Monday, May 9, 2011

The Toughest Letters You'll Ever Write

No, I'm not talking about resignation letters—I didn't even type up a formal one. Mine was just a quick e-mail to the director of associates. Short and sweet and to the point.

The death of a loved one can be extraordinarily painful for many obvious reasons. Especially if there is a bit of a checkered history between you and that person, it can dredge up a number of emotions, and the sense that “I wish I had told them ________ before they went.”

As I've been plugging along through my introspective trek through Australia (I leave Sydney for Cairns tomorrow), my thoughts have (morbidly) at times turned to “what would happen if someone died while I was gone?” Being a single traveler, the thought isn't entirely without concern with regard to yourself, either. Do I expect to croak in Australia? No. But it could certainly happen. It could also happen at home every day.

Also, I've noticed that a lot of people end up saying the things that they regret not saying to that person during eulogies, or in tribute articles. The only problem with this is they're dead. I don't know what happens to you when you die—though I do think something happens, even if we can't begin to comprehend what it is. There are too many “near death experiences” and whatnot out there to make me take the view that everything necessarily goes dark one minute, and that's it. I guess if that's the case, I won't know any better, but this column isn't meant to be a forum for me to air my thoughts on death.

Instead, what I advocate is that you write a letter or article or eulogy or whatever you want to call it to the people that matter in your life TODAY. Tell them how inspirational they are to you, or how much you love them, or that you're sorry for being such an ass. Then, either tell them what you wrote, or give them the letter, Can't Hardly Wait-style. I'm personally more comfortable probably giving the person the letter, but that's because I'm a much better writer than verbal communicator, and when writing, I find it easier to think things through so that the words come across with their intended meaning. It's probably far more “manly” to talk to the person heart-to-heart, but if you don't feel comfortable doing so, the important thing is that the person knows how you feel.

It's probably a good idea to edit things a bit before you write the person's eulogy and give it to them—otherwise they might think you're sending them a message that you're putting a contract on them. For the moment, I've been trying to do this (NOT put out hits—edit things down) with close family members through e-mails I've been sending updating my progress through the country. I haven't decided if I'm going to “practice what I preach” with friends yet or not—it seems a bit weird at the moment, but hey, if it works in the first instance, why not extrapolate it out to its logical end? When I start handing the waiter a heartfelt letter at the end of a fantastic meal, that will probably mean that I've gone too far, but until then I'm going to go as far as I feel comfortable with this thing.

At the end of the day, it's all about trying to live a life without regrets. A lot of people advocate living their own life without regrets, which is certainly admirable, but too many people pay lip service to “spending more time with family and friends,” without any sort of advice as to what that means. I think that by telling people the things that you want them to know before you kick off, you're far more likely to truly enjoy the time that you spend with them in the future. Also, it will ensure that the Reaper doesn't broadside you when he does decide that your number's up; you've already made peace with those people closest to you, so if you do meet an untimely demise, you'll be at peace. Everyone says, “on your death bed...”, like it's some kind of right. But what if there is no death bed? What if you get hit by the proverbial bus or die in a car crash? You won't even have those final moments to make peace with everyone. Far better to do it now while you have the time (and, let's face it, you really do if it's important).

Anyone going to try this? Let me know how it goes (or if you think I'm crazy) in the comments.

D.J. Gelner is a writer, entrepreneur, and recovering attorney in St. Louis, Missouri currently traveling in Australia. You can e-mail him at Follow him on twitter @djgelner. Friend him on facebook here.

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