I recently poured out my heart to a colleague about my guilt at two condolence notes left unwritten. One note was intended for a colleague whose sister had died, though I’d heard about the death long after the funeral had taken place.

The sisters had shared a close bond that I hoped to capture in writing. Choosing a plain condolence card onto which I would add my own personal sentiments, I sat down to write.

Days became weeks, and the card remained blank as I battled with indecision about what to say. In a sad turn of events, the surviving sister died suddenly, leaving me with great guilt for not having reached out in writing to let her know that I cared.

That same year, another colleague lost his wife to cancer. This time I attended the funeral service but felt a personal expression of sympathy was in order. For several hours, I painstakingly wrote and rewrote that note only to set it aside in frustration.

After all, what comforting words could there possibly be to express my sentiments about this beautiful woman taken too soon from this life? I tried again on the first anniversary of her death, and still the words would not come.

I had missed two opportunities to express my sorrow. Later, I saw my colleague and realized that he would never know how much he had been in my thoughts.

It would seem that the combination of my careers – funeral director and writer – would endow me with an effortless ability to write such notes. After all, I reasoned, funeral directors are around death all the time and should know just how to console others.

Well, despite my stock and trade, I struggle. And, I am not alone.

So, what is it about condolence notes that makes them so difficult to write? Do we fear offending in some way? Are we afraid of saying too much, or too little? Do we worry that they are not personal enough, or too personal? Do we fear falling short?

A Little History

The word “condolence” has been in the vernacular since the 1600s when it was defined as “sympathetic grief” and “sorrowing with another.” But such letters go back much further. There is archaeological evidence that the ancient Greeks wrote such letters, mostly after the death of a child.

The Victorians elevated condolence letters to an art form, writing in an elegant cursive script on high-quality mourning stationery rimmed in black. According to the book Death in the Victorian Family, “Victorian condolence letter writers offered affection and sympathy in abundance.”

In more recent times, writer Edith Wharton wrote a six-page letter to President Theodore Roosevelt upon hearing of the death of his son Quentin during WWI.

She included the important components of a condolence note, expressions of sympathy and comfort, along with a personal recollection: “We had a delightful long talk after lunch, which gave me such a sense of his vitality, his understanding, his happy face.”

While Wharton’s letter to Pres. Roosevelt flowed fluently, that is often not the case for the average letter writer, especially in this day and age of short texts and tweets. Still, there are some guidelines we can all follow.

8 Tips to Writing Condolence Notes

• Social media expressions of sympathy aren’t enough. Nothing takes the place of a handwritten note.
• Steer clear of clichés and platitudes. Telling a mourner that their loved one is in a better place may be met with “Where, the ground?” by the less spiritual.
• Well-intentioned as it may be, resist the urge to reassure the bereaved that time will lessen their grief, and they will find closure. There often isn’t any closure.
• It’s okay to admit when words fail. In fact, there are some deaths so tragic that there are no adequate words of consolation. A simple, “There are no words for this,” is honest and direct.
• Share a personal recollection, perhaps something the mourners did not know about the deceased. These reminiscences serve to remind family and friends that their loved one touched many lives.
• Quote from the great writers and poets like Shakespeare, Kahlil Gibran, Henry Wadsworth Longfellow, and Emily Dickinson, who wrote, “Unable are the loved to die. For love is immortality.”
• Offer something tangible. Reassure the mourners you are “there for them” – whether to lend an ear, run an errand, or spend some time together.
• Resist the impulse to try to compose the perfect note of sympathy. As philosopher Voltaire said, “The perfect is the enemy of the good.”

So, there you have it. It isn’t always easy to write condolence notes, but doing so will bring you peace, and may be a ray of sunshine for those who read them.

What is it about condolence notes that makes them so difficult to write? Do you fear you might offend? Or do you worry they’re not personal enough? Please use the comment box below to share your experience and thoughts.