Asklemmy

I'm a self-taught sysadmin. It took me ~3 years to get comfortable, and I'm srill learning stuff that feels like if not 100-level then at most 200-level course knowledge...

I started making a pivot to self-taught pentesting in hopes of breaking into red-teaming, but I'm stuck at finding time to practice and learn and still invest some time in the parts of life that aren't my job and/or future job. I enjoy doing it just for fun outside of the career potentials, but I've been burnt out for years from turning my current career into my hobby as well, I won't make that mistake again

I guess the only answer I have is: depends on how much time you plan on investing in self-teaching. I wouldn't say anything's necessarily out of reach, but I would say that learning the skills is only half the battle of getting employed.

I do have a little advice with my perspective: don't think of it in large timeframes, e.g. "I wan't to get to this goal within a year," do it in hours or less. Force yourself to sit down and do something that furthers that goal for X amount of hours each day; that way, you have a very clear metric and can start measuring progress by how much time you actually spent studying and applying for jobs and networking (as in building relationships with your peers and future employers... but also the other kind too).

Oh, another piece of advice: don't just read, watch videos and listen to lectures—learn by doing. Set up a home lab for whatever it is. At least a solid 80% of what you'll encounter in the field can be emulated with a good enough PC and the right software (yes, even cabling). And for everything else... Well, that's just good fun to own all those tools and gadgets and gizmos galore and so, so, SO much cable of every kind.

Last bit: are you having fun? If it's not fun to learn, it'll be soul-crushingly, mind-numbingly dull when it's your job. You don't get to do the cool new stuff most days, most days it's just replying to emails and forcing the users to restart while you observe because most of the time "Yeah, I already did that" means "I may not understand computers in the least, but I'm inexplicably dead certain that the thing the expert is telling me to do won't work." So make sure you're enjoying even those bits now

Otherwise, get out now while you still can and the Sunk Cost Fallacy hasn't kicked in.