Deathbed Letters

Two months ago I wrote a letter. I wrote it exactly as I would have from my deathbed... except that I wasn't on my deathbed and that was the entire point. Movies really love to dramatize those end-of-life-bucket-list-final-hurrah moments but the truth is that if I really was on my deathbed I'd probably be so exhausted and busy with the work of ACTUALLY dying that writing such a letter would be ten times harder, if not impossible. So, better to do it now.

It was an exercise I often walked clients through and thought, at the time, it might be a good idea if I applied it to myself. The question I always asked in that exercise was this: Imagine that you’ve just been given a prognosis of three months or less. What haven’t you said yet that you need to say? Who do you need to see, talk to, or write a letter to? Where is there “unfinished business”?

The second part of that exercise is where I ask the client to consider having that conversation or writing that letter now to any of the names that surface because the truth is that none of us are guaranteed any time other than the present. We don’t know if we’re going to get sixty more years or sixty more minutes. Not to be overly dramatic but the truth is this may be the one chance.    

So, I did the exercise myself and sure enough, someone came crystal clear into my mind followed quickly by what I knew I needed to say. I wrote it all down. Then, I found an email address, sent it into the ether, and nursed the worst vulnerability hangover of my life.

Author Tish Harrison Warren says, "We don't like people who seem too put together so many... are sure to go out of their way to show us how 'messy' they are. But it's all so very curated. Our truest weaknesses will never be a selling point."

There was nothing for sale in those words. No pride. Gratitude, yes. And grief. I waited.

Three weeks after hitting send I found myself sitting in a pub booth across from the recipient of that letter - an old friend I deeply regretted losing. I’d never been able to tease apart what happened or why it ended. It turned out there were some pretty big things that had been left unsaid on both of our parts that now we were both mature enough to see clearly and ready to say. Having that conversation wasn’t easy, part of seeing the full picture for the first time was actually painful, but if there is one thing I am committed to at this point in life it’s to trust myself and to have hard conversations. (okay, well that's two things).

It was tikkun olam, a Jewish concept which means "repairing the world". It was all things made new. It was "thy kingdom come" in a pub over burgers where after fifteen years, two old friends met and set each other free.

Challenges/Points:

  • We aren’t promised any certain amount of time in this life so it’s important to take the time now to say the things that matter to us. 

  • When we take the time to do that, we communicate a clear message to those around us that “You matter”. We also begin to live a life that has no “unfinished business” which can lead to less fear of death.   

  • We can have hard conversations and we can do hard things even if we’re scared while we do them. That’s okay. In fact that’s normal.  

Questions:

  • Consider taking the time to ask yourself the same question that I did: “If I was given a prognosis of three months or less, who would I need to say something to? What haven’t I said or done yet that really matters?”   

  • How does thinking about having that conversation or writing that letter feel? Is it scary? A relief? Overwhelming?  

  • Have you ever experienced a vulnerability hangover? What’s the hardest part for you about putting your heart out there without knowing if the other person will reciprocate?

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