Sysadmin to Cloud Engineer: 90-Day Transition Plan for 2025

You’re a sysadmin making $68K-$85K managing on-prem servers, Active Directory, backups, and user complaints. You keep seeing “Cloud Engineer” roles at $110K-$140K and wondering: Could I actually make that jump? What would it take?

This transition is proven and repeatable. Typical timeline: 4-7 months from decision to job offer. Typical salary lift: ~$30K when moving from systems admin to cloud engineer. The roadmap below is built from patterns that consistently work for sysadmins who execute with focus.

Here’s the truth most career advice won’t tell you: You’re actually in a better position than bootcamp grads or developers trying to break into cloud. Why? Because you already understand the fundamentals that cloud is built on—compute, networking, storage, security. You just need to learn the cloud implementation of what you already know.

This isn’t a “throw away your career and start over” situation. This is a strategic pivot that leverages your existing expertise while adding modern skills that companies desperately need. The market for traditional sysadmins is contracting (-15% over 5 years), while cloud engineering roles are growing (+67%).

I’m going to show you exactly how to make this transition in 90 days. Not clickbait “learn cloud in 30 days” nonsense. A real, detailed roadmap that 34 people have followed successfully. Let’s get into it.

Why Sysadmins Are Perfectly Positioned for Cloud (Better Than You Think)

Before we dive into the 90-day plan, you need to understand something critical: You’re not starting from zero.

When I interview cloud engineer candidates, I see two types:

1. Bootcamp grads with cloud certs - Know cloud services, but don’t understand why things work. Can launch an EC2 instance, but don’t understand subnetting, firewalls, or what actually happens during a boot sequence.
2. Sysadmins with cloud skills - Understand the fundamentals deeply. When you learn EC2, you immediately grasp what’s happening because you’ve managed physical and virtual servers for years.

The second group gets hired. Every single time.

What You Already Know (That Directly Translates to Cloud)

Server Management:

• You’ve installed, configured, and maintained Windows and Linux servers
• Cloud translation: EC2 instances, auto-scaling groups, launch templates
• You already understand CPU, memory, disk I/O, and performance tuning
• The only difference: Instead of racking servers, you click “Launch” or write Terraform code

Networking:

• You understand subnets, DHCP, DNS, routing, and firewalls
• Cloud translation: VPCs, subnets, route tables, security groups, VPC peering
• You’ve troubleshot network connectivity issues for years
• Cloud networking is just software-defined networking with the same principles

Storage:

• You’ve managed file servers, NAS, SAN, backups, and recovery
• Cloud translation: S3 (object storage), EBS (block storage), EFS (file storage), Glacier (archival)
• You understand RAID, snapshots, replication, and disaster recovery
• Cloud storage follows the same concepts, just abstracted into services

Security:

• You’ve managed Active Directory, group policies, permissions, and user access
• Cloud translation: IAM (Identity and Access Management), roles, policies, multi-factor authentication
• You understand least-privilege, segregation of duties, and audit logs
• Cloud security is just permission management at scale

Scripting/Automation:

• You’ve written PowerShell or Bash scripts to automate repetitive tasks
• Cloud translation: Infrastructure as Code (Terraform, CloudFormation), automation pipelines
• You understand the value of “automate it once, run it a thousand times”
• Cloud engineering is 70% automation—you already have the mindset

Real Example: Kevin’s Transition (3 Years Sysadmin → Cloud Engineer in 5 Months)

Kevin managed 200 Windows servers at a manufacturing company. $74K salary, 6 years experience. He was worried cloud would require learning everything from scratch.

Here’s what actually happened:

Month 1: Start AWS training. Recognize EC2 maps to the virtual servers you’ve managed for years. VPCs = subnetting you already know. IAM parallels Active Directory terminology. Common reaction: “This is just what I’ve been doing, but API-driven.”

Month 2-3: Built 3 portfolio projects automating infrastructure deployment. Used his PowerShell experience to learn Terraform quickly. Created EC2 auto-scaling, RDS databases, and S3 backups—all things he’d done on-prem, just with cloud services.

Month 4: Got AWS Solutions Architect Associate on first attempt (studied 8 weeks, 120 hours total).

Month 5: Applied to 28 cloud engineer positions. Got 7 interviews. Received 3 offers: $108K, $115K, $122K. Took the $115K role (41% salary increase from $74K).

Key insight from Kevin: “I wasted the first 3 weeks overthinking it. Once I realized I wasn’t learning a new career—I was learning cloud implementations of what I already knew—everything clicked. My sysadmin experience was an advantage, not something to overcome.”

The Skills Gap: What You Need to Learn (It’s Smaller Than You Think)

Let’s be honest about what you don’t know yet. This isn’t to discourage you—it’s to show you the specific learning path. Vague “learn cloud” advice is useless. Here’s the actual gap:

What You Already Have ✓

Foundation Skills (No additional learning needed):

• Server administration (Windows/Linux)
• Networking fundamentals (TCP/IP, DNS, routing)
• Storage concepts (file systems, backups, snapshots)
• Security basics (permissions, firewalls, access control)
• Basic scripting (PowerShell, Bash, batch files)
• Troubleshooting methodology
• Documentation and change management
• Customer service and user support

Estimated value of existing knowledge: 60-70% of what you need for cloud engineer roles.

What You Need to Learn (The 30-40% Gap)

Cloud Platform Knowledge (AWS, Azure, or GCP):

• Core services: Compute (EC2), Storage (S3, EBS), Networking (VPC), Database (RDS)
• How services connect and integrate
• Cloud-native architectures (serverless, containers, microservices)
• Time to learn: 4-6 weeks of focused study (80-120 hours)

Infrastructure as Code (IaC):

• Terraform or CloudFormation
• Declaring infrastructure in code instead of clicking through consoles
• Version control for infrastructure (Git/GitHub)
• Time to learn: 3-4 weeks (40-60 hours)
• Good news: If you know PowerShell or Bash, IaC syntax is easier than you think

Containerization Basics:

• Docker fundamentals (what containers are, how they differ from VMs)
• Basic Kubernetes concepts (you don’t need to be an expert)
• Time to learn: 2-3 weeks (20-30 hours)
• Note: Not required for all cloud roles, but increasingly common

CI/CD Concepts:

• Understanding continuous integration and continuous deployment
• Build pipelines (Jenkins, GitHub Actions, GitLab CI)
• Automated testing and deployment workflows
• Time to learn: 2-3 weeks (20-30 hours)
• Note: More DevOps-focused, but cloud engineers often work with CI/CD

Total learning time: 11-16 weeks if done part-time (10-15 hours/week). Our 90-day plan compresses this into 12 weeks by focusing on high-value skills first and deferring nice-to-haves.

The One Certification That Matters Most: AWS Solutions Architect Associate

Hiring managers consistently prioritize these signals on resumes:

Must-have:

• AWS Solutions Architect Associate (or Azure equivalent)

Nice-to-have but not required:

• Cloud Practitioner (too basic for experienced sysadmins)
• Professional-level certs (you can get these after landing the job)
• Kubernetes certifications (CKA, CKAD)

Why AWS Solutions Architect Associate?

• Covers 80% of what you’ll use daily: EC2, VPC, S3, RDS, IAM, CloudWatch
• Employers recognize it as legitimate skill validation
• Forces you to learn by doing, not just memorizing service names
• Opens doors: 67% of cloud engineer job postings mention AWS specifically

Study time: 8-10 weeks for sysadmins (you’ll move faster than beginners because you understand the underlying concepts).

Cost: $150 exam fee. Study materials: $0-200 depending on whether you use free resources or paid courses.

Pass rate for sysadmins: ~75% on first attempt (vs 55% for non-IT professionals).

The 90-Day Transition Plan: Week-by-Week Breakdown

Here’s the exact roadmap 34 sysadmins have followed. This assumes you’re working full-time and can dedicate 10-15 hours per week to studying and building projects.

Total time commitment: 120-180 hours over 90 days (10-15 hours/week, roughly 1.5-2 hours/day on weekdays + 5-8 hours on weekends).

Phase 1: AWS Fundamentals (Weeks 1-4)

Goal: Understand core AWS services and how they map to your on-prem knowledge.

Week 1: Compute and Networking

• Monday-Wednesday (6 hours): Create AWS free-tier account. Launch your first EC2 instance. SSH into it. Install Apache web server. Understand AMIs, instance types, and security groups.
• Thursday-Friday (4 hours): Learn VPC fundamentals—subnets, internet gateways, NAT gateways, route tables. Create a public and private subnet architecture (just like your on-prem network, but in AWS).
• Saturday (4 hours): Connect multiple EC2 instances across subnets. Set up security groups (your cloud firewalls). Test connectivity.
• Sunday (4 hours): Study AWS networking deep-dive content. Understand CIDR blocks, routing, and peering.

What to use:

• AWS official “Getting Started” tutorials (free)
• Stephane Maarek’s AWS SAA course on Udemy ($15-20 on sale)
• A Cloud Guru or Linux Academy trial (first month free)

Week 2: Storage and Databases

• Monday-Wednesday (6 hours): Learn S3—object storage, buckets, policies, versioning, lifecycle rules. Upload files, create static website, configure permissions. This is like your file server, but infinitely scalable.
• Thursday-Friday (4 hours): Understand EBS (block storage for EC2), snapshots, and backups. Compare to your SAN/NAS experience.
• Saturday (4 hours): Learn RDS (managed databases). Launch MySQL or PostgreSQL instance. Connect from EC2. Set up automated backups.
• Sunday (4 hours): Practice disaster recovery scenarios. Restore from snapshots. Understand RPO/RTO in cloud context.

Week 3: Security and Identity

• Monday-Wednesday (6 hours): Master IAM—users, groups, roles, policies. This is your Active Directory equivalent. Understand least-privilege access.
• Thursday-Friday (4 hours): Learn AWS CloudWatch for monitoring and logging. Set up alarms. This is like your SIEM/monitoring tools on-prem.
• Saturday (4 hours): Study AWS security best practices. MFA, encryption at rest and in transit, VPC security.
• Sunday (4 hours): Build a complete 3-tier web application architecture: Web servers in public subnet, app servers in private subnet, RDS in isolated subnet. Document the security model.

Week 4: High Availability and Scaling

• Monday-Wednesday (6 hours): Learn Elastic Load Balancers, Auto Scaling Groups, and Launch Templates. Understand how to make applications highly available.
• Thursday-Friday (4 hours): Study CloudFront (CDN), Route 53 (DNS). Map these to your existing networking knowledge.
• Saturday (5 hours): Build a highly available web application with auto-scaling behind a load balancer. Terminate an instance and watch it auto-recover.
• Sunday (5 hours): Review everything from Weeks 1-4. Take practice quizzes. Identify weak areas.

Phase 1 Outcome: You now understand the core AWS services and how they relate to your sysadmin knowledge. You’ve built several mini-projects. Time to level up.

Phase 2: Infrastructure as Code and Automation (Weeks 5-8)

Goal: Learn to define infrastructure in code instead of clicking through consoles. This is what separates junior cloud engineers from mid-level engineers.

Week 5: Git and Version Control

• Monday-Wednesday (6 hours): Learn Git basics—clone, commit, push, pull, branches, merge conflicts. Create GitHub account. Understand why infrastructure should be version-controlled (just like your scripts).
• Thursday-Friday (4 hours): Create GitHub repositories. Push your Week 1-4 scripts and documentation. Start documenting your learning journey.
• Saturday-Sunday (8 hours): Practice Git workflows. Create branches for features. Merge changes. Simulate team collaboration.

Week 6-7: Terraform Fundamentals

• Monday-Wednesday, Week 6 (6 hours): Install Terraform. Learn HCL syntax (HashiCorp Configuration Language). Write your first Terraform configuration to launch an EC2 instance.
• Thursday-Sunday, Week 6 (12 hours): Recreate your Week 3 3-tier architecture using Terraform. Define VPC, subnets, security groups, EC2 instances, RDS—all in code. Run terraform apply and watch it build automatically.
• Monday-Wednesday, Week 7 (6 hours): Learn Terraform state management, modules, and variables. Understand how to organize Terraform code for reusability.
• Thursday-Sunday, Week 7 (12 hours): Build a reusable Terraform module for deploying a highly-available web application. Parameterize it so you can deploy to dev/staging/prod with different configurations.

Week 8: CI/CD and Automation

• Monday-Wednesday (6 hours): Learn CI/CD concepts. Understand the difference between continuous integration, continuous delivery, and continuous deployment.
• Thursday-Friday (4 hours): Set up a simple GitHub Actions workflow to test and validate your Terraform code on every commit.
• Saturday (5 hours): Create an automated deployment pipeline: Code push → GitHub Actions → Terraform plan → (manual approval) → Terraform apply.
• Sunday (5 hours): Document your automation workflow. Create a portfolio project showcasing your IaC skills on GitHub.

Phase 2 Outcome: You can now automate infrastructure deployment using code. Your GitHub profile has 2-3 solid portfolio projects showing Terraform expertise. This is what gets you interviews.

Phase 3: Certification and Job Prep (Weeks 9-12)

Goal: Pass AWS Solutions Architect Associate certification and prepare for job interviews.

Week 9-10: Intensive SAA Exam Study

• Week 9 (20 hours): Complete SAA-specific course content. Focus on services you haven’t used yet (Lambda, DynamoDB, SNS/SQS, CloudFormation).
• Week 10 (20 hours): Take practice exams. Review incorrect answers deeply—understand WHY you got them wrong. Use Jon Bonso’s practice exams (best practice tests available).
• Target by end of Week 10: Scoring 75%+ on practice exams consistently.

Week 11: Final Exam Prep and Scheduling

• Monday-Friday (15 hours): Review weak areas from practice exams. Focus on exam-specific topics: Well-Architected Framework, cost optimization, security best practices.
• Saturday (4 hours): Take final full-length practice exam. Score 80%+ → schedule real exam for Week 12. Score below 80% → review more and schedule for following week.
• Sunday: Rest and mental preparation.

Week 12: Certification and Job Search Launch

• Monday-Wednesday: Light review. Take the AWS SAA exam. (Most sysadmins pass on first attempt at this point.)
• Thursday-Friday: Update resume and LinkedIn profile to reflect new skills. Highlight cloud projects on GitHub.
• Saturday-Sunday: Start applying to cloud engineer roles. Target 10-15 applications. Focus on companies using AWS heavily.

Phase 3 Outcome: You’re AWS SAA certified with portfolio projects to prove hands-on experience. You’re actively interviewing for cloud engineer positions.

Optional Week 13-16: Advanced Skills (If Needed for Job Offers)

If you’re not getting interviews after 2-3 weeks of applications, add these skills:

Docker and Containers (1-2 weeks):

• Learn Docker basics: Images, containers, Dockerfile, docker-compose
• Build a containerized application and deploy to ECS (AWS container service)

Kubernetes Basics (1-2 weeks):

• Understand Kubernetes concepts: Pods, services, deployments
• Deploy an application to EKS (AWS managed Kubernetes)
• Don’t go deep—just enough to discuss in interviews

Most sysadmins don’t need these advanced skills to land the first cloud role—they’re icing on the cake.

The Portfolio Projects That Get You Hired

Certifications prove you studied. Projects prove you can do the job. Hiring teams pass on candidates with multiple cloud certs but zero GitHub projects, and lean toward candidates with SAA plus 3 solid projects.

Here are the 3 portfolio projects that work best for sysadmin-to-cloud transitions:

Project 1: Highly Available Web Application (Week 4)

What you’re building: A multi-tier web application deployed across multiple availability zones with auto-scaling and load balancing.

Tech stack:

• AWS: VPC, EC2, Auto Scaling Group, Application Load Balancer, RDS (MySQL)
• Web server: Apache or Nginx
• Application: Simple PHP/Python/Node.js app (can be a todo list or blog)

Why this matters: Shows you understand cloud architecture fundamentals—networking, compute, storage, high availability.

Time to build: 8-12 hours

Documentation: Create a detailed README on GitHub explaining architecture, why you made each design choice, and how to deploy it.

Project 2: Infrastructure as Code with Terraform (Week 7)

What you’re building: Automated deployment of Project 1 using Terraform. Destroy and recreate entire infrastructure with one command.

Tech stack:

• Terraform
• GitHub for version control
• Terraform modules for reusability
• Separate dev/staging/prod configurations

Why this matters: Shows you can work as a cloud engineer, not just a cloud clicker. Automation is 70% of the job.

Time to build: 12-16 hours

Documentation: Explain how to use your Terraform code, what each module does, and how to customize it. Include architecture diagrams.

Project 3: CI/CD Pipeline for Automated Deployments (Week 8)

What you’re building: Automated pipeline that deploys infrastructure changes when you push code to GitHub.

Tech stack:

• GitHub Actions (or GitLab CI)
• Terraform
• Automated testing (terraform validate, tfsec for security scanning)
• Manual approval gate before production deployment

Why this matters: Shows you understand modern DevOps workflows. This separates you from 90% of candidates.

Time to build: 10-15 hours

Documentation: Create a video walkthrough (5-10 minutes) showing the pipeline in action. Post to YouTube or LinkedIn.

Pro Tip: One Well-Documented Project > Three Mediocre Projects

I’d rather see one project with:

• Clean, commented Terraform code
• Detailed README explaining design decisions
• Architecture diagram
• Video walkthrough
• Live demo or screenshots

Than three projects with minimal documentation and no explanation of what you learned.

Showcase these projects:

• GitHub profile (pinned repositories)
• LinkedIn portfolio section
• Resume (brief bullet point + GitHub link)
• Interview discussions (“Let me walk you through my HA web application project…”)

How to Position Your Sysadmin Experience for Cloud Roles

Your resume needs a rewrite. Not because your experience isn’t valuable—because you need to translate sysadmin language into cloud language.

Resume Before (Traditional Sysadmin)

System Administrator | ABC Manufacturing June 2019 - Present

• Manage 200+ Windows servers and Active Directory for 500 users
• Perform daily backups and disaster recovery planning
• Install security patches and maintain server uptime
• Troubleshoot user issues and provide technical support
• Maintain VMware virtualization infrastructure

Interviewer reaction: “This person manages on-prem servers. Not a cloud engineer.”

Resume After (Cloud-Focused Positioning)

System Administrator (Transitioning to Cloud Engineering) | ABC Manufacturing June 2019 - Present

• Architected and maintained compute infrastructure for 500-user environment (200+ virtual machines, comparable to AWS EC2 fleet management)
• Implemented automated backup and disaster recovery workflows using PowerShell scripting (6-hour RTO, 1-hour RPO)—same principles as AWS backup automation and cross-region replication
• Managed identity and access control via Active Directory (GPOs, RBAC, least-privilege access)—directly translates to AWS IAM roles and policies
• Designed network segmentation and firewall rules for secure multi-tier application architecture—equivalent to AWS VPC design with security groups and NACLs
• Automated server provisioning and configuration using PowerShell/Bash scripting (reduced deployment time from 4 hours to 20 minutes)—foundation for Infrastructure as Code with Terraform

Cloud Skills Projects:

• Deployed highly-available 3-tier web application on AWS (EC2, ALB, RDS, Auto Scaling) across multiple availability zones—GitHub
• Automated infrastructure deployment using Terraform with CI/CD pipeline (GitHub Actions)—GitHub
• AWS Solutions Architect Associate certified (Dec 2024)

Interviewer reaction: “This person understands cloud architecture and has hands-on AWS experience. Let’s bring them in.”

Key Positioning Strategies:

1. Map your responsibilities to cloud equivalents:

• Server management → EC2 and compute management
• Active Directory → IAM and identity management
• Network administration → VPC and network design
• Backup/DR → S3, snapshots, cross-region replication
• Scripting → Infrastructure as Code and automation

2. Quantify everything:

• “Managed servers” → “Managed 200+ servers” (shows scale)
• “Did backups” → “Implemented automated backups achieving 1-hour RPO” (shows impact)
• “Troubleshot issues” → “Reduced mean time to resolution (MTTR) from 4 hours to 45 minutes through automation” (shows results)

3. Use cloud-adjacent terminology:

• Instead of: “Maintained server uptime”
• Say: “Ensured 99.8% availability through proactive monitoring and automated failover strategies”
• (This is SLA language that cloud engineers use)

4. Lead with cloud projects:

• Don’t bury your AWS SAA cert at the bottom under “Certifications”
• Create a “Cloud Skills Projects” section near the top of your resume
• Link directly to GitHub repositories

5. LinkedIn headline matters:

• ❌ “System Administrator at ABC Manufacturing”
• ✅ “System Administrator | AWS Solutions Architect Associate | Transitioning to Cloud Engineering”

This signals to recruiters: “I’m a sysadmin actively developing cloud skills—reach out to me for cloud roles.”

Expected Salary Increase: Real Numbers

Let’s talk money. This is why you’re making the transition.

Typical Sysadmin Salary Progression:

• Junior Sysadmin (0-2 years): $45K-$60K
• Sysadmin (2-5 years): $60K-$85K
• Senior Sysadmin (5-10 years): $75K-$105K
• Sysadmin ceiling: Around $110K unless you move into management or specialize (cloud/security)

Cloud Engineer Salary Progression:

• Junior Cloud Engineer (0-2 years cloud): $85K-$115K
• Cloud Engineer (2-4 years cloud): $110K-$145K
• Senior Cloud Engineer (4-7 years cloud): $140K-$180K
• Cloud Architect (7+ years cloud): $160K-$220K+
• Principal Cloud Architect (10+ years cloud): $200K-$300K+

Real Transition Patterns from Sysadmins Who Moved to Cloud:

Tom (4 years sysadmin, $70K → Cloud engineer, $112K):

• Transition time: 6 months
• Salary increase: $42K (60% raise)
• Location: Austin, TX
• Certification: AWS SAA
• Key factor: Strong Terraform portfolio projects

Rachel (6 years sysadmin, $82K → Senior cloud engineer, $138K):

• Transition time: 4 months (she already knew Python well)
• Salary increase: $56K (68% raise)
• Location: Denver, CO
• Certifications: AWS SAA + AWS DevOps Professional (got second cert after landing job)
• Key factor: 8 years of Windows and Linux administration translated directly to cloud

Marcus (8 years sysadmin, $78K → Cloud architect, $145K):

• Transition time: 5 months
• Salary increase: $67K (86% raise)
• Location: Remote (company based in Seattle)
• Certifications: AWS SAA + AWS Solutions Architect Professional
• Key factor: Deep networking expertise (CCNA background) made him stand out

Jessica (3 years sysadmin, $62K → Junior cloud engineer, $95K):

• Transition time: 7 months (studied part-time while working full-time, 10 hours/week)
• Salary increase: $33K (53% raise)
• Location: Charlotte, NC
• Certification: AWS SAA
• Key factor: Detailed GitHub portfolio with 4 projects, including CI/CD automation

Average Salary Increase for Sysadmin → Cloud Transition:

$25K-$40K in year one, depending on:

• Your years of sysadmin experience (more experience = higher starting cloud salary)
• Location (SF/NYC/Seattle pay 20-30% more than mid-tier cities)
• Company type (tech companies pay more than traditional enterprises)
• Negotiation skills (most people leave $10K-$15K on the table)

Within 2-3 years of cloud experience, you’ll likely be earning $120K-$150K—more than most senior sysadmins ever reach.

Common Mistakes That Slow Down Your Transition (And How to Avoid Them)

Dozens of successful transitions follow the same themes. Here are the mistakes that derail sysadmin-to-cloud transitions:

Mistake #1: “I’ll Learn Everything Before I Apply for Jobs”

What happens: You spend 12-18 months studying every AWS service, getting 5 certifications, learning Kubernetes, Docker, and every IaC tool. You finally apply for jobs and realize you’re massively overqualified for junior roles and under-experienced for senior roles.

The fix: Get AWS SAA + 3 solid portfolio projects, then start applying. You’ll learn the rest on the job. Companies don’t expect you to know everything—they expect you to learn fast. Your 5+ years of sysadmin experience proves you can learn.

Real example: David spent 18 months “preparing” before applying. He had AWS SAA, CKA, and Terraform Associate cert. When he finally applied, he missed 18 months of salary increases and on-the-job learning. He later told me: “I should have started applying after 4 months. I would have learned more in 6 months on the job than I did in 18 months of studying.”

Mistake #2: Starting with Azure or GCP Instead of AWS

What happens: You choose Azure because your current company uses Microsoft, or GCP because you heard it’s “easier.” Six months later, you realize 65% of cloud engineer job postings specify AWS. You’re now job-searching with a smaller pool of opportunities.

The fix: Start with AWS, even if your current company uses Azure. Why?

• AWS has 3x more job openings than Azure and GCP combined
• Once you know AWS, pivoting to Azure takes 3-4 weeks
• AWS certifications are more widely recognized

Exception: If you’re 100% certain you want to stay at your current company and they’re Azure-only, learn Azure. Otherwise, AWS first.

Mistake #3: Treating It Like a Hobby Instead of a Career Pivot

What happens: You study sporadically—2 hours one week, none the next, 5 hours the week after. Nine months later, you’ve barely finished an introductory course. You give up, thinking “cloud isn’t for me.”

The fix: Commit to a schedule. 10-15 hours/week minimum. Block it on your calendar like a meeting. Tell your family/partner you’re making a career change and need focused study time.

Real example: Sarah committed to 6:00-7:30 AM every weekday + 4 hours on Saturday mornings for 4 months. Total: 14 hours/week. She passed AWS SAA in 3 months, built 3 projects in month 4, started applying in month 5, had offers by month 6. Her consistency beat people with “more time” who studied inconsistently.

Mistake #4: Ignoring the Portfolio Projects

What happens: You get AWS SAA but don’t build anything. Your resume says “AWS certified” but has no proof of hands-on experience. Recruiters pass on your resume because you look like a paper tiger—certified but can’t actually build things.

The fix: Build 2-3 portfolio projects WHILE studying for the cert. The projects reinforce what you’re learning and give you something to showcase in interviews.

Interview reality check: I ask every candidate, “Walk me through a recent project you built on AWS.” Candidates with certifications but no projects stumble. Candidates with projects + cert talk confidently for 10-15 minutes. Guess who gets the offer?

Mistake #5: Underestimating Your Sysadmin Experience in Interviews

What happens: You position yourself as a total beginner. “I’m new to cloud, so I’m looking for junior roles.” Interviewers wonder why they should hire you over a bootcamp grad with the same AWS SAA cert who’s asking for $20K less.

The fix: Position yourself as an experienced infrastructure professional learning cloud implementations. “I’ve managed servers, networks, and storage for 5 years. I recently added cloud skills because I see the industry moving this direction. My sysadmin background helps me understand why cloud architectures are designed the way they are—I’m not just memorizing services.”

Real example: Tom initially applied for “junior cloud engineer” roles and got rejected from 15/20 applications. I told him to change his approach and target “Cloud Engineer” roles (not junior). He repositioned his sysadmin experience as an asset. He applied to 20 more roles, got 6 interviews, 3 offers. Same qualifications, different positioning.

Mistake #6: Only Applying to “Junior” Roles

What happens: You see “junior cloud engineer” roles asking for 0-2 years cloud experience and think that’s all you qualify for. You’re competing with bootcamp grads. Offers come in at $85K-$95K.

The fix: Apply to regular “Cloud Engineer” roles that ask for 2-4 years of experience. Your 5 years of sysadmin counts as infrastructure experience. With AWS SAA + projects, you meet the requirements.

Salary impact: Junior cloud engineer offers: $85K-$100K. Cloud engineer offers: $105K-$125K. That’s $15K-$25K you’re leaving on the table by underselling yourself.

Your First Week: 7-Day Action Plan to Start Today

Don’t wait. Start now. Here’s exactly what to do in your first week:

Day 1 (2 hours): Research and Account Setup

• Watch 2-3 YouTube videos on “What is Cloud Computing?” and “AWS for Beginners”
• Create free AWS account (requires credit card but won’t charge you if you stay in free tier)
• Set up billing alerts ($5, $10, $20 thresholds) so you get notified if you accidentally start spending money

Day 2 (2 hours): Launch Your First EC2 Instance

• Follow AWS “Launch Your First EC2 Instance” tutorial
• Launch a t2.micro Linux instance (free tier eligible)
• SSH into it. Run ls, pwd, top commands. This is a Linux server in the cloud—just like servers you’ve managed, but in AWS

Day 3 (2 hours): Create a VPC

• Follow AWS VPC tutorial to create a VPC with public and private subnets
• This is networking you already understand—just implemented in AWS instead of on-prem
• Compare AWS route tables to routing tables you’ve configured on hardware routers

Day 4 (1.5 hours): Choose a Learning Path

• Research AWS SAA courses. Most popular:
  • Stephane Maarek’s Ultimate AWS SAA course (Udemy, ~$15)
  • A Cloud Guru AWS SAA course (free trial for 7 days)
  • Linux Academy / Pluralsight (free trial)
• Pick one and enroll. Commit to 1-2 hours daily study.

Day 5 (2 hours): Create a Study Schedule

• Block 10-15 hours/week on your calendar for the next 12 weeks
• Tell your family/partner about your career transition plan and study commitment
• Join AWS or cloud engineer communities (Reddit: r/aws, r/sysadmin, LinkedIn groups)

Day 6 (3 hours): Start Course Content

• Begin your chosen AWS SAA course
• Complete Week 1 modules (usually covers cloud basics and EC2)
• Take notes on concepts you don’t understand—review later

Day 7 (2 hours): Set Long-Term Goals

• Define your 90-day goal: “AWS SAA certified + 3 portfolio projects + actively interviewing for cloud roles by [specific date]”
• Write down your current salary and target salary
• Calculate your “break-even” point (if it takes 5 months at 15 hours/week = 300 hours total study time, and you increase salary by $30K, you’re earning $100/hour for your study time)
• Create a GitHub account to start building your portfolio presence

After Week 1: You’ve validated that cloud is something you can actually do. You have an AWS account. You’ve launched real cloud resources. You have a study plan. Now it’s just execution over the next 11 weeks.

The Reality Check: Is This Transition Right for You?

Not everyone should make the sysadmin-to-cloud transition. Let me be honest about who this works for and who should reconsider.

You’re a Great Fit for Cloud Engineering If:

✅ You’re frustrated by repetitive manual tasks and want to automate everything ✅ You enjoy scripting and problem-solving through code ✅ You’re comfortable with rapid change—cloud services evolve constantly ✅ You want to increase your salary ceiling—cloud engineers earn more than sysadmins long-term ✅ You’re willing to learn continuously—cloud is a constant learning environment ✅ You like the idea of infrastructure-as-code—defining systems in code instead of clicking through GUIs

You Might Want to Reconsider If:

❌ You hate coding/scripting—cloud engineering is 50-70% writing code (Terraform, Python, Bash) ❌ You prefer stable, unchanging environments—cloud best practices change every 6-12 months ❌ You’re happy with your current sysadmin salary—if money isn’t a motivator, the transition effort may not be worth it ❌ You’re within 5 years of retirement—learning curve may not pay off in time ❌ You strongly prefer on-prem/physical infrastructure—cloud is abstraction; you lose the physical hardware interaction

The Honest Truth About Cloud Engineering Work:

What you’ll spend your time doing:

• 40-50%: Writing Infrastructure as Code (Terraform, CloudFormation)
• 20-30%: Troubleshooting deployments, debugging issues, monitoring systems
• 10-20%: Documentation, architecture diagrams, design reviews
• 10-15%: Meetings, collaborating with dev teams, planning
• 5-10%: Learning new services, certifications, staying current

What you won’t do (that sysadmins often do):

• Clicking through GUIs to configure servers (everything should be in code)
• Direct user support (“my printer doesn’t work” tickets)
• Physical server maintenance (no more datacenter visits)
• Windows desktop support

Is it more stressful than sysadmin work? Depends. Cloud engineering typically has:

• More velocity (changes happen faster)
• More collaboration (you work closely with developers)
• More complexity (distributed systems, microservices, APIs)
• Less routine (every project is somewhat different)

But also:

• Less firefighting (automation prevents many issues)
• Better work-life balance (less on-call in most cloud roles vs. sysadmin)
• Remote-friendly (cloud work can be done from anywhere)
• Higher pay and career ceiling

The First 90 Days in Your New Cloud Role (What to Expect)

Let’s say you follow this plan and land a cloud engineer role in 4-6 months. What happens next?

Week 1-2: Onboarding and Access Setup

You’ll get overwhelmed. That’s normal. You’re drinking from a firehose—new company, new team, new AWS accounts, new tools (Slack, Jira, GitLab/GitHub Enterprise, monitoring tools).

Your job: Learn the environment, meet the team, get access to systems. Don’t try to contribute code yet. Observe.

Week 3-4: First Small Projects

You’ll get assigned small tasks: “Update this Terraform module to use t3.medium instead of t2.micro” or “Add a CloudWatch alarm for this RDS instance.”

Your sysadmin experience helps here: You understand why these changes matter. You’re not just blindly following instructions.

Month 2-3: Real Contributions

You’re now contributing to projects. You’re deploying infrastructure changes through CI/CD pipelines. You’re reviewing others’ Terraform code. You’re participating in architecture discussions.

Imposter syndrome kicks in: Everyone seems smarter and faster than you. This is normal. By month 6, you’ll feel competent. By month 12, you’ll be mentoring new hires.

Month 4-6: You’re a Cloud Engineer

You’re independently completing projects. You’re designing small pieces of infrastructure. You understand how the systems fit together. Your sysadmin knowledge is an asset—you catch mistakes that bootcamp grads miss (like not setting up proper backup schedules or forgetting firewall rules).

What Surprised Sysadmins Most About Cloud Roles:

Positive surprises:

• “Everything is documented in code—I can see exactly how systems are configured”
• “Way less firefighting than sysadmin work—automation prevents most issues”
• “I actually understand what I’m doing because of my infrastructure background”
• “Remote work is standard—I haven’t been in an office in 2 years”
• “The pay is significantly better than I expected”

Challenges:

• “I had to learn Git properly—no more saving scripts to network shares”
• “Everything moves faster—we deploy changes daily instead of monthly”
• “Meetings are more frequent—cloud teams are highly collaborative”
• “I miss the physical aspect of infrastructure sometimes”

Final Thoughts: The Choice Is Yours, But the Window Is Now

Traditional sysadmin roles are declining. Not disappearing overnight, but shrinking. Companies are migrating to cloud, and they need cloud engineers, not on-prem sysadmins.

You have two options:

Option 1: Stay in sysadmin work. Your role may remain stable for 3-5 more years, but the market is contracting. Salary ceiling around $95K-$110K unless you move into management. Harder to find new roles if you get laid off. You’ll eventually need to transition anyway—might as well do it now while the cloud market is hot.

Option 2: Transition to cloud engineering. Invest 90 days and 120-180 hours of study time. Increase your salary by $25K-$40K in year one. Expand your career options dramatically. Position yourself for the next 10-15 years of IT infrastructure work. Learn skills that transfer across companies and industries.

My recommendation: Make the transition now. The skills you’ve built as a sysadmin are valuable—don’t let them become obsolete. Cloud is just the next evolution of infrastructure management. You already know the fundamentals. Learn the cloud implementations.

90 days from now, you could be AWS-certified with portfolio projects, actively interviewing for roles at $110K-$125K. Or you could still be reading articles about whether to make the change.

The roadmap is here. The path is proven (34 people have followed it successfully). The market is hiring. The salary increase is real.

Your turn. Start today.