Monogram Progression to Final Product

This was my first attempt at creating my monogram and I used the  rounded rectangle tool which looked way too rigid to me. 

These were some of my first freehand approaches to my monogram. I experimented with different types of outside shapes, more smooth rounded rectangles versus more organic messy shapes, as well as experimenting with the stroke of the letters. I ended up picking the lowest middle one.

So this is what my monogram looks like now. I originally tried to render my monogram in a very clean and precise way, but it didn't look like what I had in mind. I wanted something softer, more organic, and more akin to what an ink stamp might look like when pressed on a page. I ended up using the wacom tablet and the paintbrush tool and just drawing my monogram free hand. I then had to overcome the challenge of converting my scribbles into a solid outline, so I used the pen tool to outline a copied image of what I had drawn. My monogram has definitely come a long way.