Shameless Self-Promotion

I have something to admit:

I have plugged my newsletter in every first date I’ve been on since I started it.

That may sound strange, but if you think about it, why shouldn’t I do it? This newsletter is one of the most important parts of my life, and I’m extremely proud of it. It would be weirder not to bring it up. After all, this newsletter is me.

This is not “what I do”

This is WHO I AM.

Anything I do, say, or write is me. I don’t like putting my name or reputation beside anything I’m not 100% behind.

This way of thinking has created a loop that I like:

Make work good enough to promote shamelessly, and shamelessly promote your work so that you’re motivated to keep making things that live up to the promotion.

Ryan Holiday is my biggest creative influence, and he does something I love: he promotes his work nonstop.

He provides free information through short-form content like his newsletter and Instagram videos. The idea is that if you like those short bites of philosophy, then you’ll love his books.

My favorite way that Ryan promotes his books is when he’s doing his curated book lists, he often includes his own books in those lists. To put your books in the same stack as Marcus Aurelius’ Meditations takes confidence, but Ryan has more than earned that right.

So one day, I realized something: if I don’t feel weird that Ryan promotes his work so incessantly and confidently, why should I feel bad about promoting my own work?

Ryan has worked hard to make books worth promoting, and I do the same with my writing.

These posts are short and simple, but they are the result of 10-20 hours of reading per week, not to mention the time I spend doing other forms of research and the actual writing itself.

I’m sure that given the sudden change in my life’s mission (baseball to storytelling), my self-promotion may seem like it came out of nowhere. It may even seem cringe to some people (see endnotes for a good resource on “cringe”).

But that doesn’t matter! Whether it’s cringe or cool, hopeless or hopeful, none of that is helpful to my ultimate goal of making good art.

The only question you should ask yourself before shipping your work is this:

“Can this help someone?”

If the answer is yes, you not only have a right to share your work, but you have an obligation to.

When how many people you can help is directly correlated to how much you share your work, not telling as many people about it as you can is a disservice to the world.

For a great essay on why something feeling “cringe” isn’t a bad thing, check out my friend Jason Levin’s newsletter post about it here. Jason is a G when it comes to using social media to promote your work, and I’ve learned a lot from him.

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I'd love to hear what you thought of this week’s newsletter! Reply here with any thoughts.

Also, I’m always on the hunt for new stories, so if you ever come across an article, book, movie, documentary, folktale, youtube video, instagram post etc. that I would find interesting, send it my way! That’s an easy way to make my day.