The 100th Post

Ten lessons from 100 Substack posts

Round numbers lend clarity to accomplishment. As this is my 100th Substack post, I thought I’d do something I’ve never done—write about the Substack.

On this arbitrary anniversary, here are ten lessons that I’ve learned from two years of posting on Friday at 9:00 AM:

Consistency is everything

Creatives often say they’ll do something regularly and then stop soon after. I can’t tell you how many monthly shows die after the first three performances. How many podcasts stop after the first dozen episodes.

I took a break from posting during our first tour. And after that, I vowed to never miss a week. For the past 75 consecutive weeks, I’ve published on time — through tours, Edinburgh, an Ironman, and family obligations

We make ourselves go to the grocery story when we’re out of food. And I make myself write for Friday. It’s that simple. Stop making excuses and do the work.

Don’t let facts stop you from writing

When I wrote the above paragraph, I didn’t know the exact number of weeks. Instead, I wrote “the past xxxx consecutive weeks,” and kept moving.

Stopping just to find a piece of information is a form of procrastination. Get the thoughts down first, and later you can go through and plug in the facts.

Organic advertising only

Every subscriber here is voluntary. I don’t buy ads or sign people up without their consent. But every Friday, I screenshot parts of the post for my Instagram story, and link to the article. It always gets me 10-20 extra views.

I have no interest in begging people to read. My audience is small, but dedicated and growing.

The best posts have tangible takeaways

My highest performing posts include:

• How much does the Edinburgh Fringe Cost?

• Stuck performing at house parties? Try this

• How I sold out my show with almost no effort.

Readers want novel, tangible advice. While my post about if Taylor Swift would make a good magician was interesting to me, and I believe has valuable insights, the above posts are a reminder of why I write this—for the reader.

The more I’ve made the posts for other people, and less of a journal, the more my readership has increased.

The other best posts are vulnerable

“Bombs Away—the worst performance of my career” is another post that got a lot of views. Reading about failure and overcoming it is far more interesting than a laundry list of successes.

Vulnerability is a sign of confidence and honesty.

Just do it

The easiest posts to write are the ones that draw straight from real life. Writing is retrospective.

I perform 3-4 times per week, run slightly more than that, travel and read.

By challenging myself, I’m collecting obstacles and setbacks, kindling for articles. Which means you must…

Build an idea bank

I currently have 64 unpublished drafts. Most of them are garbage and will never see the light of day. The point is the habit of collection. When Friday looms, I’m never starting from zero.

Necessity is the mother of invention

When I committed to daily posts in December, my brain adapted to the deadline.

Reality is plastic. As Ryan Holiday says, runners don’t get “runner’s block.” They run. Writers don’t need to get writer’s block, either. Just write. Speaking of…

Never write with AI

Using AI to write personal stories is pathetic. AI is not a shortcut to writing—it bypasses the creative process altogether.

Your writing improves as you actively think about it. Using AI to write your personal blog is like cooking frozen food at a restaurant—the point was for it to be hand made.

As AI grows, our need for human connection and unique, original thought will skyrocket.

If you’re using AI to write your blog, you’re better off throwing your laptop in a river. That would at least be interesting.

It improved with a human editor

My friend Nell, a professional journalist, began editing these posts in December. The quality improved because she helped me get to the point.

There is very little creative work that doesn’t benefit from a trusted, qualified second opinion. Never be afraid to ask for help.

Here’s to 100 more

I have four upcoming fringe festivals (San Diego, Denver, Hollywood, and Edinburgh) and a full creative tank. I expect to be writing post 200 two years from today.

If you’re reading this and you want more, subscribe for free. You’ll get the post every Friday at 9 AM EST, on the dot.

No matter if this is your first or 100th post, I appreciate each reader dearly. Without you, I would just be typing alone in a room. Because of you, we’re connecting for a brief moment.

Forever onward.