Like many creators, I have more ideas for projects than I have time to work on. This nice-to-have problem is exacerbated by the constraints of the monastic training structure that I live and work in. I have four or five free days a month on average. On most other days, I have about two and a half hours of free time to work on various projects. I also take one week each month to go offline to deepen my meditation practice through a silent retreat.
Historically, these constraints have forced me (and my peers) to learn to prioritize, to optimize the available time, and remove distractions. I love this structure and have benefitted from it enormously. Over the years, I’ve learned to balance the demands of the monastic structure with my own interests and side projects, finding a happy medium.
However, this theme of balancing competing demands returned with a vengeance earlier this year, when I did extensive solitary retreat in a meditation cabin at the Monastic Academy. This precious opportunity supported me in one of my lifelong pursuits, deepening my meditation practice. But it also made this problem even more acute. I didn’t post any new blog posts for the first six months of the year. I went into the cabin with an enormous backlog of ideas that I wanted to write about, and that list only grew during those six months.
Doing extended solitary retreat forced me to confront the fact that I needed to make a change in my creative process.
At first, it wasn’t clear what changes I needed to make. I knew I wanted to write and publish more posts, at higher quality, with a bigger impact on the world. I didn’t know how to do that. To diagnose my situation, I asked myself a number of open-ended, exploratory questions:
Asking these questions led me to investigate many possibilities for improving my creative process. But there was one clear theme: I had reached the limits of what I was capable of on my own.
When I started writing as a child and teenager, I loved that it was something I could do completely on my own. Unlike many other forms of creative expression, writing my words down didn’t depend on anyone else.
But the lone wolf approach was no longer working for me. I have more ideas than I can possibly write about given the constraints of the monastic training structure. To realize my ambitious visions for serving the world through my writing, I would need to start working with other people. I needed a team.
In this post, I’ll describe the changes I’ve made to my writing projects, including recruiting a group of people to support me in using my writing to have a positive impact on the world. I hope this post will give you ideas and inspiration as you examine similar problems and opportunities in your own creative process. I know many people who wish they were writing more, or putting out content of different kinds more frequently as a way to further their career, make connections, or serve the world. I believe the ideas that I share here could help you have a larger, deeper impact through your creative work.
Because I had such a large backlog of posts I wanted to write, my main goal was to double my throughput for the last six months of 2020. In 2019, I published 29 posts, for an average of 2.4 posts per month. Doubling my throughput would mean an average of five posts per month, for a total of 30+ posts in the second half of 2020. In order to produce 30+ posts in six months, I would need to create a sustainable system for drafting, editing, and publishing posts at that rate.
Focusing on increasing throughput was my major, top-level goal, and so it was worth taking the time to quantify that goal. I also listed a number of other, more qualitative goals, such as “have more fun.”
Increasing my throughput would require me to completely overhaul my creative process. Making a change required several smaller efforts, including:
- Clarifying Research Areas
- Recruiting and Managing a Team
- Managing Throughput
- Getting Started
Over the last several years, I’ve read 20+ books about strategy. I’ve done so simply by trying to always be reading one book on the topic. Reading widely within the field has helped me to get a deeper understanding of the topic than I would gain by reading just one or two books on the topic. In turn, this deeper understanding of strategy has helped me, an amateur strategist, to write about the topic in a way that even experts in the field find interesting and valuable.
For my reading this year, I decided to reproduce and broaden this success by intentionally focusing all of my reading on certain key areas of interest:
- Buddhism and Meditation
- Existential Risk
For each of these areas, I recorded a number of research questions. You can see an example in my post Monasteries Bibliography, which shares my research questions about monasteries.
Far and away, the biggest and most impactful change that I’ve made has been recruiting other people to help me. I’ve learned that I need several different kinds of help, which has led me to create four major roles so far within my organization:
- Blog Manager: I recruited my close friend and ally James Stuber as my blog manager. While I had some idea of what he could help me with, I told him his job was to level up every aspect of how I share my writing with the world, to discover ways he could help me that I couldn’t predict or anticipate. James has done a terrific job so far – I’m very grateful to be working with him, and I’m excited to see where we go from here!
- Research Assistants: I’ve asked these folks to support me in doing auxiliary research on my main topics of interest. I’ve shared my research questions and notes with them, discovered a mutually-interesting area of exploration, and asked them to dive in and report back. This has meant reading a book on my reading lists, taking progressively-summarized notes on it, and scheduling a meeting where they give me an informal, conversational “book report” on what they learned.
- Transcribers: these people take audio of me speaking on future blog post topics, transcribe the audio with Otter.ai, and turn the resulting transcript into a first draft of a post that I can revise further. This follows along the lines of my previous work with Hostwriting. You can see the procedure I’ve created for the people working with me here. While initially I hoped this would help me to speed up the writing process, so far it seems to take as much time if not more to go through this process. However, I’ve kept doing it, as it does seem to have a significant impact on the quality of my posts, as well as the ease of my writing process. It’s far easier to start writing by talking than by typing.
- Editors: initially, I wanted a “full-time” dedicated editor to review 100% of my posts. Given the rate I’m aiming to publish at, the length of my posts, the diversity of topics I’m writing about, and my budget of $0, this turned out to be a tough sell. I’ve had much more luck with recruiting people who have agreed to a more flexible arrangement. When I have posts to edit, I share it with all of them. If they have the time and interest, they edit the posts. If they don’t, they don’t.
While I can’t pay any of the members of my support team for their help, I have ensured that it is set up as a win-win arrangement. I make a point to ask what their goals are, and to find creative ways to help them move in that direction. Here are some of the goals the people working with me have:
- Start a blog and newsletter; learn from how I run my online brand
- Learn more about mutual topics of interest, e.g. meditation and Buddhism, or productivity and strategy
- Learn writing and/or productivity skills from me
- Have accountability and incentives to work on their own writing projects
Sometimes, simply getting early access to interesting blog posts, or working on a project that forces someone to learn new skills, is enough to make our arrangement win-win. In other cases, I give people free access to the Digital Productivity Coach or my Hostwriting course, and support them in moving through the relevant material at their own pace. In addition, I often give advice or support for specific, relevant issues that they are facing.
My goal is to give each person even more value than they give me – not in the form of money, but through advice, support, and mentorship in reaching their own aspirations to serve the world. This has formed what is essentially a functioning, small-scale gift economy. People trade their time and skills for the opportunity to help me (and I hope the world), in return for the opportunity to gain various skills through the project work and my mentorship. This gift economy has already changed my life and work for the better, and I hope theirs, as well.
Managing others has required me to grow new skills and capacities as a project manager and leader. Here are some of the lessons I’ve learned so far as a leader and manager:
- State “policies” as soon as possible: I have established several key values or policies for our emerging publishing cooperative, including:
- Give feedback to grow
- Use productivity best practices to DWYSYWD
- Take notes and share what you learn
- Use trial periods for recruitment: with each person that I brought on, I suggested a trial period or small deliverable as a test for both parties to see if it’s a good fit before making a further commitment. This helped me ensure that I worked well with the people I was bringing on, and gave potential candidates to see if they enjoyed the work and found it valuable. This model was inspired by Reid Hoffman, Ben Casnocha and Chris Yeh’s model of Tours of Duty (notes).
- Create procedures: Creating procedures is best practice in the business world, so it was a no-brainer to start using them for my blog. Procedures ensure that everyone working with me does quality work, but it has also helped me to develop empathy and understanding. Creating procedures has forced me to notice my assumptions and make them explicit.
Producing content at double my rate would require me to revisit how I tracked what I was writing. From a perspective of throughput, this is called Work in Progress (WIP), a concept I wrote about previously in Making Knowledge Work Visible. When I first started tracking my writing, I used the three categories suggested as a sane default for kanban: ready, doing, done. I limited my Work in Progress by working on a maximum of four posts at a time. While those three categories and a limit of four posts worked fine, I sensed that making a more granular model would support me in accelerating my publishing rate.
I broke my writing process down into ten stages in my kanban board:
- Gathering Notes / Theses / Questions
- Transcribing (optional – only for posts that start in a spoken form)
- Soliciting Content Feedback
- Soliciting Editing Feedback
- Final Polishing
Using a more granular model for my writing process has helped me to make the work visible, track work in progress, and diagnose flow issues. This resulted in me creating a new WIP limit of eight active posts (excluding the earliest stages of ideation and the final stage of distribution), which I believe will increase my overall throughput.
As an added bonus, going through each of these stages makes me feel far more confident about publishing my writing. If I go through each stage, I feel increasingly confident about my writing. I’ve thought about it, articulated my thoughts, gotten feedback on the content, revised, gotten editing feedback, and revised it further. Then it just…feels ready to publish! No one stage is too difficult or burdensome, and yet each successive stage increases the quality of each post.
You can purchase my Writing Dashboard as a Notion template for $10 on Gumroad.
To kick off this new endeavor, I took seven days of vacation time off of the monastic schedule to draft, write, edit, and publish as many posts as possible. I was inspired by Nick Winter’s concept of a Maniac Week, which is similar to what some of my monastic peers call a “Responsibility Retreat.” I didn’t work nearly as hard or consistently as Nick does on his Maniac Weeks, but the continuous effort in one direction made it possible for me to start working on reducing my backlog and increasing the number of published posts as quickly as possible. I also had a blast spending so much focused time on my writing!
I also took some time to redesign my website and newsletter. A few small tweaks – adding my name in calligraphy, adding a subtitle based on my main writing topics, rounding borders, and tweaking colors – and I felt I was signaling a new era of my work to myself and the world. How you dress matters, and not just in real life.
If you want to take some of these steps in your own writing process or other creative activity, here are a few places you might start:
- Ask yourself open-ended questions about your creative process, goals, and vision. What do you want to achieve? Why?
- Identify what areas you want to be focusing on: what topics and questions do you want to be reading and writing about?
- If you don’t already have one, capture all your existing ideas for creating content in a system. Tag them according to the different areas of focus you’re interested in.
- What is your current throughput, if any? What’s an ambitious but realistic goal for increasing your throughput?
- Ask for help from your friends, peers, allies, followers, and acquaintances, and find win-win ways to get the help you need while also helping others.
- Break your creative process down into discrete steps, track your work visually with a kanban board, and use WIP limits. Feel free to iterate on those limits over time.
- Making Knowledge Work Visible: an introduction to managing throughput using kanban, with a focus on managing reading and writing.
- The Art of Alliances: discusses the strategic concept of alliances, and how to find win-win and omni-win outcomes.
Thanks to Bill Rice, Benjamin Pence, James Stuber, Jeannette Spaulding, and Tom Critchlow for helping me to edit this post.
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