This was my original idea, however it was incredibly time consuming and turned out it was only really successful with a couple of letters. Instead, I decided I would draw out old people's faces within the letterforms. To do this, I decided instead of going straight into Illustrator, I would use pen and paper. I think these were a lot more successful, and also had a playful aspect which I thought worked really well as I didn't want it to be too serious/depressing. Below are the rough illustrations.
I then added these to illustrator and used live trace to make them into vectors. I decided I would use live trace as it would still leave the playful feel to the images. The result of this is below, and I think it was really effective.
I then added colour to the illustrations to make them even more playful. I also added a green background which made the letterforms stand out a lot more.
I presented these to my peers in a group crit and they said that they think they're really effective and that the green background was definitely neccessary. They also said that they like the fact they are really playful as it is quite a depressing fear.