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Long-Term Roadmap: 6-Month Vision

Long-Term Roadmap: 6-Month Vision

Goal: Transform from “solid portfolio” to “must-follow educator innovating with AI”

Timeline: 6 months (Month 1 = Priority Actions already completed)

Month 1: Foundation (Weeks 1-4) ✅

Focus: Core improvements from priority actions

Completed:

  • 3-5 live demos deployed
  • Homepage hero redesigned
  • Teaching Philosophy page created
  • 3 projects rewritten with narrative
  • “Educator who codes” positioning established
  • JavaScript extracted and organized
  • Warmer color palette applied

Status: Foundation complete

Month 2: Evidence & Depth (Weeks 5-8)

Week 5: Gather Evidence of Impact

Goal: Add credibility through real-world data

Tasks:

  • Contact tutors using describe_it for testimonials
  • Document Fancy Monkey metrics (sales, revenue, users)
  • Collect data from your own Spanish practice tools
  • Screenshot improvements in Spanish level over time
  • Add testimonials to project cards
  • Create “Impact” sections in project data

Deliverables:

  • 3-5 testimonial quotes
  • Quantified metrics for top projects
  • Evidence sections on project cards

Week 6: Deploy Remaining Demos

Goal: Get to 7-8 live demos total

Priority deployments:

  1. describe_it → Vercel (2 hours)
  2. subjunctive-practice → Vercel (2 hours)
  3. aves → Vercel (2 hours)
  4. open_learn_co → Heroku/Railway (3 hours)
  5. learning-agentic-engineering → GitHub Pages (1 hour)

Alternative for CLI projects:

  • Record demo videos (30 min each)
  • Add to YouTube unlisted
  • Embed in project cards

Deliverables:

  • 7-8 working demos OR demo videos
  • All demo links functional
  • Screenshots for each

Week 7: Create Project Tiers

Goal: Visual differentiation by project maturity

Tasks:

  • Identify top 3 “Featured Projects”
    • Criteria: Demo + users + compelling story
    • Candidates: Fancy Monkey, describe_it, Internet Map
  • Design full-width featured project layout
    • Large image gallery
    • Detailed description
    • Metrics prominently displayed
    • Testimonials if available
  • Redesign “Active Projects” section (5-7 projects)
    • 2-column grid
    • Standard cards with good detail
  • Create “Experiments & Learning” section (remaining)
    • Compact list or 3-column grid
    • Focus on “What I Learned”

Deliverables:

  • 3 tiers visually distinct
  • Featured projects stand out
  • Clear hierarchy

Week 8: First Case Study

Goal: Deep dive on one project

Choose: Fancy Monkey (best story: $0 hosting e-commerce)

Sections:

  1. The Problem: Can you really run e-commerce with zero hosting costs?
  2. The Approach: GitHub Pages + Vercel serverless + Stripe
  3. Technical Challenges:
    • State management without database
    • Inventory validation
    • Payment security
    • No server-side sessions
  4. What Worked:
    • Single serverless function
    • Static site speed
    • Stripe handles complexity
    • Actually profitable
  5. What Didn’t:
    • Manual inventory updates
    • Limited analytics
    • No customer accounts
    • Scaling concerns
  6. Business Metrics:
    • Sales: X
    • Revenue: $Y
    • Customers: Z
    • Cost: $0/month
  7. Lessons Learned:
    • When this approach works vs doesn’t
    • Serverless limitations
    • Static site advantages
    • Would I do differently?

Deliverables:

  • Full case study page: /projects/fancy-monkey-case-study/
  • Process images, architecture diagrams
  • Link from project card
  • 1500-2000 words

Month 3: Content Strategy (Weeks 9-12)

Week 9: Blog Infrastructure

Goal: Set up for regular content

Tasks:

  • Enable Jekyll blog functionality (already supported)
  • Design post layout with good typography
  • Create post templates:
    • Technical deep-dive
    • Educational philosophy
    • Learning reflections
  • Set up categories:
    • Education & Pedagogy
    • AI & Language Learning
    • Technical Tutorials
    • Learning in Public
  • Make RSS feed prominent in nav
  • Add “Latest Posts” to homepage

Deliverables:

  • Blog ready to publish
  • Post templates created
  • RSS feed prominent

Week 10: First Blog Post

Goal: Establish thought leadership

Title: “What I Learned Building 5 Spanish Learning Tools with AI”

Outline:

  1. Setup: Why I built custom tools instead of using Duolingo
  2. Tool 1: describe_it - Varied output practice insight
  3. Tool 2: subjunctive-practice - Context over conjugation
  4. Tool 3: aves - Content-based learning validation
  5. Tool 4: conjugation_gui - Adaptive difficulty challenges
  6. Tool 5: [another] - [lesson learned]
  7. Synthesis: 5 principles for effective AI learning tools
  8. What Failed: Honest about abandoned approaches
  9. What’s Next: Open questions I’m exploring

Length: 1200-1500 words

Promotion:

  • Share on LinkedIn
  • Post to r/languagelearning
  • Tweet thread
  • Send to education email list (if you have one)

Deliverables:

  • Published blog post
  • Shared on 3+ platforms
  • Feedback collected

Week 11: Second Blog Post (Technical)

Goal: Show technical depth

Title: “Building E-Commerce with $0 Hosting: GitHub Pages + Vercel + Stripe”

Outline:

  1. The Challenge: Can you run real e-commerce with no hosting cost?
  2. The Architecture:
    • GitHub Pages for static site
    • Vercel serverless for checkout
    • Stripe for payments
    • Architecture diagram
  3. Implementation Details:
    • Code examples
    • Environment variables
    • Deployment process
  4. Handling Edge Cases:
    • Inventory validation
    • Payment failures
    • Race conditions
    • Security considerations
  5. Real-World Results:
    • Performance metrics
    • Actual costs (zero!)
    • Scaling limitations
    • When NOT to use this approach
  6. Code Repository:
    • Link to GitHub
    • Setup instructions
    • FAQ

Length: 1500-2000 words with code examples

Promotion:

  • Share on Dev.to
  • Post to r/webdev
  • Hacker News
  • Product Hunt (maybe)

Deliverables:

  • Technical deep-dive published
  • Code examples clean and documented
  • Shared on developer communities

Week 12: About/Story Page

Goal: Tell the complete narrative

Create: /about/ or expand /work/

Sections:

  1. Four Generations (with timeline)
    • Great-grandfather → Grandfather → Father → You
    • Photos if available, illustrations if not
    • What each generation taught
    • How methods evolved
    • What stayed constant
  2. My Teaching Years (2015-2025)
    • Where you taught
    • What you taught
    • Key insights from classroom
    • Frustrations with available tools
    • Why you loved it, why you evolved
  3. Learning Spanish
    • Why Spanish?
    • The struggle (plateau at intermediate)
    • What existing apps missed
    • Building custom tools for practice
    • Progress to ACTFL Advanced
  4. The AI Turning Point
    • When you discovered Claude/GPT-4
    • Realization: “I can build adaptive tools now”
    • Learning to code (with AI assistance)
    • First projects
    • What worked, what failed
  5. Where I Am Now
    • 15 projects built
    • Still teaching (differently)
    • Educator identity + technical skills
    • What I’m building next
  6. What Drives Me
    • Continuing family legacy
    • Making learning tools that actually work
    • Empowering teachers with AI
    • Understanding pedagogy deeply, building practically

Deliverables:

  • Full narrative page
  • Timeline visual
  • Personal photos throughout
  • Link from homepage hero
  • 2000-3000 words

Month 4: Case Studies & Polish (Weeks 13-16)

Week 13: Case Study #2

Project: describe_it

Focus: Pedagogical approach

Sections:

  1. The Problem: Vocabulary plateau at intermediate
  2. Learning Theory: Varied output practice research
  3. Design Decisions: Why 5 styles? Why images?
  4. Technical Implementation: AI prompting strategies
  5. User Testing: What tutors said
  6. Impact: Quantified improvements
  7. Iterations: v1 → v2 → v3 changes
  8. What I’d Do Differently

Deliverables:

  • Full case study page
  • User testimonials
  • Before/after vocabulary data
  • Link from project card

Week 14: Case Study #3

Project: Internet Infrastructure Map

Focus: Data visualization & education

Sections:

  1. The Vision: Make invisible internet tangible
  2. Technical Challenge: 3D globe with real data
  3. Data Sources: Submarine cable datasets
  4. Three.js Implementation: Challenges & solutions
  5. Performance Optimization: Rendering 1000+ cables
  6. Educational Impact: What viewers learn
  7. Future Enhancements: Real-time traffic, AR version?

Deliverables:

  • Technical case study
  • Interactive demos embedded
  • Process GIFs showing development
  • Architecture documentation

Week 15: Design System Documentation

Goal: Professionalism and consistency

Create: /docs/design-system/ or style guide page

Document:

  • Color palette with use cases
  • Typography scale and pairings
  • Spacing system (8px grid)
  • Component library:
    • Buttons (all variants)
    • Cards (all types)
    • Forms
    • Navigation
    • Modals
    • Galleries
  • Responsive breakpoints
  • Accessibility guidelines
  • Code examples for each component

Deliverables:

  • Living style guide page
  • Component documentation
  • Design tokens clearly defined
  • Example of professionalism

Week 16: Performance Audit & Optimization

Goal: 95+ Lighthouse score

Tasks:

  • Run Lighthouse audit
  • Identify bottlenecks
  • Self-host fonts (remove Google Fonts)
  • Convert images to WebP
  • Implement responsive images
  • Generate critical CSS
  • Add service worker for offline
  • Optimize JavaScript bundle size
  • Lazy load below-fold content
  • Test on slow connections

Target metrics:

  • Performance: 95+
  • Accessibility: 100
  • Best Practices: 100
  • SEO: 100

Deliverables:

  • Lighthouse report showing 95+
  • Faster load times
  • Better mobile experience

Month 5: Community & Growth (Weeks 17-20)

Week 17: Third Blog Post (Educational)

Title: “The Fourth-Generation Educator’s Guide to AI in Teaching”

Outline:

  1. Four generations, four eras of teaching technology
  2. What AI changes fundamentally
  3. What stays the same (human connection, guidance)
  4. 5 principles for effective AI in education
  5. Common pitfalls to avoid
  6. Case studies from my tools
  7. Advice for educators exploring AI
  8. Resources for getting started

Promotion:

  • Submit to EdSurge
  • Share on education Twitter
  • Post to r/Teachers
  • LinkedIn article
  • Send to education newsletters

Goal: Establish educator credibility in AI space

Week 18: Conference Talk Proposal

Goal: Public speaking opportunity

Target conferences:

  • TESOL International Convention
  • IATEFL (International Association of Teachers of English as Foreign Language)
  • EdTech conferences
  • AI + Education summits

Proposed talk: “From Classroom to Code: Building AI Learning Tools with Pedagogical Expertise”

Outline:

  1. My teaching background
  2. The gap between ed tech and pedagogy
  3. Learning Spanish: student perspective
  4. Building 5 tools: what I learned
  5. Demos of actual tools
  6. Principles for AI in language learning
  7. Q&A

Deliverables:

  • Conference proposals submitted (3-5)
  • Slide deck drafted
  • Demo videos prepared

Week 19: Newsletter Launch (Optional)

Goal: Build audience

Setup:

  • Choose platform (Substack, ConvertKit, Buttondown)
  • Create landing page on portfolio
  • Design email template
  • Plan first 4 topics

Topics:

  • Pedagogy + AI insights
  • Project updates
  • Learning reflections
  • Tool recommendations for educators

Cadence: Monthly or bi-monthly

First issue: “Welcome: Why an Educator Builds AI Tools”

Deliverables:

  • Newsletter infrastructure ready
  • Landing page on portfolio
  • First issue published

Week 20: Networking & Outreach

Goal: Connect with education + AI community

Tasks:

  • Follow 20 educators using AI in teaching
  • Engage with their content thoughtfully
  • Share your blog posts in relevant communities
  • Reach out to 5 people for virtual coffee chats
  • Join education + AI Slack/Discord communities
  • Contribute to discussions with expertise

Targets:

  • Education Twitter
  • r/LanguageLearning
  • r/Teachers
  • EdTech LinkedIn groups
  • AI + Education communities

Deliverables:

  • 5 meaningful connections made
  • Visible presence in communities
  • Feedback on projects collected

Month 6: Expansion & Next Level (Weeks 21-24)

Week 21: Advanced Feature - User Accounts

Goal: Allow users to save progress

Choose one tool: describe_it or subjunctive-practice

Implement:

  • User authentication (Supabase Auth)
  • Progress tracking
  • Session history
  • Personal vocabulary lists
  • Settings preferences
  • Export data

Deliverables:

  • User accounts functional
  • Progress persistence works
  • Privacy policy added
  • Terms of service added

Week 22: Open Source One Project

Goal: Community contribution & visibility

Best candidate: describe_it or subjunctive-practice

Prepare:

  • Clean up code
  • Write comprehensive README
  • Add CONTRIBUTING.md
  • Create issue templates
  • Add license (MIT or similar)
  • Document API keys setup
  • Create demo video
  • Write “How to Deploy” guide

Launch:

  • Post to GitHub trending
  • Share on Product Hunt
  • Post to Hacker News
  • Write blog post about open sourcing
  • Promote in education communities

Deliverables:

  • One project fully open sourced
  • Documentation complete
  • Community can deploy it
  • Feedback loop established

Week 23: Video Content

Goal: Show personality, explain concepts

Create:

  1. Portfolio walkthrough (5-7 min)
    • Screen recording of site
    • Voiceover explaining projects
    • Personal story
    • Call to action
  2. Tool demo (3-5 min each, 3 tools)
    • describe_it in action
    • subjunctive-practice demo
    • Internet Infrastructure Map walkthrough
  3. “Day in the Life” (7-10 min)
    • Working on a project
    • Your process
    • Tools you use
    • Thought process

Platform: YouTube + embedded on portfolio

Deliverables:

  • 4-5 videos published
  • Embedded on relevant pages
  • Professional editing (basic)
  • Clear audio

Week 24: 6-Month Reflection & Planning

Goal: Assess progress, plan next phase

Retrospective:

  • What went well?
  • What didn’t work?
  • What did I learn?
  • What surprised me?
  • What would I do differently?

Metrics to review:

  • Portfolio visitors (if tracking)
  • Demo usage
  • GitHub stars/forks
  • Blog post engagement
  • Social media followers
  • Job inquiries / collaboration offers
  • Conference responses

Write: “6 Months Building in Public: What I Learned”

  • Blog post documenting journey
  • Honest about failures
  • Quantified results where possible
  • Lessons for others

Plan next 6 months:

  • What projects to focus on?
  • What content to create?
  • What skills to build?
  • What community to engage?

Deliverables:

  • Reflection blog post
  • Next 6-month roadmap
  • Clear goals and metrics

Success Milestones

Month 2 ✅

  • 7-8 live demos
  • Testimonials on 3+ projects
  • First case study published
  • 3-tier project system visible

Month 3 ✅

  • Blog infrastructure live
  • 2 blog posts published
  • Complete narrative/about page
  • Social media presence established

Month 4 ✅

  • 3 case studies complete
  • Design system documented
  • Lighthouse score 95+
  • Professional polish evident

Month 5 ✅

  • 3+ blog posts published
  • Conference talk submitted
  • Community presence established
  • Newsletter (optional) launched

Month 6 ✅

  • Advanced feature shipped
  • One project open sourced
  • Video content published
  • 6-month reflection complete

Long-Term Vision (Beyond 6 Months)

Year 1

  • Speaking: 3-5 conference talks delivered
  • Writing: 12-15 blog posts, possible book proposal
  • Projects: 3-5 with active user bases
  • Community: 1000+ newsletter subscribers
  • Impact: Measurable learning outcomes from tools

Year 2

  • Product: One tool becomes primary focus
  • Business: Sustainable revenue model (SaaS, consulting, courses)
  • Authority: Recognized voice in AI + education
  • Book: “The Educator’s Guide to Building AI Learning Tools” (maybe)
  • Company: Possible education AI startup

Year 5

  • Legacy: Continuing family teaching tradition with modern tools
  • Impact: 10,000+ learners using your tools
  • Influence: Shaping how AI is used in language education
  • Options: Product company, consultancy, academic role, or hybrid

Guiding Principles (Never Lose Sight Of)

1. Educator First

  • Always lead with teaching expertise
  • Projects informed by pedagogy, not tech trends
  • Solve real learning problems

2. Build in Public

  • Share progress, failures, learnings
  • Invite feedback and collaboration
  • Document the journey

3. Quality Over Quantity

  • Better to have 5 excellent projects than 15 mediocre
  • Depth more valuable than breadth
  • Focus on impact, not output

4. Real-World Impact

  • Users matter more than GitHub stars
  • Learning outcomes more important than features
  • Testimonials beat technical specs

5. Continuous Learning

  • You’re learning AI, coding, product, marketing
  • Embrace beginner mindset
  • Document what you learn

6. Sustainable Pace

  • 2-3 hours daily is better than weekend sprints
  • Avoid burnout
  • This is a marathon, not a sprint

Quarterly Reviews

Every 3 months, ask:

  1. Progress: What did I ship?
  2. Learning: What did I learn?
  3. Impact: Who did I help?
  4. Positioning: Is my message clearer?
  5. Goals: What’s next?

Adjust roadmap based on:

  • What’s working vs not
  • New opportunities
  • Energy and interest
  • Market feedback

Remember: Roadmaps are guides, not contracts.

Adjust as you learn.

The North Star

Your unique positioning: “Fourth-generation educator building AI tools informed by 100 years of teaching wisdom and modern pedagogical research.”

Every project, blog post, talk, and decision should reinforce this positioning.

If it doesn’t support this narrative, question whether it’s worth doing.

Stay focused. Stay authentic. Stay educator-first.

You’re not just building a portfolio. You’re building a body of work that matters.

Start with Month 1’s priority actions. The rest will follow.

You’ve got this. 🚀