How to Write a Letter of Encouragement – Personal Thoughts

The question
Which of the social letters do I find most challenging to write?

The answer
I admit I rarely send letters of encouragement not because I don’t know anyone who can make use of a few positive words, but because such letters are emotionally draining.

In my experience, it’s not enough to simply say, “You can do it!” For a letter to sound sincere, I noticed it helps if one points out why a person should keep going, should remain cheerful despite temporary setbacks, should pursue something he or she has been dreaming of, and so on. Let me give you an example.

A few weeks back, I began a conversation with a young lady who was helping me put together my purchases. While chatting with her, I gathered the following: she’s quite new in the working world; she rarely writes letters (I asked her), and she was seriously considering picking up journal writing again, but is deeply hesitant to do so.

Her reluctance, she revealed, stems from the fact that someone might accidentally read her musings. At the same time, she wished she had been keeping a diary all along so that she could’ve taken note of “recent incidents” in her life. I didn’t press for details, but something in her tone conveyed regret.

When I got home, I decided to send her a card to thank her for assisting me and to nudge her into taking up the pen again. Not surprisingly, it took me some time to put together a short message. Not because I hardly know her, but because I wanted to make sure the words I put on print will be understood and easily remembered by someone her age (24 years young) and by someone who was going through the same experience as she was.

It’s been a couple of weeks now since I put together and mailed her packet of goodies: an envelope that contains a note card and two sets of sticker sheets for her diary. I hope she uses them.

The lesson
The formula I follow for writing letters of encouragement is “one size does not fit all.” To create the most impact, think of each letter as if it’s a perfectly tailored jacket, and you want to make sure the owner – in this case, the reader – will truly treasure your gift.

What about you? What kind of letter do you find most challenging to put together?

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