Very skilled freelance sysadmin, comfy at my nice job with shitty pay. However, it's been 2 years with virtually no raises. Reporting directly to the CEO. There is no way up from here and I'm hungry for more in terms of challenges and growth/responsibility. Recently there has been a strong shift in moving towards becoming more corporate and stricter with procedures which caused us all to suffer productivity wise and slow down. Additionally, micro-management is being introduced EOY in terms of tracking everything we do (which is a red flag for me personally). "If there's no trust I don't want to work here".

I've recently started working in a fractional technical director role elsewhere and found it incredibly fulfilling. While it pays very little currently, there's room for growth both in skillset, responsibility and money down the road. My gut tells me to do these in parallel while I let it grow OR alternatively find another main sysadmin gig that would give me the responsibility and eventually the pay I want while doing my fractional role...

Both are remote.

Any opinions welcome.