Phil Simon's Blog, page 5

Moving Day

"Art is never finished, only abandoned."
—Leonardo Da Vinci

My website has always been a work-in-progress. Click here if you don't believe me.

You might notice a few changes on it today. For openers, it probably loads much faster and the menu bar now sticks to the left—not the top. Yeah, my trademark orange is still prominent, but the major changes aren't just cosmetic: today marks a new chapter for my website and, more importantly, for my business and me.

The Skinny

In June, I announced that my publishing website was adopting a subscription model. Today, I'm letting you know that I'm doing the same thing with this one.

I'll still occasionally publish free posts, but the vast majority of my new musings will live behind a paywall. That term is a bit of a misnomer. Reading almost all of my content will require no payment. Rather, you'll have to subscribe to at least the Free plan.

For more on the benefits of subscribing to my site, click here.

Why Now?

Where to begin?

Let's start with the simplest reason: the technical one.

Maintenance Fatigue

I've long known that I'm a geek. At Carnegie Mellon, even the poets know how to code. At the same time, I realize that I've spent way too much time over the past 15 years performing maintenance on my site—and hiring others to help on occasion. I'll conservatively estimate that I've put in an average of 1.5 hours per week diagnosing a bevy of issues over the last 15 years. That's 1,200 hours in total.

To be sure, my old WordPress theme Divi served a valuable purpose. Still, its future direction makes me suspect that my days of debugging wouldn't be ending. I'd much rather spend my professional time writing and ghostwriting books, speaking, creating Notion templates, and consulting.

Tech alone didn't drive this decision.

I'd be lying, though, if I claimed that tech alone drove this important (monumental?) decision.

Far from it.

Photo by Roger Ce / UnsplashProtecting My Content From Greedy Tech Companies

As an added benefit, the decision will make it harder for soulless tech corporations to illegally hoover up my intellectual property without compensating me. (Count The Guardian and Reddit among the companies that have recently filed lawsuits against these scoundrels, but I digress.) It's become such a problem that Cloudflare and other companies are launching tools that prevent AI crawlers from doing their thing.

The Core Reason

Since leaving ASU in 2020, I had been relying on white whales for clients. Maybe it was time to make a change?

A few months ago, my Carnegie Mellon friend and fellow Die Hard fanatic Moneet Singh and I were discussing evolving business models and the need to build subscription businesses.

Like all good friends, he didn't hold back when he assessed my site. In between Hans Gruber quotes, he mentioned how I had already created plenty of solid lead magnets. I just wasn't using them properly.

Moneet was being kind. I wasn't using them at all.

That conversation stuck with me over the next few weeks. I harbored no illusions about climbing to the top of the Substack Business Leaderboard and pocketing six figures per month. Still, was the idea of taking advantage of my existing blog posts, courses, Notion templates, and other assets to create a decent monthly revenue stream really farfetched?

Returning to the Tech

I didn't think so, but my website's legacy underpinnings would mean adding even more software in the form of subscription plugins and proper newsletter capabilities.

I came to a realization: If I wanted to create viable subscription business, I didn't need to tear down my website. Make no mistake, though: A more contemporary and faster content management system would certainly make it easier for me to achieve my goals.

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Award-winning, 14-time author Phil Simon chimes in with his musings on AI, the future of work, collaboration, workplace tech, and more.

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The New Foundation

With the help of rockstar developer Cathy Sarisky, I have successfully migrated my WordPress site to Ghost. (I'm hardly alone in doing so.)

You'll notice a significantly faster website. The difference between Ghost and WordPress is almost comical:

Google Site Speed Test on July 24, 2025 | Click on the image to enlarge it.

All of my old posts should render, just at different URLs that should automatically forward. I'd be mystified, however, if we caught all bugs. Let me know if you find:

Any 404 errors or dead links.Any missing images.Something else janky.

I'll get them fixed as quickly as I can.

I FOUND A SITE ISSUEWhat Has Changed

I've fused all of my prior followers into Ghost. If you subscribed to my WordPress blog, Patreon page, or Substack, I've moved you to this site's Free plan.1 I've used the email address that you gave me when you signed originally up days, weeks, months, or years ago.

My new Ghost site is a clean, lightning-fast, SEO-optimized, and responsive one that looks good on any device—all without third-party software and caching plugins. I'm kicking myself for not moving to Ghost sooner.

Check out the subscriptions part of my FAQ page here. If you don't find what you're looking for, comment here (after you log in) or contact me.

Phil Simon: AI’s Continued Lack of Transparency and ConsistencyAdventures in truly amazing, opaque software that makes basic errors.Phil SimonThe Future of My Site

Look for more frequent and longer posts from me over the coming months and years on AI, the future of work, Notion, citizen development, workplace tech, hybrid work, and the usual bouillabaisse of other work- and tech-related topics. (Future posts on writing and publishing will live on Racket Publishing. In case you're wondering, I've adopted a similar subscription model there as well for nearly identical reasons.)

Why the renewed enthusiasm for writing?

A few reasons.

First, I want people to subscribe and for some of them to pay. In order to achieve these goals, I have to bring the goods. The occasional short post just won't cut it. By all accounts, posting content irregularly leads to increased churn.

Second, on a personal level, I absolutely love Ghost's über-clean UI. It's very Notion-y. Here's a screenshot:

Notion UI of this post. Pretty slick.

Now that I'm not waiting 60 seconds for WordPress and Divi to create a new post, I'm stoked about putting more of my thoughts and creations out there.

Get your popcorn ready, and thank you for reading this post.

Phil Simon

Footnotes Medium doesn't let you export followers. ↩ ❓Finding any problems with my new website? There's no way that we caught all of the bugs. Let me know if you find any issues or would like to provide any feedback.

New Notion Template: Venture Capital & Investment Tracker

Many folks who make major investments in startups—and manage others’ investments. You’d think that they’d all track their considerable financial commitments in a systematic fashion. 

Some do, but many continue to rely upon spreadsheets and emails. It’s a matter of when—not if—things break bad. 

I can’t stop them from working inefficiently and eschewing modern solutions. I can, however, offer an alternative: a user-friendly, customizable, and affordable template to let them manage their investments, run reports, track signed documents, and much more.

So I built one. If I worked in as an investor, I’d be all over this.

VIEW THE TEMPLATE SEE ALL OF MY NOTION TEMPLATES

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AI's Continued Lack of Transparency and Consistency

This weekend I decided to overhaul the Racket Publishing website. Apart from swapping out the fonts and simplifying its appearance, I wanted to add bespoke, minimalist sketches.

I played around with a Notion-inspired GPT. It seemed promising, and I decided to upgrade for one month. I then started cranking out featured images for blog posts. I found its selection tool to be especially useful in refining preliminary sketches:

AI’s Continued Lack of Transparency and Consistency

This weekend I decided to overhaul the Racket Publishing website. Apart from swapping out the fonts and simplifying its appearance, I wanted to add bespoke, minimalist sketches.

I played around with a Notion-inspired GPT. It seemed promising, and decided to upgrade for one month. I then started cranking out featured images for blog posts. I found its selection tool to be especially useful in refining preliminary sketches:

Color Blindness

Interestingly, the GPT didn’t know the difference between grey and white.

Repeated requests pleas bore no fruit. ChatGPT was, in a word, unhelpful. Ultimately, I had to use an online image replacement tool.

Slow Down, Sparky

After a few hours and maybe 50 sketches, ChatGPT informed me that I was using its service too much. Although I paid the $20 monthly fee, I’m still subject to throttling. Evidently, I’m an excessive user. I reflexively asked ChatGPT about its limits. Here’s its response:

Why You Should Read Ghostwriters’ Previous Books Before Hiring Them

Hello, Uncertainty

AI users will have to tolerate some level of unpredictability.

First, once again, genAI is insanely useful. At the same time, it is remarkably opaque. More than one thing can be true. What I wrote in The Nine still holds true today.

Second, note ChatGPT’s use of should in the last paragraph of its response. If you’re anything like me, you value consistency in your software. Maybe ChatGPT gets there at some point. As is the case with all non-determiministic software, customers will have to tolerate some level of unpredictability. The fleas come with the dog.

The post AI’s Continued Lack of Transparency and Consistency appeared first on Phil Simon.

The Joy of Diversification and New Endeavors

Five years ago, I made the decision to leave my teaching position at ASU at the end of the semester. It was time. But how would I replace my income in the months and years ahead? Leaping before looking isn’t exactly wise. In this post, I’ll describe my strategy for the next phase of my career.

Conferences and other speaking gigs at the start of COVID were tenuous at best, although I had landed some webinars in mid-2020. My book sales were decent, but not James Clear-level. To keep the lights on, I eventually needed to add at least one more plank to my platform.

At least one.

Moneyball Lessons

I took a page from the Oakland A’s. Star slugger Jason Giambi had departed for the Yankees for $120 million in 2001. Data-savvy general manager Billy Beane knew that his decidedly frugal employer lacked the budget to sign another high-priced stud. Instead, he acquired several cheaper players who would, in theory, replicate Giambi’s individual production in the aggregate. Watch this related clip from the movie Moneyball.

The ingenious strategy worked. The A’s lost arguably their best player and won more games.

Parallels and Benefits

It turns out that Beane was on to something. I’m glad that I aped his approach.

Yeah, I still write books and speak, but most of my income today stems from new sources. I’m wrapping up another successful ghostwriting project via my publishing outfit Racket and have wowed my clients. I now develop bespoke Notion tools and and sell templates, including my pièce de résistance RacketHub. I’ve also created several courses. In the aggregate, these new lines of business have more than replaced my ASU income.

Yeah, I face more risk, but in return get far more flexibility and autonomy. (The Oakland parallels only go so far. For instance, ASU didn’t pay people like me Giambi-level salaries. I’m not its football coach.) Just as important, these new endeavors increased my professional joy. Forging my own path gels with my personality. My stress level at work is infinitesimal compared to five years ago. Today I’m a happier dude.

Why You Should Read Ghostwriters’ Previous Books Before Hiring Them

What You Need to Know

Leaving any position entails risk and tradeoffs. If you’re going at at it alone, here are five tips:

Ensure that you can pay the bills for a year.Consider several adjacent lines of business in lieu of one big bet.Be open to new ideas as they present themselves.Don’t expect immediate results. Rare is the product or service launch that immediately blows up.Be humble but enjoy your success. You’ve earned it.

The post The Joy of Diversification and New Endeavors appeared first on Phil Simon.

Why You Should Read Ghostwriters' Previous Books Before Hiring Them

Selecting a ghostwriter is a big decision. No, it's not irrevocable, but the wrong choice can set you back oodles of cash and time. If your book is timely (and it should be), then you won't be able to recoup the opportunity costs. For these reasons, if you're thinking of using any ghost—including and especially me—you should read one of the author's previous books.

Over the years, I've talked to ghostwriters who claim they can always find their clients' voices. Doesn't matter who. Let's just say that I have my doubts.

My Writing Style

In my books, I write in an active style. I despise jargon and the passive voice. I keep my sentences relatively short, and in the rare event of a long one, I will immediately truncate the next one. Long paragraphs annoy me as a reader, so why use them as a writer? Finally, I'm a big fan of case studies. Show, don't tell—to quote the great Rush song.

The client-ghostwriter relationship is very much an intimate one.

Ideally, all would-be authors would adopt the same principles. Some clients, however, insist upon a dramatically different tone. Sure, I can dial down the snark, but I can't and won't write like a pompous academic. Grammarly and other AI writing tools can easily transform text today, but the results are often synthetic. Why buy a condo when you really want a ranch?

Lessons From Previous Ghostwriting Gigs

My last two ghostwriting gigs have gone well for a variety of reasons. For starters, each client has agreed to use RacketHub and other contemporary tech. (Hello, Calendly.) They have respected the process and trusted that I knew what I was doing. More importantly, though, both of my clients knew in advance the style and content of each chapter—and, ultimately, the final product. No one has ever been surprised when I turned in a near-final draft of a 5,000-word chapter. As a result, project momentum continues. We keep moving forward.

I can't stress enough why these tenets matter so much.

The client-ghostwriter is very much an intimate relationship. Over the course of months or even years, the two parties will work together closely. From the get-go, respect each other's time and input. Disagree respectfully. Adapting to different cadences and exhibiting flexibility sure doesn't hurt. The early riser and the night owl may struggle to regularly find common meeting times. Make no mistake: this matters. All work can't be asynchronous.

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Award-winning, 14-time author Phil Simon chimes in with his musings on AI, the future of work, collaboration, workplace tech, and more.

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Simon Says

Before you even sign papers with your writing partner, though, start with something more foundational. See if you dig the ghostwriter's previous efforts. Good questions to ask include:

Does the ghost's tone generally jibe with your own?Do I write and speak in an appreciably different manner? (If so, then you'll appear off in interviews discussing the book?)If the differences are minor, then can the ghost modify his/her style? A recalcitrant writer who uses 50-cent words—like recalcitrant—may be signaling that he isn't a peach to work with. (I prefer the Oxford comma, but I won't die on that hill.)

If not, then maybe you're trying to put a square peg in a round hole.

What I Really Want From AIIn the name of all that is holy, can someone please invent a better computer diagnostic tool?Phil SimonPhil SimonFeedback

What say you?

❓Finding any problems with my new website? There's no way that we caught all of the bugs. Let me know if you find any issues or would like to provide any feedback.

Why You Should Read Ghostwriters’ Previous Books Before Hiring Them

Selecting a ghostwriter is a big decision. No, it’s not irrevocable, but the wrong choice can set you back oodles of cash and time. If your book is timely (and it should be), then you won’t be able to recoup the opportunity costs. For these reasons, if you’re thinking of using any ghost—including and especially me—you should read one of the author’s previous books.

Over the years, I’ve talked to ghostwriters who claim they can always find their clients’ voices. Doesn’t matter who. Let’s just say that I have my doubts.

My Writing Style

In my books, I write in an active style. I despise jargon and the passive voice. I keep my sentences relatively short, and in the rare event of a long one, I will immediately truncate the next one. Long paragraphs annoy me as a reader, so why use them as a writer? Finally, I’m a big fan of case studies. Show, don’t tell—to quote the great Rush song.

The client-ghostwriter is very much an intimate relationship.

Ideally, all would-be authors would adopt the same principles. Some clients, however, insist upon a dramatically different tone. Sure, I can dial down the snark, but I can’t and won’t write like a pompous academic. Grammarly and other AI writing tools can easily transform text today, but the results are often synthetic. Why buy a condo when you really want a ranch?

Custom Notion Development

Lessons From Previous Ghostwriting Gigs

My last two ghostwriting gigs have gone well for a variety of reasons. For starters, each client has agreed to use RacketHub and other contemporary tech. (Hello, Calendly.) They have respected the process and trusted that I knew what I was doing. More importantly, though, both of my clients knew in advance the style and content of each chapter—and, ultimately, the final product. No one has ever been surprised when I turned in a near-final draft of a 5,000-word chapter. As a result, project momentum continues. We keep moving forward.

I can’t stress enough why these tenets matter so much.

The client-ghostwriter is very much an intimate relationship. Over the course of months or even years, the two parties will work together closely. From the get-go, respect each other’s time and input. Disagree respectfully. Adapting to different cadences and exhibiting flexibility sure doesn’t hurt. The early riser and the night owl may struggle to regularly find common meeting times. Make no mistake: this matters. All work can’t be asynchronous.

Simon Says

Before you even sign papers with your writing partner, though, start with something more foundational. See if you dig the ghostwriter’s previous efforts. Good questions to ask include:

Does the ghost’s tone generally jibe with your own?Do I write and speak in an appreciably different manner? (If so, then you’ll appear off in interviews discussing the book?)If the differences are minor, then can the ghost modify his/her style? A recalcitrant writer who uses 50-cent words—like recalcitrant—may be signaling that he isn’t a peach to work with.1

If not, then maybe you’re trying to put a square peg in a round hole.

The post Why You Should Read Ghostwriters’ Previous Books Before Hiring Them appeared first on Phil Simon.

New Notion Template: Manuscript Word-Count Tracker

How do you write a 50,000-word manuscript?

The glib answer is one word at a time.

Here’s the longer one.

Yes, you should do your research first. Write willy-nilly and you’ll need an expensive developmental edit.

The Miscellaneous Mindset

Let the Writing Begin

There comes a point, though, when you’ll have to start the process. Over the years, I have found tracking daily word counts to be beneficial. Every day, you inch towards the massive goal of completing it. Simple charts can reinforce the notion that you’re getting closer. (The template includes two, but you’ve got to be a paid Notion plan to view more than one. Of course, you can create as many ones as you like.)

OK. I’ll take off my motivational hat.

RacketHub includes dozens of interrelated and sophisticated trackers. I’ve decided to make the word-count one available for free as a Notion template.

Here’s a quick video overview:

Click here for a demo on how to enable default daily entries by date. It’s a useful feature that takes maybe 15 seconds to enable.

 

Cross-posted on the Racket Publishing site.

DOWNLOAD FOR FREE SEE ALL OF MY NOTION TEMPLATES

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Notion Formulas Based on Attachments

Here’s a way to circumvent this current Notion limitation.

I use these powerful formulas extensively in RacketHub.

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The Better Collaboration Question

Which tool will we use to do X?

After all, modern organizations use dozens of overlapping applications and systems—and sometimes nearly 200. As but one example, Zoom, MS Teams, and Webex are viable videoconferencing options. Don’t get me started on the vast array of task-management tools.

Once a firm lands on a magnet app, however, the question shifts. It becomes: Where in [insert name of tool] should we put X?

That’s not to say that people don’t make honest mistakes while using Notion, Loom, Coda, and other magnet apps. They do. But moving a database, drawing, PDF, document, or other file from one location to another within the same, universally used app is simple. Choosing a new tool altogether (and fighting myriad internal battles over the move) is a very different kettle of fish.

A Better Way to Work

Training people to use a tool isn’t difficult. Getting everyone to agree upon it in the first place is.

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