Regret is a long dismal road that it's easy for all of us to get dragged down. The fact is that your life as it has been is what made you the terrific person you are. Yes, transition may be harder for us than it will be for JJ, but we're older and better able to deal with it.
There will always be people who have it easier than we do, whether having to do with transition, or job, family, looks, money, talent, or just dumb luck. I find comparing my lot in life with someone else's is never a productive activity.