AWS Cloud Engineer Career Transition Plan - Final Version

Executive Summary

Timeline: 56 weeks total with sustainable 25-hour weekly commitment
Investment: $600-800 with 80-90% success probability
Target: Mid-level Cloud Engineer ($120K-150K) transitioning to federal contractor opportunities

Phase 1: Foundation and re:Invent Preparation (Weeks 1-14)

AWS Solutions Architect Associate (Weeks 1-6)

September 19 - October 29, 2025

  • Already worked through Cantrill’s AWS SAA course with labs and extensive notes
  • Resources
    • Whizlabs Quizzes and Tests
    • Tutorial Dojo Study Guide, Videos, and Tests
    • Cantrill’s Tests
    • Sybex Study Guide with Quizzes
    • AI Generated Flash Cards and Study Guide
  • Days 1-10 (Sybex Phase):
    • Flashcards (15 New Daily)
    • Sybex chapter + quiz
    • Daily practice test or 2 quizzes
    • Review Tests/quizzes
  • Days 11-26 (Tutorial Dojo Phase):
    • Flashcards (review)
    • Tutorial Dojo study guide review (25 pages)/AI study guide
    • Tutorial Dojo videos (90 minutes)
    • Daily practice test
    • Review Tests
  • Target: Wednesday, October 25, 2025

Cloud Resume Challenge - re:Invent Demo Version (Weeks 7-11)

October 27 - November 29, 2025

Week 7: HTML/CSS development and S3 hosting setup + Python Programming for AWS with Boto3 (Neal Davis) course integration Week 8: Lambda function, DynamoDB, and API Gateway integration Week 9: Terraform infrastructure as code conversion + AWS SimuLearn: Serverless Foundations scenario
Week 10: Basic CI/CD pipeline and testing (Thanksgiving week - lighter schedule) + AWS SimuLearn: Single-Page App scenario
Week 11: Documentation, portfolio integration, and demonstration preparation

Target: Working demonstration ready for AWS re:Invent networking

AWS re:Invent Conference (Week 12)

December 1-5, 2025

Conference Objectives:

  • Network with Solutions Architects and federal contractors
  • Demonstrate working Cloud Resume project
  • Gather market intelligence and feedback
  • Build professional relationships for job search phase

Demo Strategy: 2-minute mobile demonstration of serverless visitor counter with architecture explanation

Security+ Certification (Weeks 13-14)

December 6-19, 2025

  • Week 13: Security fundamentals and risk management (25 hours)
  • Week 14: Implementation and exam preparation (25 hours)
  • Target: Friday, December 19, 2025

Phase 2: Project Development (Weeks 15-34)

Cloud Resume Challenge - Production Enhancement (Week 15)

December 20-26, 2025

Enhance re:Invent demo version based on conference feedback:

  • Advanced monitoring and alerting implementation
  • Security hardening and compliance validation
  • Performance optimization and testing
  • Comprehensive documentation and architecture decisions

Cruddur Social Media Platform (Weeks 16-30)

December 27, 2025 - April 10, 2026

Follow FreeCodeCamp 13-week bootcamp with 2-week buffer:

Weeks 16-17: Containerization and application foundations + AWS SimuLearn: Container Services scenario
Weeks 18-19: Distributed tracing, authentication, SQL implementation + AWS SimuLearn: Core Security Concepts scenario
Weeks 20-21: NoSQL, serverless containers, load balancing + AWS SimuLearn: Databases in Practice scenario
Weeks 22-23: CI/CD pipelines and infrastructure as code + AWS SimuLearn: Decoupling Applications scenario
Weeks 24-25: Advanced features and monitoring + AWS Solutions Architect: Designing a Three-Tier Web Architecture (4.5h course)
Weeks 26-27: Security implementation and compliance + AWS Solutions Architect: Designing a Compliant, Secure, and Governed Architecture (3.5h course)
Weeks 28-29: Performance optimization and testing + AWS SimuLearn: Connecting VPCs scenario
Weeks 30: Documentation and portfolio presentation

Enhanced Implementation Standards:

  • Comprehensive monitoring and alerting
  • Security scanning and compliance validation
  • Performance testing and optimization
  • Detailed operational procedures
  • Business impact documentation

Skills Gap Bridging (Weeks 31-34)

April 11 - May 8, 2026

Week 31: Linux for DevOps, Cloud, and SRE Engineers (Pravin Mishra) course completion + Java fundamentals and Spring Boot basics
Week 32: DevOps toolchain (Jenkins, SonarQube, GitLab CI)
Week 33: Terraform Associate 003 Hands-On Labs (Bryan Krausen) course completion + Advanced Terraform and container orchestration
Week 34: Portfolio refinement and presentation preparation

Phase 3: Job Search (Weeks 35-50)

May 9 - August 21, 2026

Application Strategy (Weeks 35-42)

Target Volume: 8-12 applications per week
Focus Areas:

  • Federal contractors (Huntsville, remote)
  • Mid-size companies (100-500 employees)
  • MSP-to-cloud transition opportunities

Weekly Schedule:

  • 15 hours: Job applications and networking
  • 10 hours: Interview preparation and skills maintenance
  • BeSA Interview Preparation: Watch “AWS Solutions Architect Interview Process” playlist (8 videos, 4.5 hours total) during Week 35-36

Network Development (Weeks 35-50)

Month 1: LinkedIn optimization, AWS community engagement + BeSA: “How to Transition from IT Roles to Cloud Architect?” (30 min)
Month 2: Local meetups, informational interviews
Month 3: Technical portfolio demonstrations + BeSA: “How to Run a Successful Workload Discovery Meeting?” (34 min)
Month 4: Offer management and negotiation

re:Invent Network Activation: Leverage contacts made during conference for referrals and opportunities

Interview Preparation

Technical Focus:

  • Architecture discussions with trade-off analysis
  • Troubleshooting scenarios and problem-solving
  • Portfolio project deep dives
  • MSP experience translation to cloud context

Phase 4: Advanced Development (Weeks 51-58)

August 22 - October 16, 2026

Continued Job Search + Advanced Skills

If Employed: Transition to role while completing advanced certifications
If Searching: Extended search with additional specialization

Advanced Certifications (choose one):

  • AWS Solutions Architect Professional
  • AWS Security Specialty
  • Terraform Associate

Investment Breakdown

Certification Costs

  • AWS SAA: $150
  • Security+: $370
  • Study materials: $400
  • Subtotal: $920

Infrastructure Costs

  • Domain and hosting: $100
  • AWS usage (8 months): $300
  • Development tools: $150
  • Subtotal: $550

Professional Development

  • Networking events: $300
  • Professional memberships: $200
  • Subtotal: $500

Total Investment: $1,970

Weekly Schedule Framework

Sustainable Learning Approach

Technical Learning Maximum: 25 hours/week (intensive cognitive work) Career Support Activities: 10-15 hours/week (networking, documentation, applications) Total Career-Related Time: 35-40 hours/week

Daily Structure Template

Morning Block (8:00 AM - 11:30 AM): 3.5 hours intensive technical work

  • 90 minutes: Core learning (AWS, coding, architecture)
  • 15-minute break
  • 90 minutes: Hands-on labs or project development
  • 30 minutes: Review and documentation

Afternoon Block (1:00 PM - 3:00 PM): 2 hours supplementary learning

  • Course videos, reading, or lighter technical content

Evening Block (5:00 PM - 6:30 PM): 1.5 hours career development

  • Networking, job applications, portfolio updates, planning

Phase-Specific Allocation

Weeks 1-14 (Certifications + re:Invent)

  • Technical Study: 25 hours
  • Career Development: 10 hours
  • Conference Preparation: 5 hours (Week 12)

Weeks 15-34 (Projects)

  • Development/Coding: 20 hours
  • Learning/Research: 5 hours
  • Documentation/Portfolio: 10 hours
  • Applications/Networking: 15 hours
  • Interview Preparation: 10 hours
  • Skills Maintenance: 10 hours

Success Metrics

Technical Milestones

  • Month 2: AWS SAA certification completion
  • Month 3: Working Cloud Resume for re:Invent demonstration
  • Month 4: Security+ certification completion
  • Month 8: Cruddur project completion
  • Month 14: Job search launch readiness

Market Response Targets

  • Application response rate: 30%+
  • Phone to technical interview: 50%+
  • Technical to offer conversion: 25%+
  • Starting salary: $120K-150K

Risk Management

Timeline Protection

  • Quality gates: No advancement until current phase complete
  • Extension triggers: Family emergencies, learning difficulties
  • Buffer weeks: Built into each major phase

Burnout Prevention

  • 25-hour weekly maximum with hard stops
  • Sunday rest: Absolute family time commitment
  • Monthly reviews: Progress assessment and plan adjustment

Financial Security

  • Emergency fund: Maintain 6-month expenses
  • Income continuity: Current work balance during transition
  • Investment limits: Stay within planned budget

Support Systems

Professional Network

  • AWS User Groups: Monthly participation
  • LinkedIn content: Weekly posts documenting progress
  • Mentorship: 2-3 professional relationships

Personal Support

  • Family communication: Regular updates on progress
  • Health maintenance: Exercise and stress management
  • Social connections: Maintain relationships outside tech

Learning Resources

  • Primary: FreeCodeCamp, AWS documentation
  • Secondary: Udemy courses, YouTube tutorials
  • Community: Reddit, Discord, AWS forums

Federal Contractor Positioning

Security Clearance Track

  • Security+ certification: Federal contractor requirement
  • Background preparation: Clean financial and legal history
  • Clearance application: Initiate after job offer

Market Research

  • Target companies: Research Huntsville area contractors
  • Skill alignment: Match portfolio to federal requirements
  • Networking: Connect with federal contractor employees

This plan balances realistic timelines with market opportunities, incorporating lessons from documented career change experiences while maintaining sustainable practices for long-term success.