A friend of mine has been pondering his career path, and I honestly have no idea how to guide him. He has degrees and certifications in web development, IT administration, and PC applications, along with nearly 20 years of experience in tech support roles. While he can solve problems, he's more of an IT generalist than a skilled programmer, having dabbled in languages like Python and JavaScript but not really excelling at coding.
His job titles have ranged from general manager to marketing assistant to IT lead, and he even has some background in GIS. Surprisingly, he seems to flourish in challenging roles where everyone thinks he won't succeed. Despite being a bit slow at implementing solutions, he ensures what he does works reliably in the long run. Now, he's reached out to me for career advice, and I honestly don't know how to categorize him. What should I tell him?
3 Answers
Given his mixed bag of tech and management experience, he could be a great fit for an IT Manager or even an IT Director role in a small to medium-sized company. As an IT generalist, he doesn’t need to be an expert coder—just knowledgeable enough to understand tasks and delegate effectively. Plus, he should have the business acumen to explain technical details to execs. Suggesting he explore IT Manager roles or even technical project management could be beneficial. "Jack of all trades, master of none" fits him well!
Honestly, I'd have a hard time recommending him for roles beyond helpdesk until he proves more experience. If he can troubleshoot effectively and has decent interpersonal skills, maybe he could consider helpdesk escalation. His background doesn’t quite convince me he’s ready for a sysadmin position just yet without gaining more hands-on experience.
Fair point! I forgot to mention he has experience as an O365 admin and manages his current company's Active Directory.
With 20 years of troubleshooting under his belt, he's got a solid foundation! If he wants to dive into coding, starting a portfolio of personal projects could really showcase his skills. If he's more into problem-solving, he might want to consider focusing on problem management. It’s more rewarding to tackle the root causes of issues rather than just putting out fires. Regardless of the path, I’d suggest he prioritizes reliability and communication, which he seems to be doing already! Not everyone is cut out for management, and that's perfectly fine. Staying consistent is key, so it sounds like he’s already on the right track!
Exactly! Consistency is vital, but he needs to figure out his direction too. Maybe he should take a moment to assess his goals.

That definitely makes sense! I’ve heard that saying before, and it fits his situation.