u/voidedzim

I am a director of IT for a very very small company (5 people total), but I love it. I have complete autonomy over what I do and how I do it, and the actual work that I do is really fun (creating automation/workflows, building data dashboards, managing online courses, creating internal tools, web development, platform administration/PM/CRM management, and lots of other random stuff.) However, I've been here a while now and I don't feel like the company is growing. I also currently feel like the Mario of IT, which for a while was great because it introduced variety and threw me in the deep end with learning some new things, but now I would like to have a focus or specialization that moves me into the next level. I don't really care about leadership roles, I more-so enjoy doing the work, specifically around API & automation if I could choose that.

Can anyone recommend types of jobs that I might be well suited for, or knowledge-gaps that I can improve to be able to jump to other roles? I am also a contractor currently and while I make decent money, I seem to run into walls applying to jobs. I'm not sure if its because of the contracting angle or the "you've been at some company no one has heard of for years" angle. But I am willing to do whatever I need to to make a jump.

I've never been more stressed out my whole life

What other areas can I jump to at this stage in my career?