Career Launch + 10-Year Plan Overview

May 2025

Hello everyone, this is my ten year plan I've created with the help of ChatGPT, any feedback would be greatly appreciated, Thanks!

I recently graduated with an Associate Degree in Computer Information Systems from Holland College. Through this program, I gained hands-on experience in IT, cybersecurity, programming, and systems management. I’ve also been lucky to stay in touch with former co-workers who referred me to a lucrative industrial painting job in Alberta, working a 20-days-on, 8-days-off rotation with full living expenses covered.

This role is a strategic first step. With expected savings of $40,000–$60,000 in the first year, I plan to leverage the income and downtime to start side work in AI/data annotation and begin investing early through a TFSA and ETFs. Below is my full 10-year roadmap, combining career growth, military training, real estate, and multiple income streams.

My 10-Year Career + Income Plan

Year 1 – Alberta (Max Income + AI Side Work)

• Job: Industrial painting (20/8 schedule, 12-hour shifts + overtime)
• Earnings: ~$90K–$110K/year
• Living: Covered or low (housing, meals, flights paid)
• Save: $40K–$60K minimum
• Side Hustle: AI training (Remotasks, Scale, etc.) = $300–$600+/mo
• Invest: Open TFSA, invest in ETFs (VFV/VEQT)

Years 2–3 – Military + Paid Computer Science Degree

• Join CAF and complete a 2-year paid CS degree
• Pay: ~$50K/year while in school
• Certs: Security+, CySA+
• Invest: $10K/year
• Start research: Halifax real estate market for duplex/triplex

Years 4–5 – Full-Time Military Cyber Role

• Serve in cyber/IT role
• Save/Invest: $15K–$20K/year
• Capital by Year 5: ~$100K
• Finalize plans: Buy Halifax rental property (duplex or triplex)

Year 6 – Buy Halifax Rental Property

• Down payment: $60K–$80K
• Target property price: $400K–$500K
• Rental income: $2800–$4000/month
• Strategy: House hack or fully rent
• Continue investing: ETFs + AI side income

Year 7 – Final Year of Military Service

• Manage or outsource rental
• Advance cyber skills: more certifications (e.g., CISSP, Cloud+)
• Prep for 2nd property purchase

Year 8 – Transition to Civilian Cyber Career

• Exit CAF with:
  • Paid CS degree
  • Security clearance
  • 4+ years cyber experience
  • AI freelance work
  • Investments + real estate income
• Target salary: $100K–$150K+ in civilian cyber role
• Option: Freelance/consult part-time

Years 9–10 – Scaling Up

• Buy 2nd rental property
• Target net worth: $250K–$400K+
• Grow income streams:
  • Real estate
  • ETFs
  • Cyber job
  • AI gigs / freelance consulting