I was a college-student BOFH, an ISP sysadmin, and an academic IT manager. If I wanted a curmudgeonly sysadmin, I could just look in a mirror. Most developers were unlikely to be granted root on any systems whatsoever, and servers were carefully hand-whittled works of art. You know, The Way Things Were.
Moving to a role doing operations at a developer-centric startup was both a culture shock and a great learning experience. I'll discuss what worked for me (and what was challenging!) in terms of my transition to a DevOps practice.
Spoiler alert: change is scary, but awesome developers on the team make it much easier for an old-school sysadmin to be assimilated into the DevOps of Borg. Wacky hijinx ensue, and there's a hilarious coda: as it turns out, having your startup acquired means that in IT's view, you're the cowboy now! All sorts of empathy potential!
Bridget Kromhout does operations at Fluid after years as a sysadmin at ISPs and in academia. Software engineering was optional when she studied Computer Science at the University of Minnesota, so she took more math instead; this ensured that she'd end up in software. She likes HBase, Graphite, FreeBSD, bicycle-powered camping, and butchering pumpkins for home canning. In what remains of her free time, she's the lead organizer for DevOpsDays Minneapolis.