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What I wish I had known when I was starting out as a developer

As I get older, I wish I could reach back and give myself advice. Some of it is life advice (take that leap, kiss that girl, take that trip) but a lot of it is career advice.

There’s so much about being a software developer that you learn along the way. This includes technical knowledge like how to tune a database query and how to use a text editor. It also includes non technical knowledge, what some people term “soft skills”. I tend to think they are actually pretty hard, to be honest. Things like:

  • How to help your manager help you
  • Why writing code isn’t always the best solution
  • Mistakes and how to handle them
  • How to view other parts of the business

These skills took me a long time to learn (and I am still learning them to this day) but have had a material impact on my happiness as a developer.

I am so passionate about this topic that I’ve written over 150 blog posts. Where are these? They’re over at another site I’ve been updating for a few years.

And then I went and wrote a book. I learned a bunch of lessons during that process, including the fact that it’s an intense effort. I wrote it with three audiences in mind:

  • The new developer, with less than five years of experience. This book will help them level up.
  • The person considering software development. This book will give them a glimpse of what being a software developer is like.
  • The mentor. This book will serve as a discussion guide for many interesting aspects of development with a mentee.

The book arrives in August. I hope you’ll check it out.

Full details, including ordering information, over at the Letters To A New Developer website.

Lifehack Mistakes Programming | moore |

How I use GenAI for my memes

I’ve been trying to do a themed funny meme a day for the past few weeks, every day when I work. I share them on my Twitter, Bluesky and LinkedIn accounts.

Here’s my process:

  • Find a meme I understand. I know a lot of memes, but also check Know Your Meme to make sure I understand the context.
  • Use ChatGPT to brainstorm meme ideas. This usually takes 1-2 tries, but the prompt looks something like this: “can you provide 15 funny meme ideas around saml, jwts, passwords, oidc, rbac, or other authentication or authorization related topics. The meme I am trying to use is the epic handshake meme, where the hands in the middle show agreement between two parties on something.”
  • Review the 15 suggestions, modifying as needed based on my knowledge and the memes I’ve posted recently. If I just posted about SAML, I don’t want to do so again.
  • Create a meme using imgflip.
  • Post to the areas above, making sure to use alt text descriptions.

This process takes about 5-10 minutes, with a big chunk of the time being the actual posting. I created memes before all on my own, but it took longer, probably 20-30 minutes. The brainstorming took much longer. I’ve also done meme brainstorming in a committee, and that took person-hours, cycling through ideas.

I sometimes wonder: is this cheating? I’m still part of the creative process, but am more of an editor/refiner than the creator, though I do set the bounds by selecting the meme and creating the prompt. The quality of the memes are at least as good as what I did without any genAI help, so I don’t think this is AI slop, though of course the people looking at the memes are the ultimate arbiters of that.

Would it be cheating if I had an agent do all of this? Would it still be valuable? I also don’t know.

As the cost (in time) of content creation goes down, more and more will be created.

The human attention that I’m competing for hasn’t increased, though.

Content Useful Tools | moore |

How To Plan For A Big Educational Project

I was talking to someone about a big educational project they were considering, something like a book or a course.

They asked about how I’d think about starting such a thing. I wrote this up in a DM and wanted to share it, lightly edited, with the public. Yup, that’s you, dear reader.

For any serious big project that was educational, I’d probably start with a rough topic outline. Then turn chunks of that into ten blog post titles on the topic.

Then I’d write those ten blog posts. This is because I’m a text driven person 🙂 . If you are a video driven person, you might consider making ten videos. If you learn by coding, maybe ten different projects or features in an app. I think that blogging is the best because words are way easier to change or update than video or code, but you do you.

If you are wrirting, Leanpub can be a good way to do this too, because it is easy to publish from markdown. You can also set a price that changes as you write more content. I wrote more about Leanpub here.

I’d also set up an email list so that you can get interested folks’ email and send them updates. Leanpub takes care of this, but any email list tool (buttondown, mailchimp, substack, beehiiv) can do this. Don’t get hung up on the tools, the goal is to have an easy way to collect interested folks’ emails.

Finally, I’d think about how you are going to publicize the project, beyond the email list. Options include but are not limited to:

  • Post regularly on LinkedIn or other relevant social network
  • Share on slacks (in a commercial channel or other blessed way)
  • Go on podcasts
  • Submit a bunch of CFPs
  • Spend time in the relevant reddit or Stackoverflow answering questions
  • Contribute to an open source project applicable to the topic
  • Answer questions on a relevant mailing list

Spend at least 10% of your time thinking about how to get the word out (and doing it!) over the time you’re working on the project. If you don’t, you will end up with a nice project that no one knows about.

Content Podcast | moore |

Documentation For Devtools

I have been spending a lot of time working on documentation for FusionAuth over the last couple of years. It’s been a learning experience for me. While it hasn’t been a full time position, I have worked on various aspects of our technical documentation. Some of the things I’ve done include:

  • Modifying or extending the tech stack with components or plugins. We used Jekyll and then Astro for our docs. They each have different strengths.
    • Jekyll feels long in the tooth but has a solution for everything because it has been around so long.
    • Astro feels shiny and new and has nice build time errors. It also evolves more quickly. On the downside, there have been times we had to build our own solution because no one had built it for Astro yet.
  • Extracting out common text to share across document sections, including using variables.
  • Reading lots of code and trying tasks with the product to make sure I understood behavior.
  • Building diagrams using PlantUML and Mermaid.
  • Revamping the user navigation and experience multiple times.
  • Looking at common questions that have surfaced from support tickets, sales conversations and the community and writing doc to answer those questions. This serves multiple purposes:
    • Someone can self-serve the answer to their question, using Google, and may not need to talk to us at all. Devs love that!
    • Support or sales engineers can point questioners to the documentation. They can then spend time adding nuance, rather than copy pasting or worse writing answers from scratch.
    • They help anyone in the company understand product features, including people who might work on a different part of the codebase.
    • By being public and used, these docs stand a good chance of staying up to date.
  • Worked on long guides for deep technical topics, such as one about sessions and another about searching. These are fun to begin with and then become more and more repulsive to me over time. I can barely make myself read the final draft “one more time”. But that kind of write-review-refine-hate-publish cycle is so important for quality doc.

I think we’ve done a good job of documenting our product from a technical perspective. One data point: a competitor said that a challenge of using our product is that the doc can be “overwhelming”. I agree, it is voluminous but sometimes confusing; there’s definitely there’s room to improve. But they are critical. Our docs are the main way people find us and evaluate our solution. They are read and referred to by developers inside and outside of our organization.

On the flip side, one founder I respected when I worked for her a few years ago said “no doc is the best doc”. Her reasoning: the goal of any tool should be to make usage so intuitive that there is no need for a user to read the documentation. Hard to disagree with this, right?

Wait, but I just said docs are critical to FusionAuth’s adoption. What gives?

It comes down to what devs want, when. It should be no surprise that devs want different things at different times.

Keith Casey did a good job of outlining it here, saying we need to answer two questions to help sell to devs:

  • How does our tool help developers build something useful or go home?
  • How do we demonstrate that and speed them along?

If we can’t speak to and demonstrate both, we have a toy, not a tool.

Having an intuitive interface primarily helps with the first goal. When someone is using your tool, can they build something useful? If a dev can’t figure out how to move around and accomplish what they want to do, whether that is because of jargon, bugs or overwhelming complexity, they can’t.

Good UX also helps with the second part of the second question. An interface so good docs are superfluous means it is quick to build something.

Therefore, the “no doc is the best doc” founder was right.

However, devs are not always going to take the time to poke around your tool, especially if you require them to sign up or download something. Great docs, in contrast, help with demonstration. A dev will believe your documentation, at least until you give them reason to distrust you. Statements like “tool X can help you solve problem Y” with instructions on actually doing so, help devs. These developers might be evaluating multiple tools, or even just curious and wanting to learn about your solution. Doc can help them decide whether to invest more time and take the next step. It’s far quicker to scan a doc than it is to sign and navigate a tool.

You can also, with doc and example applications, show how to integrate your devtool into existing architectures or systems. This is relatively easy to do with documentation, sample code and screenshots. It is more difficult to do inside an application UX. You can also cover nuanced topics in-depth and using doc in ways that would be tough to do inside an application’s interface.

Doc also helps with discovery via SEO or LLMs, both of which ingest text. Google is the main way I navigate many devtool focused docs.

(Discovery does assume your devtool docs are public. Requiring registration or payment to view documentation is quite a high barrier for evaluation. I’d avoid that unless you have a monopoly or captive market of devs who must use your software.)

Therefore, the “doc is important” experience I mentioned above is also correct.

You want both an intuitive interface and great docs for your devtool. They serve different purposes.

Content Devrel FusionAuth | moore |

Extracting Written Content From Podcasts And Livestreams

I wrote before about not wasting content that you’re creating as you answer questions or interact on communities like Twitter, Bluesky, Discord or Slack.

One great source of content for your newsletter or blog is podcasts or livestreams that you are on. Here’s how I’d do that with an example podcast interview I did a few months ago.

First you need to transcribe it. Most podcasts and livestreams are posted to youtube, and my go to tool there is youtubetranscript.com. Here’s the transcript of the interview. I know people who are happy with Descript and I’m sure there are other solutions out there.

Most podcasts are a wide ranging conversations with multiple possible newsletters or posts contained within them. Sorting out these topic areas is a great use case for AI.

Paste the transcript text into Claude.ai and ask for topic grouping as well as verbatim text for the beginning of each of the topic groups.

Here’s an example of the Claude output:

Content Creation and Repurposing Strategies
Starting text: “I think that the reason I wrote this blog post is because I am a member of a lot of different slack communities or follow people on again on some of those platforms that I shall not mention and I see some great great content that comes out and great answers great wisdom and then it just and then it goes poof away”

Themes:

  • Leveraging existing content from platforms like Slack
  • Low-effort content creation
  • Transcribing podcasts for newsletter content
  • Maintaining authentic voice while repurposing
  • Best practices for newsletter creation

Claude identified five topic areas in this transcript. Once you have this, go back to the raw transcript. Search on a unique text string and. Pull out an interesting, relevant section.

I use the youtubetranscript site to understand where I stop talking and other people start. You can click on a section in the text and view the corresponding part of the video. There may be an AI solution or a specific GPT to do the transcription and have it include speaker names, but I haven’t found one yet.

Here’s an example section that I extracted:

I think that the reason I wrote this blog post is because I am a member of a lot of different slack communities or follow people on again on some of those platforms that I shall not mention and I see some great great content that comes out and great answers great wisdom and then it just and then it goes poof away and even on some some like I follow the ietf emailing lists around ooth and things like that I see some great content there but it it especially in in slack but even in those other places it just gets lost and so my point was by picking up and putting it onto um a newsletter you can and maybe you do some editing right because most stuff that you you um write off in a slack it might not be as Pol as you would normally put a newsletter but you can basically take this um wisdom exhaust right like it’s like kind of like data exhaust from the early 2000s but you can like pick it up and put it together and even if you don’t think you have enough content for a newsletter I think you do if you are active on those channels and by taking it from these walled Gardens of the platforms or slacks or discords and putting it out on a in a newsletter you do a couple of things one is you just showcase Bas your knowledge um the same way a Blog would you can deliver it to people you have a low effort way to connect with folks right if you ever run into somebody a conference or whatnot instead of asking them to follow you on something you can say hey I have a newsletter about real estate in Atlanta or I have a newsletter about how developers are the new king makers or AI or whatever it is and that’s just a lower ask than some other things and it will start to build up a longer term relationship with anybody that you’re um engaged with at low effort to you so that’s kind of the the purpose of the blog post is people are creating all this beautiful content and it’s just trapped especially stuff in slack

This one section is 383 words. This is the kernel of a newsletter edition or a blog post. However, this needs some work. I can’t copy it directly into a newsletter or blog post because I don’t talk as clearly as I write.

Let’s take the above content and lightly edit it to be something I’d feel comfortable publishing.

The reason I wrote this blog post about not letting your content go to waste is because I am a member of a lot of different slack communities where people post great content. I also follow people on Bluesky, that which was formerly Twitter, and other platforms where, again, people are dropping lots of knowledge. This even occurs on IETF mailing lists. There the content is available but it can be difficult to separate the gems from the dross.

I see great great content published and great answers for common questions. Then it goes “poof” away.

Especially in slack but even in those other places, this content just gets lost.

By picking up and putting it into a newsletter you save it. You have to edit it, because most Slack posts are not as polished as newsletter content would be.

But even with that work, you can basically take this “wisdom exhaust” and repurpose it. It’s kind of like data exhaust from the early 2000s. Even if you don’t think you have enough content for a newsletter, you do, if you are active on those channels.

By taking it from these walled gardens of the platforms, slacks or discords and putting it out on a in a newsletter, you do a couple of things.

  • you showcase your knowledge
  • you deliver it to people’s inboxes so they remember you
  • now you have a low effort way to connect with folks; if you ever run into somebody a conference or whatnot instead of asking them to follow you, you can ask them to subscribe to your newsletter
  • you start to build a corpus of knowledge and a set of people interested in hearing from you.

I edited to clarify and expand on the content. I added links where appropriate, and also updated it–Bluesky wasn’t a big thing when I did this podcast.

This is fewer words, but a firm foundation for writing a longer blog post. I could also review the transcript for more of my words.

So, that, in a nutshell, is how you can easily generate written content from a podcast, recorded presentation, or livestream.

Blog Content Newsletter | moore |

Startup Opportunity Gains

As a former startup founder and an employee or early contractor of five other startups, there are costs an benefits to joining a startup. But first, what is a startup? Investopedia says:

The term “startup” refers to a company in the early stages of its operations. Startups are founded by one or more entrepreneurs who want to develop a product or service for which they believe there is demand.

Startups can be either bootstrapped (hard) or raise money (hard). But they are focused on growth. In my opinion, if a business isn’t scalable, it is not really a startup.

  • A laundromat: not a startup.
  • Laundromat management software: startup.
  • Being a real estate broker: not a startup.
  • Building a tech focused real estate brokerage: startup.
  • A web development consulting company: not a startup.
  • A company building product that makes web development easier: startup.

The lines can be blurry of course; if you start a laundromat and make a custom app to improve operations, you can perhaps use that software as the foundation of a laundromat software startup.

I know there is absolutely an opportunity cost to starting a startup, but I don’t want to focus on those. Buy me a beer sometime and I can chat with you about that.

This growth is the key to the benefits. Because of the growth, you’ll learn a ton about a bunch of different parts of building a company. These can include:

  • devops
  • hiring
  • product
  • creating process
  • conflict resolution
  • customer support
  • sales

Of course, what you learn depends on what stage you join a startup and the role you are hired for. But in my experience, especially at startups under one hundred employees, there’s so much work to be done that you can help almost anywhere. (If you are an engineer, talk to your manager before jumping into a sales call, though.)

All of this is exposure you won’t get at a bigco.

Of course, you need to ask yourself if that is what you want to do. Some people are happy building a system and business, while others are more content when embedded in a system which can make them productive.

And even for the same person, you can be ready for different challenges at different times of your life.

 

Startup | moore |

Is A Piece Of Software Ever Done?

I was thinking about this in the context of the Bending Spoons list of acquisitions.

When you are starting out writing any piece of, it seems like there is a limitless amount of new, useful functionality to add. Yes, even sometimes reading email.

But just as a building goes through phases of construction and ends up done, I believe software can be finished too.

I do not mean that the software is abandoned either because it isn’t used any longer or because an adequate substitute for custom built software is purchased. In these cases the software is unused, not finished.

I also don’t mean theoretically complete, where it is bug free and does exactly what is in the spec, as discussed here on Reddit about /bin/true. I don’t think any non-trivial piece of software ever reaches that point.

My definition of finished is when the software is still being used, but the long term value of adding new features to the software package is exceeded by the cost of adding those features.

Finishing software in this manner is different than finishing in physical construction because:

But just as there’s value in personally ending projects, I think there’s value in calling software done.

What would this mean?

  • the software would continue to be valuable
  • the value of the software would depreciate over time
  • some users would continue to use it, others would not
  • most of the team which built it would move on to different endeavors
  • there would need to be a team to do maintenance

Wait!, you say. Software is bits, and those don’t decay, so why would depreciation happen? It would happen in a similar way to how it happens in buildings. A building can become less useful because of:

  • wear and tear, breaking down the physical infrastructure
  • changing styles, making it less desirable
  • new needs of inhabitants/users that it has difficulty meeting because of the way it was built

The latter two apply to software as well as buildings.

While I think it is easy to vilify companies like Bending Spoons for buying software up, laying off most folks, and changing the business model, I’m struggling to understand how it is it any different than buy up a finished building and renting it out while doing minimal maintenance.

What am I missing?

Programming Technology | moore |

Paying attention to competitors

How often do you check out your competitors? And how deeply?

If you are working at any kind of business, you need to know what the market looks like. This includes the services offered, new features or capabilities and pricing. Pricing is very important, and you should try to know both the public pricing and the real pricing. The latter is tough and part of why secret shoppers are a thing; your customers who have talked to competitors but chose you might also be able to help.

If you work in devtools, you also need to know about how competitors are actually used:

  • integration time
  • migration complexity
  • long term ROI/issues

How can you find out about this? You can:

  • read their website
  • read their code (if they expose it)
  • read their forums or slack channel
  • subscribe to their newsletter
  • set up a google alert for them
  • use the tool

However, all of these have flaws.

A marketing website can be tough to extract information from. And technical documentation can lie^H^H^H^H be inaccurate or out of date.

Reading code to understand it is helpful if you are zooming in on specific feature, but most users of whatever the tool is are going to be interested in solving a problem, not the intricacies of how a problem is solved. Code isn’t always available or in a language you know, either.

Reading feedback and questions from a community around a product can be fruitful, but you will only see problems, because happy users rarely post. It is a good way to find out about longer term challenges, though. If you do this and reply to messages, you should 100% never shill your product. That’s like going into a Wal-mart in a Target shirt and walking up to customers and trying to get them to leave with you. Not a good look.

Getting a newsletter keeps you on top of their messaging. However, understand that a newsletter will show them in the best light.

Setting up a google alert can be helpful in getting you an understanding not just of what they are saying about themselves, but what the wider internet is saying. However, there can be a a lot of garbage in there. If the competitor is a public company, you’ll get more stock tips than technical evaluation.

I think the last choice, using the tool to solve a problem, is the highest effort, but will teach you the most. You’ll have to spend money and time.

Since you aren’t using their software in a production context, you won’t get a full picture, but you’ll have an idea of the integration joy and pain that their users will feel. You should ideally do the integration on a cadence so that you keep up with changes and features.

Great. You should learn about the competition.

But how do you figure out how your competitors are? That’s what I’ll cover soon.

Business Startup | moore |

Don’t Let That Content Go To Waste

If you are a member of an online community and you participate, you’ll often write a few paragraphs in response to a comment or question. This is also true if you use a social network like LinkedIn well. Both of these let you share your knowledge and experience with low effort.

While you can definitely gain visibility, your wisdom will only benefit a few people.

If you posted to a synchronous community, the people who happened to be around when you posted will benefit, but no one who visits the site in a few months or years will. Okay, if someone is determined, they might struggle through a search for the topic and find it. If what you write is really memorable, other people might link to your post. But most of what you share will go straight to the Slack memory hole.

If you post to a social network, you are at the not-so-tender mercies of the algorithm. What you write might surface for your followers a day or week later, but a month or year later it’ll be gone. Detritus floating on the scouring stream of witty content and pleas for attention, if you will.

But you spent precious time creating that post. You’re an expert in your field, and you post about it. You shared your experience and your wisdom. Why should you let it go by the wayside? Is there a way to leverage it without too much effort?

Yes.

Capture it in a newsletter or blog post. I prefer a newsletter, which has the following benefits:

  • you can easily build an audience of people who want to hear from you
  • you can have your ideas posted to a permanent URL that Google can find and others can share
  • a newsletter can be casual

First, you need to select a theme, usually related to your professional goals, and then set up a newsletter. Examples of themes can range from database optimization to product marketing; it doesn’t matter what the theme is as long as you have expertise and plenty to say. The nuts and bolts of setting up a newsletter and adding a subscription form to your website are well covered by the newsletter providers (Beehiiv, Substack). Therefore, I want to focus on the next step, gathering and publishing content.

After you read this post, you’ll know how to gather and publish the scraps of insight your share around on communities or social platforms in a sustainable regular way. You can start getting the first one hundred subscribers to your newsletter; people that want to hear from you.

Doing so is a four step process:

  • gather sources
  • schedule scouring
  • tell a story
  • schedule it

It’s important to not let the perfect be the enemy of the good. Finding, editing and shipping existing content in a newsletter is a process that you’ll get better at, but you don’t need your newsletter to be perfectly manicured like one of the big newsletters, or a newsletter from a large company. You may build your newsletter into that, but to get started, the goal is to enable you to send a regular newsletter. Remember, we want to avoid letting that great insight languish.

Let’s look at each of these above steps.

Gather Sources

First, gather your sources. I start with a google doc and write down links for everything that might be a source of newsletter content.

This includes social media platforms where long form posting happens, such as LinkedIn or Facebook. Also, include sites where you write substantive comments, such as Hacker News or Reddit.

The real gold is often in private communities such as slack or email lists. Make sure you respect community rules and never use someone else’s content. But your long, detailed answer to a common technical question is perfect for touching up and publishing to your newsletter list.

Another place to look for newsletter content is livestreams or podcasts you are a guest on. The technical conversations are a great source of content for a newsletter.

Any fully-formed GitHub project READMEs can also be good content, especially if they talk through the use cases of a particular tool or project.

Wherever you share insights related to your newsletter theme, especially if it is long-form and ephemeral, is fair game.

Add these to a list. Keep it up to date; as you appear on a new podcast or start posting thoughts elsewhere, add the links.

Scouring

Next, find some regular time to review these sources. I suggest doing this once every two months, but the right frequency depends on how many newsletters you want to send and how often you post.

In the google doc, do the following:

  • mark the date you reviewed
  • copy and paste the text
  • capture the link

Don’t grab one to two line comments or anything that is off-topic of your newsletter . Instead, look for the multi-paragraph insightful comments. If there was a discussion, grab all your comments. Don’t forget to grab any links you mention as well.

How exactly you grab the text depends on the source:

  • If you are looking at LinkedIn, you can search for all posts and comments you have made.
  • If you are using a podcast or video stream as a source, For these, you can use a tool like Youtube Transcript to extract text and then scan to find insights that you can repurpose. You can use GenAI tools to group the text into high level topics that you can portion up into newsletters.
  • If you are posting on a slack, you can search for all your posts using the from modifier.

Each source will have a different way to find your content, but after the first few times it’ll be second nature to grab it.

Tell A Story

The next step is to take the raw text and turn it into a coherent story. You want to do this every month or so, though you may need to front-load this if you are starting a newsletter.

You’ll need to spend some time on this process. The goal is to create something worth sending out to your readers.

Each post should be:

  • 500-1000 words
  • coherent; if you are merging together more than one comment, make sure tense and pronouns agree
  • edited; remove fluff words and anything that distracts from the point, especially if you are condensing a podcast section
  • on theme; if you are a devops consultant, don’t post about ice cream stores, unless they relate to devops

You will end up with a solid newsletter post. Mark this fragment with the date you reviewed and turned it into a story. This will prevent you from using the same text in six months.

In my experience, this is an AI-aided manual process. You can use the AI to condense podcast text, think of alternate angles, or give you feedback on any other areas to cover. But what you should not do, unless you want a newsletter that sounds robotic, is paste your text into ChatGPT and ask for a newsletter-length block of text.

Don’t rewrite the text. The whole point of this process is to leverage existing content you have created in a low-effort, sustainable way.

Since you have all your content in one place, you can repeat this process to get many newsletters ready. I like to get as many ready as I’ll send out in the next month.

Then, schedule them out.

Schedule It

You’ve done all the hard work, scheduling is easy.

Make sure any platform you select supports scheduling out newsletters.

Test sending them to yourself to see what they look like.

Schedule each story on a regular interval. I like to send on the same day of the week every time. Once every two weeks to once a month is sustainable but will keep you top of mind.

If there’s timely news that you want to address, you can bump one of the other newsletter editions.

Summing Up

This process is the start of a journey that will end with a permanent, searchable corpus of your insights, at relatively low cost in terms of effort and time. It also ends with you having a list of people who want to hear from you about the topics you cover.

You will no longer be letting your content go to waste.

It is not, however, a quick process. You may send newsletters to hundreds of subscribers for years. There are two ways to think about that:

  • oh man, I only have 200 subscribers and therefore I compare poorly to people who have tens of thousands of subscribers or more
  • oh my, I have 200 subscribers who want to hear what I say and are willing to let me into their email inbox regularly

Which do you think is the better perspective?

Content Newsletter | moore |

Great GitHub actions for techdocs sites

There are two main options for techdocs sites. You can use a SaaS solution like Readme or DeveloperHub. Or you can use a static site generator like Jekyll, Hugo or Docusaurus. There are strengths to each approach, but for this post I want to look at continuous integration/continuous deployment (CI/CD) tasks you can run on staticly generated tech documentation.

Why use CI/CD for your docs site? CI/CD tools let you automate code or documentation tasks. For documentation, you can run checks to ensure consistency and correctness which make your documentation better.

GitHub Actions is the CI/CD tool I’m going to refer to, but similar functionality is available with other CI/CD solutions such as CircleCI or Jenkins. Additionally, I’ll talk about the content living on GitHub in a repo, but you could use self hosted git, gitlab, bitbucket or other version control solutions.

This post has a couple of assumptions:

  • Your content is in version control.
  • Your content is in a format that needs to be processed before it is ready for publishing. In other words, you are editing text files in a certain format (markdown, asciidoc, etc) that are then processed, rather than using a WYSIWYG editor.
  • The people writing your content are comfortable using version control and tools like markdown.

Here are tasks you should automate:

Deploying The Documentation

This is the first one and the easiest win. You should have a workflow which automatically deploys changes when a PR is merged to your primary branch. This lowers the barrier to entry for contributing to documentation, because you only need to get a GitHub PR approved. Similar to continuous deployment of a SaaS application, it makes it easy to push changes regularly. Because it is a GitHub PR, it also is easy to roll back–you just revert the PR.

You may wonder at my including this, because it seems so obvious, but I’ve been on teams where the deploy process included sshing to a server, pulling the branch, and running a script.

Automating deployment was well worth it, because it changed “I found a typo, oh man, what a pain” to “I found a typo, I can push a PR and fix it in 3 min”.

Vale

Vale is an amazing, free linter for your prose. I haven’t witnessed it used at its full potential, but it is a spell checker, word police and living style guide all in one. It’s kinda imposing to start with since there are so many “nerd knobs”, but start simple and add to it as you learn it.

Vale runs fast enough you can have it run on every PR.

Spelling

Deploy a spell checker to run against your documentation to prevent misspellings and typos.

You have two choices here:

  • spell check just the changes (vale is good at this)
  • spell check the entire site (pyspelling is good at this)

The former lets you block a PR if there’s an issue, while the latter takes a lot longer and should run on a schedule. The latter is a good fit if you have non-technical docs (perhaps from a marketing site) that you also want to check for correctness.

You should plan to add a lot of words to the ‘known words’ file because most techdocs have jargon or names that aren’t in standard dictionaries.

Look For Dead Links

Running a link checker regularly will help your users avoid 404 pages. No matter how cute they are, they annoy folks because a 404 is a dead end. Techdocs are all about enabling end users to solve their problems and a 404 page doesn’t help.

You should run the checker periodically and fix busted links as soon as possible. I haven’t found a way to run it quickly enough to link checking on a PR. (Update July 7: someone on a slack pointed me to this open source partial link checker. I haven’t tested it, but they say they use it.) I like this fast link checker which catches 404s but also will error on page anchors that don’t exist. The latter are not as annoying as the former, but still impact developer experience.

Side note: link checkers only prevent internal linkrot. You can prevent external linkrot by being assiduous about your redirects. Never let an external link be sent to the home page or, worse, a 404 page.

Check For Closed Issues

Often documentation references an externally facing issue tracker, such as GitHub issues or Jira. After all, if there is a known problem that has a workaround or enhancement planned, adding a link to an external tracker lets the dev audience know and can help them accomplish their goals or know to wait for a future release. Often issues are closed but are still referenced in the docs, which means that the link is confusing.

This job mitigates that by iterating docs, looking for issue links, then checking to see the status of the issues. If the issue is closed, this task reports the problem that the doc can be updated.

Shrinking Images

Small images lead to a faster experience for your users, but it can be hard to remember to shrink the images as you are creating documentation. Automating such image shrinking using a tool like tinypng is an easy way to improve user experience.

This is best done on a pull request, but will require committing the changes using a tool like git-auto-commit.

Generic Content Checking

You can write a shell script using grep to look for known content issues. Examples:

  • Images without alt text.
  • Documents without a title or description tag.
  • Alt text that is not a full sentence.
  • Descriptions that are not a full sentence.
  • Enforcing that every blog post is in a known category.
  • Absolute URLs that point to your docs site. Everything should be relative so it’s easy to stand up locally.
  • Markdown syntax issues

In practice, this looks like: exit `find astro/src/content/ -type f -name "*.md*" | xargs grep ']()'| wc -l |sed 's/[ ]*//g'`

That one liner looks for a markdown link with an empty URL. The above GitHub action will fail if there is a non-zero exit code.

Custom Checks

Once you start automating content quality checks, you’ll find opportunities everywhere. Some ideas:

  • If you show example applications on your techdocs website, but store the code elsewhere in a repository, you can check to see that the numbers from each source are equivalent.
  • If you have handcrafted JSON examples, making sure they parse using a tool like jq. It can be easy to miss an errant comma.
  • Making sure every API page has example code on it.

As you look at your docs, I’m sure you’ll think of others.

How To Handle Errors

Many of these tasks will throw an error when something is incorrect, such as a misspelling or syntax error. There are two ways to handle these errors.

  1. If you can run the check quickly enough, run it on every push or every opened PR and provide feedback for fixing the issue. The doc author can then handle it immediately before the PR is merged.
  2. If the check takes a long time, like spell checking your entire site, then run it on a schedule. The last person to edit the workflow will get the notification, so it’s best to catch the error and have it send an email to a shared alias to capture the issue and then fix it.

Also, configure these tasks to be run manually (the workflow_dispatch event for GitHub actions). This helps with troubleshooting or testing when a fix has been made.

Conclusion

All of these tasks can help you remove some of the toil from creating an excellent techdocs site. You don’t have to do them all at once, but adding them will reduce your effort and increase your documentation quality.

Content Devrel | moore |

Open source is code escrow on the cheap

I read this article a while back about the VC backed open core playbook. Worth a read.

If you haven’t had a chance yet, the playbook is:

  • start an open source product
  • create a company around it
  • use the siren of open source to drive adoption
  • take VC money
  • continue to developer the open source solution
  • build out closed source functionality, typically as a hosted SaaS
  • over invest in the closed source edition
  • let the open source version wither on the vine
  • profit !?!

The crux of the argument is that the open source version of whatever software is being sold is a pure marketing play, and that all the focus will eventually arrive on the closed source extensions or functionality. After all, that is what drives the revenue, and since the company took VC money, they need outsize revenue.

There are a few flaws in the argument, including, but not limited to:

  • it is possible, and even likely if a project succeeds, that there is a community of other companies that will drive the open source project forward under another name (see Opensearch or Valkey)
  • the marketing value of the open source project doesn’t necessarily recede as the closed source functionality drives more revenue; it may even grow
  • not every open source company is VC funded

But I’m going to set all those aside for now, and focus on the value of open source for the end developer. In particular, why is that so attractive to devs? Why is it such a powerful marketing tool to drive adoption?

There are two reasons OSS is important for dev focused tools:

  • permissionless access
  • derisking the future

Let’s dig into each of these.

Permissionless access

When a product is open source, a developer can access it, typically by downloading and running the code, without talking to anyone. They don’t have to fill out a ‘contact sales’ form or give any information to the vendor. By the way, marketing departments hate that, not because they want to spam developers, but because it’s really hard to do modern marketing when you have no idea who your users are.

Just as importantly, a developer downloading an OSS project does not have to ask for money or permission from their own organization either. They are spending time, which is an opportunity cost, but for typical developers that isn’t an expense that is tracked too closely. Even agency developers billing by the hour have time to explore and can justify investigating a tool if they think it will speed delivery.

Decreasing the friction of trying a tool means, all other things being equal, more people will try it. If the product is good, and by that I mean it solves a need, this is the first step to adoption.

Derisking the future

Whenever a developer picks up a tool, whether it is a SaaS product or a library, they do so with the knowledge that the tool and the uses for it will break something in the future. This is an unfortunate side effect of the fluidity of software and anyone who has spent days or weeks upgrading from one version of a framework or library to another will understand that it is part of the job.

Using an OSS tool derisks this unpleasant task in two ways, and therefore makes the future better for the developer, increasing the attractiveness of using OSS.

The first is bug fixes. It is quite frustrating to be stopped by a bug in a software library you are using. I still remember decompiling java classes two decades ago to characterize a bug in a software package we were using. I found the bug and then had to raise an issue with the vendor; in the meantime I had to code a workaround.

When you have access to the source as a developer, you can do the fix yourself. You typically want to upstream it to the vendor to ease the burden of maintaining a fork, but you are not stopped in your tracks. And finding the fix is easier because the source and build instructions are available.

The second is operations. If pricing gets punitive or the vendor has a hard time operating the software in a way that meets your availability needs, you can run it yourself. Or, if you don’t want to, you can pay someone else to do so. If the software is successful enough, a hyperscaler may offer a managed service (hello Elasticsearch!). Having  competition for running the product makes it less likely you’ll be stranded engaging with a vendor that doesn’t meet your needs. It’s code escrow without paying Iron Mountain truckloads of cash.

Conclusion

I think the risk of relying on OSS companies that take funding is real. VCs aren’t in the business of giving away value, so there will eventually need to be a business model and I think that the author of the original post described what is unfortunately a pattern. But developers justifiably value the benefits of OSS highly too. Permissionless access lets them get on with doing their job while source code availability derisks future problems.

I predict we’ll see more OSS companies started in the devtools space because of these factors. But the long term trend of successful companies moving from OSS licenses to more restrictive ones will also continue.

Business ElasticSearch SaaS | moore |