My Condolences

My thoughts and prayers are with you.

Really?

We mean well, but those words resonate with the timbre of wet dough dropped onto a countertop. Seriously, is there a more banal cliché?

But what’s the alternative— buying an equally clichéd Hallmark card to affix our name to?

I’ve always found condolences awkward. I mean, what can one write or say to properly express feelings at one of the worst moments of a friend or family member’s life? Some people, however, excel at them.  Every once in a while, we receive a sympathetic message that touches our hearts.

When I get a message like that, I’m inspired to do the same the next time it’s my turn to extend condolences.

Recently —embarrassingly recently —I committed to being that person. 

The occasion was a wake.  I didn’t know the bereaved very well, only seeing him sporadically over the years. He had lost the love of his life to cancer. Other friends were there, and when my eyes met his, I found myself at a loss for words. We shook hands, his eyes filled with tears, and I muttered a feeble, “I’m sorry, man.” 

That was it. 

Upon returning home and extracting myself from dress slacks and a necktie, I muttered, “That didn’t cut it.” 

I had the bereaved’s email address, so I opened my laptop and started typing.

Sending an email would be awkward, but I was determined to do this condolence right. I abandoned conventional boundaries and personal safeguards and wrote a lengthy, heartfelt message. I had never done anything like this before. Was it too much? Guys, for the most part, don’t do intimate, heartfelt, or emotional. 

When finished, I re-read the email several times, and nearly hit the delete button. Then, I mustered my courage, like jumping off the dock into the cold water of early Spring, and hit send. 

I regretted sending the email almost immediately; it was almost certainly too much. But it was too late. 

A few months later, I saw the recipient at a large social gathering. “Ok, let’s get this over,” I thought. Steeling myself for an awkward encounter, I walked across the room. He saw me and rose to give me a bear hug. 

“I can’t tell you how much your email meant to me,” he offered. “I printed it out, put it in my desk drawer, and reread it from time to time. I will keep it forever. Thank you!”

We then talked about his wife, how much he missed her, and how difficult the months following her passing had been. There was no embarrassment, no awkwardness —just a powerfully authentic sharing.

So what did I learn?

1. Cliche’d thoughts and prayers don’t cut it— don’t be that person!

2. Authentic connection requires vulnerability

3. I must work harder at leaning into discomfort in intimate personal situations. 

That doesn’t necessarily mean writing lengthy condolences — maybe that was over the top — but opening my soul to connect with him made an impact. You know the saying: “People don’t remember what you say, only how you made them feel!”

I’m going to remember what I learned and try to do better. 

Sorry, Hallmark, but you’re outa here!

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Former blog posts can be found here by subject category and here chronologically. 

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My first book, Towards A Life Well-Lived, can be purchased by clicking this link. Proceeds from sales are donated to Peace In Schools, a Portland, Oregon-based organization that supports mindfulness training in high schools. 

Stay tuned for my new book, The Secret Within, which I expect to make available in time for the Holidays.