A key concept I learned when I worked at Xtreme Labs was the idea of agility. Agile development was one of the distinctive features of their services. Xtreme believed that this style of programming, driven by weekly releases of a project to their clients at the end of every week, enabled better speed and quality. Xtreme Labs made mobile apps, for companies like Facebook, Uber, and Twitter — amongst many others.

A simple example: a client project might start as a set of wireframes the first week, then a rapid prototype the second, a core app the third, with new features being built every week. Through client meetings and internal demos, the project teams also took in feedback every week. 

Image via: Hackernoon

This stands out in contrast to the “old way,” waterfall development, in which clients wouldn’t see updates on a project until it was close to completely finished.

I started working at Xtreme Labs during my fourth year in college, and it really imprinted the virtue of speed into my mind. (It would be years before I recognized the virtues of slowness as well. More on this another time.)

The philosophies and ideas of agile are straightforward enough, but in practice, it takes focus, discipline, and critical thinking. Executing on this simplicity provided Xtreme Labs with many clients, and ultimately a $65 million acquisition.

As the pace of the world accelerates, being “agile” will matter more to every field and all sorts of work. The people who are quick enough to keep up with change, and adapt, will be the ones that can exploit the marketplace. This applies to the craft of writing. People are applying the principles of agile into their work. Here are three ways they manifest agility in their writing process to take their work to the next level: 

Constant Releases Enable Experimentation and Understanding

The benefits to agile are the constant releases, which ensures constant feedback, which ensures constant progress. In The Phoenix Project, a business fable about continuous improvement (another theme in agile programming), an operations guru tells the protagonist to, “Figure out how to get to ten deploys a day.” I recently heard entrepreneur Gary Vaynerchuk say to Shopify founder Tobi Lutke that he wanted to ship 4,000 pieces of content a day. 

Erik, probably invoking the same thinking behind Gary, elaborates, “If you can’t out-experiment and beat your competitors in time to market and agility, you are sunk. Features are always a gamble. If you’re lucky, ten percent will get the desired benefits. So the faster you can get those features to market and test them, the better off you’ll be.” Features, like content, are also a lottery.

The constant smaller, less promoted, releases create opportunities for active learning, but it requires working smaller and writing in serials. Every piece of writing you make is an opportunity to get feedback. Similar to agile programming, writing can be a team sport. And more importantly, don’t promote everything the same way — save your promotional efforts when you know you’ve worked on something that will resonate.

Define Your Criteria to Preserve Quality

The challenge is, it’s not difficult to make something fast; rather, it takes time for good work to get done. Thinking. Re-thinking. Writing. Re-writing. Author Robert Caro deliberately writes by hand so he can slow himself down. He triple spaces his words and edits by hand. It’s important for the material to make a good first impression; for him to craft it in the way that he meant to. 

It’s arguable that products and features are more objective; they either work, or they don’t. But that’s not entirely true, either. There is an art to building a product roadmap, and choosing the path to roll out the product. If the product team takes shortcuts, design and technical debt accumulates, and the user experience eventually breaks.

Certainly, for testing apps, quality assurance can be automated; and there’s always Grammarly to automate proofreading. But if you’re going to write and release more, you need to define what’s acceptable to you and to meet those goals — not necessarily to aim for perfection, every time.

Collect Feedback from People

Agile doesn’t mean thrashing away at creating high quantities of meaningless features. In the world of agile development, there is a product manager who plans and guides the roadmap, there are developers and designers who execute it, and there’s a product owner (or client) who provides feedback.

The agile writer doesn’t have (or need) such a large team, so they need to do this themselves. They need to integrate the roadmap of their writing, and the execution; they need to decide what their goal is, what to write, and then actually write it. They will need feedback, which an audience will provide. 

Having followers is absolutely invaluable; I’ve seen Daniel Vassallo, and Nat Elaisson, both test out and validate their new product ideas with a single tweet — practically on the fly. 

Even without such large audiences, the agile writer needs to work harder to collect feedback, which takes away from their agility. Instead of live feedback from a single tweet, an agile writer without an audience can search for readers. It might be at a forum, a subreddit, or their friends.

The agile writer works to build this audience with their work. They execute and release new content continuously. They scope and size their creative work, so they can make sure they don’t bite off more than they can chew. And of course, they also take in feedback and understand which articles do well, and which do not.

With this continuous release comes lower stakes, less pressure, and a greater flow of creativity. When every day provides an opportunity, the next release doesn’t seem so ominous. 

The Elements of an Agile Writer

Agile programming is full of weekly milestones and feedback points, but the promotional efforts take place when the app is finally launched. Similarly, an agile writer may take time to show people — individually, at first, if they must — and to gain an audience. 

As they continue writing and learning, the agile writer can eventually plan and work their way to make something big. Something that they know will resonate, based on their learning and the feedback. 

Then, they can put their full efforts into promoting that piece of work, and growing their audience with a massive promotional effort. 

When the circle comes to an end, they start the journey back around again. Such is the life of an agile writer.

When your skills evolve, so does your fear. Here’s what you can do 

Image: Eunice De Guzman/Unsplash

“Failure is the condiment that gives success its flavor,” Truman Capote’s saying goes. The inversion is equally true; even just a sample of sweet success provides failure with its bitterness. 

Three weeks ago, I decided to make a screencast, film it, and sell it for money. It was an idea my friends and I’ve had for years; some of us run ecommerce businesses, some of us run studios, but none of us have actually tried selling information products. Almost immediately I decided, the thoughts came into my head… 

What an Evolved Fear of Failure Sounds Like

Eight years ago, I got takeout sushi with my friends, went upstairs to the Xtreme Labs office, and worked from sunset till dark to write and launch an ebook. I didn’t have a worry in the world; I was with friends, and even if I launched to a beautiful, round, zero, I would just figure it out after that. Hell, I was supposed to fail. I was a student. When else was I going to experiment?

But this time, I heard myself harshly critiquing the idea from the start. All those things I didn’t know eight years ago — the joys of ignorance — stood up and spoke out.

“Your audience isn’t big enough.” 

“You haven’t validated this idea.” 

“There’s not enough time to promote.”

The truth is, these voices weren’t even wrong. They all had valid points. But they were also just sophisticated ways of saying the same thing:

“I’m scared. Don’t do it!”

In accumulating my own expertise, I realized that my own fear of failure had evolved as well; I could point out flaws and reasons why things wouldn’t work much easier than I could eight years ago. 

My fear knew all the right, logical, things to say to talk me out of this. And in many ways, it was what I’d say to a friend or client in my situation.

As I worked throughout the week, I realized that I had lost agility compared to eight years ago, when I was a beginner. I was a student, and I’d never tasted success; I’d gotten used to the taste of failure. At least I was doing something. 

But now, my career, client list, and body of work grew, and I developed what I call.. 

The Intermediate’s Fear of Failure

As we get better at what we do, we expect to fail at it less and less often. We lose our connection with failure. The more work experiences a person accumulates, the stronger their reputation, and the greater their own expectations for the things they work on. The more we learn, the more we earn, the more we feel like it’s normal. 

For example, in the few weeks I focused on this experiment, I know the amount of money I could have made, if I wanted to get a job. A month not making that money can feel like I lost it. It’s tempting to expect my hourly rate to be the quantity I need to get back from my projects to justify my earning. Opportunity cost forces me to realize I’m investing all the potential earnings into my own life and learning experiences. 

Outside comparisons play a part, too. But now, eight years after my student side project, things seem scarier. People take on corporate VP titles. (I didn’t realize Goldman Sachs had 12,000 VPs in 2012.) They’re flexing on LinkedIn. They’re making down payments.

The fear of failure kept me doing the things I know I was good at, and didn’t support me in exploring the things I could be great at. Plus, it wasn’t real; nothing bad would actually happen if this project didn’t make a single dollar. Rather than enable me to develop new skills, it was keeping me in a silo. I needed to break out.

It really took this project to really encourage me to apply what I knew. I’ve watched Gary Vaynerchuk yell at 30- and 40-year-olds, “You’re a kid!” I think it’s an admonishment to return back to the mindset of a student. Like Amazon, everyday is day one. 

Return to the Beginner’s Mindset

A beginner’s mindset has no expectations. It is, by default, loosened up. It doesn’t worry about how the work or experience will turn out. 

The beginner’s mindset is about being okay with zero. Zero Likes. Zero views. Zero sales. Zero expectations. It’s purely about the experience, and zero results. You are a student again; you are a beginner again. 

In conventional linear progression, beginners accumulate experience. Other people may see them becoming intermediates, and then experts. But with the beginner’s mindset, even the most veteran experts are humble. They know that there are so many things they don’t know; so they’re always open to exploring, or re-exploring, an old idea. 

A beginner’s mindset can’t be read about; it takes practice. This experience meant a lot to me; it wasn’t the same as reading a book about the beginner’s mindset, it was a lot better. 

Keep Your Expectations Small

Paul Graham once wrote about keeping your identity small. I think it’s important that as we start excelling at the things we do, that we not throw away our experimental and playful side to preserve our reputations and expectations. In short, make something just for the hell of it, and ship it. 

It might not help your legacy; Andre 3000’s meticulous body of work is an example of that. But it will keep you creative; in his podcast with Rick Rubin, Andre talks about the pains of his legacy and how he feels stifled by external expectations.

The solution is to do something new, even if you think it might suck. Adopt a beginner’s mindset to overcome your intermediate fear of failure. What you’re working on today will limit or expand the things you can work on in the future. Keep your expectations small, and build the skill sets you need to do the things you want to do.

When the writing process met the theory of constraints

Image: Damir Spanic/Unsplash

“Should I write at my own blog, or at Medium?”

Of course, the question is worth considering if you’re a new writer. But a more pressing question you need to focus on is:

“How do I write something I’m proud of?”

Writing is meant to be fun and stimulating. It turns out best when you enjoy the process. Not only do you write better, but you keep writing. So the best place to start writing is wherever you get the most enjoyment from. It doesn’t really matter where it is, especially when you’re just starting out. Here’s why:

When You Start, Your Constraint Is Your Writing

In The Goal, author Eliyahu M. Goldratt introduces the theory of constraints:

Improvements made anywhere beside the bottleneck are an illusion.

In case you’re scratching your head, I made a diagram to illustrate this idea. Lastly, let’s say each piece of writing starts off as an idea, and your goal is to move it downwards as quickly as possible to add value to it (and make money). The pink bars are the measure of capacity. The red bars are the actual flow of effort and value produced and extracted:

Let’s unpack what each of these mean, starting at the far left:

The inefficient writing process: This process involves a lot of writing and editing, but is bottlenecked first by its opportunities to publish. For example, maybe the writer using this process writes only for Fast Company or New York Times. They’ve developed a strong reputation which enables their promoting capabilities. But because they don’t sell their own products (e.g., books) or offer services (e.g., speaking), they’re not maximizing what they earn. Writers pursuing this method are not interested in monetizing. Instead, they choose to focus on the craft of writing. 

The suboptimized writing process: This is the process of the cautious new writer we talk about in the opening section. They’re often so fixated on the place they publish, they don’t consider developing the critical parts of the writing process (ideating, writing, and editing). This process shows them eventually becoming capable of promoting and building an audience, but the underdeveloped early phases limit the amount of value they create. I see that first question, “Should I write at my own blog, or at Medium?” as an attempt to optimize for:

• Promoting (e.g., SEO, network effects, etc.)
• Monetizing (e.g., Medium pays for writing, whereas WordPress doesn’t)
• Building audience (e.g., You can speak directly to readers in a newsletter, but if you write at Medium their algorithm determines your distribution)

But really, this person is best suited by focusing on writing better. Once they widen those parts of their capabilities, they’ll be able to create a larger volume of, which enables them to produce and eventually extract a lot of value.

The optimized writing process: The third is an expert writer; one that’s able to earn most of what each piece is worth. They still aren’t making the maximum money on everything they publish, but they’re getting close. Maybe they haven’t gotten their back catalog organized, so they don’t circulate (i.e., syndicate and republish) their work as much as they’d like to. Or, maybe they have so many ideas and drafts, but they’re not able to edit fast enough to keep publishing going. A lot of professional authors fit into this mould.

The high impact writing process: This process creates the maximum amount of value with each article, and extracts every single dollar out of it. This person publishes amazing work, perfectly optimizes their SEO, has a group of core fans that promote their work, sets up sponsorships and affiliate links without messing up their own reputation, and regularly attracts a ton of new readers to their audience. They also have a back catalog they often excerpt or republish at other places. This is the perfect writing process. I know of only a few people who have come close to mastering this mythical process. (I’d love to hear suggestions.)

When You’re Starting, Focus on Ideating, Writing, and Editing 

Nobody starts off writing their first article at the “optimized writing process.” When you’re first starting off, you shouldn’t worry yourself about all of those factors anyway; the main constraint is how much you’re actually writing. It’s about ideating, writing, editing, and publishing your work. 

If you’re not ideating, writing, editing, and publishing regularly, then the rest doesn’t matter: 

• Your distribution won’t matter because you won’t have any writing to distribute
• Your payment won’t matter because your work is not worth paying for yet
• Your audience won’t matter because you won’t have anything to send to them

At the beginning, focus on writing better, faster, and more. The “better” part is the most important (quality), but shouldn’t come at so great a sacrifice that the other two (speed and quantity) aren’t always slowly improving. Make acceptable, not perfect; and always make sure you keep publishing.

Of course, when you write regularly, and you’ve got an audience, you might need more time to polish each article up. You can then reset your speed and quantity metrics (e.g., instead of four times a week, just once a week). Juggling these three factors will balance you out. 

When to Focus on an Ideal Place to Publish

Let’s say you’re writing regularly, and notice that each of your articles are producing the results of an inefficient writing process. You’re starting to ideate, write, edit, and publish good writing that you’re proud of. But, you’re only monetizing a small part of it. 

This is the time to focus on where you’re building your home on the internet. By then, writing should no longer be too serious a constraint; you’ve developed your skills as a writer, your ideating, writing, and editing capabilities are there, and you’ve refined your skillset. 

You’ve also likely developed a body of work that’s starting to get readers, hopefully passively through search engine traffic or social media. In situations like that, migration can be painful (e.g., you might be kicking yourself for not setting it up at your own blog), but it’s important to remember… 

You could not be writing at all.

It’s a challenge I face, and I see others wrestling with too. Starting to write is easy; constantly figuring out something worth writing, and polishing it up, is hard. It needs to stay enjoyable if you’re going to succeed at it. It’s easy to give up from the discouragement, or from a sense of overwhelm. The enjoyment and intrinsic motivation can counterbalance this.

When you’re first writing, it’s important to dial back; it’s the same as learning to cook. Signing up for a meal kit delivery plan can be crucial to starting the habit of cooking and building capacity. Eventually, when you’ve gotten a grip on cooking, you’ll make your own meal plans and order your own groceries. But if you give up, then you lose a chance to build a rewarding habit (and to enjoy the results).

The Key is Focus

Naturally, in a lot of situations, you can improve more than one thing at any given moment. In theory you can become a better writer, find more places to publish, and promote better at the same time. 

But focus can be the difference that makes or breaks your efforts as a writer, especially for anyone starting this part-time. When you identify your focus, then you can also set more realistic and reasonable goals, level your expectations, and move forward with a plan. At the beginning, every extra drop of effort needs to be focused into making something you’re proud of. You can sort everything else out after.

4 Ways to Gain Clarity When Opportunity Knocks

Last week, a friend had a job offer come up. It was a stable job opportunity in a chaotic time. It would be a step up in his field of work, it promised good money, and it could open up very interesting doors.

He also experienced high stress while interviewing for the opportunity, he wasn’t sure about this specific career, and he wasn’t desperate for the money. 

He wasn’t sure yet about what he should do.

He called me because I was in a similar situation just a year and a half ago. Long story short, I decided to take on a big work contract. I was lucky things unfolded the way they did, but I should have known how to make that decision more deliberately. 

We chatted for an hour or so. I talked about my experiences, and almost started wandering down the path of what I’d do in his case. Then, I smartened up. 

In my note-taking system, I started a thread about how to make difficult decisions. I ran to get it, and read the notes in it to my friend during the call.

A few days later, he texted me and said he knew what he needed to do, and that our call gave him a lot of clarity into his situation. 

I was happy. I wrote the thread for myself, and I knew it would be useful for him, but didn’t realize how clarifying it could be. 

Here’s what I’ve written down in my notes, and what I told him:

Define the Important Areas of Your Life

I really like Skillshare and Otis founder Mike Karnjanaprakorn’s post on setting goals. The short of it is, he defines the areas of his life that are important to him, and sets goals he wants to achieve. Each week, and quarter, he checks in on his own progress.

The key to this is not just in the goal-setting portion, but actually in quarterly and weekly reviews. Are you actually making progress on those goals? What are you doing that’s working and not working?

In my experience, setting the initial goals can take maybe even less than an hour. The best way to come up with the best answer you can in that moment, then think and improve it the next quarter. Goals and plans are guesses, and you can always improve them. This way, whenever you check on your goals, you have the best version of them.

These goals will determine what you want your life to look like, as well as how you evaluate your opportunities. If, for example, my friend was interested in mental health, he’d consider that the interviewing process created a stressful experience for him. He might consider whether or not it was indicative of how the job would be, and decide deliberately whether or not it was worth it to him.

Define Your Anti-Goals

Metalab and Tiny founder Andrew Wilkinson writes about the power of knowing what you don’t want to do. He figured out what he wanted his days to look like by calling out the things he didn’t like (e.g., long meetings, packed calendars, etc.).

Back to my friend — he could quickly list the worst parts of his days. Or, if he wasn’t sure, he could look back at the worst 5 days of the month (or year), and see what they had in common. 

For example, if he hates meetings as much as Andrew does, and the job clearly requires a lot of meetings with stakeholders, etc., then he’d know this opportunity might not be worth his time. On the other hand, if there were no meetings at all, then this opportunity could be interesting. 

Work Backwards from the Future

In 2013, Pixar set a goal to make their movies cheaper and faster. On average, each movie cost them 22,000-person weeks, and they wanted to bring that down to 18,500. In Creativity, Inc., Pixar co-founder Ed Catmull shares how he prompted his team for suggestions: 

“The year is 2017. Both of this year’s films were completed in well under 18,500 person-weeks. … What innovations helped these productions meet their budget goals? What are some specific things that we did differently?” 

It’s a simple prompt, but one that I really like. They forecast the setting four years later, and ask for suggestions on specific things done differently. Without a realistic way to get there, a vision remains little more than just that. It won’t become reality.

If my friend had defined his goals, he could use this to determine how to get there. He’d have an idea of whether this opportunity sets him up to achieve his goals, or takes him further away.

Assess the Current Situation

Ryan Holiday asks, what’s the absolute worst thing that could happen? What would you miss out on if you did it? 

The answers need to be clear here. If they’re not, go ask someone who has either done something similar, or knows someone who did. Ask them what happened with the decision and what the outcome was. Or, go read a book about it. 

And as Ryan advises, most people can’t see your goals and vision beyond their own experiences. Don’t outsource your decision-making to them and ask, “What would you do?” They’ll give you an answer for what they’ll do, which they might position as what they would do if they were you, but neither is the same answer as what you should do.

I emphasized this to my friend, calling myself out, cognizant I might’ve biased him towards one decision or another. (Of course I had an idea what I would do in that situation, but that doesn’t mean I knew what was best for him. There is a subtle, but very important, difference.)

Clarity Makes Hard Decisions Easy

If there’s a common thread in all of these exercises, it’s that they clarify your goals, desires, and enable you to put a plan together for yourself. Whenever an opportunity comes up, you at least have a destination you’re working towards. 

From there, it’s just a simple matter of figuring out whether the opportunity supports you to getting closer to it, whether you can finesse it into such a vehicle, or whether it’s a trap — a swamp that will keep you stuck, forcing you to chase something you didn’t want to in the first place.

Remember, 10% Is Better than 0%

“I wish I knew about this 10 years ago!”

I exclaimed this after I started organizing my notes and writing with them. And I only did that because after I read parts of How to Take Smart Notes. The book had been on my shelf for years; I’d even moved a couple of times with it. Yet I only picked it up after I resolved to spend 20 minutes reading it; I couldn’t put it down until two hours later.

The main subject of the book is a man named Niklas Luhmann, who wrote 60 books and published a two-volume grand theory, The Society of Society, on time. He did all this, as you can probably guess, with the help of his note-taking system.

I don’t know what Niklas ate for breakfast, or how he solved specific note-taking problems (like adding a card between 1 and 1a), but I started my note-taking system right after reading just a portion of that book. I also completely see a better way of doing it; a system that can be both analog and digital, and how to make time to maintain it. If a contemporary disciple of Niklas Luhmann had a look at my slipbox, they’d probably:

• Turn me into a meme and laugh themselves silly
• Cringe so hard they give me access to their thousand-dollar courses so they never have to see it again
• Make a note to add to their thread about the deteriorating nature of notes… 

Hell, maybe all three. (Some note takers have big personalities!) But without having been willing to read parts of the book, and apply a lesson imperfectly, I’d never have learned or experienced any of this. So I propose a method to reading now, moving forward:

The 10% Read

The 10% Read idea is useful to everyone, but probably most useful to people who aren’t already reading 25 pages per day, and want to get value out of books: 

Read 10% of a non-fiction book, and apply one lesson from it.

The point of the 10% Read is to give yourself permission to speed-read through a book. Get acquainted with its best ideas, through looking at the table of contents, the index, and just randomly flipping through it. Accept a superficial understanding of an idea, and acknowledge it’s just the start. 

Take action on what you learned. If you’ve read 10% of Deep Work, start blocking chunks of time in your calendar. If you read Radical Acceptance, pay attention to your self-talk. Put reminders of these applications and ideas in your phone notes, your wallpapers, and your journals.

The 10% Read is meant to lower the barrier of reading a book so aggressively that you can’t help but show up. Then, apply just one lesson to apply to your life in some way. 

Most of us are taught to read cover to cover, and you may think it’s not worth your time to read just part of a book. But the truth is, even just getting one of a book’s best ideas are better than leaving it on your shelf and getting none of them. (And more importantly, not every book is worth your time to read in full!)

Ideas are worthless to you as mere words on a page. They’re only useful after you understand and apply them somehow.

The Power of Taking Away Just One Idea

It’s so tempting to say, “If I’m not going to remember this whole book, I might as well not read it. Why bother?” 

Curtis Jackson writes in Hustle Harder, Hustle Smarter:

“After you finish this book, you might only take a few of the principles with you. Even just one. That’s fine. That was the case when I read Robert’s 48 Laws of Power. Ask me today what that book was about and all I can really tell you is, ‘As the student, never outshine the master.’

“There were forty-seven other laws in that book, but that’s the one that stayed lodged in my brain. And because it’s never left me, I’ve been able to apply it so many times over the years. I’ve literally made millions by remembering to follow that principle.”

Similarly, when Joss Whedon admits to never finishing the Getting Things Done book, he still says that he applies the principles constantly. He says, “‘Next actions’ is one of the most important things that you can say in any endeavor.” 

Both of these people took away one important thing from their books, applied it, and used the techniques to great success. 

Each Application can Change Your Life

Imagine if Curtis had decided not to read The 48 Laws of Power until he had a proper note-taking system in place. Or Joss decided because he couldn’t finish Getting Things Done, that it wasn’t worth reading. Sure, they might’ve succeeded nonetheless, but they each would be missing an incredibly valuable tool in their belts. (After all, Curtis directly attributes earning millions to his adherence of the principle.)

Oftentimes, you just need one opportunity to exploit, or an idea to connect two dots. The more dots you expose yourself to, the greater the connections you can make, and the more value you can get from a book. 

Don’t leave a book closed because you don’t have time to finish it. Open it, skim it, and get what you can out of it.

Of course, even in Curtis’s and Joss’s cases, you could say that they might be even more successful if they read or retained the whole book. That’s why it’s worth considering the next evolution after you’ve mastered and gotten value out of the 10% Read.

From 10%, to 100%

Without the 10% Read, How to Take Smart Notes would still be on my shelf, and I’d still be without a note-taking system. I wouldn’t have gotten any value out of it. But after my read, I know that there’s much more value that I can get out of it.

 The 10% Read is all about starting at 10%. It’s not about staying there. And it certainly isn’t conflating 10% with 100%. It’s very clear I haven’t grokked some of the important ideas and philosophies yet. As Philip Stanhope, the 4th Earl of Chesterfield, wrote, “Whatever is worth doing at all, is worth doing well.”.

Understanding and applying 10% of a book might not be as powerful as understanding and applying 100%. I’ve now learned that How to Take Smart Notes is worth my time; I’m applying it every day, and I know how to improve it. Reading 10% of the book and applying the note-taking system already improved my writing process drastically. I can’t wait to read, and apply, the rest of it.