Putting pen to paper: collecting your ideas into a book
Barry O’Reilly, entrepreneur, business advisor, keynote speaker, and best-selling author, shares how he got started and his tips for other aspiring authors.
Did someone in your network publish a book recently? Are you thinking of doing the same? We speak to Barry O’Reilly, entrepreneur, business advisor, keynote speaker, and best-selling author, about how he got started and his tips for other aspiring authors.
Q. Hi Barry, thanks for taking the time to chat with us! Could you introduce yourself to our readers?
I started as a software engineer in Scotland, working in a pioneering mobile games development startup. There, I was figuring out on the fly how to build, test, and iterate using early Agile methods. When that ended, I spent time travelling in South America and ended up in Australia where I worked on an $800m Asia Pacific government-funded education initiative to create next-generation eLearning content for teaching and schools. I gained insights into building and leading cross-functional teams during my time there.
I continued to work in different parts of the world, including London, San Francisco, Melbourne and Manila in the Philippines. I joined ThoughtWorks, pioneers of technology and product development practices, in London. There, I ran business transformation globally, working with brands like British Airways and The Economist. I saw that many large corporations were struggling to adapt to changing markets and customer needs. This formed the basis of Lean Enterprise: How High-Performance Organizations Innovate At Scale, a book coauthored with two on my colleagues at ThoughtWorks, Jez Humble and Joanne Molesky.
The publication of our book led to work with senior business leaders all over the world. I moved to the US and started ExecCamp, an outcome-oriented immersion program for executives and business leaders who are willing to get comfortable with being uncomfortable to make a lasting cultural impact on themselves and the organizations they lead. This work then led to my next book, Unlearn: Let Go of Past Success to Achieve Extraordinary Results. This opened more doors to more consulting work.
I’ve also recently embarked on a new challenge, cofounding Nobody Studios, a venture studio that seeks to make entrepreneurship and venture building accessible for all. We aim to create 100 compelling businesses in 5 years. No one has attempted what we’re doing, so it’s an exciting time for me.
Q. It sounds like the two books played an important role in your journey so far. How did the first book opportunity come about?
I was lucky. One of my colleagues at work reached out to me and he was working on a book. He just sort of said, “Look I’m working on this book. I’d love if you could write a chapter or two”.
I’m dyslexic so I was quite nervous about trying to write a book. I had a solid history of D minuses in English literature. I never considered myself a writer. But writing a book is this thing that you always imagine, “could I get to do that”? So I said yes and instead of writing one chapter, I ended up writing probably about half of the book. We just started to collaborate on the entire thing. That was just a really great experience.
I’m dyslexic so I was quite nervous about trying to write a book. I had a solid history of D minuses in English literature. I never considered myself a writer. But writing a book is this thing that you always imagine, “could I get to do that”?
We also had another co-author and the fact that we were a team working together made the process both easier and harder. It was easier because we shared the workload by taking on different themes in the book, writing our portions and then reviewing each other’s work until we created a harmonized whole. But it was also harder because there were schedules to coordinate, ideas to debate, and more editorial decisions to agree on.
I did feel like my own voice wasn’t always present. I can see my voice coming through in some places, but because our writing process was a cross-functional collaboration, the final result was that our individual voices got merged.
Lean Enterprise launched and it was really successful. I learnt a great deal from my coauthors and achieved something that I once thought was never going to be possible. There was a great sense of accomplishment.
Writing a book is like eating a potato chip. You know they’re not good for you and you should avoid them because they are bad for your health, disrupt your life, and cause more frustration than you can imagine. Yet once you had one, you just want one more.
Q. Was it different when you wrote your second book?
I wrote a book in a team, but then could I write one on my own? Would I even have enough to say? I was also starting my own business, so I thought right, let’s do it. Let’s write the next book.
I see writing as a personal retrospective of my work. It is a chance for me to reflect and capture my own thoughts and experiences. I wanted to write about what I experienced, in my own words, in my own way.
I tried many different ways to write this book. At first, I tried getting up earlier than usual so I could spend the first one or two hours of the day on writing. I also tried staying up late to do the same. I tried writing the ending of the book first, and I also tried to write the beginning of the book first. I tried to commit to a certain number of words per day. But I still struggled to build and maintain the momentum I would need to complete the book.
This actually continued for six months and I found myself stuck. Then I decided to add a skilled writer to build my own writing team because the team approach worked well for the first book. I wanted to find someone who could provide the spark to keep things moving forward, and work as a collaborator and also as a coach.
I realized that my strength was in speaking and presenting. So instead of writing the book, I spoke it. I created mini-keynotes for each chapter and the writer created sets of questions which he used to interview me. We got the interviews transcribed and suddenly we were flying. He would get the transcription, edit it and then send it back to me. We were in this great fast feedback cycle.
I realized that my strength was in speaking and presenting. So instead of writing the book, I spoke it.
I applied many of the same practices I use for product development. Writing a book is similar to building a software product. You’ve got customers, a vision and features to bring to life. The vision is a big idea, but I started small by doing the proposal, outlining the chapters, and working in small batches. We shipped material to each other quickly and often to create a fast feedback loop between me and the writer. This became an iterative and experimental process for writing the book.
Q. Who should consider writing a book?
There’s sort of a romantic idea about writing a book. It is kind of special because it lasts. It feels like a contribution to society at some level. It’s one of those things that feel like milestones or achievements that people might find inspiring.
If you have the inclination to do it, just do it. There are so many mediums to share your ideas now, whether it is podcasting, writing, or making micro-content as creators. There are so many ways for people to communicate ideas.
The thing I’d make people aware of is that it is a long and lonely process. It’s a lot of work to formulate your ideas, put them down, share them with people, get feedback, and understand what feedback to take on board and what to disregard.
It’s actually hard. You share your ideas with bright people that you respect and they may have different opinions than you. But you have to remember it’s your book and it’s your opinion. Sometimes you have to go against the opinion of people you really admire.
You ask for critique and you hear things that you don’t want to hear. Can you see past it, take in what’s important and discard what is not? Those things can be hard when you’re trying to create something.
You do put yourself out there and it’s a huge vulnerability, but it’s a massive achievement when you complete the book and it’s very rewarding.
You do put yourself out there and it’s a huge vulnerability, but it’s a massive achievement when you complete the book and it’s very rewarding.
Q. There are many people writing blogs, doing podcasts, and writing books. Is it important to have a standout idea?
You either need a unique angle or a really strong audience already. There’s a reason why when Stephen King publishes a book, everybody buys it. For publishers, even if you have an amazing idea, they’re still going to back people who have an established following, credibility and path to book sales.
You either need a unique angle or a really strong audience already. There’s a reason why when Stephen King publishes a book, everybody buys it.
When you’re touting your book to publishers, you have to write a whole marketing plan about who you are, all the people you know, and what your following on social media is like. You need to write this plan and also give them one chapter of the book. It’s pretty hardcore.
But a good idea is table stakes. If you don’t have a good idea, people won’t be interested in your book even if you already have a following. You also have to create authority and awareness around the idea. The process of raising awareness of the idea brings people to you.
Q. What tips do you have for people who’re thinking about writing their first book?
You can start by testing your idea. You publish blogs which show that these are the areas you’re interested in or this is what you’re writing about. The blogs are really good because while you’re testing out the content, you’re also building an audience around the ideas that you’re interested in and passionate about. If you can start to connect with people who’re interested in the same things that you are, it’s a great way to get people excited about what you’re going to share with them. This also helps to get you into the habit of writing.
You can start by testing your idea. You publish blogs which show that these are the areas you’re interested in or this is what you’re writing about…If you can start to connect with people who’re interested in the same things that you are, it’s a great way to get people excited about what you’re going to share with them. This also helps to get you into the habit of writing.
For me, that was a big one. It gave me a way to formulate my ideas and get them better. The more I did that, the more confident I was that this was an idea that people really resonated with. It also taught me how to talk about my ideas. Before blogging, I didn’t really know how to speak about my ideas. It was kind of interesting teaching myself how to describe the ideas and see which ones landed with people.
When you launch your book, you have these super fans who are already cheering you on. The minute the book comes out, they often buy it. That gets you up and running.
One of my friends, Theresa Torres, wrote a book called Continuous Discovery Habits. She had an early review club where people would get access to chapters as she was writing them to give her feedback. She had also been blogging about the topic for over four years, making videos about it, and conference talks about it. Eventually, she self-published the book and it was a success because her followers bought it. People already knew about the book and were excited that the book was finally here.
There’s another tip I can share. Not many people read 300 pages anymore. Part of the trick is to write something that’s probably about 100 pages because it makes you focus on a niche that you can get right.
Q. Not every book becomes a big success overnight. What would be a realistic expectation after the book gets published?
There’s always nervousness. Even when I was publishing blogs, I would think “oh nobody would care about this stuff”, or “who’s going to read this”. You always have to deal with the vulnerability of writing. The thing is, if you just write a book and never tell anyone about the idea, suddenly just launching it to the world, there’s no on-ramp for people to understand you and what you’re writing about. Why should what you’re writing matter and what would be interesting about you?
That’s why I’d really encourage you to start telling the story even as you’re writing the book. Be out there talking to people about it because that’s what gets people aware of what’s exciting about what you have to say. Then they’re with you during the journey and they want to be part of it. The more people you can get involved in that community, the more successful it’s going to be. That’s my ultimate hack with all of this stuff.
The other thing is you don’t really make money from the book sales itself. Most people are going to pay between US$10-$15 for a book and sometimes you give it away for free. You make money from people asking you to present or run workshops around it.
The book is one tool in your marketing strategy of what you’re trying to create. For example, if you wanted to work with startups, then you write a book targeted at startup founders. When they see the content, then they call you to do the work you want to do. The book becomes your ultimate business card because it has credibility to it.ays nervousness. Even when I was publishing blogs, I would think “oh nobody would care about this stuff”, or “who’s going to read this”. You always have to deal with the vulnerability of writing. The thing is, if you just write a book and never tell anyone about the idea, suddenly just launching it to the world, there’s no on-ramp for people to understand you and what you’re writing about. Why should what you’re writing matter and what would be interesting about you?
That’s why I’d really encourage you to start telling the story even as you’re writing the book. Be out there talking to people about it because that’s what gets people aware of what’s exciting about what you have to say. Then they’re with you during the journey and they want to be part of it. The more people you can get involved in that community, the more successful it’s going to be. That’s my ultimate hack with all of this stuff.
The other thing is you don’t really make money from the book sales itself. Most people are going to pay between US$10-$15 for a book and sometimes you give it away for free. You make money from people asking you to present or run workshops around it.
The book is one tool in your marketing strategy of what you’re trying to create. For example, if you wanted to work with startups, then you write a book targeted at startup founders. When they see the content, then they call you to do the work you want to do. The book becomes your ultimate business card because it has credibility to it.
Many thanks to Barry for sharing his book-writing experience and tips! Read more of Barry’s thoughts on other topics at his blog or listen to his podcast which also features many other thought leaders.