My case didn't involve a gap of a few years between initial applications and eventually getting a role, but I did apply for (and get rejected from) a lot of roles before I was accepted to one, so it might still fit the spirit of your question.
I learned about EA in 2018, and started applying for EA-aligned roles in 2019. I applied for ~30 roles that year, ~25 of which were at EA orgs, most but not all of which were research or research-ish roles. Some were things like internships, but most were jobs.
I ended up with 2 offers, both jobs at EA orgs. One was an operations role and one was a research role. I took the research role.
In contrast, in 2020, with some EA research experience under my belt, I applied for ~11 roles at EA orgs (mostly research roles), and ultimately received 4 offers (all research roles).
So I got ~28 rejections before my first EA-related job offer, but then I got one, and since then I've been very happy with how things have gone.
I say a bit more about this process here, and about how I "got up to speed" on EA ideas here (which was probably part but not all of how I ultimately got these job offers). I also collect some readings and notes related to doing high-impact research here. Hope some of that's helpful!
And I also endorse Khorton's comment that the EA community probably overemphasises working at EA orgs. I'd add that it probably overemphasises research roles too. (I of course do think that research roles and roles at EA orgs can be highly impactful, and that some people should be doing them! I just think many other things can be highly impactful too, and will fit some people better.) So I think EAs who haven't yet tested their fit for many things should probably consider and apply to a lot of non-research roles and roles outside of explicitly EA orgs.
I was never bent on getting an EA job. I wanted to test out many different jobs and see what fits me. I also wanted to have some impact. I didn’t write those two articles or criticize ACE and other organizations in order to increase my chances of getting a job at an EA org. I’m not sure that thought even crossed my mind. I did it because I wanted to have an impact.
When I was doing EA community building internship, my manager would ask me every week: “what have you learnt about your personal fit as an EA community builder?” Because that was the main goal. After he read my articles, he was like “I think you have a better fit for this kind of stuff”. And some other people said similar things. And I did feel that the research that I did had more potential to make an impact than other things I’ve tried. So I decided to try to do more research. I started applying for researcher jobs partly because I was running out of savings. But when I got the offer for the RP job, I still wasn’t sure if I should take it. What if they tell me to research something that I don’t feel is impactful or exciting? That happened during my ACE internship. I was considering living in CEEALAR and just doing research by myself instead.
I’m still unsure if I should be doing research. I feel like I’m having more expected impact but still not that much. When I talk to people at animal charities about what they are doing, it sounds much more impactful. Also, I don’t like looking at a screen all day, especially when it’s sunny outside. I’m set on doing research for now, but I’m thinking that maybe I should try to found a direct work charity or something some time in the future.
Because I got bored of programming and I wasn’t that good at it. I also thought that I only have one life and it would be a shame if I never tried a different job. I considered trying out jobs like door-to-door salesman because they sounded fun, but since I also cared about impact, I applied for internships at EA orgs first.
I just happened to be a good enough personal fit to be a researcher despite being rejected from it at first. Maybe you are a better fit at something else. Being rejected in early hiring rounds is evidence that maybe this path is not for you. It’s not conclusive evidence, but it is evidence.
Do you like reading research? When you read it, do you spot mistakes? Are you a good writer? I think you can test your personal fit for being a researcher quite a bit by asking yourself questions like these. That’s one other thing you can use to make a decision on whether to persevere and try more to become a researcher, or whether to try something else. And different questions for different roles. And if you do decide you want to be a researcher, maybe you need to do something different than things I needed. E.g. a writing class or talking with other EAs more.
Another thing to base your actions on is experimenting - trying different things and seeing if you like them, and if you have an impact. I tried many different things to make an impact before (temporarily) settling on research. For example:
When doing most of these things, I had a feeling that I’m not doing that much impact. So I stopped. Note that none of these required being employed at an EA org.