Day 110 of 1000: Writing a book that solves someone’s problem

I’m undertaking a 1000-day reinvention project, blogging here daily to track my progress. In Wednesday Writing, I consider my writing practice and skills and how to improve upon them.

Yesterday I started sharing ideas from Write Useful Books: A Modern Approach to Designing and Refining Recommendable Nonfiction by Rob Fitzpatrick. I’m going to continue today.

Fitzpatrick suggests that the two most important elements of writing a useful book that gets recommended by people who read it to other people who need it are to (1) make a promise to solve an important problem for a well-defined category of readers and (2) effectively solve that problem for the readers, with front-loaded value in the book.

The problem my book will solve is this: what if you reach midlife and you don’t have the love and intimacy you want? Perhaps you’re divorced, or never married, or stuck in a relationship that’s stagnant. What do you do? The conventional approaches of online dating and building relationships have failed.

The solution: approach finding and building love with recklessness rather than reckfulness, where reckfulness involves caution, calculation, and prediction. Recklessness on the other hand calls for acknowledging the unpredictability of life, choosing a partner that will challenge and change you, and approaching love with open-hearted presence instead of cold-hearted calculations.


Fitzpatrick suggests that before writing a first draft, you develop and test a detailed table of contents that includes takeaways for every chapter and section you’re going to write.

For my book’s first chapter, that looks something like this:

  1. In Praise of Reckless Love
    1. What is reckless love? Introducing Lloyd Dobler, patron saint of reckless love, from the Gen X classic love movie Say Anything
    2. Defining reckless vs reckful love
    3. Diane Court’s dilemma — she learned to be reckful from her dad, but Lloyd offers recklessness
    4. My story: I was Diane Court — choosing reckful love didn’t work but what’s the alternative
    5. This is not pop psychology — draws from philosophy, sociology, cultural criticism, classic literature, and modern movies
    6. Preview of the ten mistakes of reckful love and the ten antidotes of reckless love
    7. The need for courage in love at midlife
    8. A call to adventure to get reckless

Fitapatrck suggests you then test this with people from your target readership, in conversation or even in teaching them. Sounds to me like a good idea but I’m not sure I’m going to do it. I’m going to ponder how I might try something like that in a way that is fun and easy.


The next thing he suggests, for writing the first draft, is to write based on the detailed table of contents and ensure each subsection isn’t too long. He notes:

Readers aren’t buying your useful book for its storytelling or suspense. They are buying it as the solution to a problem or a path toward a goal. They’ll stay engaged for as long as you are regularly and consistently delivering on that promise.

Many nonfiction books start with a history or theoretical foundation for the practical advice to come. Like Fitzpatrick, that sort of set up drives me crazy. I want to get to the advice and pragmatic tips!

Fitzpatrick writes:

At least every few pages, you want your reader to be thinking, “Oh wow, I can use that.” …

Your book can be as “boring” as you like; readers will feel engaged and rewarded so long as it regularly delivers the next piece of whatever they were promised on the cover.

He suggests tracking word counts by section so you see how many words are sitting between any two pieces of value. This works if you created a detailed table of contents with each section designed to provide value.

Using these word counts, you can see if the book or chapter has a slow start (too many words before the first major piece of value), long slogs (back-to-back sections without important ideas), and fluffy sections (sections with too many words relative to their value.


I’m well on my way to crafting a book that I think I will feel confident putting some marketing time and resources behind. I think it’s probably time to start finding some “beta readers” for the book: people who have the problem I’m targeting with my book (people at midlife who haven’t found the love and intimacy they wanted). That is scary, but it shouldn’t be any scarier than thinking about promoting the book itself once its done. It’s just an early version of that. It’s where I can see if people really want this kind of book and if the advice makes sense and helps them change their lives.