. . . a person's wisdom should be judged by the effect it has on his or her life. If that wisdom doesn't have the effect of settling the problems and difficulties in one's life – of creating a sense of ease, well-being, space, happiness, peace, and freedom – then it cannot be the real thing. - Ajahn Brahm (The Art of Disappearing)
My immediate reaction was to ask myself whether whatever wisdom I have is the real thing, followed by a quick, emphatic nöpe! Mind you, I absolutely do not disagree with him. Reading things like that, it rings right. And I have no problem with anyone, myself included, telling me my wisdom is flawed.
But that was just my quick answer and pondering it with more nuance, it turns out to be more perplexing than that.
Does my purported wisdom or practice have an effect that settles the problems and difficulties in my life? What problems do I really have? Obviously it seems and feels like I have many, but when I have a goal of bringing my life to a close, my "problem" is just being here. Not to put too fine a point on it, the reasons why bringing my life to a close is the goal are not a problem.
Within being here, all the normative things that might be perceived as problems don't amount to much. The role mindfulness plays is that it keeps me from being overly neurotic or angsty about it like I have been in the past. It keeps negativity and negative reactions in focus and at bay and promotes the opposite, or at least neutrality. There has been a settling effect on the problems, but it may not look like it.
What difficulties do I have? I can't say I don't have difficulties. There are things that I find difficult, but they're mostly neurotic things that are difficult only because I create them or let them be difficult. Again, mindfulness just observes the perceived difficulties and tries to understand they're my own creation and not to get bent out of shape over them. Rainy days are difficult. My neurotic reaction about my neighbors is difficult. They're not really difficulties. If pressed, they fly out the window.
How about separately considering sense of ease, well-being, space, happiness, peace and freedom? That's where it gets perplexing because contemplating dying brings exactly those feelings: sense of ease, well-being, space, openness, happiness, peace and freedom.
They aren't what psychiatrists might point out in some suicidal cases where there's a feeling of euphoria once they've made the decision to kill themselves. That's a false sense of those feelings because it's conditional on knowing they're going to be released from their pain, rather than having a settling effect on their problems and difficulties.
Contemplating death, those feelings are very real for me. The feelings aren't contingent on having made a final decision and looking forward to it as a relief. They are there with the very contemplation and vary in intensity depending on the depth of it. But are they connected to wisdom?
Some would say true wisdom would make me want to live. I would call that dogmatic, judgmental attachment to living just for the sake of preserving life that's ephemeral by nature. That's not wisdom, either. Wisdom is an understanding, it doesn't make people do or not do anything. It's morality's job to police behavior, not wisdom's, and I've never cared much for human or social constructs of morality.
I think it is very possible for practitioners to contemplate death and connect deeply with the reality that one day we will die and feel that sense of freedom and peace; that letting go. It's not an abandonment or a 'why bother?' letting go, but it's based on wisdom understanding, accompanied with mindfulness training to not be attached or overly sentimental about our lives.