I'd say there's a few key steps in order to get where you need to go. Firstly therapy or councelling is a must! Or if your in the UK speak to your GP about refferal to a GIC - I'm sure there's like 7 in the UK or something.
At the moment I am working on voice - it's hard because there's so many good videos on Youtube but I want my voice to sound like me. I often get mistaken for a girl on the phone and sometimes when speaking publically. When I worked in a local supermarket people often said "thanks hen" and I'd be like umm ok? I almost never corrected anyone about this so I guess my voice is femanine enough to pass most of the time.
I would advise work on that as it's free and can take time to get it sounding right.
I'm also saving for Laser hair removal, that's at the top of my billing right now in terms of financially getting things sorted. Having bought clothes and makeup already I can start experimenting but not until this facial hair is gone - for me it's just a waste of good products at the moment as my fuzz always stands out.
Losing weight is also a concern for me, I am not fat or greatly overweight or anything like that but I want a more slimeline waist. Kicking exercises and running are two things I want to keep on doing. I don't drive so I walk everywhere - it's free and allows me to lose alittle weight too.
Seeing as my councelling just ended, I no longer feel the need to constantly bottle things up. I've taked openly with my family about my plans to transition in a slower paced way. I'm watching Youtube vids, joining forums to ask for advice and help others with their GID. I actually feel alot happier since doing that - like I can finally find a place where I belong in

To the OP - I'm currently unemployed as well, I left my job in March - went through hell the last few months but having seen a councellor & finally just been open and honest about what I want in life I've been able to move forward and am starting to look for work again. Being on the Joncentre is annoying, all the people who don't give a fudge about finding work while your there applying left right and centre! Trust me I know when I go I'm one of the few whose actually looking into getting abck into work. Although we can't just lump everyone in the same bucket - there's alot of honest people looking for work today as well.... just those lazy ones who annoy me the most!
Keep your chin up, there's jobs out there for people who really want them! Also if your palnning a transition it might be best to remain in "boy mode" for just now - after you change your name by deed poll all your work history and employment records go out the window... unless you put Transgender o your CV. But to me it's a moot point... I'll never, EVER work with the public again unless I
absolutely must! Still presenting as "boy" is a good way until you are 100% ready to commit to living life as a girl, everyday.
For myself I just cannot do it without the hair removal, no way!
Best of luck xx