Thoughts on starting a digital garden

Years ago, I loved Mike Caulfield’s explanation of how many internet platforms today are streams, not gardens. This concept re-emerged in this tweet today.

This is inspiring me to make my own digital garden.

As I said in my twitter reply, there are so many amazing resources in this list of digital gardeners. I’m going to be digging into this for a while.

Exploring the concepts of digital gardens and how to implement one

The following here is my 3,600-word exploration of how to add a digital garden to my existing WordPress blog of 2,500 posts. As with the nature of the digital garden, I’ll be updating this post as time goes on. This is a little rough, because I’m streaming through ideas, trying to figure things out. But I did try to categorize various thoughts. Eventually I might take this draft and write an essay, “How to increase quantity and quality on your blog”. For now, feel free to explore.

Also, I should note, I use the terms “digital garden” and “notepad” interchangeably. On my site, I’m calling the digital garden as a notepad.

This article is awesome, “My blog is a digital garden, not a blog“.

I’m convinced that paginated posted sorted chronologically fuckin’ sucks.

What makes a garden is interesting. It’s personal. Things are organized and orderly, but with a touch of chaos around the edges.

Just like plants in the garden I’ve got posts that are in various stages of growth and nurturing. Some might wither and die, and others (like this one you are reading) will flourish and provide a source of continued for the gardener and folks in community that visit 👋

Chronologically sorted pages of posts aren’t how people actually use the internet.

and this, “Stop Giving af and Start Writing More

It’s not a fucking blog.

Seriously. The idea of a “blog” needs to get over itself. Everybody is treating writing as a “content marketing strategy” and using it to “build a personal brand” which leads to the fundamental flawed idea that everything you post has to be polished to perfection and ready to be consumed.


This idea is toxic and led me to publish less and less over time.
Instead my approach now is to publish my thoughts more freely with less premeditation. Particularly in this space, which is mine, for me, by me.

I can so relate to this. I should just treat for what it is. A garden. It’s always been a random thoughts garden. I do need to learn the art of focus. I also need to get back to basic structures that I adhere to.

The basic structures I follow in my life

  • Creativity
  • Helping
  • Understanding
  • Patience
  • Observing

How do I really demonstrate and explain these structures? I think part of getting to structuredness is better organizing what I have. And yeah, that pagination thing just doesn’t make much sense. But it’s also writing specifically about these topics. Sure, when I write something fun, it’s loosely tied to my idea that everyone can live a creative life.

Lately I’ve been thinking about what it takes to write a book. Like, really get a topic, and write on that topic. Things that are helpful, insightful. Not just random stuff. But then my blog isn’t really a place where I FREELY capture interesting things. I moderate it down. I water down what I write.

I’ve been living between two worlds:
1) Not being focused
2) Not being totally free

My blog is in that limbo land between those two points. I don’t write super-long focused pieces. And I don’t let myself be completely free. I do moderate what I write. So I end up writing these middle-ish pieces. Nothing great. Nothing totally small.

Now that I discovered this “digital gardening” resource, with lots of links on how to build one, I feel like I should just install one of these tools and start posting and posting and posting more!

Build the garden for me first. And then if anyone wants to come into my garden, cool!

I mean, really, that’s what I’ve been doing all along. I just curb myself way too much. I need to be more free.

Plus, I get frustrated when people don’t read my stuff. But screw that. What if I just made it for me first? It’s my way of figuring things out. Getting themes together. Making it about the process. I’ve always been about the process.

Let’s add that to my list of structures/themes

  • Creativity
  • Helping
  • Understanding
  • Patience
  • Observing
  • Process

My filters for if I should write about something

When I find interesting things, sometimes I feel like, “why should I blog about this? People can already find out lots of stuff about this. Why should I blog about it? I would only cover one grain of sand in this beach of vector paintings.”

For instance, today I found these vector painting textures. It’s like, “this is a painting and a vector?” No way. It was fascinating to me. But I didn’t write about it, because I feel like it’s been done.

But if I’m writing to a garden site—MY garden site for ME, then it’s just me capturing what I find. And then as I find other vector painting stuff, I add it. It’s just my personal experience that I’m putting together.

Keep a digital garden. Post to it freely.

The doubts

Will people read it? My mind keeps thinking, “how will people read this? how will they follow this? Matt. People don’t read your blog now. Screw all that. Just do it for how you want to do it.

Will I organize the garden? I’ve been using Evernote to capture stuff for YEARS. How often do I go back and tag things to connect stuff together? Answer: NEVER.

Will this make money? The nagging question… will this make me money? Because I know I have other projects that could actually make me money.

Tools to build the digital garden

I was thinking of installing one of these garden tools like TiddlyWiki or Roam at a directory like, Heh. is available.

A list of tools to use to build the garden (along with my comments):

  • TiddlyWiki (doesn’t really seem up my alley.)
  • Roam (Roam is $15/month forget that.)
  • Hypothesis for annotating (I already use this, I love it. But it’s not a platform for my own site)
  • Gatsby Brain Theme (Really, I don’t want to start up a Jekyll or Gatsby site.)
  • Simply Jekyll theme
  • Quotebacks for quoting

Create my digital garden in WordPress?

By keeping the garden in my WordPress, I can better connect my existing blog posts. Really, most of my current blog posts are really garden items anyways.

There might be better tools other than WordPress to annotate and connect ideas together. But for now, I’ll stick to WordPress. Maybe as I read more about digital gardens, there might be organizational concepts that could be implemented into my WordPress install. I know how to bend WordPress around pretty well on the backend.

Formats, structure, focus

I should seriously start thinking about what it’s like to publish a book. Or getting focused on things. That would really make me go back and pull stuff out my archives. Getting me to reformat things.

Or the notion of making these posts into RESOURCES. Like a downloadable PDF. Or a class.

Thoughts on how to organize my site with a garden would be a collection of this:

  1. The free-for-all posting garden
  2. The blog for medium sized stuff to share with people via email.
  3. Highly polished, in-depth articles/pages

Wouldn’t it be funny if 1 and 3 started to dominate my site? 2 would become a place for me announce stuff. Announce when I have a new in-depth article. Or when I make a major update.

Maggie Appleton has an interesting way of organizing her digital garden. Every post is in one of three categories of development:

  1. Seedling
  2. Budding
  3. Evergreen

Heh. That takes my 3-pronged approach and puts it all into the garden terms.

Sidenote: I’m subscribing to her newsletter. Curious to see what she puts in there. Will it be just links to the posts on her site?—like what I do with the newsletters? Will it be her writing specifically to an audience like a Substack?

Side-side note: Is there a Gutenberg block in WordPress where I can make these sidenotes appear literally off to the side, like marginalia? [to do]

Do I transition over most of my blog to a garden?

I have over 2,500 blog posts. What if the entire blog was a garden? And then the only items that go to rss/email are tagged?

Oh wait. here’s the distinction.

  1. Garden (Unfinished drafts, in progress. Or small minor posts that I don’t want to share to email/rss)
  2. Blog posts (Finished, published. I want to go to my email list and RSS subscribers)
  3. In-depth articles (Very polished and finished, but always in progress. A compilation of both garden posts and blog posts. Continually update these articles. Major releases are announced via blog posts)

The blog posts sit in a weird in-between land. What purpose do the blog posts serve? Just the email/RSS? If nobody really reads the email/RSS is there a point of me continuing it? There might be some cases where a blog post is like an in-depth article.

Since blog posts sit in this in-between land, wouldn’t everything be just in the garden? I guess if there are some cool garden posts that I really like, I can make it a blog post. Then, in theory, people see it via email or RSS.

URL problem

All my wordpress posts get put under the URL of Thus, my essays and my garden posts would have “blog” in the URL. Maybe that’s weird to have the categories be: garden, blog, essays.

Maybe I could just rename the “blog” category. Everything on this site is a blog post. Hmmmm. Spitting out some ideas:

  • Notepad, Published, Essays. “Published” sounds too weird, like it’s been published in an external magazine.
  • Notepad, Shared, Essays. I’m sharing the blog posts to email and RSS. But “Shared” is weird. It sounds like social media.
  • Notepad, Newsletter, Essays. Essentially all my blog posts are newsletters. But not really. They are blog posts.

I’m going to have to think this through more. [needs work]

Categories and tags for the garden and blog

I already have a garden with the posts categorized as “notepad“. I started that about a month ago. Any post that is categorized “notepad”, it does not appear on the homepage, RSS feed, or email newsletters. I’m left free to post whatever I want.

Right now, the blog posts on use both categories and tags. Here’s an example:

Categories on the blogTags on (some of the tags)
Art (779)
Chicago (890)
Comics (35)
Design (367)
Etc (112)
Healthy living (188)
Illustration (64)
Life (214)
Money (79)
Notepad (9)
Outer space (125)
Podcast (10)
Pop culture (208)
Sports (303)
Tech (429)
Words (361)
Art Institute of Chicago (54)
ASCII art (9)
Baseball (170)
Chocolate (19)
Croquet (64)
Dodgeball (10)
Football (8)
New words (44)
Numbers (42)
Origami (7)
Postage stamps and mail (24)
Questions (335)
Receipts (9)
Sidewalks (23)
Star Wars (50)
Transformers (27)
Walgreens (30)
Work (56)

My categories and tags are messed up. What’s really the difference? Plus, my Garden posts are in the notepad category, so any Garden posts won’t have an additional category. That’s kinda weird.

Maybe I should just delete all the categories, and just have:

  1. Essays
  2. Blog
  3. Notepad

Does Google like my existing category pages? I don’t think so, really.

I could just make all my existing categories be tags. For instance, the art category would become the art tag.

This is interesting

A quick way to get into specific areas of a garden. This is just a list of tags.

Can the creative categories of synectics be an organization system for my blog/garden?

Although, the synectics categories might prove useful—maybe. I could potentially unify a bunch of my posts under some of these categories. Like, the category of subtraction and cropping. Searching through my blog posts for the word “crop”. I have five posts that involve cropping:

Ok, so all those posts have something to do with cropping. But they don’t help the reader learn anything about cropping. It’s not specific to say, “here, this is what could happen when you crop something)

The synectics categories might be too abstract. Like when uses the categories of “how we create, how we share, how we discover” Like, who gives a crap about those categories? Ummm, who is actually looking up “how we share”? NOBODY does that.

Photos section

If I posted all 4,000 of my Flickr photos on, how does that play into this new structure?

Would people use the photos section?

To Joel Hooks’ point on pagination—nobody is clicking through pages on your site. And to extend that further, nobody is coming to my site to search for something like photos. (People only use the on-site search if they came to your site, and didn’t find what they wanted). My site is not a place where people come and look for photos. My site is not like Google or AP.

Although it would be interesting is someone googled for an image, came to my site, and then the related photos showed more stuff they may want. Plus, I like the idea of owning the place where all my online photos reside. Right now my photos are splintered between Flickr, Instagram, Yelp, and Swarm.

Creative commons?

Another thought is that I make all my photos Creative Commons usage. I offer up low-res photos–all watermarked with my url. If someone wants to professionally use my photos in their book/site, I can offer a high-res version without the watermark. In some cases for money, in other cases for free.

The point is just to make more connections with people. I miss the days of when my photos would be used more. Now they just sit in the closet.

How would a photo section fit into my site?

Anyhow, so how would I incorporate the photos section into my site? I’d imagine it would be a custom content type.

It would be interesting if i could make photo galleries on, so i can easily feature curated photos in groups. If I tagged photos, then they would essentially be in a group. But that’s not really curated per se. It would be nice to make specific galleries, in addition to the tags.

Process of my garden

To make the garden effective for me, I need a better interface. I need a quicker way to skim over all my posts and to review items. Like, I actually need to update stuff!

  1. Post, post, post lots of garden posts.
  2. Review.
    I need to go back and regularly review garden posts. See which ones need to be extended. I rarely go back to my drafts. I need a way to really dig up previous drafts and find ways of expanding them. Sometimes a draft just simply needs a photo for it to become a published blog post. Now my drafts are going to be garden posts. I need a way of skimming through these garden posts.
  3. Grow garden posts into blog posts.
    Some garden posts automatically grow into a blog post. By the very nature of writing lots of garden posts, often they will already be a blog post when I’m done with a session of writing. I’ve seen this happen a bunch already with the notepad category. I was writing for something to go into the notepad. When I was done writing, I thought, “wow, this is actually pretty good to share. I’ll make it a blog post”.
  4. Grow garden posts into essays.
    I also need to sit down and look as a whole which COLLECTION of blog and garden posts can become a master article. Find the commonalities between garden posts and blog posts. Then combine them together into one big resourceful article

Part of the trick is having these posts in front of me. I already have 1,800 unpublished blog drafts in Evernote. That program is really great for giving a condensed view. Yet, I the drafts sit unpublished.

That 4th one is the trick. Aggregating a bunch of stuff all together. In some cases I might leave the original post alone. Like the post about Shutterfly’s unlimited free prints offer. Google gives me lots of traffic to that one post. I don’t want to mess anything up with that one post. but I should write more Shutterfly stuff. Garden & blog posts. Eventually making some master article(s) on Shutterfly.

Will I REALLY go back to old archives of blog posts and make them into master articles? Really? Have I ever really wrote stuff that can be mashed together into something useful?

Most of my stuff is spur of the moment stuff. And just fun stuff. Not a resource of things.

What is an essay?

Do I really have “essays”? I think I have only one essay. It’s a collection of photos and blog posts about my Star Wraps art. But this essay doesn’t really serve any utility value. It’s just a collection.

Let’s lay out the qualities of essays.

  • Long
  • Continually updated over time
  • Collection of blog posts and images scattered across my blog and online
  • Utility value to reader (Maybe?)

Is the main identifier of an essay that it’s always updated? Is the static/flexible aspect the main quality of my three categories?

  • Notepad–Static quick captures (although sometimes updated to become a blog post)
    Not worthy of sharing. Not worthy either because it’s incomplete, or because it’s off-topic/random. If it’s not updated into a blog post, then the notepad is just a slice in time. A pebble that remains a pebble.
  • Blog post–Static longer posts.
    Worthy of sharing with my readers.
  • Essay–Continually updated.
    Keep loading on and onto each essay. Or sharpening the essay so it’s more clear.

There might be situations where I update a blog post. But for the most part, those are static. I’d like to focus my time on making the more comprehensive essays. Hmmm… actually, how about that…. THAT should be my focus. Making these essays. Everything else should hang from the essays.

I might have had this flipped the whole time. I was putting the blog first. And today I’ve been putting the notepad first–write, write, write, more! But really, what would happen if I spent my time on the essays? Thinking through specific topics…. Hmm, that might give me the direction I need.

The question I need to be asking myself is: “What do I want to be writing about?” Instead of “Oh, I found something neat, I’ll write something about this.”

This garden post is helping me to really think through two key points.

  1. I have a blog. How do I add on a digital garden to my blog?
  2. I have a blog. How do I start writing comprehensive essays on my blog?

With these two questions, I’m allowing myself to have the quantity of capturing lots of things. But also the focus and intent of writing longer informative essays.

Now, these essays should probably fall under some sort of strategy. A sort of guidance. Right? Or can these essays just be like the Star Wraps essay? It’s just a collection of all my images and stories about making this artwork? What does that really do for the viewer? Am I am encouraging them to make Star Wraps? Or am I merely sharing a comprehensive view of this artwork?

My view of essays needs more thought.

This notepad post is getting so long, it’s almost like an essay. I spent a lot of time organizing my thoughts in this post, but it’s still too loose. It needs more structure. Maybe at some point this post can become an essay about “how to take your blog, and add a digital garden, and essays.” Ok, that’s too long and awkward.

Maybe this analogy:

  • A garden post is a seed.
  • A blog post is a tree.
  • An essay is a forest.

Lots of seeds are cast onto the ground. Many won’t grow. Some will grow. The blog post is a grown tree. Some are small trees. Some are large trees. Some give barely any shade. Others are lots of fun to hang out in. A forest is a bunch of trees together that you can explore through. You spend time in the forest.

Then what’s the website? A nature preserve? The website is really the forest. You got from one essay to the next.

Ok, let’s try this.

  • Garden post = seed
  • Blog post = small tree
  • Essay = large tree with lots of shade and fruit
  • Website = forest to explore

The snappy title for this: Get more seeds for your blog and grow it into a large tree. LOL. Ok, that sounds weird. Or this. How to increase quantity and quality on your blog. Whoa. Check that out. Pretty snappy. That’s exactly what i’m doing. I’m increasing quantity (notepad posts) and increasing quality (essays).

What can be helpful for…

My gap… My issue is really making resourceful content.

  • Fun art projects (mine)
  • Fun art projects (others) — although I don’t think i’ve written much about that really
  • [I need to add to this list]

I’m just so spur of the moment on things.

You know what’s funny? I’ve always wanted to be a teacher. Yet, does my blog actually teach anything? Or have any resources to educate?

But then sometimes I love that sort of stuff. Like Om’s posts. Or Dave Winer’s posts. A lot of their posts wouldn’t be aggregated into one master resource. They are thought nuggets.

To do items for me in digital gardening research

  • Look up all the digital gardeners.
  • Make a list of their sites.
  • Look them up on Twitter (although, not sure if that’s really of any use to me)
  • Look them up on podcast episodes (via
  • Google: “digital garden” WordPress. I did a little bit of this.

It would be really nice if somehow there was a to-do list built into WordPress. I’d like each of these items inside this blog post to be elements that would flow into a master to-do list.

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Bob Irving
11 months ago

What did you decide about using WordPress for your digital garden? I’m looking for platforms for my personal yet-to-be-launched digital garden and have my biz site on WordPress.

Would love your thoughts, please comment.x