I have a similar story:
When I left school, I started working as a Lotus Notes developer, and administrator afterwards. I switched jobs quite a few times, but I always stayed in the Lotus/IBM world as this had become my area of expertise. I wasn't the most sexy or modern technology, but it paid quite well as people with this kind of expertise were hard to find.
A few years go, I got tired of working with Lotus technology (mostly in a sysops-role). IMHO this technology is way overdue its experiation date, and I got frustrated that I didn't get the chance with more "sexy" technologies. I was applying for other jobs but I never got hired as I didn't had the required experience with new technologies (I was trying to get into the cloud-computing areas).
I took quite a drastic and impulsive decision: I quit my job. I started doing AWS courses on my own time and money, and earned my AWS certifications. I decided to give freelancing a try, and went scouting for cloud/AWS projects.
The first 2 years were hard. I had my certifications, and despite the fact that I had a lot of experience with sysops in general, companies were reluctant to hire my due to lack of AWS experience. So I "under-priced" myself a bit, and luckily I managed to get a few projects and prove hands-on that I knew this stuff.
I'm now freelancing for almost 4 years (I'm 39 now), and I'm happy with what I'm doing now and I no longer need to "under-price" myself.
This way of performing a career-change is not for everyone. If you want to go this route, my advice is:
Still, I do not regret my decision and I would never go back. So far my freelance experience is going great. The first 5 months however, were the one of the most stressful months in my life. I'm not sure I would be so impulsive again.
Good advices. It's true companies are dumb shy at recruting programmers with no experiences that's understandable. When I had my own company in the past I had helped people find job by recruting them for getting some experiences in it then they were recruitable after that :)
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