When I transition (won't be for another 5 years at least) I know for sure I want T shots (obviously) and top surgery. I know the cheapest surgery (by Dr. Garramone I think you guys were saying?) is around $5,000 and the T shot are $150 each I think? Plus on top of that, I have to save up money to go out of country for surgery (basically like a vacation). I'm wondering, what if there's things you still want to do in life like travel, see places you haven't been to yet or something? Is it possible to still have money to do these things after you transition? I've heard money can be quite the problem sometimes. I hope this question isn't too personal but it has been something that's been on my mind lately...

Alot depends on things ... for example...I thought I would never be able to afford having chest surgery ... but I am switching insurance where I have a medical savings plan (HSA) that I will never loose ... so I started setting money aside for it ... well I just learned that my top surgery will be covered by my new insurance.  I also learned that my T shots once I get the prescription will be covered as well.  Times are changing ... who knows in 5 years it no longer will be a struggle for insurance to cover things - it might be normal everyday medical stuff by then.

Live you life -- don't worry about affording things in the future ... one thing I have learned in life .. if you really want to do it - you can find the money to get it done

Like Rob said, who knows what will happen in 5 years? Go ahead and save up, but don't worry about the money right now.

As for the rest of your question - I'm not sure what you're getting at. Yes, sometimes those with a trans past may face discrimination, but it's not like you can't succeed financially after transition. If anything, you'll be more confident and comfortable with yourself and better able to focus on getting things done.

The cost of everything will go up in 5 years. That is virtually certain. Whether insurance will cover more or whether you will have this type of insurance? That all depends.

Also note that the cost of getting T is not just what you're thinking (the price of the injection or gel). It's the price of paying the doctor prescribing it for you, the cost of the blood work that the dr. will order to make sure you don't have any contraindications for T & will use as followup to check your levels after some time on T, and maybe even the cost of a therapist (if the method is still getting a letter and if you can't find informed consent doctor options near you).

Transitioning doesn't happen at one moment in your life. Transitioning is an ongoing process - how you present, how you are called, what your ID says, and so on...all in addition to the medical stuff. There is no magical fairy of transitions who waves a wand and decides that "Aha! Today you are a man." A lot of this stuff can cost money, not just the medical stuff. Doing a name change petition is expensive in most places, for example.

I am very fortunate that I have reached the point in my life to transition where I have: (1) job security of a sort; (2) a strong education & career experience to fall back on if I want to switch jobs anyway; (3) good health insurance; and (4) a fair amount of savings. I have traveled somewhat extensively in my life, and I plan to continue to do so. Many people are not so lucky.

I am confused about what you mean when you say you plan to transition in 5 years. Do you mean medically? Or otherwise? Whatever you mean, though, you should expect it to be expensive to transition, and you should plan now to have education & a career path & insurance that will help you as much as possible down the line.

Essentially what you're asking is "is it possible to be well off financially?". For that, you're going to want to build a good career.

Study hard, work hard, don't live above your means, and you'll get the money to do what you want.

Being trans isn't a life killer - it's just another annoying set of bills to pay .

Personally, I went about my career "backwards" compared to most people here.

I did my name change and started T while I was a broke student (made possible by a good public healthcare system, a very cheap shrink, and living off cheap instant ramen... literally! My pre-T blood tests came back saying I was anemic! ).

Then I went and started a good career in a new city with enough to my transition done to pass as myself without a problem.

Things were really tough when I was a broke student, but in the end it worked out really well. I started my career with an almost clean slate.

If you can find a way to afford it, and you're of a young age (as in, you don't have history already), changing as much as possible before you start a long term career is something to seriously consider. For one, you never have to worry about "coming out" at work and losing your paycheck over it - and that buys you a fair bit of financial stability.