Q. & A. with executive coach and author Joe Casey 

Client success story


Joe Casey hired me for one year as his book coach in order to complete the draft manuscript of “Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy,” published in 2022. Despite his busy practice as an executive coach, Joe drafted chapter after chapter, month by month, with my editorial feedback and direction. 

But all credit for the creative narrative that drives his book goes to Joe. The book tells the engaging story of a composite figure, Pete, as he works with coach Rick through the many obstacles (“the 9 forces”) to a satisfying retirement. 

It’s rare that you actually get the behind-the-scenes story of how a book was written and published. Joe bares it all
in this Q & A with me. 

Before becoming an executive coach, Joe spent 26 years at Merrill Lynch where he ended his career as head of HR for Global Markets and Investment Banking. So he understands the corporate mindset as well as the many challenges that senior leaders wrestle with. 

Joe’s dry humor and wit (in his writing and in person) made it a privilege and a pleasure to work with him! – Debbie



Joe Casey

Joe Casey



All Q.s are from Debbie; all A.’s from Joe.


Q. You’ve been an executive coach for 13 years. What prompted your idea of writing a book about retirement?

A. I was inspired to write the book because of the new lives I see my clients creating after they decide to leave the world of full-time work. Many people’s 401(k) are better prepared for retirement than they are – and they’re surprised by some of the obstacles that pop up once they retire. The good news is you can anticipate many of them and outsmart them if you’re prepared.


Q. Do you consider your career as an executive coach the first step in your own creative retirement?

A. Yes. I had an exceptional executive coach in my corporate career, and I knew it was what I wanted to do after my HR career. When I had the opportunity to take early retirement at 52, it allowed me to invest in going back to school to learn about the profession and how to redirect my skills and experience in a new way to help others.


Q. Once you had decided to write the book, what was your next step? (i.e., did you sit on the idea for a while? take notes? start writing? procrastinate??)

A. Over the years, many people had said to me “You should write a book!” I filed that away. But the catalyst for me was Designing Your Life by Bill Burnett and Dave Evans. When I went through their training to add to my coaching toolkit, in the middle of my first Odyssey Plans (which are three  alternative visions of your future) in Year 3 I drew a picture of a book and that made it real – and it became a goal.

The first step after that was to envision who it would be about and who specifically it would help. I reflected on the clients I’d coached and their stories. I noticed they had faced a number of common challenges. The challenges had a progression to them with increasing degrees of difficulty. It reminded me of a sports tournament, where you’d defeat an opponent and then go on to the next level and face an even tougher one. Then I started to take inventory of what research would be relevant and what more I needed to find out.


Q. You ultimately wrote your book as narrative nonfiction. There are a number of other successful business books written in that format including The Go-Giver: A Little Story About a Powerful Business Idea by Bob Burg and John David Mann. What inspired you to take that approach?

A. I started with the research. But once I took stock of what I saw in my client’s experiences, I felt it needed to be in a story form, like each of their journeys had unfolded. So, I created a fictional character named Pete, who takes on all nine of the challenges one by one. I created a fictional coach named Rick, who helps Pete along, as a device to bring in the research on each challenge. They’re different people and Pete finds Rick annoying at times. But like any good coach, Rick helps Pete think differently and step out of his comfort zone to get to where the growth lies. People sometimes forget that we don’t stop growing when we retire, and Rick keeps Pete on a growth path.



Q. Once you started writing, how long (or how many words!) did it take before you felt you had traction with your draft?

A. I began to hit my stride when I was writing the fourth and fifth chapters. There was a better sense of the writing process. I had created a process that worked for me in writing a chapter and that streamlined it compared to the early chapters. The funny thing is the first part I wrote, the Introduction, ended up being the one I revised the most. I must have written eight or nine different versions of it. I wasn’t able to nail it until the rest of the book was drafted.


Q. What was your biggest challenge once you started writing the book?

A. The biggest challenge was time management, scheduling time to write consistently. I ended up scheduling two separate weeks where went away (in the middle of the pandemic) and dedicated a week to nothing but writing. My book coach was very helpful in structuring a detailed and realistic schedule with goals and deliverables for each day. I discovered that immersing myself in writing worked best for me. I’ll do more of that next time.

Another challenge was keeping the book true to my clients’ experiences. Creating a new life isn’t a linear thing. There are twists and turns and highs and lows – and times of frustration and uncertainty. It doesn’t unfold neatly. That created a conflict at times with telling a compelling story, but I chose to err on the side of how I see it play out in real life, even if it was at the expense of the storytelling.


 Q. What was the most fun, perhaps unexpectedly?

 A. It was creating the characters and then seeing where the story would go next and how things would unfold.


 Q. You chose to work with a book coach (aka moi); was that for accountability as much as editorial feedback?

A. It was very helpful on many fronts. Having interim deadlines was a huge help and it was great to get feedback along the way, especially “reality checks” on some of my ideas and where they needed to be rethought, refined or scrapped entirely. It was valuable to work with someone who really understood the process and could provide guidance and oversight and point out where some course corrections and adjustments would be helpful. It provided a good balance between the structure and discipline needed to write a book with the flexibility it took to evolve it properly.


Q. When you started writing, how long did you think it would take to complete your first complete draft of the book? How long did it take??

 A. I didn’t have an idea of what a realistic timeframe would be. It took about 18 months, but I was not in a hurry to complete it.

If I had it to over again, knowing what I know now, I think it would take a year.


Q. After we finished working together on your draft manuscript, the process of final edits, proofreading, choosing a title and cover, and production of the book took about a year, didn’t it? 

A. I started working with the hybrid publisher Scribe Media in late December 2021 and the book was published in early August 2022, so about 7 1/2 months. It was a great collaborative process working with specialists for each phase, with an overall coordinator who was the point person for the project.

I learned how valuable it is to have talented, experienced people to partner with. I learned about the different types of editing and the value of each.

The book cover designer I worked with had been an album cover designer earlier in her career and had created album covers for David Bowie and other rock stars, which got our teenage son interested.

Note: there was some lag time between finishing his manuscript and starting to work with a publisher. – Debbie


Q. What is your best advice for someone with a book idea in their head? What should they be aware of as the biggest challenges to going from “idea in your head” to a draft on paper?

A. Work with someone, such as an experienced book coach like Debbie Weil, who’s written books and really knows the creative process. Work with that person to craft, critique and refine an outline. Test the process. Then see where you want to go next.

Be open to critical feedback – early and often. An excellent coach, like I had, will both support and challenge you. Work with a partner who can provide the structure and guidance that will bring out your best and help make your book a reality.