Progress on My Upcoming Book About Learning From Mistakes (and Possible Mistakes I’m Making)

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I've mentioned before that I'm writing a book based on — inspired by — the interviews, stories, and insights from my guests on the My Favorite Mistake podcast.

The book isn't just a collection of transcripts of those stories. That would be a long book, and I'd like to add more value to the reader by distilling and sharing common themes, lessons, and advice — backed by some of the lessons from my insightful guests.

At the end of this post is a one-question survey about what you'd hope to learn from a book like this.

You might choose to read the post and then come back to answer this question:

A Mistake About a Book Title for a Book About Mistakes?

When writing a book about mistakes, there are many mistakes (and possible mistakes) to make along the way. And that's fine. When doing something new, we're unlikely to “do it right the first time.”

Books always have mistakes like typos (even on page 1). More meaningful mistakes that are harder to fix in a re-print (or a quick update of a Kindle Book).

One thing that's difficult for an author is deciding on a title. It's hard to do early pre-marketing of the book without a title.

For a few reasons (that I'll share in the book, or in a standalone article if it's cut from the book), I think the name “My Favorite Mistake” was a bit of a mistake for the podcast.

I think the book would be better served by a different title, for different reasons. Each episode of the podcast is a guest's “favorite mistake.” The book is more than a collection of favorite mistakes.

I considered “Our Favorite Mistakes” as a book title (and an opportunity to re-title the podcast). Having a podcast with the same name as the book seems like it would be mutually beneficial. Or changing the podcast name would be a mistake.

After going through alternatives, I think this will be the title (and subtitle — another tough decision to make).

Mistakes That Make Us: How Getting Things Wrong Can Make it Right — For Leaders and Organizations

This is just a prototype cover. I won't make the mistake of thinking I am a graphic designer. An old friend is a professional artist and created the cover image for the podcast, and I want the book to reflect that style.


Questions for debate about the title have included:

  • Have the word “The” or not at the start of it
  • The Mistakes That Made Us (the work “Make” implies a more ongoing process)
  • Should the subtitle have the word “culture” in it?

A particular book title could be a mistake. That's one that's hard to test in the market. I can survey people, but hearing what people prefer may or may not correlate to what grabs their attention as a book buyer.

I do want to make sure the book title suggests a positive focus. That was one benefit of the word “favorite” in “My Favorite Mistake.” Or “Our Favorite Mistakes.”

It's not too late to change my mind, though. I'd be curious to hear what you think.

Please comment on this post or contact me directly with any ideas or feedback.

It Was Tough Getting Started

I had the idea for the book in the spring of 2022. I was quickly reminded that it's difficult to juggle regular work with book writing regardless of my enthusiasm for this project.

It's a mistake to think I can find an open 45-minute block between meetings and then “get into book mode.” I've learned that blocking off big chunks of time — at least a half day — makes it easier to get my head into book mode. Editing, perhaps, can be done in shorter intervals, but writing requires dedicated time.

After deciding I wanted to write this, I was working with a healthcare client that had me on the road at least two weeks a month. The work was rewarding, but I decided to step back from that travel in August to focus more on the book and some other work. Then, work-from-home work managed to get in the way. The book is “important but not urgent,” where there was always some work that was “urgent and sometimes also important.”

When I got a few things behind me and off my mental plate, I made more progress in November and December.

I'm reminding myself to not beat myself up over slow progress. I don't have an arbitrary publisher deadline to hit. I'll publish it myself (meaning I'll form a team of contractors and partners to work with me instead of relying on a traditional publisher). I don't think that's a mistake based on past experiences doing books with a publisher and being my own publisher (for Practicing Lean and Measures of Success).

Overproducing Words?

I've written about 64,000 words. It might be a mistake to publish a book of that length, given how busy people are these days. My book coach is trying to convince me that 30,000 to 40,000 words is ideal these days. I've perhaps made the mistake of overproducing words. My editor thinks the book should be as long as it should be, given the focus and quality of the writing.

My initial concept was a book that would cover lessons that benefit:

  1. Individuals
  2. Organizations

It's a mistake to think your initial book concept or outline is the one that makes sense as the final book. It was a mistake to think in terms of “part 1” and “part 2” because the stories and lessons for individuals and organizations are very intertwined. When a CEO makes a mistake at work, that's both a personal story and an organizational story.

An Iterative Process

So, I tweaked the outline and flow to have those lessons more intermingled, ending with two chapters about building a culture of learning from mistakes (although some culture-building lessons appear throughout the book). I think it helps a leader to get better at processing their own mistakes before they work to help others build and strengthen that culture in their team or company. Physician, heal thyself.

For a while, I made the mistake of thinking about the book instead of putting my fingers to the keyboard to write the book. I know, from past experience, that nobody ever writes a great first draft. Publishing a first draft might be a mistake, even with copyediting. So, I got more disciplined about “just write and figure it out.” At some point, I had to write to process what I was thinking about my guests and their stories.

There are higher-level questions to answer about the focus and the high-level flow of the book. I'm grateful to have an excellent “developmental editor” working with me on this: Tom Ehrenfeld, who has worked on many great LEI publications and more.

Creating a book is an incremental PDSA process, at least for me. A book is like software, in that the design and creation is an iterative process — based on my reflections and input or feedback from others.

When to Start Sharing Content?

With previous projects, including Practicing Lean and Measures of Success, I used the “Lean publishing” approach to share my progress and to let early readers actually buy the book and give feedback. I don't think that was a mistake. But those books progressed much more linearly than this new book. So I haven't yet shared early material through LeanPub, even though I set up a page to do so. Maybe it's a mistake to be holding back that way.

“Publish early, publish often,” as a startup would release software?

I'd like to get the book to a “more ready” state before sharing via LeanPub. It might be a mistake to wait until it's “totally ready” yet alone “perfect.” I'm just starting to feel confident sharing some material with friends — aiming to get honest and constructive feedback, not just praise and reassurance.

It's often said about software that if you aren't a little bit embarrassed by the product when you launch, then you've waited too long to launch.

Tightening the Focus?

As I go back through the book — the structure and the words, I'm thinking I should tighten up the focus to lean in on the cultural aspects. I'm not looking to write a self-help book, and I don't think I'm qualified to do so. I do feel qualified to write a management book (whether some of you think that's a mistake or not).

I think this book will be better off serving a smaller and more focused audience — those who want to get better about learning from mistakes in a workplace. My podcast was focused on professional mistakes. Some of those stories, while compelling, were examples of career mistakes or other mistakes that ended up having a positive impact on them. Maybe I could, later, partner up with one of the many psychologists who I interviewed about doing a book that's more focused on individuals.

There are so many insights and stories from my guests about creating and sustaining the culture of learning from mistakes. My passion is strong (stronger?) about creating a culture of psychological safety and learning from mistakes, as I've written about here on the blog.

One author friend thinks tightening the focus could be a mistake in that it shrinks my audience. Maybe, but I can mitigate the risk of that error by saving stories and material that I cut from the book, so it can be reused in some other forms.

What's Next?

Tom is doing a deep dive into the manuscript. I don't think I'll need a complete rewrite. Sometimes, authors have to do that. But, I'll probably have to re-write parts of Chapter 1 in ways that better tee up the organizational culture focus.

I'll probably cut some stories and tighten up others to get the word count down without being too terse.

I want the book to be helpful to my readers, not just interesting. It should be an enjoyable way to pass time, but it needs to be more than that. I'm not in a rush to get this to print — I'd rather make it “right” than “right now.”

That said, it's important to me to get the book out there sooner than later, personally and professionally.

But as Tom so helpfully reminded me: I need to focus on enjoying the book writing, editing, and publishing process as it's happening. I do enjoy writing. I am super excited about this topic… so I'll make sure I get the book published instead of playing around with it forever.

Maybe in April.

You can sign up here to get more updates.

Please feel free to comment on this post or contact me directly with any ideas or feedback. The draft book description can be found below the one-question survey:

Survey: What Would You Hope to Learn?


Draft Book Description (A Work in Progress)

Everybody makes mistakes, but the most successful people (and companies) learn from those mistakes, Mark Graban explains in The Mistakes That Make Us. Individuals often say, “We learn the most from our failures,” but many organizations have unreasonable (and counterproductive) expectations of perfection. It's better to expect to make mistakes — we're all human — and react constructively in a way that turns them into stepping stones to success. 

Many entrepreneurs say we should “fail early, fail often.” It's better to, instead, “fail early, learn, and be more likely to succeed.”

Drawing on his “My Favorite Mistake” podcast interviews of CEOs, entrepreneurs, and other leaders from wide-ranging fields including healthcare, software, and professional sports, Graban illustrates how to:

  • Shift from shaming ourselves (or others) to learning and improving after mistakes
  • Take ownership of mistakes instead of blaming others
  • Avoid making the same mistake twice
  • Be proactive about trying to prevent mistakes, while realizing they might still happen
  • Stop saying with certainty, “we know that's a great idea,” and, instead start recognizing and saying “we could be wrong”
  • Test ideas and assumptions in a way that mitigates risk
  • Embrace (and learn from) small mistakes so we avoid the catastrophic ones
  • Create a workplace culture where it's safe for people to disclose mistakes, ensuring learning instead of coverups

Graban's book shares compelling stories about how a culture of learning from mistakes, built upon psychological safety, means we can learn more and reach greater heights. As the subtitle says, “getting things wrong can make it right” — if we can lead with grace and humility.

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