkedIn / Facebook Groups full of people in their target audience.

We had planned to do organic sharing on Twitter and LinkedIn. Plus some organic stuff on Hacker News and Reddit.

But the idea of finding dedicated groups on LinkedIn or Facebook had completely escaped me. I think Discords or Slack communities would be good too.

Overall, it was a super helpful meeting, and JP was really generous with his time. I pulled a few key ideas that I think will help us get more reach, and tighten up our funnels a bit. Both of which will definitely save us time in our goal to grow the site.

How To (Actually) Make Money Writing Online

By Ethan

On April 23, 2023

In How-To, Newsletters, Writing

From 2020 to 2023, I helped run a multi-million dollar newsletter called Trends, which is the sister-publication of another even bigger newsletter called The Hustle.

While there, I had the chance not only to see behind the scenes of a successful media company, but also to help literally write the book on how 7-figure newsletters make money, interviewing leaders at other major publications like Axios, Buzzfeed, The New Yorker, Morning Brew, Motley Fool, Washington Post, and more.

I’ve also talked to lots of people you’ve never heard of, who still make 6- to 8-figures each year on their writing.

Do you want to know what they all have in common? It’s NOT a big audience, a fancy website, or even very good writing.

The people who make the most money from their writing understand one simple business model…

…Oh, and by the way, this works for different kinds of media too. Podcasters, TikTok-ers, Instagram influencers, and more – the ones that make money all do it by adhering to the same simple framework.

Here it is – there are three ways to make money from media:

Free products: Monetized via ads and affiliate deals
Low-cost products: Known as “front end” products, these are typically $100 or less (cheap enough to be an impulse buy) and designed to reach large audiences.
High-price products: Known as “back end” products, these are typically $500 and up (can go all the way up into the many thousands of dollars). Because of their price, they’re often designed for much more narrow audiences.

That’s it.

Anyone who’s making serious money is doing it through one or more of those 3 levers, whether they realize it or not.

And that’s the problem – big companies understand that this is how the model works, but a lot of smaller creators or media startups don’t realize that this is the game they’re playing. They feel like they’re taking shots in the dark.

On their own, any of the three can be a multi-million dollar business. You can also mix and match them. For example, 1440 makes money from ads alone, The Browser has both free and low-cost subscriptions, whereas The Motley Fool uses all three.

Once you understand how these pieces fit together, you’ll have a much easier time deciding what to create, and when.

I like to think of it as a bullseye.

Here’s how it works…

Each ring of the bullseye represents one of the three monetization methods (free, front-end, and back-end).

The size of the circle correlates to the breadth of the audience that you can capture with that product. The depth speaks to how detailed and specific your content has to be at each stage.

Let’s break down each…

Free Products

When I say “free products” I’m talking about media properties you run that your audience can access for free.

For writers, this is primarily free newsletters and blogs. But it can also be free YouTube channels, podcasts, Twitter accounts, etc. – really anywhere you can build an audience and place ads.

To keep things simple, let’s just use the example of a free email newsletter.

Your free publication represents the outer ring of your bullseye. It will always be your biggest audience because it has the lowest barrier to entry. There’s no cost, and people don’t need to love you to subscribe. They just need to be somewhat interested in your work.

Because of the broad reach, the content will be fairly broad too. You can typically cover several different topics if you want, and the depth of coverage doesn’t have to be super deep.

There are two ways this free audience can make you money:

Showing them ads & affiliate deals
Selling your paid (front- and/or back-end) products to them

Important: When it comes to your free audience, bigger doesn’t always mean better.

I’ve seen publications with 1k highly targeted subscribers make 6-figures a year. The Newsette did more revenue with 500k readers than Morning Brew did with over a million.

The key is understanding what makes an audience valuable. There are three factors that contribute:

Size: How big is the audience?
Trust: Are they taking action based on what you say?
Budget: How much do they have to spend?

You basically need two of the three for a valuable audience. Of those, No. 3 is the most important, since it dictates everything else (e.g. the kinds of advertisers you can work with, the products you can create/sell, etc.).

But if you have any two, you’re ready to start monetizing a free publication.

Affiliate ads are typically the easiest place to start. Or you can sell direct advertising to brands, or develop paid products for your audience to buy. Speaking of, let’s take a look at those…

The Basics of Paid Media Products

There are two types of paid media products – front end and back end.

The difference between them is their cost, as well as the depth, specificity, and value of the content you create. We’ll look at the particulars of each below.

For now, just know that both can be sold on either a one-off or subscription basis. The main benefits of subscriptions are that they create recurring revenue for your business, and they can scale in a way that other media can’t. But they also typically require you to continue creating new content over time, which can be tough. You’ve got to weigh your ability to do that when thinking about how to structure your offer.

Front End Products

The so-called “front end” products are paid products that are typically priced in the $50-$100 price range – cheap enough to be an impulse buy.

Most often, these are something like a short course, downloadable guide, or paid newsletter. But they can be other things too – a book you sell, images you license, even subscription apps or software. The distinguishing feature is that the price is in that impulse zone under $100.

Because they’re paid, the potential audience is narrower than your free product. But because the price is somewhat low, the aim is typically to reach several thousand customers (at minimum).

The content also tends to be more in-depth than whatever’s provided at the free level.

For example, at The Hustle, our writers reported on tech and business news every day in quick, pithy pieces (typically 150-250 words). That was the free newsletter. Our paid newsletter, Trends, offered deeper coverage specifically focused on emerging business opportunities for startup founders (usually in a longer format, and with much more data, insights, etc.)

Millions of people could subscribe to The Hustle because they enjoyed general business coverage. But Trends was for a narrower group that wanted to go deeper – people actively trying to build businesses.

In a similar way, your front-end product will be a paid solution that you know a sub-set of your free audience is interested in.

There are two big mistakes people make with front-end products:

1) Pricing: People often price these willy-nilly. For example, at Trends, we priced the subscription at $300 for the year because we didn’t know any better.

That price point is kind of a no man’s land – you don’t know if you’d earn more by dropping the price (going after a bigger audience) or increasing it. So stick to $100 or less on your front-end product unless your audience is big enough to do proper A/B tests.

2) Value Prop: The bigger problem people face is not getting clear on the value prop. SO many creators offer a “paid” tier which is just more of the same kind of content they give away for free. It often goes something like this…

“Welcome to my newsletter. You’re on the free plan, which is just one email per week. But if you sign up for my patreon, you’ll get two emails per week, plus access to the archive.”

DONT do this.

The problem here is that you’re not really offering anything unique to the reader. Just more of the same. If they do sign up for the paid subscription, they’re often only doing it because they like you as a personality, and that’s not a sustainable way to do business.

Instead, use your relationship with your free audience to figure out what their main frustrations and pain points are (the valuable ones you can solve), then solve those with your paid products.

Back End Products

Much more specific, much deeper coverage, and much more expensive.

Back end products typically start at $500-$1000 and can go up into the many thousands of dollars per year.

How, you ask?

Well, back-end products are typically very focused on value creation. Think insider-business know-how, or industry data. They can even be high-end consulting packages, or expensive live events.

What ties them all together is that they’re typically focused on helping customers make money, save money, or save time. That’s why they command a high price.

For example, James Altucher has several back-end newsletter subscriptions that run $4-$5k+ each year. They’re focused on specific stock trading strategies he’s developed, and the allure for buyers is that one great trade can return many times what the newsletter costs them.

In a different example, Industry Dive licenses content to other companies for thousands of dollars a year. They also have custom research services they offer. Companies know they’re saving tens- or even hundreds of thousands of dollars not having to create the content themselves, and they believe it’ll help them attract more customers, so they’re willing to pay.

Your back end products will always have the narrowest audiences, so it’s important to price them high enough that they can make money with relatively few subscribers (often <1% of whatever your free audience is).

Pulling It All Together

Generally speaking, your free product sells your front-end, and your front-end sells the back-end, so that the whole system is set up to attract free readers and gradually convert the most dedicated ones to high-paying customers.

You can have multiple free, front- and back-end products if you like.

The most important thing is to know that you’re not obligated to have any of them. This model is a choose-your-own adventure.

For a long time, Morning Brew did tens-of-millions with just free products. On the other end of the spectrum, someone like Kevin VanTrump makes millions on just a paid newsletter about corn and soy (there’s a free trial, but no permanently free subscription).

A really robust media company, like Motley Fool or Agora might look something like this…

When you know how the model works, you can pick the pieces you want and spend less time guessing.

Wrapping Up

So that’s it.

Obviously, there’s a lot more that could be said about the nitty gritty of pricing, growth, content strategy, technology, and more.

But you now know the model used by all media companies to thrive.

Dive deeper into this site for case studies that show this model in action.

A Mistake I Made

By Ethan

On January 2, 2023

In How-To, Newsletters, Writing

Back in the spring of 2021, I published a Twitter thread about some research I’d done on 7-figure newsletter companies.

I had been lucky to get unprecidented access to leaders in that industry, and over the course of about six months, I’d boiled down the business model in a way no one had really shared up to that point.

Newsletters were very popular, and the tweet spread fast.

A friend at the time recommended that I publish another thread. And another, and another. One a day for the next 30 days or so, in order to ride the wave, build my Twitter following, and establish my name as a go-to resource in the field.

It would have been easy enough. I had 500+ pages of edited insights, plus hundreds more in interview transcripts, P&Ls, and more.

In about twenty minutes, I wrote an outline of what the publication schedule would look like.

The first few days went well, I was stacking followers like never before. But then two things happened:

I hit a day where I didn’t feel like writing, and
I worried, “What if I run out of things to say?”

That was two years ago, and in a lot of ways, my career went on pause that day.

I’ve continued to work (a lot). And learn. And publish in other places.

But my personal audience-growth (especially on that topic) mostly stalled, and I still haven’t worked my way through that original list of 30 threads. And now I think that was a mistake.

Giving in to number one is always a mistake. Any pro knows that.

But number two was more complex.

Because in a weird way, it became a self-fulfilling prophecy. I was worried about running out of things to say. So I didn’t say anything. And the effect was the same, except now, my research isn’t out in the world working for me like it could. And I’m also sort of stuck, because I can’t possibly move on to anything new until I get this out in the world.

Don’t feel too bad for me. The last two years have been fun.

But the lesson is an important one: It is both selfish and self-destructive to hold back your ideas just to make them last longer.

If I were giving advice to my younger self, I’d say, “Do the opposite.”

Share a little more than you think you can sustain.

Not only will that help strengthen your creativity muscle. But staying out at the leading edge of your content ideas will help ensure that you can continue to evolve and reinvent yourself as the situation demands. Whether that’s because the industry changed, or because you find something you’re more interested in.

This game, of audience building and idea-sharing for money – it’s all about movement. You need to stay moving. Stay curious. Stay publishing.

As in life, stagnance is death.

Do You Want To Make Cake?… Or Progress?

By Ethan

On November 26, 2022

In Cooking, Life Lessons

I have a health problem: It’s called SPHS — Spontaneous Procrastinative Hunger Syndrome.

It’s very serious.

Basically, whenever I have a lot on my to-do list, and I’m not quite sure what to tackle next, I get hungry.

Not for just anything.

Usually, I get hungry for something that I don’t have in the fridge. Something that would require a trip to the store, and (if the to-do list is particularly complex) cooking.

Often, it’s a multi-pan affair. Something going on the stovetop, while something else heats in the oven, with several mixing bowls, measuring cups, knives, and cutting boards to match, all of which need cleaning before I can get back to my to-do list (obviously).

The problem for people who suffer from SPHS is that the food never quite hits the spot (because you weren’t hungry in the first place). Instead, you spend a bunch of time only to find yourself standing there two or three hours later, tired(er), to-do list still undone, and that much less time left in the day.

Doesn’t matter. The disease persists.

Today, the craving was cake.

I don’t even like cake. But as I was working I had a turkey cooking down into stock on the stove, and something about the smell reminded me of the first hint of a cake that’s been in the oven for a few minutes.

The SPHS stirred.

My better brain objected. It might have even prevailed. But then my other disease, SPCS, kicked in.

If you haven’t heard of it, SPCS is short for Spontaneous Procrastinative Chore Syndrome. Basically, that’s a condition where you think of little chores you can do that feel useful but actually just distract you from the thing you’re supposed to be working on.

It’s not fatal (though it can be for your career).

Anyways, I have both of these. And the sum result was that this afternoon, I was craving cake, trying to resist a trip to the supermarket, when I suddenly remembered the supermarket is next to the hardware store, and the hardware store sells fireplace logs, and I’m kind of low on fireplace logs, so if I go to get cake stuff, I can get fireplace logs too, and then it’s not a distraction but a very useful trip.

Plus I end up with cake at the end.

I won’t bury the lead here: I’m not eating cake right now.

I made my way to the hardware store, perused the aisles for fireplace logs, all the while thinking about what kind of cake I should make, and what would be involved in that. Cracking the eggs, mixing batter, filling pans (oh, I need pans).

And as I did, a voice appeared in my head.

“You’re going to do all that,” it said, “just to make yourself feel better about this to-do list which is out of control?”

I paused as the thought occurred to me.

“Would you rather make cake? Or progress?”

Go Re-Write Your Tagline Now

By Ethan

On November 13, 2022

In Newsletters, Writing

Agora does an estimated $1B per year in income across a range of one-off and subscription info products.

Evaldo Albuquerque is one of their best copywriters. His sales letters have driven ~$120m+ in business.

He wrote this great book on the framework he uses to write killer copy.

In it, he says that the foundation is built on one specific thing:

The single most important thing you can do when you write a sales letter is to make the reader believe that:

This new opportunity is the key to their desire and it’s only available through my new mechanism.

As soon as I read that, I was struck by how many newsletters and info-products miss the mark when we try to hook subscribers.

Because doing this means you need to get clear on two things:

What’s genuinely unique about your newsletter?
And what is it that your readers truly desire?

How many of us can say we’ve really done this?

Substack is the first thing that comes to mind. Because all the landing pages are roughly the same by design, the only thing that could possibly set a newsletter apart is the title/description.

Here are the landing pages of 3 random Substacks:

Notice anything?

All of these focus mostly on what the writing is about. Not what the prospective reader desires, or what makes the newsletter different from anything they’ve ever seen before (even in similar genres).

That’s not a knock on these writers. As the screenshots show, several of these have thousands of paying subscribers. So something is working.

But I’m left wondering how much bigger the audiences could be if more of us tried Albuquerque’s method.

I say “us” because even huge newsletters are not immune to this. Check this out. Here are the landing pages for a handful of the most popular free tech/business newsletters.

Yikes.

Okay, so the first thing we should say is that there might be a reason these are all practically identical:

They work!

These are all big publications with audiences ranging from ~100k to 4m+. They’ve all got smart teams split-testing their home pages, and optimizing for what performs.

So we’ll give ’em that.

It’s also worth pointing out that when a reader lands on one of these pages, they’re typically not simultaneously looking at all the others. So in that moment, the hook might truly seem unique and enticing.

But you have to admit that when you stack ’em up next to each other, it’s a little…

Can we do better?

If we look at this through Albuquerque’s model, it seems like we’ve all (as an industry) decided that the only thing readers want is to “get smarter,” and they want to do it in 5 minutes or less.

Obviously, readers’ desires go far deeper than that.

Ads come closer to capturing this. Because they have to. An ad is competing way harder for your attention out there in the wild. So the hooks on high-performing ads are worth looking at.

For example, readers don’t just want to be smarter. They want to be perceived as smarter by people they respect.

They also want to be on the inside…

But really, I think most of us could afford to think a lot more about this.

What is it your readers actually desire? What’s truly different about your newsletter that represents a “new opportunity” for them to get the thing they want? Why is it that they can only get it with you?

Answering these won’t just help you land more readers. It’ll improve your newsletter (or book… podcast… course… whatever!) content.

Story Is About The Gap Between Expectation and Reality

By Ethan

On April 8, 2021

In Uncategorized

The first two pages of White Fang are more captivating and thought-provoking than anything I read on Twitter all day.

How is it that one or two pages from a story-teller, long-dead, can change you more profoundly than an endless scroll of the most profound thoughts of today’s most profound thinkers?

I’ve been obsessed with this question recently.

I sat down to record a video for work a few days ago. I was telling the story of a small company in Europe who started the world’s first carbon footprint credit card.

It was so hard.

I stumbled. I got side-tracked. Even the editors couldn’t save it. A total failure of storytelling.

The funny thing is, I used to be a great story-teller. It was like wood-working, or machining. I could feel a story’s angles and edges, knew how it fit together, sense the audience’s anticipation.

It seemed like the most natural thing in the world, and I remember the feeling of holding a group’s attention, wrapped, around a campfire or over drinks at a party.

I remember getting boring too.

All of a sudden, telling a story felt like treading water in a snow-suit. I pawed at the surface, trying harder and harder to keep my head up. Slipping further down into the darkness, flailing and thrashing, until finally all that was left was calm water as far as the eye could see.

I wish I could remember exactly what happened, that way I could change it back. I don’t know for sure, but I have a guess…

When I was 23, after a quarter-century of adventures, I suddenly found myself struggling with a case of soul-crushing anxiety. To survive, I learned to give up my expectations. Let go of my ideas about right and wrong. Embrace the messiness of life.

There’s a problem though…

At its core, story-telling is about exposing the gap between expectation and reality. If there’s no difference between what happened, and what the audience expects would happen, then there is no story.

For a story-teller, giving up expectations is like trimming the whiskers on a cat. All of a sudden, the world seems just a little out-of-reach. And that’s enough to ruin a great story.

So this blog is about exploring the craft of storytelling, and maybe, about learning to open myself back up to expectations after nearly a decade spent surviving.

The $300 Coffee: Understanding the Value of Money

By Ethan

On February 28, 2020

In Freedom Project

When was the last time you tipped $54 on a $5 coffee? If you’re 30 years old, the answer is probably more recently than you’d suspect.

Any time you buy something, you’re trading away money that could have been invested. If invested, that money would have grown over the next ten, twenty, even thirty or more years. So a dollar today is usually worth quite a bit more down the line.

This is known as the Future Value of Money and it’s an important tool in making financial decisions. If you understand what $1 or $100 today could be worth in the future, you can (supposedly) make better decisions on how to spend (or not spend) your cash.

To understand the Future Value of your money, you only need to know three basic things: how much money you have, what interest rate it could be earning, and how long it could be earning interest (how long you could leave it invested).

The calculation is very simple, and looks like this:

FV = Future Value
PV = Present Value (how much money you have right now)
i = Interest Rate
n = Number of Time Periods (years you could leave the money invested)

$FV = PV(1 + i)^n$

So if you have $1 today, and you have the option to invest it at a 5% return for 5 years, the math would look like this:

$FV = 1 (1 + .o5)^5$

$FV = 1 (1.05)^5$

$FV = 1 \times 1.27$

Future Value = $1.27

This means that if you invest that money, rather than spend it, in five years you could have $1.27. Put another way, if you spend that dollar today, you are choosing not to make a $0.27 five years from now.

Now, the promise of twenty-seven cents five years in the future may not seem like a compelling reason to save that dollar. But where this math starts to get very interesting is when you think about retirement.

Retirement planning changes two very important variables in this equation: the interest rate (i), and the number of compounding cycles (n).

Interest rates on quality long term investments are generally higher than 5%. Because the time-span is also much longer, the money has more time to grow. If you want to get a whole new take on the value of the money you’re spending today, consider this:

Many estimates say that, on average, over the last 40 years, a strong, safe index fund can earn you about 10% per year before inflation. Sometimes it’s higher. Sometimes it’s lower. Sometimes the market falls and you take a short-term hit. But over the long haul, the trend has been about a 10% return.

If you are 30 years old, then you have 42 years (minimum) to leave your money invested. After that point, various laws regarding retirement accounts begin to complicate things. But for the time-being, lets say your money can grow for 42 years, until you’re 72. The math, therefor looks like this:

$FV = PV (1 + .1 )^4^2$

$FV = 1 (1.1)^4^2$

$FV = 1 \times 54.76$

Future Value = 54.76

This means that every dollar you have today could, if invested, be worth more than $54 when it came time to retire.

Even that by itself doesn’t seem so compelling, so bad is our ability to grasp the consequences of the long-term. But think about it like this: Each time you spend a dollar today, rather than investing it, you’re not just spending a dollar. You’re spending $1, and taking an additional $53.76 away from your future self.

That coffee you bought this morning for $4.33? If you had invested the money, it would have been $237.11 when you hit retirement. If you add a $1 tip, it would have been $291.87.

That drink at the bar last night for $10.65? That would have been $581.55 when you turned 72.

Dinner for $47.19? You just took away $2,584.12 from little old future you.

Am I trying to tell you to avoid spending? To pinch every penny and never tip?

Of course not.

But it is a fascinating way to think about the money you have today. Even if you don’t feel wealthy, looking at your money through the lens of its Future Value shows you that you wield significant buying power, as long as you’re patient enough to let your money grow.

More than that, Future Value acts as a gut-check for compulsive spending, or purchases you’re unsure about.

Let’s say there’s a conference you think you want to attend, but the ticket costs $500.

One way to make the decision easier would be to look at the Future Value of that $500 (which is $27,380 using our math above) and ask whether you feel the conference is worth that much.

If it is, great! You just made your decision easier. Go buy the ticket and get on with your life. If it isn’t, that’s fine. Skip the conference, and put the money towards something more worthwhile.

Even a dinner with friends takes on a whole new shape when you understand the money you’re spending. Even a cheap meal, say $50 in the average US city, has a Future Value of more than $2,500. In a very real way, you’re spending thousands of dollars for that experience. Savor it.

Understanding the Future Value of your money probably won’t end your coffee habit. Nor should it. If you enjoy coffee, then go buy coffee. You can’t live your entire life deferring things to your 72-year-old self.

But what if this knowledge leads you to buy one less coffee per month?

Well, if your coffee’s $5 (and we all know that’s conservative these days), buying one less coffee per month would give you $60 per year to invest. That may not seem like a terribly imposing sum. But through the power of compounding interest, if you were to invest that $60 each year for the next 42 years, it would grow to $32,258.

That is the power of compounding annuities, and that is a story for another time.

The Locked Door: Krakauer, Seneca, and the Challenge of Coming Home

By Ethan

On September 7, 2019

In Exploration

Deep in the heart of the Swiss Alps, overlooking the Oberland villages of Grindelwald and Lauterbrunnen, there lives a giant. Six-thousand vertical feet of imposing black rock and ice, edged by glaciers, and buffeted by winds that are said to drive people beyond the brink of insanity. This is the Eiger and its north face is the stuff of legend.

It rises straight up for more than a mile; up, up out of the surrounding landscape, reaching out to scoop the clouds from the sky and hold them in its arms like a child’s stuffed toy. Dozens of the world’s greatest climbers have died in those arms, earning the North Face the nickname of “mordwand” — murder wall.

In the side of the mountain, looking quite out of place thousands of feet above the valley floor, there is a small wooden door. This unlikely hatchway, which is never locked, is known as the stollenloch and leads off the menacing face into a train tunnel, offering deliverance to stranded climbers.

In the opening pages of his book, Eiger Dreams: Ventures Among Men And Mountains, Jon Krakauer mentions the door, saying that it reminded him a little too much of:

“…a scene from a recurring dream I’ve been having for years in which I’m fighting for my life in a storm on some endless climb when I come upon a door set into the mountainside. The doorway leads into a warm room with a fireplace and tables of steaming food and a comfortable bed. Usually, in this dream, the door is locked.”

Something about this passage grabbed my imagination and wouldn’t let go. For who of us has not felt at some time like we were stumbling through the very same stormy climb, with happiness and warmth on the other side of a door we can’t seem to open?

In my life it has often manifested as a restlessness. Behind the door is a place called “home”. A settled life with a loving partner and people who know my name at the local coffee shop. It seems nice. I think to myself that I’d like to go there. And yet, for whatever reason, the door is locked, and I’ve misplaced the key, and somehow continuing to climb seems easier than knocking.

I’ve written before about why people choose to venture. But what about the challenge of going home? What about the challenge of staying home? When that particular door seems locked, journeying can quickly turn into drifting and a darkness gathers — a darkness like that of Krakauer’s unending climb.

In his interview with adventurer and extreme endurance athlete Ross Edgley, Joe Rogan once said:

“There’s something about a lot of these endurance people… I always consider [them] like dark… They’re running from some darkness. You know what I mean?”

This was shortly after Edgley finished The Great British Swim. For one-hundred and fifty-seven days he swam day and night, in six-hour shifts, through thousands of miles of cold, dark, jellyfish-infested waters all the way around Great Britain. He used neither fins nor snorkel, his wetsuit chafed the back of his neck into a deep, raw gash that regularly re-opened in the salt water, and constant exposure led to continual exhaustion and such unpleasantries as “salt tongue”, a condition in which one’s tongue literally begins to disintegrate.

For five months he endured this. He has also endured such harrowing feats as pulling a car the length of a marathon, completing a triathlon whilst carrying a hundred-pound log, climbing up and down a rope for a total of 8488 meters (the height of Everest), running thirty marathons in thirty consecutive days, and many others.

“You seem so normal,” Rogan said. “That’s what’s so confusing to me.”

Indeed, aside from the fact that he’s built like a Greek statue’s idea of what a Greek statue should look like, Edgley does seem exceedingly normal. He is warm, hospitable, cheery, and uplifting with an easy smile and the natural movements of a lifelong athlete. One of the mottos of the Great British Swim was “swim with a smile,” and he commonly sites research about how even forcing a grin can release biochemicals that aid in muscle recovery and boost immune function (both critical under such trying conditions).

And yet when he met with Charlie Pitcher, a fellow adventurer who rowed alone across the Atlantic in 2013 setting a new world record, Edgley didn’t ask about endurance or mental toughness. Instead, he asked Pitcher for advice on how to transition back into the civilized world. Proof that, even for those who swim with a smile, the door back to everyday life can sometimes be difficult to open.

“Do you think it is unusual,” Edgley asked Rogan, “or do you think that we now think it’s unusual because society has got real comfortable?”

It’s a good question. Anyone who’s tossed their life into a backpack and stepped out onto the road has had similar misgivings about society. We take to the road, we think, to get away from here and to find more of what we’re looking for out there.

This is not new though. For as long as there have been societies, there have been men and women who wandered away from them in hope of finding something more. Seneca spoke of this two-thousand years ago, warning about something that sounds uncannily like the darkness that Rogan mentioned.

“All that dashing about turns out to be quite futile,” he wrote in a letter, going on to say:

“And if you want to know why all this running away cannot help you, the answer is simply this: you are running away in your own company.”

Socrates put it similarly nearly five-hundred years earlier when he said:

“How can you wonder your travels do you no good when you carry yourself around with you? You are saddled with the very thing that drove you away.”

If the ancients are right (and let’s face it, they often are) then perhaps the door we face is not locked at all. Perhaps it is us on both sides of the door, at once trying to pry it open, and simultaneously pulling with all our might to try and hold it closed.

It is this struggle against ourselves which makes it seem as though the door is locked, and for as long as it continues, we are trapped, like Krakauer in the stormy endless climb.

The key to opening it, according to Seneca, is not found out in the world, but rather by turning inward. “You have to lay aside the load on your spirit,” he says. “Until you do that nowhere will satisfy you.”

The good news is that, if we can figure out how to do that, the future (both on the road and at home) looks pretty damn bright.

“…every change of scene will become a pleasure. You may be banished to the ends of the earth, and yet in whatever outlandish corner of the world you may find yourself stationed, you will find that place, whatever it may be like, a hospitable home. Where you arrive does not matter so much as what sort of person you are when you arrive there… the thing you are looking for, the good life, is available everywhere.”

-Seneca, Letters from a Stoic

I can’t tell you how to lay aside this load. It’s something I’m far from figuring out myself. But maybe it’s enough to remember that way up on the Eiger’s murderous north face, amongst rockslides and avalanches and maddening foehn winds, the most unlikely door in the world, the stollenloch, always swings free.

Mark Twain and the Value of Journals

By Ethan

On August 26, 2019

In Writing

“If you wish to inflict a heartless and malignant punishment upon a young person, pledge him to keep a journal a year.”

-Mark Twain, The Innocents Abroad

For anyone who has ever been frustrated by their inability to keep a journal, or, after keeping a journal, by the surprising gaps and useless information one finds upon revisiting those pages a few months or years later; For anyone who has ever known this frustration, we have Mark Twain.

When we think of Twain, most of us think immediately of Tom Sawyer or Huckleberry Finn. But during his lifetime, The Innocents Abroad sold more copies than any of his other books. A humorous account of his travels through Europe and the Holy Land, it is one of the bestselling travel books of all time.

Among the many observations he made during the trip, one that will likely resonate with writers of all kinds is that of the difficulty of keeping a journal…

“At certain periods it becomes the dearest ambition of a man to keep a faithful record of his performances in a book; and he dashes at this work with an enthusiasm that imposes on him the notion that keeping a journal is the veriest pastime in the world, and the pleasantest.

But if he only lives twenty-one days, he will find out that only those rare natures that are made up of pluck, endurance, devotion to duty for duty’s sake, and invincible determination may hope to venture upon so tremendous an enterprise as the keeping of a journal and not sustain a shameful defeat.”

-Mark Twain, The Innocents Abroad

Starting a journal is easy. Finishing it is the hard part. What’s more, all the value of the thing is pretty much bound up in the finishing of it. As Twain wryly points out to a young shipmate in his book…

“Yes, a journal that is incomplete isn’t of much use, but a journal properly kept is worth a thousand dollars — when you’ve got it done.”

The same can be said about writing projects in general. They are easy to start, hard to finish, and not really worth anything until you’ve got them done. So the question naturally becomes How do you go about finishing a journal? What is the “right” way to do it?

As with so many things, the answer seems to be “It depends.”

Twain himself tended to keep a single notebook in which he wrote everything from fictional sketches, to shopping lists, to accounts of his travels far and wide. During a single month-long voyage from San Francisco to New York, he filled an entire notebook with his thoughts and observations (the seventh of forty-nine surviving notebooks which scholars still study and transcribe to this day).

Hemingway, on the other hand, spent more than a month shooting big game in Africa (the trip which eventually became The Green Hills of Africa) and wrote nothing but a few jotted notes and a tally of animals seen scribbled on the end-papers of a bird-book he was reading during the trip. His wife, Pauline, kept a faithful account (which is itself worth a read, and can be found along with Hemingway’s own notes inside the Hemingway Library edition of The Green Hills of Africa) which he used while writing Green Hills.

Perhaps your style lies somewhere in between. Perhaps it’s different entirely.

In the end, it seems that great writing can come from just about any kind of journal, so long as the journal is complete from the writer’s perspective and the style of journaling jives with the mind doing the writing.