I'm a community college IT student in Ontario, Canada, and I'm trying to figure out whether freelancing could be a realistic way to start my career after graduation. The entry-level job market seems extremely competitive, so I wondered whether local managed service providers might be more willing to use me as a freelancer or contractor than hire me as a permanent employee. I also have ADHD and tend to work best with flexibility and independence.
My current skills include Microsoft 365 administration, Entra, Intune, SharePoint, Exchange, Graph API, Python, REST APIs, PowerShell, Active Directory, AWS, networking fundamentals, and Linux scripting. I'm also learning about LLM applications such as retrieval-augmented generation and vector databases, with the goal of eventually helping automate MSP tasks. Before graduating, I'm hoping to learn ServiceNow and its API as well.
I've used many of these technologies separately, including Microsoft 365 during an internship, but I still need more hands-on experience combining them in a home lab. I've applied for roughly 150 internships and only found one through a family connection, so I'm considering cold-emailing MSPs and contacting people I know in the industry. Is freelancing or contract work a realistic option for someone in my position, or should I focus on internships, entry-level employment, or another path?
5 Answers
Instead of pitching yourself as an independent consultant to an MSP, look at small businesses that need occasional IT help and could hire you directly as a contract worker. Be clear about the limited scope of your experience, start with low-risk tasks, and make sure expectations, access, payment, and liability are defined in writing.
Temporary employment agencies and technical contract marketplaces may be another way to get a first foothold. The work can be inconsistent and location-dependent, and some platforms have questionable project management, but completed jobs can still help build references and a work history. Compare the pay and reliability carefully against ordinary entry-level employment.
It’s worth trying, and your technical foundation sounds stronger than what many entry-level help-desk applicants bring. That said, make sure you can demonstrate the skills with a home lab, documented projects, scripts, and practical examples rather than just listing technologies on a résumé.
An MSP is unlikely to hand a freelancer with no professional track record access to client systems. They usually need control over scheduling, security, training, and accountability, so they tend to hire inexperienced people as employees and train them through help desk or junior support work. Expect the first few months to involve basic tickets, password resets, hardware, and documentation.
Keep applying for internships, co-ops, junior support roles, and temporary IT positions even if the process is discouraging. Networking with people already working at MSPs can help, but ask about openings or referrals rather than assuming freelance work will bypass the normal screening process. Your strongest pitch will be a small portfolio showing exactly what you automated, configured, or troubleshot.
That makes sense. I’ve had a hard time even getting internships despite applying widely, so I’ll focus on proving what I can do through a lab and practical projects.