Transitioning or not really depends on your own emotional reserves and determination. We need a strong support system, time, money and patience in order do it. I know you hate when people say, "as long as you're happy," but they mean it. In reality, the people close to you won't define their happiness based on whether or not you transition. You have to find your happiness, and hold onto it.
If your choices are: be miserable and stuck wondering if you should or shouldn't transition, or starting to transition and finding out whether you can handle it. I'd say the second choice is the better chance to stay true to yourself. Although it's a bit reductive to say you have only two choices. In reality, transitioning is a series of steps you take. Finding a therapist, getting an evaluation for HRT, researching if you want to do surgery, learning new fashion, hair and makeup style, etc.. It's not anyone one first step and it can be very slow and frustrating.
I can't answer your question for you, only you can determine when and if you're ready.
Hugs,
- Katie
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