How to write thoughtful messages

Set a reminder

We’re all busy and we all forget, but it would be a shame to miss out on this opportunity, so don’t leave it to chance and set a reminder (or two) for a few days before the contribution deadline.

Set your mind

It’s often hard to just launch into something like this and expect a great result. Just in the same way you psych yourself up for a workout or a productive work session, you might find you need to perform similar rituals to tap into your emotional core. Set some time aside for when you know you have a quiet moment alone. Or get your wheels going by thinking about this when you find yourself in a mind-wandering situation – in the shower or as you’re falling asleep. Relax, perhaps with a glass of wine, or ambient music and really think about what this person means to you and the impact they’ve had on your life.

Be yourself

Most people aren’t as eloquent as they would like to be when it comes to putting pen to paper, but you don’t need to be a poet or a “good writer” to write a meaningful response to these questions. In so many of our daily interactions we talk facts not feelings, we stay on the surface talking about what we did or we you saw (rather than how we felt) and we receive those same facts passively. In your responses try to steer things down an emotional path. Trim away what’s superfluous to get at what’s really at stake. Contrary to what you might assume about maintaining a perception of personal success, we actually like it when others show vulnerability. Talking about your great life is actually not as appealing as talking about your difficulties. It’s not that we don’t want good things to happen to others, but it’s just really comforting to know we’re not alone in our gloom – vulnerability builds and solidifies friendships.

Make sure that your words are something you truly think and would actually say out loud, otherwise it will come off as hollow.

Get personal & specific

Try to draw from specific memories that you’ve shared with this person. For example, something funny you did in high school. Specific references will bring back those memories. By describing a personal memory or experience you will ensure that nobody else will write that exact same message, it will be truly unique to you.

The difference between an okay and a great response often comes down to how thoughtful we be about including small personal details and observations.

The most memorable responses come from finding the super specific details that you love about the recipient and letting them be known. Your observation could be the first time in the recipient’s entire life that this quality has been brought to their attention. And every time they notice that detail about themselves, the thought will be linked back to you and your thoughtful words. What are the teensy tiny, detailed things that the recipient does/is that make your heart light up?

This is a great opportunity to prove that you listen to them by recalling specific advice or words that you remember this person saying.

Prove you’re human

A quick way to make your responses warmer and less mechanical is by using a natural and human tone, almost as if you were speaking the words in conversation.

Focus & keep it simple

Small digressions — no matter how well written — tend to make make stories unfocused and tiring to read. A trick for cutting away stuff is to create a “Leftovers” area either in a separate note or at the bottom of the field. When you consider cutting something away, move it to the that section temporarily, to see how the response works without that bit. We all like to get creative with words, sentence structures and punctuation, but often simplicity is best and less is more.

Avoid clichés

Things like Happy wife, happy life!, Stop to smell the roses or Live each day as if it were your last are fine sentiments, but literally anyone could say them and if the words on your page sound like a copy/paste job from a greeting card it will be meaningless. The goal is to express yourself and communicate how much and why you care about this person so focus on your truthful feelings and emotions. Your own words may share the same sentiment as the cliché, but the difference is that only you will have said them.

Integrate moments of lightness

It doesn't all need to be so serious. Even if you’re writing to remember someone who has recently passed, sharing a funny personal story can be just as heartwarming as a memory of their more professional accomplishments.

Don’t overshare

It’s important to remember that your responses will be read by the recipient of the Fondfolio, but may also get passed around for others to read. This is not the place to divulge sensitive information or personal details that might hurt, embarrass or incriminate the recipient, yourself, or anyone else

Use natural language

The most important thing when you’re writing these personal words not to get too fancy. Don’t get addicted to the thesaurus. Sometimes, saying that you were out for a “stroll” might be the most appropriate word, but calling it a “walk” will sound a lot more natural.

Be thoughtful

In your opinion what does this person not get told enough? Often some of the things that are presented most obviously in plain view are the things that get taken for granted the most. If you are more prone to complimenting them on just one thing or one area (i.e. only their physical appearance or abilities) then this can be a good exercise for expanding your awareness of all of the other things that you love about them. Bonus points if you can recall something that he or she may have forgotten over time.

Avoid negativity

If you’re written anything defensive or aggressive, take it out. Even if you are expressing anger, there shouldn’t be any aggression in these words. Even if you have some sort of beef with this person, this is not the time or place for that – write words you want to be remembered forever.

Talk about them

Let’s face it, we’re all the center of our own universe, but if you put important stuff in the middle of a ramble about your life, your news, your feelings, it may get overlooked and miss the mark. If your feelings are an important subject in the story state them succinctly and — where possible — draw connections to the recipient’s role in those feelings. Everything you say should make the recipient think, “Wow, this is so true, sweet, and thoughtful. They really see me for who I am.”. Think about what exactly this person brings to your life and how they specifically make it easier/better. Some writing prompts: “I appreciate you most when you…” “Your greatest strength is…” “The thing I think of first when your name comes to mind is…”

Offer support, if neccessary

If this person is going through something difficult, you might want to let them know that you are there and want to offer your support. Again, be specific if you can. You could say something like “Give me a call whenever you like,” or “Let me know if there’s anything around the house that needs doing.” rather than the well meaning, but rather less helpful “let me know if there’s anything I can do” which puts responsibility on them to assign you a task. Think of specific things you could do to make their life a bit easier – “I’ll make you my famous veggie loaf and mash as soon as you feel like seeing people. We usually eat dinner around 6, and you are welcome to join us anytime.”

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