If you know any of those hobby designers, please let me know.

If not, just copy a mainstream program as closely as possible. There’s a reason why that’s designed the way it is. And if not, people are used to that design anyway. (I’m thinking ‘different bgcolor toolbar with left oriented icons’, tabs, standard iconset (eg some flopydisk as save), statusbar or other lower delimitation of window…)

interface design is a whole science for itself I’m afraid…

1) many programs these days utilize themes – so the user can pick their own gui – you could try that

and
2)i use outlook for my to do list (aka goals) and there is a very important function that you have overlooked: the checkbox. another implementation might be a to-do tree (aka goal implementation tree)

a real life example would be: i wanted to:

1)become a travel writer (top of the tree) so i:
A) returned from china [where i was living la vida fengkuang]
B) went to harvard and studied travel writing
C) got an internship at National Geograpic traveler
and
D) got a job at fodors writing their beijing guide.
Now D) had some subcatorgories, which i still havent implemented:
A) Visit my grandma in LA,
B) drive home to ny, and see my parents
C) sell the van (this one got checked off today)
D) buy a plane ticket
E) pack
F) go.

Grey looks better.