If I had to start over...which IT path would I take?

Starting over in IT today, NetworkChuck’s core recommendation is to build a broad foundation fast, land a first help-desk job quickly, then pivot into cloud—using Linux and Python (or PowerShell for Azure) as the real career accelerators. The practical logic is simple: early certifications mainly help get interviews, but the first job and hands-on proof matter more than stacking credentials. From there, cloud offers the most momentum for both pay and flexibility, including the chance to work remotely.

The path begins with CompTIA A+ as the baseline. The emphasis isn’t on becoming a desktop technician forever; it’s on using A+ to qualify for entry roles while learning the fundamentals needed across IT. Immediately after starting the A+ track, the advice shifts to job searching—apply broadly for help desk and IT support roles, even if postings list “preferred” experience. Networking is treated as part of the job hunt: find hiring managers and employees at target companies on LinkedIn, connect, and lean on familiarity because hiring often follows relationships.

Once the first IT job is secured, the certification strategy becomes more selective. The “kicker” is timing: if the first job arrives before finishing A+, the A+ can be dropped and completed later, since the credential is most valuable for getting that initial interview. The next step is still framed as breadth. Instead of doubling down on a single networking vendor track, the recommendation favors CompTIA Network+ for wide networking coverage, followed by CompTIA Security+ and Linux+ to round out the skill set. The CCNA remains valuable for its name recognition and industry pull, but the guidance is that Network+ may be the better early choice because it can cover what many entry networking roles need without relying on Cisco-specific depth.

After the networking-and-security foundation, the plan pivots decisively to cloud. Cloud is positioned as the future “someone else’s data center” model that enables faster scaling, redundancy, and easier experimentation—especially compared with building and maintaining physical infrastructure. The job-search lens becomes cloud-specific: choose AWS or Azure based on local demand and available roles, then start with entry-level cloud credentials (AWS Cloud Practitioner / Azure fundamentals) before moving to associate-level certifications like AWS Solutions Architect Associate. The goal is not to collect every cloud exam, but to reach the point where a first cloud job becomes realistic.

In the cloud phase, the real differentiators are Linux and Python. Linux supports the operating environment behind many cloud services, while Python is framed as the automation glue that turns cloud knowledge into practical engineering work. For Azure paths, PowerShell is highlighted as the scripting language that pairs with Linux skills (including Linux on Windows through WSL). The advice also stresses staying employable: if the help-desk role doesn’t offer a clear upward path within about a year or two, move to a company where cloud exposure exists.

Finally, the guidance addresses emerging trends and tradeoffs. Network automation is expected to become increasingly GUI-driven in many environments, with vendors packaging automation into easier tools—though deeper scripting still helps. Traditional networking remains relevant, but the “bet” for excitement and long-term opportunity shifts toward cloud. Hacking is acknowledged as interesting, yet treated as less clearly aligned with the most lucrative, safe, and remote-friendly trajectory compared with cloud engineering. The overall message: prove skills with projects (often via GitHub), keep learning while working, and use the first job as the launchpad rather than waiting to become “certified enough.”