This is the situation I am currently finding myself in. I work as a telephone switch administrator for an independent phone company in Canada. I've had this just for 13 years now, it was the only job I've had since university. My undergrad is in computer science. I ended up with this job because the company bought out a friend's ISP that I was helping run when I was in high school. It was a good job, nice company, they treat me very well. Pay isn't quite at industry standards, but back then I was living in an isolated Northern Ontario Community, so it was a decent job. Plus it allowed me to work from home.

But I love programming. I've been doing it ever since I was a kid on a Commodore 64. While I do get to do a good amount of programming, I wish I could do more. It would be awesome to get more into systems or embedded programming. I recently moved to Ottawa, one of Canada's major tech hubs, and I've been sending out resumes everywhere. So far I've only gotten one interview, which was at Shopify. But I didn't make it past the initial interview--there were too many other applicants with more experience than me. I've applied to other telecom related vendors as well, like Cisco, Genband, Nokia, etc. but I've never gotten a callback.

Now I find myself wishing that after graduating university I'd taken an internship at Nortel or someplace like that, so that I'd have it on my resume, and focused on my programming career rather than just keeping the same job. I find that all entry level job postings are for new graduates only. I've contemplated doing my masters so that I could "reboot" my career so to speak and become a "new graduate."