Hi, Everybody!
I've been following this thread without comment so far, but at this point I've decided to throw in my 2c worth. My remarks aren't directed at any one individual or any one viewpoint, but address this question generally.
My feeling is that when this issue is raised, there's a risk of it becoming a biased question. That is, we regard a successful transition as a "full transition" that allows the person in question to live happily ever after.
My feeling is that we shouldn't look at it this way. The goal should be finding a way to live as happily as possible, and it doesn't necessarily imply fully transitioning. We all know this. We all know that we're all individuals with different needs, and we each need to find our own individual path to happiness.
I generally find the whole discussion of "transgender regret" unsatisfactory, mainly because it's usually presented as an all-or-nothing affair: either you totally regret transitioning or you don't regret it in the least.
This is simplistic. It's a rare person who finds pure and unalloyed happiness after transitioning. This doesn't imply that they regret having transitioned. It simply means that you never get everything in life.
Consider this analogy: not long ago my son was considering a job offer. The job he was working at the time was making him extremely unhappy, so unhappy that he actually collapsed at work one day and had to be taken to the hospital. Obviously, he needed another job. The problem was that he couldn't be sure that the offer he was considering would be any better.
Now he did accept the offer and, sad to say, it did actually turn out to be worse. It was so bad that he eventually expressed regret at having accepted it. But I pointed out to him that in my view he had made the right decision. His first job was so bad that he had no choice but to change. It's just that he couldn't possibly foresee whether the second would be better or worse. In life there are simply too many variables. You can't possibly accurately weigh them all. You make the best decision you can and hope for the best.
And that's what he did. It's just that he was extremely disappointed with the result. I think we need to draw a distinction between disappointment and regret. It can happen that you'll be very disappointed with the consequences of a correct decision. That's simply the way life is.
This is the case with transitioning: you can be quite clear in your mind that you need to do it and still be disappointed with the results. Those who have transitioned can discover that they're actually less happy afterwards than before—often for reasons that are entirely outside their control: people are harassing them, they find a lack of acceptance from their families, friends, colleagues, etc.
This doesn't mean that their decision was wrong: it simply means that, as so often happens in life, they're disappointed with factors that they couldn't possibly assess beforehand.
Rather than regard "regret" as an all-or-nothing matter, we should see it as nuanced, perhaps ask ourselves the question, "As regards gender, how satisfied am I currently with my life in general? On a scale of 1 to 10, how happy am I at present?" There's always going to be some sort of disappointment, but that doesn't mean that on the whole you won't be satisfied with where you are.
As soon as I came out of the closet and began living full time I started facing difficulties that I'd never had to face before. The fact is that transwomen have certain problems that ciswomen don't have. But does that mean that I regret having come out? Not at all. I'm much, much happier now than I was before. Happiness often comes with a price attached. You simply have to decide whether the price is worth it. If it's not, then you might not be finding happiness.
And consider: do cispeople never have any regrets or disappointments? Of course they do. You can regret the career choice you made. You can regret having bought the car you did. You can regret having married the person you did. Whenever people are making any kind of decision, it's inevitable that there's going to be a certain level of disappointment.
For me, these points are extremely important for two reasons: (1) We need to avoid putting undue pressure on ourselves. We need to decide what we mean by "making it". The definition is different for each one of us.
If we could all go back to the moment of our conception and be given a choice, how many of us would choose to be trans female rather than cis female? Probably none of us. Which means that none of us is really going to "make it". None of us is ever going to get where we'd really like to be. That's what being trans implies: unavoidably there's going to be some unhappiness in your life that cispeople don't have to face.
So we need to be realistic. We need to seek happiness on our own terms. Right now, in terms of gender, on a scale of 1 to 10, I'd rate my satisfaction in life at an 8. Now 8 is pretty good, and it's going to be hard to improve upon. It may be that for me this is as good as it gets.
So I need to think carefully about imposing on myself the goal of full transition. I'm an "all-or-nothing person": I recognize that if I can't be cis female, I'm never going to be truly happy in life—and I can't be cis female. So if I go further with my transition, I might be putting myself through a lot of time, trouble, expense and pain and find out at the end of it I'm no happier than I am now.
We shouldn't put pressure on ourselves by setting goals that won't be conducive to our happiness. Fully transitioning isn't necessarily "making it".
(2) Second reason: if we posit a full transition as the goal for each and every one of us, we're playing into the hands of our bitterest (and most ignorant and vindictive) of our enemies. Our enemies have the idea that the goal for every transperson is fully transitioning. Thus when they see that not all of us do that, or that many of us who do have various regrets and disappointments, in their view it invalidates ->-bleeped-<- altogether.
They love stories about "transgender regret" and "detransitioning". "X regretted his transition. Therefore nobody needs to transition." Or "Y detransitioned. Therefore nobody needs to transition."
They're wrong because they don't have a correct view of the situation—and we shouldn't contribute to their incorrect view. We know that not everybody needs to fully transition and that among those who do there will inevitably be some disappointment. This doesn't prove that nobody needs to transition.
Also, we shouldn't be surprised when somebody detransitions. Transitioning is a step-by-step process, and it's often hard to know when you've taken enough steps. That's the position I'm in now: I'm quite pleased with the steps I've taken so far, but would I be better off by taking the next one? I'm not at all sure.
Often in life there's only one way to be sure: you try it and see how it works out. If it doesn't work out, then you know you've gone too far and you need to back off. If certain transpeople find themselves in this position, it should occasion no surprise. The goal is not necessarily to travel the entire road, but only to travel as far as you need to. Finding your spot along that road can be difficult, and at the end of the day there may be nothing for it but to put it to test. Going one step too far doesn't invalidate the steps you've already taken nor the steps that somebody else has taken.
At any rate, those are my views, whatever they're worth, on this question.