Long post incoming.
I think it is absolutely essential to find a place / group of people that you can experience full time with outside of your friends / family. For me, I went to school (cosmetology... probably the smartest thing I've ever done). 6 months later, I'm full time there and I'm learning as I go in a very safe and kind environment.
IDK what the equivalent of that is for you, but find anything... volunteer work, school, support group... anything that is out of reach of the people you know. I have my 5 year plan somewhere but tbh I haven't looked at it in over a year.
Words of advice to everyone. My sister told me something once that I will always remember and so far it has been the absolute truth in this journey. "When things are meant to happen, they will just fall into place." They have for me. I haven't forced anything in my transition. To get the ball rolling, all I've had to do is blow on it, while some people I have noticed have been trying to bulldoze that ball and it's breaking them and everything in its way. Don't force anything, when something is ready to happen, it will without much effort whatsoever.
----------------------------------------------------------------
My transition so far:
Started going to a therapist august 2010.
Therapist told me to find support.
September - last boy haircut.
October 16th - Came out to my sister in law in hopes she would support me. I forced it and that caused some serious issues. I stopped trying because I just didn't know what to do about a support system.
November - HRT letter from therapist - waiting list VERY LONG with recommended doctor.
December 2010 - I thought "I'll go into cosmetology. If I decide to transition 1 day I can be myself in that class and I'll learn so much girl stuff just due to the course being what it is" ... but I drug my feet on it because I'm the worlds #3 procrastinator.
In July 2011, Something happened that made me HATE my job, and apply to cosmetology school.
Early August 2011 - I got my drivers license renewed. I looked at it and said "This will hopefully be the last time I have to have a male license". This caused me to get sick of the waiting list. That night I ordered estradiol.
August 19th - took my first E pill, 3 days later ordered Finasteride. 2 weeks later Spiro. Full dose HRT by September 2nd 2011.
Sept 10th - made appointment with endocrinologist.
October 5th - started school. Was open about my girliness, but not my GID.
November 2nd - prescribed HRT.
January 2012 - After not caring about the consequence, I came out to mom. She was very accepting.
February - First time maamed by a stranger.
March 24th - while in class, I asked my best friend to give me a full makeover. While this was happening I came out to everyone in class. I looked in the mirror and decided that night I was going out in public as female, and I did.
March 26th - came out to the entire cosmetology area at school. Started going to school in make up. Asked people to please start referring to me as a female and with my female name. Everybody respects this.
April 15th - Obtained letter from therapist suggesting to my school director that I should be considered female for my own psychological benefit. School director complicit and respectful of the request.
Today - First day full time as a girl at school. Coincidentally it's also the first day of clinicals (where I see clients), so it's technically like I'm getting OJT as a girl.
So far, so good... very little push from me at all. BTW I live in Louisiana... right by Texas and Arkansas. IE redneck god fearing dip spitting "God Hates Queers!" mecca. If it can be done here, it can be done anywhere in the US.