Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart.But if you want to get unstuck and break free from that rut, it’s important to take risks. Hard work and determination only gets you so far, you also need imagination and willingness to step outside of your comfort zone.
I grew up in poverty and fought to get out of it. I am well aware at any point I could fuck up and fall back into it permanently. I have everything to lose and long term stability is more important than taking risks in the hope they work out.
That's iffy, you might need to pick one, but "healthy" is also a pretty wildly varying thing and being able to work doesn't mean someone will give you work. Ya, maybe a temp agency will get you something if you're lucky, but then you also need to get rather lucky to get a place even if you can pay for it sometimes.
Sucks to say it, but if the majority of your work history is as a programmer and you fall on hard times, you're not at the top of any hiring list for a low-wage entry-level position.
Cultivate wisdom so that you can live a good life and die without regrets is better to me than following your heart.