personal-website/content/drafts/2025-03-12-lessons-learned-custom-ssg.md

title	date	tags
Lessons Learned: One Year with a Custom Static Site Generator	2025-03-12	web development javascript static-site node tailwind lessons

It's been just over a year since I transitioned from Haunt to my own custom static site generator for this website. What started as an experiment to gain more control over my publishing workflow has evolved into a valuable learning experience that has shaped how I approach web development projects.

In this post, I'll share the key lessons I've learned, challenges I've faced, and insights I've gained from building and maintaining my own static site generator.

The Technical Evolution

Initial Implementation vs. Current State

When I first built my static site generator, it was a simple Node.js script that converted markdown to HTML and injected it into a template. The feature set was minimal:

• Basic markdown parsing with marked
• Simple templating with string literals
• Manual asset management
• Command-line build process

Today, the system has evolved considerably:

• Enhanced markdown processing with syntax highlighting and custom extensions
• Tailwind CSS integration with optimized builds
• Automated image optimization
• Tag-based organization and filtering
• RSS feed generation
• Incremental builds for faster development

This evolution wasn't planned from the beginning—it emerged organically as I used the system and identified pain points and opportunities for improvement.

The Power of Incremental Improvements

One of the most valuable lessons I've learned is the power of incremental improvements. Rather than trying to build a comprehensive system upfront, I started with the minimum viable solution and gradually added features as needed.

This approach allowed me to:

1. Get the site up and running quickly
2. Learn from actual usage rather than anticipated needs
3. Focus development efforts on genuine pain points
4. Avoid overengineering and unnecessary complexity

For example, I didn't initially implement an image optimization pipeline. Only after manually optimizing images for several posts did I recognize the value of automating this process. The resulting solution was more practical and tailored to my specific workflow than if I had tried to design it upfront.

Unexpected Challenges

Dependency Management

One of the most surprising challenges was dependency management. While I deliberately kept external dependencies minimal, even the few libraries I did use occasionally introduced breaking changes or security vulnerabilities that required attention.

For instance, when updating the marked library for markdown processing, I had to adapt to changes in its API and configuration options. This highlighted the importance of:

• Carefully evaluating dependencies before adoption
• Writing good tests to catch breaking changes
• Considering the long-term maintenance implications of each dependency

Browser Compatibility

Another unexpected challenge was ensuring browser compatibility. While static sites are generally more resilient than complex web applications, I still encountered issues with:

• CSS features not supported in older browsers
• JavaScript syntax compatibility
• Image format support (particularly with WebP and AVIF formats)

These challenges led me to implement better progressive enhancement strategies and more thorough testing across different browsers and devices.

Content Management Workflow

Perhaps the most significant challenge was refining the content management workflow. While I initially focused on the technical aspects of generating the site, I quickly realized that the author experience was equally important.

Pain points included:

• Managing front matter consistently
• Previewing content during writing
• Organizing and reusing images
• Maintaining consistent formatting

To address these issues, I developed additional tools and scripts to streamline the content creation process, including a front matter template generator and a live preview server.

Community Engagement

Sharing the Journey

One unexpected benefit of building my own static site generator has been the community engagement it has fostered. By documenting my process and sharing code snippets, I've connected with other developers interested in similar approaches.

These interactions have:

• Provided valuable feedback and suggestions
• Inspired new features and improvements
• Created opportunities for collaboration
• Helped others solve similar problems

I've received numerous emails and comments from readers who have adapted aspects of my approach for their own projects, which has been incredibly rewarding.

Open Source Contributions

Working on my own static site generator has also led to contributions to open source projects. As I encountered limitations or bugs in the libraries I was using, I often found myself submitting pull requests or opening issues.

This has not only improved the tools I rely on but has also deepened my understanding of the broader ecosystem and connected me with other developers working on similar problems.

Performance Insights

Build Performance vs. Runtime Performance

An interesting lesson has been the distinction between build performance and runtime performance. Initially, I focused primarily on optimizing the runtime performance of the site—ensuring fast page loads, minimal JavaScript, and optimized assets.

However, as the site grew, build performance became increasingly important. Slow builds hindered the content creation process and made it less enjoyable to update the site.

This led me to implement:

• Incremental builds that only process changed files
• Parallel processing for independent tasks
• Caching of intermediate build artifacts
• More efficient asset processing pipelines

These optimizations significantly improved the development experience without compromising the performance of the published site.

The Value of Measurement

Another key lesson has been the importance of measurement in performance optimization. Rather than making assumptions about performance bottlenecks, I've learned to rely on data from:

• Lighthouse scores and reports
• Chrome DevTools performance profiles
• Build time measurements
• Real User Monitoring (RUM) data

This data-driven approach has often revealed surprising insights, such as the significant impact of font loading on perceived performance and the importance of optimizing the critical rendering path.

Security Considerations

Building and maintaining my own static site generator has also deepened my understanding of web security. Even though static sites are inherently more secure than dynamic applications, there are still important considerations:

• Content Security Policy (CSP) implementation
• Secure handling of third-party resources
• Protection against common vulnerabilities in dependencies
• Secure deployment processes (as detailed in my recent post about my development environment)

I've implemented a comprehensive security strategy that includes regular dependency audits, strict CSP headers, and secure deployment practices using GPG encryption for credentials.

Future Roadmap

As I look to the future of my custom static site generator, several areas of improvement stand out:

Content Management Improvements

• Better support for content types beyond blog posts
• Enhanced media management
• Improved drafting and scheduling capabilities
• Better support for content updates and versioning

Build System Enhancements

• Further build performance optimizations
• Better incremental build support
• Improved error reporting and diagnostics
• Integration with modern build tools like esbuild

Frontend Innovations

• Enhanced progressive enhancement strategies
• Better offline support with service workers
• Improved accessibility features
• More sophisticated interaction patterns without sacrificing performance

Conclusion: Was It Worth It?

The question I'm most frequently asked about my custom static site generator is whether it was worth the effort compared to using an established solution like Hugo, Eleventy, or Next.js.

My answer is an unequivocal yes, but with an important caveat: it was worth it for my specific goals and learning objectives.

Building a custom solution has provided:

1. Deep learning opportunities across the full web development stack
2. Complete control over the implementation and feature set
3. Minimal dependencies leading to a more maintainable codebase
4. Tailored workflows specific to my content creation process
5. Performance optimizations focused on my particular use cases

However, I wouldn't recommend this approach for everyone. If your primary goal is to get a site up quickly with minimal development effort, established static site generators offer tremendous value and a wealth of community support.

The key is to align your tooling choices with your specific goals, constraints, and learning objectives. For me, the journey of building and evolving my own static site generator has been as valuable as the destination—a fast, secure, and maintainable website that perfectly suits my needs.

I'd love to hear about your experiences with static site generators, whether custom-built or established solutions. What lessons have you learned? What challenges have you faced? Share your thoughts in the comments or reach out via email.