How would you go about starting a font design?

I personally sketch, scan, and outline the fonts I make. If it were something in the Sans family, I would only start with an existing font if I wanted to change that font slightly, not all together.
Personally I always ether start with a blank piece of paper or a blank document. My favorite thing to do, actually, is draw strange fonts on odd objects, like dirt or wax, or in ink and blood on wood and what-nots, then photograph them, import them into FontLab and outline their images.

My friend took a free font and worked off of it. Tweaked it, changed it, remade it. Keep it vector based, that way it can be blown up to any size.

Any particularly favorable letters to begin with? (My questions are getting dumber and dumber)

@ makemo.
Ok, so the process that I am about to say is totally lifted from Matthew carter’s interview in the movie “Helvetica” But it makes sense and can really help you flesh out a font.
First you start with the lowercase h. An “h” can tell you whether the font will be a serif or a sans, the amount of thick/thin contrast in the letter form, and the proportion of the ascenders (the neck of the “h”.) to the rest of the letter. then, because the “h” is a straight sided letter, the next letter that you should make is something with a curve. The lowercase “o” is perfect for the second letter. With just these two letters you can see how the weight of the curve in the “o” relates to the straight part of the “h” and get a good idea of where the font is going. Next you make a “p”.... because they are half straight and half round and they have a descending stroke… not to mention the fact that “p” can help you knock out “q” “d” and “b”. while your at it you can make “n” and “u” out of the “h” that you created. then you make an “e” so you can start figuring out how the terminals on the open letters will look… this will help you make “s” and “c”. And then you really want to figure out what you are going to do with “a” because they can throw in a few tricks. finally, make a lower case “w”, because this often is either dictated by the u or will specify the “v”. As far as the rest, just make them follow suit with the design that you have already started to create.

P.S: I would strongly suggest you watch the film Helvetica if you are interested in font design and its history.

something else I also thought off as I was working:
Starting with a “solid” font, like a built in font, (Times New Roman… ect…) means you will have an ENTIRE font set to work with, including symbols most people never make, like æ, Æ, or å, or ¥.

I have recently created a typeface and while it is not at all uncommen to simply ‘tweak’ an existing one I prefer creating something completely new. Here is my technique:

1) Identify fonts, certain letters, ligatures and style (kerning, tracking,..) in existing font you like and collect them and print them out as big as possible.
2) Look at the fonts you have printed out and analyze the parts that fascinate you, use those key identifiers to decide what direction your font should go. I for example love swashy ligatures, slab serifs as well as strong serifs such as Didot or Bodoni, so after looking at all them I decided to make a cross of the line strength variation found in the serifs I like with the swashyness of the ligatures while retaining the srong presence of a slab typeface.
3) sketch out a few letters first. Start with: (all lower case) h,o,p,n,u,q,b,d then go from there. These lettershapes have most of the basics of a font. h has ascenders, p has descenders and the o covers the round letters. From there the h almost includes n, the n the u and so on…
4) Sketch on tranparent paper. that way you can make adjustments on top (a new layer) and try things out without having to redraw all of the shape over and over again.
5) once happy with the letter, scan then trace (pen tool) it — i use Adobe Illustrator — then copy it into FontLab or other font program to set it.

et voila! your own font.

I recommend the movie “Helvetica by Gary Hustwit” a great film about typography!

These are great answers!

re: Helvetica movie. I’ve seen it, and it was very inspiring. Although, my personal feeling these days, are that good ole Helvetica is starting to smell a bit like 5 days old pizza salad in the refrigerator. Can’t help it.

But, if using your hints (shadowfelldown’s and meemorizes), is your workflow regarding said letters, when doing the caps? Or is there by any chance, a different approach you might take there? I don’t expect you to write long answers with step by step instructions (although I don’t mind). Just some thoughts will do just fine.

True true, I have somewhat moved on from the original Helvetica but still like to use Helvetica Neue sometime, though even that happens more and more rarely.

Have a look at the type foundry “Hoefler & Frere-Jones” they are probably my favourite typographers at the moment. Fonts like Archer or Gotham / Gotham Rounded are simply awesome.

In regards to the captial letters, define the elements of the typeface first, for example if it is a serif, draw a I (i) to see the extend of the serif on a simple shape. Then do H which is somewhat two i’s plus a line, which will also define the x-height. From there on do an O for some roundness then you are pretty close to Q and then you can do an K by now you have straights, x-height, serifs and bowls defined, time to draw a P then R and M,N…

Sans-serif is obviously somewhat easier in this regards as it tends to be relatively straight with clean beginnings and ends though a swashy serif can be quite rewarding once it’s done.

Begin with the capitol H then E then A then O. the reason being that these are the letters that most closely represent the basic visual shapes: square, rectangle, triangle, and circle. Determine what these look like and you have the basis of your typeface. From here the lowercase of the heao will give you the curves, counters, lengths ext. for the rest of the family.