I planned and planned and planned once the soul-searching was pretty much complete. Like Melan said, this was something I thought about often, but just moved on with different parts of my life and didn't pay much attention to it. I almost transition at 30 but didn't. I completely focused on my career instead. When I knew I was going to transition I set up a loose timeline. I knew that once I started, I would not stop...ever. I knew there was no "just jump in and see how it goes." I took my time and focused on therapy first to have someone probe my brain. As I thought was the case, I knew what I was doing and considered pretty much all angles.
HRT was next, knowing I wouldn't go off of them. Electrolysis four hours a weekend for 9 months followed by FFS then full time. It's been over a year now since full time and I haven't looked back. Well, I look back, but no regrets at all. I'm happy. I'll probably end up with SRS late next year, planned in my overall timeline of course.
I'm posting the timeline I used just so you can get a sense of my planning process. I left my started/completed/Estimated date of completion and notes out of here so it didn't lose it's point:
Subject Started Completed Est. Date Completion Notes
Research/Support Learn about my transition options
Set up a long-term plan
Become active in online TS community
Join a support group
Decide my future role in TS community, if any, & act on it
Therapy Come to terms with my feelings
Continue therapy through transition, stay grounded
Get two SRS letters
Personal relationships Come out to family
Reach a compromise with my partner
Get a divorce
Explore possibility of relationship pre-op
Have loving relationship with someone after SRS
Get married after transition
Electrolysis Begin Laser Hair Removal on Face
Complete Laser Hair Removal on Face
Begin electrolysis
Achieve 100 hours of electrolysis
Complete my facial electrolysis
Begin body laser
Complete my body/genital electrolysis prior to surgery
Voice Improve voice though self-practice
Improve voice through lessons
Have completely passable voice on phone & in person
Legal Change name on Driver's License, all other financial records
Change gender marker on government records
Hair Grow my hair longer
Regrow some lost hair
Get hormone levels into female range
Evaluate hormone levels, take action if needed
Face surgery Do thorough research on FFS (forum, boards, face-to-face, etc.)
Get full FFS (forehead, jaw, chin, trachea, nose, upper lip)
Get breast augmentation, only if needed to be proportional
Lose weight
Going full-time Go full time 24/7
Feel comfortable with FT living
Employment Come out to business partner, ensure continued employment
Come out to rest of employees
Transition at current job
SRS Have reassignment surgery (bottom) surgery
Sorry it's so long, I just figured I would get the point across that there are varying degrees of preparedness. I approached my transition like I've faced every other thing in my life: with a lot of planning, an optimistic approach that things will work out in the end and a basic belief that I am a good person and know what's right for me. That's me

Meghan