Have you tried wear it over-ear?
Hippo foam is recommended by few but not sure if that will help solve your uncomfortable issue, especially if your ear is small like mine, I have tried many methods and settled with over-ear while need to adjust the insertion slightly.
Btw I'm using the double-flange ear-tips.

Yes you can try comply foam without problem, technically it is more comfortable compare with rubber sleeve.

LOL.. I'm also a spec guy so yeah, it's slight awkward but you'll get use to it.
Trying is.. erm, I'm not too sure about this, but SLCG did want to give me a try but I bit reluctant due to my ear wax, lol... anyway now I'm all good with double-flange, it keeps a distance of the housing from my ear so it's all good.
The housing finish is not the rounded one so it can be quite hurt when wear it for very long.

Try not to stick in it in your ears too deeply. To get a good fit, just put it in and adjust the pressure until it feels right. When it's too deep, it creates much pressure. You know if you're sticking in too deep when your world goes a little too 'silent' I guess. It kind of mutes the sound with the pressure in your ear canal. So, adjust the span of reach to get the right fit. If it still wouldn't work, get the hippo foam. It's comfortable, and  with a great seal too.

Hippo Foam will provide much comfortable compare with Shure Olive.