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Hacktoberfest 2025 Reflection: Three Years, Three Lessons, One Evolution

Hacktoberfest: Open Source Reflections

This is a submission for the 2025 Hacktoberfest Writing Challenge: Open Source Reflections

The Three-Year Journey

This was my third Hacktoberfest, and each year taught me something different about what open source really means.
Hacktoberfest 2023: My first year—excited, overwhelmed, hunting for "good first issues"
Hacktoberfest 2024: More confident, making targeted contributions, starting to understand project ecosystems
Hacktoberfest 2025: Finally clicked—focused on impact over activity, documentation as infrastructure, solving problems at scale

Hacktoberfest 2025: What I Built

This year, I contributed to goose (Block's open source AI developer tool) by creating comprehensive documentation addressing enterprise adoption gaps.

My 2025 Contributions

Four-part documentation series (40,000+ words):

  1. Getting Started with goose on Windows - Platform-specific guide with troubleshooting
  2. Best Practices for Prompt Engineering - 6 techniques with 50+ production examples
  3. Deep Dive into MCP Extensions - Complete technical reference with production patterns
  4. Team Configuration Guide - Enterprise deployment frameworks
  5. Docs: add Linux and Windows paths to uninstall section - Add Linux and Windows paths to uninstall section
  • Updates the 'Uninstall Goose or Remove Cached Data' section to include
  • platform-specific paths for Linux and Windows alongside existing macOS paths.

Plus production-ready tools: setup scripts, cost tracking, configuration validation, security frameworks.

The Evolution: What Changed Year Over Year

2023: Hunting for Issues

  • Focus: Finding "good first issues" I could solve
  • Mindset: "What can I contribute?"
  • Success metric: Number of merged PRs
  • Learning: How to make a pull request, work with Git, follow contribution guidelines

2024: Understanding Projects

  • Focus: Contributing to projects I actually used
  • Mindset: "How can I help this project?"
  • Success metric: Quality of contributions
  • Learning: How projects work, what maintainers need, how to write better code

2025: Solving Real Problems

  • Focus: Identifying gaps and filling them completely
  • Mindset: "What's stopping adoption of this tool?"
  • Success metric: Measurable impact on users
  • Learning: Documentation IS infrastructure, production matters more than demos

The Pattern: Each year, my contributions got fewer but more impactful. 2023 was many small PRs. 2024 was fewer, better PRs. 2025 was comprehensive solutions to complex problems.

What I Learned This Year

1. Documentation is Infrastructure (Not Afterthought)

In 2023-2024, I saw documentation as "nice to have." In 2025, I realized it's infrastructure—the foundation that enables adoption.
goose works great for maintainers but was hard for teams to deploy at scale. My documentation bridges that gap: configuration management, security, cost tracking, governance. Without these pieces, enterprises can't adopt AI tools no matter how good they are.
Lesson: The best contributions remove barriers. Code that works but can't be deployed is just potential.

2. The Meta-Loop: Using Tools to Improve Themselves

This year's unique insight: I used goose to contribute to goose.

  • Used goose to analyze documentation gaps
  • Used goose to research common problems
  • Used goose to draft content and iterate
  • Used goose to create production scripts
  • Used goose to refine technical accuracy This taught me: the best way to understand a tool is to use it to improve itself. You can't fake this depth of understanding—it comes from actually solving problems with the tool. Lesson: Use what you're contributing to. Real usage reveals what docs miss.

4. Community Amplifies Everything

In 2023, I contributed and moved on. In 2024, I started engaging with maintainers. In 2025, I realized community feedback makes contributions better:

  • Comments revealed what I'd missed
  • Users shared their workarounds
  • Platform teams asked about patterns
  • Other contributors built on my work

Lesson: Open source isn't a solo activity. The community improves what you create

How My Perspective Changed

What Open Source Meant to Me in 2023:

Contributing code to repositories, fixing bugs, adding features

What Open Source Means to Me in 2025:

Building infrastructure that democratizes access—to tools, knowledge, and best practices

The shift: from contributing to projects to contributing to ecosystems.
goose isn't just a tool—it's part of an ecosystem:

  • MCP is an open standard (works across Claude, Cursor, etc.)
  • Extensions are composable (build once, use everywhere)
  • Documentation helps everyone (users, contributors, enterprises)
  • Improvements compound (each contribution builds on others)

When I create documentation, I'm not just explaining features—I'm:

  • Lowering barriers for Windows developers
  • Helping small teams access enterprise-grade AI
  • Giving companies frameworks to adopt tools safely
  • Contributing to collective knowledge

The realization: Open source's power isn't free code—it's that improvements compound. My docs help teams deploy faster, they discover better patterns, they share them, someone improves on that, everyone benefits.

Three Years of Lessons

Year 1 (2023): The Mechanics

  • How to find projects
  • How to make PRs
  • How to follow contribution guidelines
  • How Git/GitHub work
  • How to communicate with maintainers

Year 2 (2024): The Context

  • Why projects make certain decisions
  • What maintainers actually need
  • How to write quality contributions
  • How projects are structured
  • How to think about tradeoffs

Year 3 (2025): The Impact

  • What stops tool adoption
  • How to solve problems at scale
  • What production means vs demo
  • How documentation enables adoption
  • How contributions compound

The Lesson: Open source is a journey from mechanics → context → impact. Early years teach you HOW to contribute. Later years teach you WHERE and WHY to contribute

Advice for Different Stages

For First-Time Participants (Where I Was in 2023):

  1. Start with Tools You Use - Don't just hunt "good first issues." Contribute to tools you actually use—you'll understand the problems better.
  2. Read the Contribution Guidelines - Every project has them. Following them shows respect and gets your PR merged faster.
  3. Start Small, Ship Often - Fix typos, improve docs, add tests. Don't aim for perfect—aim for shipped.
  4. Learn Git Properly - It's worth the time investment. You'll use it everywhere.
  5. Engage Respectfully - Maintainers are volunteers. Be patient, be kind, be helpful.

For Second-Year Participants (Where I Was in 2024):

  1. Go Deeper, Not Wider - Instead of 20 small PRs, make 5 substantial ones. Quality over quantity.
  2. Understand the Project - Read the architecture docs. Understand why it works that way. Your contributions will be better.
  3. Fix Related Issues Together - If you find one bug, look for related bugs. Fix them together in one PR.
  4. Ask "Why?" - When maintainers suggest changes, ask why. Learn their reasoning. It makes you better.
  5. Think About Maintainability - Your code will be maintained by others. Make it clear, well-tested, document ed.

For Experienced Participants (Where I Am in 2025):

  1. Find the Adoption Gaps - Look for what stops people from using great tools. That's where impact lives.
  2. Think in Complete Solutions - Don't just answer one question—create comprehensive resources that solve all related problems.
  3. Use the Tool to Improve the Tool - If contributing to AI tools, use AI. If contributing to testing frameworks, test them. Meta-usage gives deep understanding.
  4. Focus on Production Patterns - Demos are everywhere. Production-ready solutions are rare and valuable.
  5. Measure Impact, Not Activity - Did your contribution actually help people? That's the metric that matters.
  6. Build for Scale - Individual use is one thing. 50 developers is another. Address the latter.
  7. Engage Long-Term - Don't disappear after October. Answer questions, update docs, help others.

What This Year Taught Me About Open Source

Open source is about compound improvements.
When I document how to deploy goose:

  • Teams deploy successfully
  • They discover better patterns
  • They share those patterns
  • Someone improves on them
  • Documentation gets updated
  • The next team starts higher
  • The ecosystem improves

This compounding is why open source is powerful. We're not building in isolation—we're building on each other's work. Each contribution makes the next easier.

The best contributions make the next contribution easier.

That's what I focused on in 2025: creating infrastructure that others can build on. Not just solving my problem, but creating frameworks that help thousands of teams solve similar problems.

The Three-Year Arc

2023: Learning the mechanics of open source
2024: Understanding how projects work
2025: Creating infrastructure for adoption
2026 (Goal): Contributing code that solves the problems I documented
The progression is clear: u_ser → documentation contributor → code contributor → maintainer._
Each step builds on the previous. Each year, I understand more about what makes open source work.

Looking Forward

Three Hacktoberfests taught me that the best path is:

✅ Use the tool (learn deeply)
✅ Document the tool (help others)
→ Build the tool (next step)
→ Maintain the tool (future goal)

This year showed me I want to go deeper with goose. I've documented the gaps—now I want to fix them at the source. Move from explaining problems to solving them in code.
That's the beautiful thing about open source—there's always a next level, always a way to contribute more, always an opportunity to increase impact.

Final Reflection

If 2023 Me Could See 2025 Me:
2023 Me: "Look how many PRs I made!"
2025 Me: "Look how many teams I helped."
The shift from quantity to quality, from activity to impact, from contributions to infrastructure—that's the three-year journey.

What I'd Tell 2023 Me:
"Stop hunting for issues. Find a tool you love, use it deeply, understand where it struggles, then fix that. One impactful contribution beats ten surface-level PRs. Quality compounds. Activity doesn't."

What Excites Me About 2026:
Moving from documenting problems to solving them in code. Contributing to goose's codebase. Building features that make enterprise adoption easier. Helping the next wave of contributors.


Three years in, one lesson clear: Open source isn't about heroic individual contributions. It's about collective progress. It's about building infrastructure others can stand on. It's about making the next contribution easier.
Thank you to every maintainer, every contributor, every person who answered my questions, and every team that made open source better. Here's to year four. 🚀

Top comments (2)

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ben profile image
Ben Halpern

Good stuff

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stoic-ankush profile image
Ankush Khakale

Great !