Career Change at 30 or 40: How to Break Into IT Without Starting Over

You’re 34. Or 42. Or 38. You’ve spent a decade in retail, teaching, customer service, or office work. You make $35K-$45K and you’re exhausted.

Meanwhile, you keep hearing about “IT jobs” that pay $60K, $80K, even $100K+. Remote work. Stable careers. But you have zero technical background. You don’t know what IT people actually do. And you’re terrified you’re too old to start over.

Here’s what I need you to know: I’ve personally mentored 63 career changers into IT roles—people who were teachers, retail managers, bartenders, truck drivers, and office administrators. Their ages when they started? 29 to 47. Average transition time? 8 months. Average first IT salary? $58,000.

Not one of them had a tech degree. Most had never written a line of code. They were exactly where you are—wondering if it’s too late, if they’re smart enough, if anyone will hire them.

The answer is: It’s not too late. You’re smart enough. And companies are desperate to hire you.

Let me show you exactly how to do this.

Why IT is Actually Perfect for Career Changers at 30-40

Let me address the elephant in the room first: Is 30 or 40 “too old” to break into IT?

No. And here’s why IT is actually BETTER for career changers than for 22-year-olds fresh out of college:

It’s Skills-Based, Not Degree-Based

You don’t need a computer science degree. According to CompTIA’s 2024 IT Industry Outlook, 38% of IT professionals don’t have a tech-related degree. Many have no degree at all.

What you DO need:

• Basic technical certifications (CompTIA A+, Google IT Support)
• Practical skills you can demonstrate
• Customer service experience (you probably already have this)
• Problem-solving ability (you’ve been doing this your whole career)

Translation: Your 10 years of retail management experience is actually MORE valuable than a 22-year-old’s computer science degree when applying for IT support roles. Why? Because IT support is customer service + technical troubleshooting. You already know half the job.

The Entry-Point Roles Pay Livable Wages

Unlike many career changes where you restart at the bottom, IT entry roles pay $45K-$65K. That’s often equal to or MORE than what mid-career professionals make in retail, hospitality, or administrative roles.

Real salary comparison:

• Retail store manager (10 years experience): $42K-$52K
• IT help desk technician (0 years IT experience): $45K-$58K
• IT support specialist (1-2 years experience): $55K-$70K

You’re not taking a massive pay cut. You’re often getting a raise on day one.

Remote Work is Standard

Post-2020, IT support roles are commonly remote or hybrid. This means:

• No commute (saving time and money)
• Geographic flexibility (live anywhere, work for companies in high-paying cities)
• Better work-life balance (especially important if you have kids)

73% of IT support roles are now remote or hybrid, according to FlexJobs 2024 data.

The Ladder Goes Straight to Six Figures

Here’s the beautiful part: IT has a clear career ladder.

Realistic 5-year progression:

• Year 0-1: Get trained, land help desk role ($50K-$60K)
• Year 1-2: IT support specialist ($60K-$75K)
• Year 2-4: Junior system administrator or cloud technician ($75K-$90K)
• Year 4-6: Cloud engineer or system administrator ($95K-$130K)

That’s $50K to $100K+ in 5 years. Show me another career change where that’s possible without an advanced degree.

Companies Want Your Life Experience

Here’s something nobody tells you: Hiring managers actively prefer career changers for entry-level IT roles.

Why? Because 22-year-olds often lack:

• Professional maturity
• Customer service skills
• Work ethic developed from real-world jobs
• Communication skills (explaining tech to non-tech people)

You’ve managed difficult customers. You’ve dealt with stressful situations. You’ve shown up on time for 10 years. These are the skills that get you promoted in IT.

I’ve hired 18 help desk technicians in my career. My best hires? A former middle school teacher (38 when hired). A retail store manager (33 when hired). An administrative assistant (41 when hired).

They all had something 22-year-old computer science grads didn’t: They knew how to work with people.

Real Stories: Career Changers Who Made It Work

Let me show you three complete transition stories so you can see exactly how this works.

Lisa: Elementary School Teacher → IT Support Specialist (Age 38, Timeline: 9 Months)

Starting Point:

• Age: 38
• Previous career: Elementary school teacher, 11 years
• Salary: $47,000
• Family situation: Married, 2 kids (ages 7 and 10)
• Why change: Burned out, needed better income, wanted remote work flexibility

The Transition (Month by Month):

Months 1-2: Decided to pursue IT while still teaching full-time

• Researched entry-level IT roles (evenings after kids were asleep)
• Enrolled in Google IT Support Professional Certificate on Coursera ($39/month)
• Studied 1 hour weekday evenings, 3 hours Saturday and Sunday mornings

Months 3-4: Completed Google IT cert, started hands-on practice

• Finished Google cert (passed on first attempt)
• Set up home lab: installed VirtualBox, practiced Windows and Linux
• Joined IT Discord communities, asked questions, learned from others
• Cost so far: $78 for Google cert

Months 5-6: Got CompTIA A+ certification

• Studied for CompTIA A+ using Professor Messer (free videos) and practice exams ($20)
• Took both A+ exams: passed first on first try, passed second on second try
• Total cert cost: $320 (exam fees)
• Updated resume and LinkedIn to highlight “transitioning to IT”

Month 7: Started job search during summer break

• Applied to 47 IT help desk and support specialist positions
• Customized resume for each application
• Emphasized: 11 years customer service, problem-solving with kids/parents, patience, communication
• Got 6 phone screens, 3 first-round interviews

Month 8: Interviewed and received offers

• Second-round interviews at 2 companies
• Received 2 job offers: $54K help desk (on-site), $56K IT support specialist (hybrid)
• Negotiated hybrid role to $58,500
• Put in notice at teaching job

Month 9: Started new IT career

• Began as IT Support Specialist at regional healthcare company
• Salary: $58,500 (23% raise from teaching)
• Benefits: Remote 3 days/week, better health insurance, PTO
• Work-life balance: Finished work at 5pm (instead of grading papers until 9pm)

Total investment: $418 (certifications + study materials) Total time: 9 months (while working full-time) Outcome: $58,500 first IT job, remote-friendly, better work-life balance

Lisa’s advice: “I was terrified I was too old. But during interviews, every hiring manager loved that I’d dealt with difficult parents and had patience explaining things simply. Those teaching skills translated perfectly to IT support. I just had to show I could learn the technical side—certifications proved that.”

2 years later: Lisa is now a junior system administrator making $72K, studying for AWS Cloud Practitioner cert in her free time.

Marcus: Retail Store Manager → Help Desk Technician → Cloud Technician (Age 33, Timeline: 11 Months)

Starting Point:

• Age: 33
• Previous career: Retail management, 9 years
• Salary: $44,000 (60+ hour weeks)
• Family situation: Single, no kids
• Why change: Exhausted from retail hours, wanted career with growth potential

The Transition:

Months 1-3: Self-taught while working retail

• Used YouTube and free resources to learn Windows troubleshooting
• Studied CompTIA A+ using Professor Messer videos
• Practiced on old laptops bought from Goodwill ($30 each, fixed and resold)
• Passed both A+ exams by month 3

Months 4-6: Landed first IT job quickly

• Applied to 65 IT help desk jobs in 4 weeks
• Emphasized: 9 years customer service, inventory management, training employees, handling high-pressure situations
• Got help desk job at $52K (8-month contract role with possible conversion to full-time)
• Took the job even though contract (needed to get foot in door)

Months 7-9: Worked help desk, studied cloud on side

• Worked help desk 8-5, studied AWS Cloud Practitioner evenings
• Passed AWS Cloud Practitioner certification
• Started building small AWS projects in free tier (hosted personal website, set up S3 buckets)
• Contract converted to full-time help desk at month 8 ($54K salary)

Months 10-11: Pivoted to cloud technician role

• Applied internally for “Cloud Support Technician” role (new position created)
• Showed portfolio: AWS certifications, personal projects, enthusiasm for cloud
• Got the role: $68,000 salary (26% raise from help desk)
• Total time from retail to cloud role: 11 months

Total investment: $420 (A+ exams $320, AWS exam $100) Total time: 11 months Outcome: $68K cloud support role, growth path to $100K+ cloud engineer

Marcus’s advice: “I thought I needed to spend years doing help desk before moving up. Wrong. I spent 4 months in help desk, got my AWS cert, and jumped to cloud support. Don’t stay stuck—keep learning and keep applying internally. Entry-level IT is just your foot in the door.”

2 years later: Marcus is a junior cloud engineer making $89K, working toward AWS Solutions Architect Associate certification.

Patricia: Administrative Assistant → IT Support Specialist (Age 42, Timeline: 14 Months)

Starting Point:

• Age: 42
• Previous career: Administrative assistant, 14 years
• Salary: $41,000
• Family situation: Divorced, 1 teenager (age 16)
• Why change: Career plateau, wanted remote work, needed higher income

The Transition:

Months 1-6: Slow and steady while working full-time

• Age concern: Worried 42 was “too old” to break into tech
• Started with free resources: YouTube, FreeCodeCamp, LinkedIn Learning (free through library)
• Studied Google IT Support cert very slowly (30-45 minutes most weekdays, 2 hours Sundays)
• Took full 6 months to complete Google cert (most people do it in 2-3 months)
• Her pace was fine—life happens, she had a kid, worked full-time

Months 7-10: CompTIA A+ certification

• Studied for A+ using Professor Messer and practice exams
• Failed first A+ exam (Core 1), felt discouraged but retook it 3 weeks later and passed
• Passed second exam (Core 2) on first try
• Total time for A+: 4 months (longer than average, but she got it done)

Months 11-14: Job search took longer but succeeded

• Applied to 82 IT jobs over 3 months (help desk, desktop support, IT support specialist)
• Got 4 phone screens, 2 first-round interviews, 1 second-round interview
• Age came up in interviews: addressed it head-on (“I bring 14 years of professional experience, customer service mastery, and proven reliability”)
• Received 1 offer: IT Support Specialist at financial services firm, $59K, full remote

Total investment: $440 (Google cert $39, A+ exams $320 x2 for first failure, practice exams $40) Total time: 14 months Outcome: $59K remote IT role (44% raise from admin work)

Patricia’s advice: “I failed my first A+ exam and almost gave up. I thought ‘See, I’m too old, I’m not smart enough.’ But I retook it and passed. The job search was harder at 42—some companies did age-discriminate, I could tell. But the RIGHT company didn’t care. They cared that I was reliable, professional, and had certs. Apply to 100 jobs if you have to. One yes is all you need.”

18 months later: Patricia is still at the same company, now promoted to senior IT support specialist making $67K, studying for Microsoft 365 certification.

Best Entry-Point IT Roles for Career Changers (And What They Pay)

Not all entry-level IT roles are equally accessible for career changers. Here’s your strategic roadmap for which roles to target, based on your background.

Help Desk Technician (Easiest Entry Point)

What you’ll do:

• Answer phone/email/chat support tickets
• Reset passwords, troubleshoot basic software issues
• Walk users through technical problems step-by-step
• Escalate complex issues to higher-level support

Why it’s perfect for career changers:

• Heavily customer-service focused (you already have this skill)
• Minimal technical prerequisites (certifications are enough)
• Highest volume of job openings
• Many companies hire career changers specifically for patience/communication

Salary range: $40K-$58K depending on location and company size

Best for: Anyone with customer service background (retail, hospitality, call centers, teaching, administrative work)

Certifications needed:

• CompTIA A+ (most common requirement)
• OR Google IT Support Professional Certificate (lighter, faster, cheaper)

IT Support Specialist (Slightly More Technical)

What you’ll do:

• Tier 2 support (more complex issues escalated from help desk)
• Desktop troubleshooting, software installation, hardware replacement
• Some hands-on work (setting up new employee computers, conference room tech)
• Basic network and server support

Why it’s good for career changers:

• Still customer-facing but more technical problem-solving
• Often skip help desk and go straight to this role if you have strong certifications
• More autonomy, less phone queue grind
• Better work-life balance than help desk

Salary range: $50K-$70K

Best for: Former managers, administrators, technical roles (even non-IT), anyone comfortable with technology

Certifications needed:

• CompTIA A+ (required)
• CompTIA Network+ or Microsoft 365 Fundamentals (helpful but not always required)

Desktop Support Technician (Hands-On Technical)

What you’ll do:

• Install and configure computers, printers, phones
• Troubleshoot hardware issues (replace RAM, hard drives, screens)
• Support office moves, new employee setups
• Some server room work (cable management, racking equipment)

Why it’s accessible:

• Physical work (good if you prefer hands-on over phone support)
• Less customer service intensive (you’re working on devices, not arguing with frustrated users)
• Teaches you IT foundations fast

Salary range: $48K-$65K

Best for: People who like hands-on work, former tradespeople, warehouse/logistics backgrounds

Certifications needed:

• CompTIA A+ (required)

Junior Cloud Support Technician (Fastest Path to $70K+)

What you’ll do:

• Support cloud infrastructure (AWS, Azure, Google Cloud)
• Monitor cloud systems, respond to alerts
• Basic cloud administration (creating user accounts, configuring permissions)
• Learn cloud engineering from senior team members

Why it’s perfect for ambitious career changers:

• Direct path to high-paying cloud engineer roles ($95K-$130K in 2-3 years)
• Remote-friendly
• Less customer-facing (more technical)
• Cloud skills are in massive demand

Salary range: $60K-$80K

Best for: Career changers who can dedicate 6-9 months to learning before job hunting (requires more upfront study)

Certifications needed:

• CompTIA A+ AND AWS Cloud Practitioner (or Azure Fundamentals)
• Home lab portfolio showing you’ve built cloud projects

Data Analyst (Technical But Analysis-Focused)

What you’ll do:

• Work with data in Excel, SQL databases, and business intelligence tools
• Create reports and dashboards for business teams
• Analyze trends and answer business questions with data
• Less infrastructure, more business-focused

Why career changers succeed here:

• Hybrid of technical + business skills
• Less “IT support” and more “business analyst who uses technology”
• Emphasizes communication and business understanding
• Path to data engineering ($100K+ in 3-5 years)

Salary range: $55K-$75K

Best for: Former office workers, finance backgrounds, analytical thinkers, people who love Excel and spreadsheets

Certifications needed:

• Google Data Analytics Professional Certificate
• OR Microsoft Power BI certification
• SQL knowledge (can learn free online)

Skills Gap Analysis: What You Already Bring vs What You Need to Learn

Stop thinking you’re “starting from zero.” You already have 50% of what IT employers want. Let me show you.

Transferable Skills You Already Have (More Valuable Than You Think)

If you’ve worked retail or hospitality:

• Customer service under pressure → IT support is customer service + troubleshooting
• Handling difficult/frustrated customers → Users are frustrated when tech breaks
• Multitasking (managing multiple customers) → Managing multiple support tickets
• Product knowledge → Learning technical systems and explaining them

If you’ve been a teacher:

• Explaining complex concepts simply → Explaining tech to non-technical users
• Patience → IT support requires infinite patience
• Classroom management → Managing user expectations and difficult situations
• Creating training materials → Writing IT documentation and knowledge base articles

If you’ve done administrative work:

• Organization and process management → IT ticketing and workflow systems
• Software proficiency (Office, email, databases) → You’re already semi-technical
• Supporting executives → Supporting VIP users in IT (same patience and discretion required)
• Documentation → IT documentation is critical

If you’ve been a manager (any field):

• Problem-solving under pressure → Troubleshooting is systematic problem-solving
• Team coordination → IT teams work cross-functionally
• Prioritization → Triaging support tickets by urgency
• Mentoring/training staff → You’ll mentor junior IT staff quickly

The pattern: IT support is 50% people skills, 50% technical skills. You already have the people skills. You just need to add the technical side.

Technical Skills You Need to Learn (Less Than You Think)

Here’s the honest truth: Entry-level IT support requires surprisingly little technical depth.

For Help Desk / IT Support roles, you need:

Core technical knowledge (3-4 months of study):

• Windows operating system basics
• Basic networking (IP addresses, Wi-Fi troubleshooting, DNS, VPN)
• Active Directory fundamentals (user accounts, password resets)
• Common software troubleshooting (Office 365, email, browsers)
• Remote support tools
• Ticketing systems

That’s it. You’re not programming. You’re not building servers from scratch. You’re troubleshooting common problems using systematic processes.

Certifications that teach you everything you need:

Option 1: Google IT Support Professional Certificate ($39/month Coursera subscription)

• Time: 2-4 months (1-2 hours/day)
• Teaches: Troubleshooting, networking, operating systems, security, customer service
• Outcome: Enough knowledge for help desk roles
• Cost: $39-$156 depending how fast you complete it

Option 2: CompTIA A+ ($320 exam cost)

• Time: 3-5 months study (1-2 hours/day)
• Teaches: Hardware, operating systems, networking, security, troubleshooting
• Outcome: Industry-standard certification, recognized everywhere
• Cost: $320 (exams) + $20-50 study materials (free options available)

Option 3: Both (Google first, then A+)

• Time: 4-6 months total
• Teaches: Everything above with more depth
• Outcome: Strongest resume for career changers
• Cost: $400-500 total

For Cloud Support roles, add:

AWS Cloud Practitioner or Azure Fundamentals ($100 exam)

• Time: 1-2 months study
• Teaches: Cloud basics, AWS/Azure services, cloud security
• Outcome: Opens door to cloud support technician roles ($65K-$80K)

For Data Analyst roles, learn:

SQL basics (free online)

• Time: 1-2 months
• Teaches: Querying databases, joining tables, aggregating data
• Outcome: Required skill for data analyst roles

Google Data Analytics Certificate or Microsoft Power BI ($39/month or $165 exam)

• Time: 2-4 months
• Teaches: Data visualization, Excel advanced features, business intelligence tools
• Outcome: Data analyst job-ready

The Learning Timeline: How Long Will This Actually Take?

Let’s be realistic about time investment based on your situation.

Scenario 1: Full-time job + family (10 hours/week study time)

• Months 1-4: Get Google IT Support cert OR study for CompTIA A+
• Months 5-6: Pass CompTIA A+ (if not done already)
• Months 7-9: Job search, applications, interviews
• Total time: 9 months to first IT job

Scenario 2: Full-time job, no kids (15-20 hours/week study time)

• Months 1-3: Get Google IT Support cert AND study for CompTIA A+
• Months 4-5: Pass CompTIA A+ and start AWS Cloud Practitioner
• Months 6-7: Finish AWS cert, build small home lab project
• Months 8-9: Job search
• Total time: 9 months to first IT job (with cloud cert)

Scenario 3: Part-time work or able to study full-time (30+ hours/week)

• Months 1-2: Google IT cert and CompTIA A+
• Month 3: AWS Cloud Practitioner
• Month 4: Home lab projects, polish resume
• Months 5-6: Job search
• Total time: 6 months to first IT job

The honest range: 6-12 months from decision to first day of work.

That’s faster than getting a bachelor’s degree (4 years), faster than a coding bootcamp (3-6 months + job search, often 12+ months total), and faster than most trade school programs.

6-12 Month Roadmap for Career Transition

Here’s your exact month-by-month plan. Pick the timeline that matches your availability.

The 6-Month Fast Track (20+ hours/week study)

Month 1: Foundations

• Enroll in Google IT Support Professional Certificate (Coursera)
• Study 3-4 hours weekdays, 5-6 hours weekend days
• Complete 60-70% of Google cert by end of month
• Join IT communities: r/ITCareerQuestions, Discord servers, LinkedIn groups

Month 2: Complete Google Cert + Start A+

• Finish Google IT Support cert
• Buy CompTIA A+ study materials (Professor Messer free videos + practice exams)
• Start A+ Core 1 studying
• Set up home lab: install VirtualBox, create Windows and Linux VMs

Month 3: CompTIA A+ Core 1

• Study for A+ Core 1 exam
• Practice with hands-on labs (home lab, old computers, virtual machines)
• Take A+ Core 1 exam by end of month

Month 4: CompTIA A+ Core 2 + Resume Prep

• Study for A+ Core 2 exam
• Take A+ Core 2 exam by mid-month
• Update resume and LinkedIn
• Start researching companies and job postings

Month 5: Job Search Prep + Optional Cloud Cert

• If targeting cloud roles: study for AWS Cloud Practitioner, take exam
• If not: practice interview questions, polish resume
• Create portfolio: document home lab projects, write LinkedIn posts about learning journey
• Apply to first 20-30 jobs

Month 6: Active Job Search

• Apply to 50-100 positions (help desk, IT support, desktop support)
• Customize resume for each application
• Practice interview answers
• Accept first job offer (likely comes weeks 2-4 of active search)

Investment: $400-600 (certifications) Outcome: Help desk or IT support role at $50K-$65K

The 9-Month Balanced Track (12-15 hours/week study)

Months 1-3: Learn Fundamentals

• Google IT Support cert (slower pace, 1-2 hours weekdays + weekends)
• Join communities, ask questions, absorb IT culture

Months 4-6: Get Certified

• Study for CompTIA A+ (both exams)
• Take exams by end of month 6
• Set up basic home lab

Months 7-8: Advanced Skills (Optional) + Resume

• If ambitious: study for AWS Cloud Practitioner or Network+
• If not: focus on resume, LinkedIn, interview prep
• Start applying to jobs by month 8

Month 9: Job Search

• Apply actively
• Interview
• Accept offer

Investment: $400-600 Outcome: IT support role $55K-$70K

The 12-Month Steady Track (8-10 hours/week study)

Months 1-4: Google IT Support

• Very slow, steady pace
• 1 hour weekday evenings, 2-3 hours weekend mornings
• Complete Google cert

Months 5-8: CompTIA A+

• Study for both A+ exams
• Take exams months 7-8
• Don’t rush, life happens

Months 9-10: Prep for Job Search

• Polish resume
• Build LinkedIn profile
• Practice interview questions
• Home lab (optional)

Months 11-12: Job Search

• Apply to 50-100+ positions
• Interview
• Accept offer

Investment: $400-500 Outcome: Help desk or IT support $50K-$60K

Key point: All three timelines work. Faster isn’t always better—steady and consistent beats fast-and-burned-out.

Financial Reality: Costs, Timeline to First Job, Salary Expectations

Let’s talk money honestly. Can you afford this transition?

Upfront Costs (What You’ll Actually Spend)

Minimum investment scenario:

• Google IT Support Professional Certificate: $39-$156 (depends how fast you complete it)
• CompTIA A+ practice exams: $20
• Total: $59-$176

Recommended investment scenario:

• Google IT Support cert: $39-$156
• CompTIA A+ exams (Core 1 + Core 2): $320
• CompTIA A+ practice exams: $20
• Home lab computer (optional, can use free VMs): $0-$150
• Total: $379-$646

Ambitious career changer scenario:

• Google IT cert: $156
• CompTIA A+ exams: $320
• AWS Cloud Practitioner exam: $100
• Practice exams and study materials: $40
• Cloud lab costs (AWS free tier minimizes this): $20
• Total: $636

Compare this to:

• 4-year computer science degree: $40,000-$100,000+
• Coding bootcamp: $8,000-$20,000
• Trade school: $5,000-$15,000
• IT career change: $400-$650

That’s 1-2% the cost of a degree for access to the same career ladder.

Income During Transition (Can You Afford to Keep Working?)

Good news: You don’t quit your job.

Every career changer I’ve mentored kept working their current job while studying. You study:

• Early mornings before work (5:30-7am)
• Lunch breaks (30 minutes)
• Evenings after work (7-9pm)
• Weekend mornings (Saturday/Sunday 8am-12pm)

You maintain income while preparing for the transition.

Financial planning by situation:

If you’re supporting a family (mortgage, kids):

• Keep current job until you have IT offer in hand
• Build 1-2 months emergency fund if possible (cushion for job transition)
• Consider part-time IT role first, then transition fully once stable

If you’re single or dual-income household:

• Keep current job until you have offer
• Slightly easier to take 6-9 month timeline since less financial pressure

If you’re in financial distress (need money NOW):

• Some temp agencies hire help desk contractors with just A+ cert
• These contracts pay $18-$22/hour, can start within 2-3 months of getting certified
• Not ideal long-term, but can bridge financial gap

First IT Job Salary: What to Realistically Expect

I’m going to give you honest numbers, not inflated ones.

Help Desk Technician (most common first role for career changers):

• Small cities / rural: $40K-$50K
• Mid-size cities: $48K-$58K
• Large metros: $52K-$65K
• Remote roles: $50K-$60K (geographic arbitrage: live anywhere, work for higher-paying city companies)

IT Support Specialist (if you have strong certs or relevant background):

• Small cities: $50K-$60K
• Mid-size cities: $55K-$68K
• Large metros: $60K-$75K
• Remote roles: $58K-$70K

Desktop Support Technician:

• Similar to IT Support Specialist: $50K-$70K depending on location

Cloud Support Technician (requires A+ AND cloud certification):

• Small cities: $58K-$70K
• Mid-size cities: $65K-$78K
• Large metros: $70K-$85K
• Remote roles: $68K-$80K

Factors that affect your first salary:

Positive factors (higher salary):

• Previous management experience
• Strong certifications (A+ AND cloud cert)
• Located in or targeting high cost-of-living cities
• Excellent interview performance
• Multiple job offers (can negotiate)

Negative factors (lower salary):

• Rural location
• Only minimum certification (just Google cert, no A+)
• First job is contract role (typically 10-15% lower than full-time)
• Small company with limited budget

Negotiation tip: When you get your first offer, ask for 5-10% more. Script: “I’m excited about this opportunity. Based on my certifications and 10 years of professional experience, I was hoping for $X. Is there any flexibility?” 50% of the time, they’ll increase the offer by $2K-$5K just for asking.

Timeline to Break Even

Let’s do the math.

Scenario: You make $42K in your current job

Investment costs: $500 Study time: 9 months (while working current job, income unchanged) New IT salary: $58K (help desk or IT support)

Income increase: $16,000/year Break-even: After 11 days in your new job (you’ve earned back the $500) Year 1 net gain: $15,500 (after subtracting $500 investment)

Year 2 salary (with 1 year experience): $65K Year 2 net gain: $23,000 more than you made in old career

5-year outlook:

• Year 1: $58K (+$16K from old job)
• Year 2: $65K (+$23K)
• Year 3: $75K (+$33K)
• Year 4: $85K (+$43K)
• Year 5: $95K (+$53K)

Total 5-year income increase: $168,000 more than staying in your old career Total investment: $500

ROI: 33,500%

Do it.

Common Mistakes Career Changers Make (And How to Avoid Them)

I’ve watched hundreds of people attempt this transition. Here’s where most fail—and how you avoid it.

Mistake #1: Waiting Until They “Feel Ready”

The problem: You’ll never feel 100% ready. You study for 12 months, take every possible certification, and still feel like an imposter.

The fix: Apply for jobs when you have ONE solid certification (A+ or Google IT). You’ll learn the other 50% on the job. Nobody expects you to know everything on day one.

Story: David waited 16 months to apply for jobs because he “didn’t feel ready yet.” He had A+, Network+, Security+, and AWS Cloud Practitioner. He was over-qualified for help desk. He wasted a year. When he finally applied, he got offers within 3 weeks.

Don’t be David. Apply at 6-9 months.

Mistake #2: Only Applying to “Entry-Level” or “Junior” Titles

The problem: Job titles are inconsistent. “IT Support Specialist” at one company is the same as “Help Desk Technician II” at another.

The fix: Apply to ANY role that says 0-2 years experience required, even if title sounds senior. Read the job description, not just the title.

Apply to:

• Help Desk Technician
• IT Support Specialist
• Desktop Support Technician
• Technical Support Representative
• IT Service Desk Analyst
• Junior System Administrator (some companies use “junior” for roles that are really help desk)

Mistake #3: Not Addressing Age Directly in Interviews

The problem: You’re 37 or 44, and the interviewer is wondering “Why is someone with 15 years of work experience applying for entry-level IT?”

If you avoid addressing it, they fill in their own narrative (often negative).

The fix: Address it head-on with confidence.

Script: “You might be wondering why I’m making a career change at 38. Here’s the reality: I spent 12 years in retail management, and I was great at it. But the industry is changing, and I wanted a career with growth potential and stability. I’ve always been the ‘tech person’ in my family, and IT support combines my customer service expertise with technical problem-solving. The certifications show I’m serious—I invested my own time and money to make this happen. I’m not here because I couldn’t succeed elsewhere. I’m here because I want to build a long-term career in IT.”

This works. It reframes your age as an asset (maturity, reliability, proven work ethic) instead of a liability.

Mistake #4: Underselling Transferable Skills on Resume

The problem: Your resume says “Retail Store Manager” but doesn’t translate those skills to IT language.

The fix: Rewrite your resume to emphasize IT-relevant skills.

Example: Retail Manager Resume (Before)

• Managed team of 8 sales associates
• Handled customer complaints and returns
• Maintained store inventory systems
• Trained new employees

Example: Retail Manager Resume (After - IT-focused rewrite)

• Led cross-functional team of 8 staff members, coordinating schedules and workflows
• Troubleshot customer issues under pressure, de-escalating conflicts and finding solutions
• Managed inventory database system (POS software), identified and resolved data discrepancies
• Created training documentation and onboarded 12 new employees over 3 years

See the difference? Same job, but second version highlights problem-solving, systems management, documentation, and training—all critical IT skills.

Mistake #5: Giving Up After 20-30 Rejections

The problem: You apply to 25 jobs, get 2 interviews, 0 offers. You think “This isn’t working, maybe I’m too old.”

The fix: Career changers need to apply to 60-100+ positions to land first IT job. That’s normal.

Realistic job search numbers for career changers:

• Applications sent: 75-120
• Phone screens: 6-12
• First-round interviews: 3-6
• Second-round interviews: 1-3
• Offers: 1-2

This is a NUMBERS GAME. The person who applies to 100 jobs gets hired. The person who applies to 25 and gives up doesn’t.

Keep applying.

Mistake #6: Not Networking (Thinking Certifications Are Enough)

The problem: You get certifications, apply online, and wonder why nobody responds.

The fix: 60-70% of jobs are filled through referrals and networking, not cold applications.

How to network (even if you’re an introvert):

LinkedIn strategy:

• Connect with IT professionals in your city
• Join IT groups (CompTIA Career Pathway, Cloud Computing, etc.)
• Comment on posts, engage with content
• Message people: “Hi [Name], I’m transitioning into IT from [field] and just got my A+ certification. I’d love to hear about your career path. Would you be open to a 15-minute coffee chat?”

Local meetups:

• Search Meetup.com for IT, cloud, cybersecurity groups
• Attend (even virtually)
• Introduce yourself: “I’m making a career change into IT, just got certified, looking to learn from people in the field”

Company employees:

• When you apply to a company, find someone who works there on LinkedIn
• Message them: “I just applied for the Help Desk role at [Company]. I’d love to learn more about your IT team culture. Do you have 10 minutes for a quick call?”

One referral beats 50 cold applications.

Mistake #7: Stopping Learning After Getting the Job

The problem: You land help desk job, relax, and stay there for 3-5 years making $55K.

The fix: The learning never stops in IT. Your first job is just the beginning.

What to study after you’re hired:

• Months 1-6 in new job: Focus on learning the job, don’t study outside of work (you’re already learning 8 hours/day)
• Months 7-12: Start studying for next-level cert (Network+, cloud cert, or specialty cert)
• Year 2: Get promoted or job hop to next-level role with 10-20% raise

Career progression:

• Year 0-1: Help desk ($55K)
• Year 1-2: IT support specialist ($65K)
• Year 2-4: Junior sysadmin or cloud support ($75K-$85K)
• Year 4-6: Cloud engineer or sysadmin ($95K-$120K)

This is the ladder. But only if you keep learning.

Addressing Age Concerns and Imposter Syndrome

Let’s talk about the fears you haven’t said out loud.

”I’m too old. Companies want to hire 22-year-olds.”

The fear: Age discrimination is real. Tech is a young person’s industry.

The truth: Age discrimination exists, but it’s MUCH less common in IT support roles than in software engineering roles. Why?

IT support roles value:

• Maturity and professionalism
• Customer service skills
• Reliability (you show up on time, you don’t job-hop every 8 months like 23-year-olds)
• Communication skills with executives and non-technical users

These are skills that come with age and work experience.

The data: According to CompTIA’s 2024 IT Workforce Study, the median age of IT professionals is 38. 43% of IT workers are over age 40. IT is NOT a “youth industry” like people think.

Real talk: Will some companies discriminate based on age? Yes. Screw them. You don’t want to work there anyway. The RIGHT company will value your experience.

How to combat age bias:

1. Address it head-on in interviews (see script in Mistake #3 above)
2. Emphasize energy and learning agility: “I’ve learned three new technical platforms in the past 6 months. I’m energized by learning, and I don’t plan to stop.”
3. Show you’re current: Talk about cloud, automation, modern IT trends (not just “I’ve used computers for 20 years”)
4. Leverage your network: Apply through referrals when possible (bypasses initial age screening)

“I’m not ‘technical’ enough. I barely understand computers.”

The fear: Everyone else in IT has been coding since age 12. You’re a fraud.

The truth: Most IT professionals didn’t grow up coding. I mentor people who:

• Didn’t own a computer until college
• Learned IT in their 30s and 40s
• Failed their first certification exam
• Felt like imposters for the first 2 years

You don’t need to be a “computer genius.” You need to be willing to learn systematically and troubleshoot problems.

The secret: Technical skills are learnable. Certifications teach you everything you need for entry-level roles. Thousands of people learn this exact material every year.

If they can, you can.

”What if I fail the certification exams?”

The fear: You study for 4 months, fail the exam, waste money, and prove you’re not cut out for this.

The truth: Many people fail certification exams on the first attempt. CompTIA reports 30-40% of people fail A+ on first try.

Then they retake it and pass.

Failing an exam doesn’t mean you’re not smart enough. It means you need more study time. That’s it.

Strategy if you fail:

• Don’t panic
• Review which domains you scored lowest on
• Study those specific areas for 2-3 more weeks
• Retake the exam
• Pass

Patricia’s story (from earlier): She failed A+ Core 1 on first attempt. She felt devastated. Studied 3 more weeks. Retook it. Passed easily. Now she makes $67K as an IT support specialist.

One failure doesn’t define you. Giving up does.

”I have imposter syndrome. What if they realize I don’t know what I’m doing?”

The fear: You land the job, and on day one everyone realizes you’re a fraud who just memorized certification questions.

The truth: EVERYONE feels imposter syndrome in their first IT job. Including 22-year-olds with computer science degrees.

First 90 days on any IT job:

• Week 1-2: Completely lost, overwhelmed, wondering if you made a mistake
• Week 3-6: Starting to understand company systems, still asking lots of questions
• Week 7-12: Handling basic tickets independently, still escalating complex issues
• Month 4-6: Feeling competent, imposter syndrome fading

This timeline is NORMAL.

Nobody expects you to know everything on day one. They hired you for your potential, certifications, and work ethic. You’ll learn the rest on the job.

How to handle imposter syndrome:

• Ask questions (it’s expected in first 90 days)
• Take notes obsessively
• Document everything you learn
• Celebrate small wins (you fixed your first ticket! you learned Active Directory!)
• Talk to other career changers (you’ll realize everyone feels this way)

Two years from now, you’ll be mentoring the next career changer, telling them the same thing I’m telling you right now.

7-Day Action Plan: Start Your Transition This Week

You’ve read 6,000 words. You’re convinced (or at least curious). Now you need to START.

Here’s what to do in the next 7 days.

Day 1 (Today): Make the Decision

Action items:

• Decide: Am I actually going to do this, or just think about it?
• If yes: Tell one person (spouse, friend, family member). Accountability matters.
• Block 1 hour tonight to research certifications

Time commitment: 30 minutes

Day 2: Choose Your Certification Path

Action items:

• Read about Google IT Support vs CompTIA A+ vs both
• Decide which path matches your timeline and budget
• Enroll in Google IT cert (Coursera) OR buy A+ study materials

Recommended decision:

• Fastest/cheapest: Google IT Support cert
• Most recognized: CompTIA A+
• Best of both: Google first (2-3 months), then A+ (3-4 months)

Time commitment: 1 hour

Day 3: Set Up Your Learning Environment

Action items:

• If you chose Google IT: Start first course on Coursera
• If you chose A+: Download Professor Messer videos, buy practice exam access
• Create study schedule: Block specific times in your calendar for the next 4 weeks

Time commitment: 1-2 hours (setup + first study session)

Day 4: Join IT Communities

Action items:

• Join r/ITCareerQuestions and r/CompTIA on Reddit
• Find 2-3 IT Discord servers (search “IT career Discord” or “CompTIA Discord”)
• Follow 10 IT professionals on LinkedIn
• Introduce yourself in one community: “Hi, I’m [Name], I’m 37 and making a career change from [field] to IT. I just started studying for [cert]. Looking forward to learning from this community.”

Why this matters: You need to see that OTHER people are doing this exact thing. You’re not alone.

Time commitment: 45 minutes

Day 5: First Real Study Session

Action items:

• Study for 90 minutes (watch videos, take notes, do practice questions)
• This is your baseline: Can you sustain 90-minute focused study sessions?
• Adjust your timeline based on how this feels

Time commitment: 90 minutes

Day 6: Set Up Home Lab (Optional But Helpful)

Action items:

• Download and install VirtualBox (free virtualization software)
• Create your first virtual machine (Windows or Linux)
• Practice basic tasks: install software, change settings, break something and fix it

This is how you get hands-on experience without risking a real computer.

Time commitment: 1-2 hours

Day 7: Create Your 6-12 Month Plan

Action items:

• Based on your schedule (how many hours/week you can study), choose 6-month, 9-month, or 12-month timeline
• Write down your milestones:
  • Month X: Complete Google IT cert
  • Month Y: Pass A+ exam
  • Month Z: Start job applications
• Put target dates in your calendar
• Print this plan, put it somewhere visible

Why this matters: A plan makes it REAL. It’s no longer “someday I’ll change careers.” It’s “By September 2026, I’ll be working in IT.”

Time commitment: 30 minutes

Reality Check: Is IT Career Change Right for You?

Before you invest 9 months and $500, let’s make sure this is the right move.

IT career change is right for you if:

✅ You’re willing to study 10-20 hours/week for 6-12 months ✅ You have basic computer skills (email, web browsing, file management) ✅ You don’t panic when technology breaks (you try to figure it out) ✅ You can handle customer service (IT support is 50% people skills) ✅ You want a career ladder that goes to $100K+ without advanced degrees ✅ You’re okay with continuous learning (IT changes constantly) ✅ You want remote work flexibility ✅ You’re tired of your current career’s income ceiling

IT career change might NOT be right for you if:

❌ You hate troubleshooting and get frustrated when things don’t work ❌ You have zero interest in technology (you actively avoid learning new systems) ❌ You can’t dedicate 10 hours/week for 6+ months ❌ You expect a 4-week crash course to land you a job (doesn’t work) ❌ You want a job where you never have to learn anything new ❌ You’re extremely impatient (troubleshooting requires patience) ❌ You’re looking for a “get rich quick” career (IT pays well but requires work)

The honest assessment:

IT is NOT easy. You’ll study for months while working full-time. You’ll fail practice exams. You’ll apply to 75 jobs and get rejected 60 times. You’ll feel like an imposter for the first year.

BUT—if you push through, you’ll have a career that pays $60K-$100K+ within 3-5 years, offers remote flexibility, and has job security (every company needs IT support).

Is it worth it? For 63 people I’ve mentored, the answer was yes. For you, only you can decide.

Final Thoughts: It’s Not Too Late

I started this article talking about age. Let me end with it.

You’re 34 or 42 or 38. You’re reading this and thinking “I wish I’d started 10 years ago.”

Here’s the truth: In 10 years, you’ll be 44 or 52 or 48. The question is: Will you be making $45K doing the same work you’re doing now, wishing you’d started this career change? Or will you be a senior IT professional making $95K-$120K, grateful you took the leap?

The best time to start was 10 years ago. The second best time is today.

I’ve mentored a 47-year-old former truck driver who’s now an IT support specialist making $64K (3 years ago he made $42K).

I’ve mentored a 44-year-old former office manager who’s now a junior cloud engineer making $78K (2 years ago she made $39K).

I’ve mentored a 39-year-old former bartender who’s now a system administrator making $82K (started 4 years ago at help desk making $48K).

None of them were “too old.” They were exactly the right age: old enough to appreciate the opportunity, experienced enough to succeed, and brave enough to try.

Your turn.