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Beyond Writer’s Block: 3 Challenges Writers Face in Their Careers

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It’s been more than a decade since I could call myself a professional writer. #timeflies To be sure, writing has done more than help me pay my bills. On the whole, it’s been enormously rewarding and saved me thousands of dollars on psychiatrists. (Writing is far cheaper than therapy but largely serves the same purposes.) With ten books and oodles of articles and blog posts under my belt, I’ve spent more time writing than I can count.

Still, it would be folly to claim that it has all been puppy dogs and ice cream. In this post, I’ll explain a few of the biggest challenges that I’ve faced as a scribe over the years. (Note that I’ve anonymized the individuals and companies involved.)

Pleasing Multiple Masters

In 2011, a large telecommunications company commissioned me to write a white paper about emerging technologies. In the abstract, the project seemed straightforward enough: Pen 3,000 words on some of the most important trends. 

I did what I always do. I held a call to paint broad strokes. I then sketched out an outline of the paper based on that discussion and provided a working draft of white paper consisting of 1,500 words.

Boy, was I naive.

Before long, eight executives were chiming in with their thoughts—and their comments clearly exceeded the scope of the project. (If you think that this process resembles sending around a PowerPoint deck to a bunch of partners at a consulting firm, trust your instincts.) 

I remember one particularly galling example: This is all fine, but what are the security ramifications of all of this?

Answering that question alone would require writing several books (plural).

Ultimately, I had to tread lightly. I gently reminded the bigwigs of the scope of the project and offered to do additional work—for a fee, of course. My final draft of the white paper consisted of an additional 600 words, give or take. 

In the end, I learned firsthand about the perils of scope creep on writing projects. Also, it’s virtually impossible to please so many different masters. As my next yarn illustrates, satisfying one can be challenging enough. 

The Constantly Moving Target

A while back, I took on a ghost-writing project to write a 220-page non-fiction book for a successful C-level executive determined to enter the ranks of the author club. (I’ll call him William here but it’s a pseudonym.) During our initial conversations, William was only sure of one thing: the title of the book. He had only a rough idea about what the book would actually entail.

No problem—or so I thought. That’s why I was there. To quote from Die Hard, they didn’t bring me along for my charming personality.  

Over the course of the first two-and-a-half months, our progress was decidedly uneven. We routinely would take a step forward and then two steps back. We’d settle on the book’s 300-word synopsis and then move on to the book’s outline. The next week, though, William would express doubts about the book’s general direction and want to revisit it. For example, something newsworthy would happen and he’d ask to include a new chapter about it. And could we—and by that, he meant I—give him some more subtitle ideas and another new synopsis. 

More than two months in, I still didn’t know if I was writing a business book, a memoir, a psychology book, a self-help book, or some combination of each. I would ask William that question and he couldn’t respond. I told him that I knew what I was doing: If a book is about everything, then it’s about nothing. All authors need to pick a lane, and William was no exception to that rule. 

He also once sent our agreed-upon book synopsis to several friends for feedback. Predictably, they all had different ideas about the book’s direction. Big red flag. I was writing a book for him, not his well-intentioned friends. I advised William of the drawbacks of doing this and he agreed not to do it again. 

I expressed my concerns to a few professional writer friends of mine, one of whom told me immediately cut bait.

I decided to stick it out. I could get this guy to come around.

During the third month, things became increasingly tense. Throughout our time together, I kept reminding William that I was an architect building the equivalent of a house. It couldn’t be a colonial one day, a duplex the next, and a ranch after that. (No, you can’t keep noodling with the number of bedrooms.) Changing so many foundational elements would sink the project. No one would be happy. That was our come-to-Jesus conversation. William claimed that he understood and vowed to keep his commitments from now on.

Based upon that discussion, I quickly churned out a solid 5,000-word chapter based upon the eighth—and ostensibly final—version of our outline. It went over well and I believed that we had finally turned the corner. 

Boy was I wrong. 

Not long after, he sent me some weekend messages in Slack. William’s additions would represent yet another new direction. Before signing off, his last question was, “What’s this book about?”

As I was about to type a response in Slack, my fingers froze. His question at this point in the project was a bridge too far.

It became clear to me that William liked the idea of writing a book, but would never reach the finish line—at least with me involved. For two reasons, the situation had become downright untenable. It was hard enough to deal with William’s chronic uncertainty. He repeatedly showed his unwillingness to respect our process—and that I couldn’t abide.

I informed William that I was leaving the project the following Monday and wished him the best of luck. Yeah, I walked away from a considerable amount of money, but I bought my sanity. 

Much like my experience in the consulting world, sometimes a client needs to hear the same thing from a second or third expert before it really sinks in. Basketball teams change coaches all the time for similar reasons. 

The Unreliable Partners

Like many authors, I have worked with different publishers. I even started a little micropublisher before selling it in 2017.

In total, Motion Publishing published six books, including my fourth: The Age of the Platform: How Amazon, Apple, Facebook, and Google Have Redefined Business. As I did for all Motion books, I hired a well-regarded editor who brought along her “best” interior designer. That is, I wasn’t self-publishing and doing everything myself. I was paying professionals—or so I thought

I received the proof of that book from the printer and couldn’t believe my eyes. The book was rife with errors. Most appalling to me, the designer actually introduced some of them himself. These alleged experts even got the size of the book wrong. (I had requested 5.5” x 8.5”, not 5” x 8”. As a result, the book just plain looked weird.) 

Frustrated doesn’t begin to describe how I felt. Remarkably, the designer didn’t use proper InDesign styles for formatting the book—a rookie move, to be sure. 

My book was a mess, and I was about to kick off a marketing campaign with my PR firm. What to do?

I put aside my frustration and searched for solutions. I got my files back and settled up with my partners. Thankfully, I found two angels who helped salvage my book. Marlowe Shaeffer came to the rescue on the editing end and Juanita Dix did the same on the design end.

The new book proofs arrived a few weeks later and it looked great. In fact, The Age of the Platform wound up winning an award, selling a bunch of copies, getting translated thrice, and taking my career to the next level. 

Simon Says 

Geddy Lee of Rush fame released a solo album in 2000 titled My Favourite Headache. He both loves and hates creating music. That phrase has always stuck with me. It perfectly encapsulates my feelings on writing—and golf for that matter. In each case, it can be both remarkably challenging and rewarding at the same time.


Phil Simon is a frequent keynote speaker, dynamic trainer, recognized technology authority, and ghostwriter. He is the award-winning author of ten books, most recently Slack For Dummies and Zoom For Dummies. His contributions have appeared in The Harvard Business Review, The New York Times, and many other sites.

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