is a big can of worms! or not!
I thought I might throw out some creative Project Management topics for discussion.
Creative projects cover a huge range of possibilities and technologies nowdays, and estimating is a key part of undertaking any project.
Even exploratory play um, R&D! has to be timeboxed in the busy world we live in.
(which leads into a separate but related topic of constraints being a creative enabler...)
Here's a couple of good articles on estimating (albeit from a sw developer perspective):
http://simpleprogrammer.com/2014/10/27/5-ways-software-developers-can-become-better-estimation/
http://www.toptal.com/agile/software-costs-estimation-in-agile-project-management
Some questions to ponder:
1. How good are you at estimating your specific skill(s) [sw, hw, 2d/3d art, writing, illustration, etc] ?
2. How do you go about estimating different project types, from web apps to 3D/2D to cross-platform whatever?
3. How do you manage estimates vs project reality?
4. What tools do you use?
5. [insert here]
My quick answers:
1. Depends on the project. The more uncertainty/risk the bigger the buffers
2. Break it down as far as possible, articulate the risks, ballpark them in task terms based on experience/skills available
3. Related to #4
4. I've used lots but I'm liking the combo of Trello + Plus for Trello atm atm. Lightweight, agile, + visual.