Two Possible Directions for My Book

Do I Go Deep on a Single Topic, or Keep it More Broad?

Last week I started reflecting more deeply about my reasons for writing a book for illustrators. I started by unpacking why I wanted to give other fellow illustrators, especially those starting out, the “leg up” I wish I had when starting out. It turns out that was pretty simple: I just want to be a positive presence in an industry that can sometimes seem opaque and inaccessible. I am empathetic to the struggles of the beginner, and I think I have something to offer.

Today, I started to work out the second reason I listed in my original purpose statement. As a refresher, this one was to make available my most essential guiding principles as an illustrator. The idea here is inspired by my observation that many so-called thought leaders have their flagship book, a gathering of the ideas or principles that underline their success. Or, a book that epitomizes their most defining qualities. I think of James Victore’s Feck Perfuction, or Austin Kleon’s Steal Like an Artist. Or Simon Sinek’s Start With Why. Or the hugely controversial Jordan Peterson’s 12 Rules for Life. The list goes on. Whether you love or hate them, think of almost any thought leader in any category or industry, and you’ll probably find they have a book.

For me, the question of what leads to these books comes up. What was it that pushed them to write a book? Or, what came first—the thought leader or their book? Did any of these writers have to write the book first, and then became known for their ideas, or did they already have these ideas circling around other aspects of their practice, and through various influences they realized there was a demand for their book? My guess is the latter: a book doesn’t just get written out of nowhere. These experts were already known for something else, within their niche or industry, and then there came a time when having the book was almost inevitable. James Victore was a well respected designer, and then speaker, before he started writing his books. I actually don’t know what Austin Kleon did before he wrote books and spoke on stages, but I do know his books stem from his talks. What pushed these leaders to get up on stages in the first place is a whole other subject, but I think it’s clear that if you are going to write as an expert on a subject, your chances of success really depend on how well known and respected you are already. The book does not come first. It flows naturally from your growing, existing record of leadership.

So, the question here is obvious: do I have the necessary pool of respect and experience in my industry to warrant a book? Do I have ideas that are cohesive enough to put into book format, and do I have an audience who will listen? Beyond my current audience, will I be able to reach new readers? Are my ideas universal enough to speak to a broader audience?

Of course, I believe the answer to all of the above is yes. Yes, I believe I have a proven pool of experience and respect, as evidenced by my over 90,000 students taught on Skillshare and 22,000 followers on Instagram. I receive notes every week from friendly strangers who tell me how my classes have helped them break through their own creative struggles. I have growing audiences on YouTube and here on Medium. (I’m thankful to report that over the last weekend, I became a Top Writer in the Art category here on Medium!). All signs are pointing to this: my messages and content are resonating with more than just a few people.

The next question, then, is what are my most essential guiding principles as an illustrator? As I continue to grow my body of classes and other resources for illustrators, what are the common themes or principles underlying everything? It is clear to me that I don’t just show people how to do stuff in a purely instructional way. There’s always some deeper insight, some foundation of understanding, on which the how-to part is built. Whatever these are, these are what I need to examine more closely. These are my clues to my own guiding principles. The real work I need to do: summarize these under a single, cohesive idea. The real power of any set of guiding principles is in being able to name what ties them together. This name must simultaneously 1) give an identity to my ideas, and 2) deeply relate to questions or pain points my audience struggles with. Ultimately, my book needs to offer guidance and resolution to a key issue faced by my audience.

To this end, I have two possible directions:

Option 1: Go Deep on a Single Topic

In this option, I choose one topic that I feel has underpinned all my success as an illustrator. I identify the overarching idea and summarize it as a system. For instance, most of my classes, and indeed, my illustration process itself, is based on breaking down larger, more intimidating projects into smaller, more easy-to-do parts. I always start by naming the key struggles or problems to overcome (both in my classes and my own work) and then move forward through a series of steps that help me forward. Taking this approach to my book, I would give this overall tendency of breaking things down and stepping through them a name, which clearly positions it as a solution to a key struggle creatives face in their own work or career path.

When my wife and I were new parents, one of the biggest struggles for us was helping our baby get enough sleep, and well, more to the point, getting enough sleep ourselves. There are many books on this topic. Some of the most popular titles include:

• The No Cry Sleep Solution: Gentle Ways to Help Your Baby Sleep Through the Night
• Healthy Sleep Habits, Happy Child
• The Sleep Easy Solution

All of these address the main area of struggle: getting your baby to sleep! We definitely chose to read some of these books based on their titles. The point here is that, with this direction (of choosing a single topic and creating a system out of it), I need to find one of the key pain points of aspiring and working illustrators and address it head-on in my title. The title of the book serves as a pithy and powerful one-line summary of what my book is about. Rather than having to explain the book idea with an elaborate setup and examples, it is self explanatory in 15 or fewer words.

Option 2: A Set of Guiding Principles

In this option, I gather a set (perhaps 10) of the most powerful insights I have learned or which have pushed me through my creative career. Or perhaps they are a set of principles that I abide by (whether I do so cognizantly or not) when making my art. These would be more like Austin Kleon’s 10 overall chapters in his book, Keep Going, or Paul Arden’s It’s Not How Good You Are, It’s How Good You Want to Be, with its 7 or 8 sections containing several shorter essays. Another inspiring title along this line is Paul Rand’s A Designer’s Art. While Rand’s and Arden’s ideas are not gathered as numbered lists (as Kleon’s chapters tend to be), all three of these book examples provide a cohesive group of inspiring ideas, all leading you to key insights that have made these writers the successes that they are. If you admire the writer and their other work, you will be interested in and receptive to their guiding principles a.k.a. their books.

This second direction is what I first envisioned when I thought of writing a book. I think it’s easier to imagine just writing a series of mini essays and packaging them up as a book. If this were to be my approach, I’m already well on my way, given all my writing and class content so far. The trick here is to identity the principles that have truly been instrumental in my success and which speak to what my audience is truly going through. It would be about finding one singular concept to frame around everything else. I think for this one, I would have to identify what it is I am already known for, and then name it accordingly. My best guess so far: I am known for breaking things down and explaining them clearly and empathetically—for people who feel they are not talented or good enough. This is the same as what I already described in the first option above. What’s different, however, is that instead of creating a system to solve one root issue or struggle, this book would be more generally about the daily experience of being an illustrator for a living. Whereas the first direction is about tackling a single topic head-on, this second direction is about more of a mindset, a way of being.

Clearly, I have some more thinking to do around this point, of 1) what my most essential guiding principles are, and 2) whether to write about them under the guise of one “pain point” topic or more as a listing of keys to success.

Today, I’m feeling more excited about the first direction. It seems like if I can nail that one big idea, it could not only become the basis for a successful book (in that it would help many creatives break through in their work), it could also become a platform for public speaking—something I also want to become better at and invited more to do.

My next step is to play out these options a bit more (likely offline in my physical journal). I hope to write more posts this week that are more topical and less self-reflective.

Thank you for reading!