Putting words on paper—or pixel, as the case may be in high-tech communications—can be difficult at times. Especially at the times that matter most, those milestone moments we want our sentiments to perfectly convey what's in our hearts and be cherished forever by loved ones.

I often get email requests from grandparents to help them write the right words in greeting cards, letters, baby books and more at important junctures in the lives of their grandchildren. Grandparents have reached out to me (or searched my site) for advice on formulating memorable messages for:

• notes to a yet-to-be-born grandchild

• greetings upon a grandchild's birth

• best wishes for a grandchild's first day of school

• best wishes for a grandchild's graduation from first grade, twelfth grade, college

• hopes and dreams for a grandchild's wedding

• advice during a grandchild's difficult time, illness, separation from the family

• inscriptions in books that will (one hopes) be cherished forever

• and everyday moments in which Grandma or Grandpa just wants to share the pride, love, and joy they feel for their grandson or granddaughter.

For each of those moments and milestones, these are the steps I suggest for crafting a memorable message to a grandchild:

Consider and clarify the point you want to make. Do you want to express pride, congratulations, love, advice, or simply joy surrounding a particular moment? Think through exactly what you hope your grandchild will feel, recall, remember about your message.

Be yourself and be brief. Long-winded notes—especially on occasions when the grandchild has numerous cards to read through—are more likely to be skimmed than savored. So condense your message in your head, then write it how you might say it. A few flowery words and lofty lines are fine, but if you "speak" on paper in a manner far different from how you typically speak aloud, your grandchild won't "hear" you in the message. So be you—the grandparent your grandchild knows and loves.

Preview on paper. Write your message on a separate piece of paper before writing it in the book, card, note or more that you plan to give the child. Doing a first draft not only allows you to scribble out and replace words to get the phrasing just right, it helps gauge how much space you'll use when handwriting the permanent message. There's nothing worse than beginning with large text then getting tinier and tighter as you realize you'll run out of space soon.

Write it again... in a word processor. Type up another draft on the computer or tablet or such using a processing program (such as Word) then run the spell check. Grammar check is helpful, too. And the thesaurus if you want a more succinct word than first chosen here and there. We all hope to be wise when sharing heartfelt thoughts with grandkids; misspellings and incorrect word usage will do the exact opposite. Plus, be sure to manually check the following which might get through a spell check but not exactly what you meant:

• its, it's — its is possessive (a book and its pages) while it's is the contraction of the two words it is.

• your, you're — your means belonging to (this is your year) while you're is the contraction of you are.

• there, their, they're — there designates a place or location (his car is over there); their designates ownership (it's their car); they're is really the two words they are, scrunched together.

Want more? If you feel your message needs a bit more punch, additional meaning, a memorable phrase, consider adding a relevant quote, some scripture, perhaps even a song lyric. Search online for the perfect punch by using the word for the feeling or quality you want conveyed and the word "quote" or "lyric" or "scripture." Then write the chosen passage just above your signature (including attribution, of course). If it's a greeting card you're signing, consider writing the quote on the blank left inside page.

Sign, seal, deliver. A simple declaration of love works fabulously for a closing. For me, that's usually Love, Gramma. Choose one that befits your style, add it, and you're done.

Congratulations! You've completed a heartfelt and memorable message for your granddaughter or grandson.

One final suggestion: Don't be offended, disappointed, or resentful if the recipient of your hard work and sweet sentiments doesn't jump for joy, shed a tear, grin big, or gush forth praise and thanks. What matters most is that you let your grandchild know your sincere thoughts and feelings at an important time—thoughts and feelings that will sincerely last for all time.

(Need advice for longer formats? See my How to write a keepsake letter to a grandchild.)

Today's question:

On what occasion did you find it most difficult to write an inscription in a greeting card or such?