I'm getting so familiar with your write ups that even if it was read to me without prior information of the author I could guess right that it's you.
I remember writing on something similar about living my best life in one of your weekend-engagement topics in weekend experience community, I know I'm not yet leaving my best Life, but everyday I'm striving to get there, I also know what the limitations are and hopefully we'll scale through. Ideally we shouldn't measure ourselves and our life goals based on the values that other people set for themselves. so before I get into anything, knowing the amount of my life I'm about to commit to it, I make sure I'm the one wanting this and not someone else, and whatever the outcome, I try not to have a regret. That's me leaving my best life.
Regret isn't a very good companion so it makes a lot of sense to act in ways that minimise the risk of it occurring; in that, I think you're on the right track.