Contributing to Holloway

Holloway Editorial Team
▪︎ 17 minutes read time

Photo credit: Patrick Michael Chin

When you face obstacles, it’s a wonderful thing to remember you’re not alone. Invariably, someone else, somewhere, has faced down and overcome a similar challenge before. Unfortunately, deeply helpful and practical resources are exceedingly rare despite how valuable they can be when you’re trying to figure something out. These days, so much of what you read online is written not to help, but to get you to buy something—content marketers and SEO specialists have thoroughly gamed a system where ads and impressions are the bottom line.

At Holloway, we’re on a mission to provide the knowledge needed to enable people to do their best work. People read Holloway because they’re highly motivated and staring down a high-risk professional challenge. They want to learn, make good decisions, and get somewhere. We create our Guides to help readers orient themselves in a complex landscape, solve problems, and avoid dangerous pitfalls (or even just looking silly because they don’t know industry jargon!).

We hope you’ll join us in making something different at Holloway.

No individual or organization should have a monopoly on wisdom, which is why we’re looking for deeply knowledgeable experts willing to be published on Holloway. There are many ways to get involved, with different degrees of commitment and compensation.

This post lays out the benefits of contributing, makes it clear what Guides are and are not, explains the different roles you could take on as a contributor, and provides a high-level look at the process of producing a Guide.

By contributing, you’ll be giving readers a step up. They shouldn’t have to climb the same mountain you did—your knowledge should be their foundation.

Why Contribute

Helping write the Holloway Guide to Technical Recruiting and Hiring was one of the most fulfilling experiences of my career. Initially, writing something as comprehensive as a Holloway Guide sounded daunting, but the support of the Holloway team and community made the experience tractable and rewarding. I had an opportunity to talk to dozens of the best recruiters in the Valley, learning more about a complex topic than I think I would have through (potentially decades of) direct practice.Ozzie Osman, Lead Author of The Holloway Guide to Technical Recruiting and Hiring

There are many benefits to contributing to Holloway:

  • Help others learn: When you contribute to Holloway, you’re helping out every single one of our readers. While our readers may be self-directed learning sponges, they’re reading Holloway because they’re staring down a hell of a challenge. They need help. Think of your contribution like an outstretched hand to each of our thousands of readers.
  • Create something a lot of people read: Why should you write for Holloway and not write a book? Most non-fiction books don’t ever get more than 5,000 readers. A huge part of why we built a browser-based reading experience is so we could take advantage of search engines as a distribution channel and reach a much wider audience.
  • Grow your professional network: Everyone who takes on a writing role with us is already an expert, but writing with Holloway is a rare opportunity to interview, exchange ideas, and learn from others who are deeply interested in and knowledgeable about a topic. Producing a work of knowledge together is a powerful way to develop relationships.
  • Practice your writing skills: Some authors describe writing as a lonely experience, locked up at home with little contact with the outside world. That’s not how Holloway works. Writing is a team sport. No matter their experience level, all contributors work closely with our editorial team to produce great writing that can fit with the all the material that makes up a Guide.
  • Establish yourself as a subject-matter expert: You’ve spent years learning, working, and growing. You know what you’re talking about. As a Holloway contributor, you’ll have a highly respected, deeply researched work to point to and say, “I helped make that.” If you don’t yet have the name recognition you hope to when it comes to a field or topic, it’ll help to be associated with some of the well-known experts who will share the masthead with you. Writing with Holloway can open up opportunities to speak at conferences, advise companies and individuals, be interviewed on podcasts, and more.

What You’re Contributing To

Before you dig into the various ways to contribute, make sure to familiarize yourself with what a Guide is and is not.

A Guide is

  1. A whole made of parts: Each Guide we produce is a comprehensive collection of knowledge. Most material is broken down into sections that can stand on their own and be read over a lunch break or before putting the kids to bed. Other parts are reference material you might return to when needed. We work with many different authors and contributors to create this variety of material, and our editorial team works with a lead author to assemble it all into a unified Guide.
  2. Exceptional: This is our internal bar of quality. By definition, does it form an exception? Each section of a Guide must meet this bar, and the Guide as a whole must meet this bar. Are our definitions authoritative? Does each section exceed the existing bar for what’s been written on the subject? Is the Guide internally consistent and does it make narrative and logical sense if read from introduction to conclusion? What will each section and the Guide as a whole help someone accomplish? Does this work offer something that no other resource on the topic does? Does it answer the failures of poor resources, and exceed the bar set by the best ones?
  3. Hard work: Readers rely on our content to move their professional careers forward, which means we have a responsibility to publish the absolute best knowledge ever created on whatever subject we’re writing on. That means no fluff, no corner cutting, no self-promotion, no nonsense. It means fact-checking, having your opinions challenged by other experts, and reconciling a wide range of potentially conflicting perspectives. Contributors work with editors who will ask detailed questions and request changes to push your work from good to great. Our team is flexible and human, but does set deadlines we hope contributors will respect.
  4. Always improving: Our Guides are never “finished.” We update our content just like software. At its genesis, a Guide is Draft 0.1 (revisions follow 0.2, 0.3, etc.). When a Guide first becomes available for purchase, we’ll ship Edition 1.0, and we’ll continue updating it based on feedback (Edition 1.1, 1.2, 1.3, and so on.). That also means largely different teams might be involved with Edition 1.0 and 1.6.

A Guide is not

  1. A book: Guides are not books. Traditional reference books are out-of-date immediately after being published, difficult to search or engage with, and limited in scope, typically reflecting the experiences and perspectives of one or two people.
  2. A one-person show: Producing a Guide is an iterative and collaborative process. Some authors are used to being able to draft a table of contents and head to the woods to write for months without submitting work to an editor or getting input from others. That’s not how writing with Holloway works. Contributing authors and lead authors collaborate with each other and Holloway editorial staff on a regular basis.

How You Can Contribute

Assembling a mountain of expertise is no small endeavor. We need lead authors to anchor the production process, contributing authors to fill in where the lead author has gaps in their knowledge, writers to create subject-specific glossaries, fact-checkers, graphic designers, folks who can help out with data visualization, copyeditors, proofreaders, and more.

Ways to contribute

We get a lot of offers to help for quick bursts of time, and Holloway couldn’t be Holloway without those folks. That said, those who contribute in deep ways—whether it’s choosing to take on a lead author role or reviewing an entire Guide front to back—create immense value for the community by helping beginners learn from seasoned experts. On top of that, benefits accrue to those who really dig in. Lead authors, for example, are paid contributors, get to meet and work with some of the best people in their industry, get invited to speak at conferences, and have even gotten job offers from companies that find out about their work with Holloway.

If we listed out every single role someone could hold while contributing to Holloway, you’d be staring at a list like a film’s closing credits. Here are the main ways you can get involved with Holloway:

Writing roles

Lead authors

Lead authors are at the center of every major Holloway production. While no Guide is a one-person show, we’ve found that it works better if a few people take a leadership role and drive the bulk of the writing. Lead authors are experienced and knowledgeable to the point that they can untangle technical nuances, and empathetic—focused on making them easy for novices to grasp.

  • Outcomes: If you’re a lead author on a brand new Guide, we expect you to get us to at least a second draft of an edition, known as Draft 0.2. Lead authors typically write at least 3+ full sections of a Guide and help recruit contributing authors to write sections outside their zone of expertise.If you’re a lead author on a Guide that’s already been published for paid access, we expect you to lead the work on at least three full edition updates (Edition 1.1, 1.2, and 1.3, for example).
  • Time Commitment: 40-60 hours per month for at least three months.
  • Compensation: All lead authors are paid for their contribution.

Contributing authors

A contributing author is deeply interested and an expert in a specific subtopic of a Guide, and they usually come in where the lead author doesn’t have the direct experience to write with authority.

  • Outcomes: Produce a full draft of an entire section and work with our editorial staff through two rounds of revisions. For representative examples, see Taxes on Equity Compensation and Fundamentals of Product Market-Fit.
  • Time Commitment: 40-100 hours, depending on the length of the section and revisions.
  • Compensation: All contributing authors are paid for their contribution.

Definitions writers

Definitions writers are obsessed with technical accuracy and nuance. This expert writer comes on to help create a glossary for each Guide. They research to a deep, technical, nuanced degree in order to write definitive explanations of key terms.

  • Outcomes: Each Guide has between 50-100 key terms in its glossary. In some cases, you’ll take existing definitions from lead and contributing authors and improve them, while in others you’ll be writing the definitions from scratch. Either way, you’ll be responsible for the precision, clarity, and quality of all the definitions in a glossary.
  • Time Commitment: 80-100+ hours.
  • Compensation: All Definitions Writers are paid for their contribution.


At various stages of production, subject matter experts and target audience readers take apart drafts, provide multi-paragraph feedback, point out factual errors and confusing prose or structure, and mark where there are differing opinions that should be included. Often, reviewers come back to go through another draft a few weeks later. Working with great reviewers is the difference between putting our feet in our mouths and publishing something our readers can rely on.

  • Outcomes: Either review one entire section in-depth or review the entire Guide from top to bottom, leaving feedback in Google Docs and a summary of what we can improve.
  • Time Commitment: 3-15 hours.
  • Compensation: Reviewers are not compensated, but appear in Guide credits and get complimentary lifetime access to the Guide they review.


We recognize not every expert can set aside the time required for a lead or contributing author. Contributors are experts who write something for us in any way smaller than writing an entire 2,000+ word section. They might write a subsection, write in to us with a multi-paragraph addition, participate in an interview or off-site, or contribute in a meaningful way that’s hard to put a label on.

  • Outcomes: Contributor roles vary so much that it’s impossible to list outcomes. The key is that you helped us make the Guide materially better.
  • Time Commitment: Time commitment for contributors ranges drastically. It could be anything from a 15 minute interview to several hours worth of reading and comments.
  • Compensation: Contributors are not compensated, but appear in Guide credits. For some, becoming a contributor will be the first step toward a bigger role like becoming a contributing author.

Production roles

Copyeditors and proofreaders

We’re always looking for freelance copyeditors and proofreaders to ensure accuracy, coherency, clarity, and consistency of our Guides and work with Holloway editors to resolve style, grammar, and related issues in the Guide.

  • Outcomes: Run through an entire Guide top-to-bottom at least once.
  • Time Commitment: 10-40 hours.
  • Compensation: All copyeditors and proofreaders are paid for their contribution.


Fact-checkers help make sure we get things right.

  • Outcomes: Run through an entire Guide top-to-bottom at least once.
  • Time Commitment: 10-40 hours.
  • Compensation: All fact-checkers are paid for their contribution.

Data visualization and graphics

If you’re a graphic designer and you’d like to get involved, we’d love to talk with you. While we have our own libraries for things like charts and graphs, we’re always interested in new ways to visualize data.

  • Outcomes: Help us take a dataset from a table and bring it to life in either a static or interactive visualization that fits with our visual vocabulary.
  • Time Commitment: 20+ hours.
  • Compensation: All data visualization and graphic design is paid work.

Data partnerships

We partner with data providers when seeking unique datasets to help our readers understand a subject, problem, or solution.

  • Outcomes: Provide us with access to a unique dataset.
  • Time Commitment: 1+ hours.
  • Compensation: All data partnerships are either in exchange for attribution or negotiated on a one-off basis.

Advisory and community


Subject matter experts who have one to four hours available per month. Advisors may meet with our lead and contributing authors for two hours once a month, or be interviewed for several hours by an author or editor.


Maybe you don’t have a lot of time on your hands, but you’re well connected. You may have noticed our announcement that we’re producing a Guide on a subject where you know some top experts, and you think they should be involved. Please introduce us!

Getting in Touch

Please drop us a line at or check out our jobs page. If you don’t see the role you’re looking for on the jobs page, we may not have gotten around to posting everything. Whatever your creative idea, we’d love to hear from you.

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