Life By the Mile: Gifts to Mark Major Milestones

Life By the Mile: Gifts to Mark Major Milestones

Based on the definition and a handful of related words, I’d say milestones are something of a big deal.

Milestone: a significant point in development. Also see: highlight, climax, turning point, transformation, crossroads.

And big deals should be celebrated. The funny thing about milestones is how sneaky they are. Not only do they seem to come up out of nowhere — when did you get old enough to be engaged? — they differ from person to person. To help you out, I’ve put together a gift guide for important events you might soon find on the horizons of your nearest and dearest.

Life By the Mile: Gifts to Mark Major Milestones


High School: Perhaps you’ve forgotten, but surviving high school is major! There’s the cafeteria food, student drivers, and the million pop quizzes also known as everyday social interaction. Oh, and those reading, writing, ‘rithmatic classes that put students to sleep during the day and kept them up all night. Who knows what might be next: college, a job, world travel… The best gift for a fledgling adult spreading his wings in a brave new world is an opportunity to escape from said world and recharge.

Consider noise-canceling headphones. High-end headphones offer a comfortable (and grown up) alternative to ear buds when trying to block out a roommate’s three-hour call to mom or a crying baby on your flight to Europe. Not only do they keep unwanted sounds out, they do a damn good job of piping her favorite tunes in so she can totally check out.

Alternatively, a tablet makes an awesome graduation gift. Whether he wants to connect with everyone on the planet or disappear into a world of his own, there is an app for that. Books, games, and Facebook are all literally at his fingertips.

Life By the Mile: Gifts to Mark Major Milestones

College: It doesn’t matter if you are celebrating an undergrad, masters, vocational school, etc. This milestone marks an entrance into “THE WORLD.” The capitals tell you this step is even bigger than the first one taken after high school. The two things she needs to know most are what to do and how to look doing it.

With so many possibilities the former can be daunting. I recommend you check out Diane Pauley’s revolutionary site, Postgradolescence. She has designed an entire program to help seekers “do work that you love & live life on your own terms.” This month she’s releasing a toolkit to guide the bewildered into their new life.

As for what to wear, get that grad a snazzy new coat or fabulous shoes. Of course, it is what’s on the inside that counts, but employers and potential clients see the outside first. Looking smart instills confidence in the wearer and the viewer alike.

Life By the Mile: Gifts to Mark Major Milestones


New job: That’s right; somebody actually hired that formerly scabby-kneed kid who used to deliver your papers. Good for him! You should reward him with the tools to help him get from “new guy” to “boss man.” How about a book of flowcharts to streamline the decision process? You might also throw in a map to success (of sorts) such as Steve Jobs by Walter Isaacson or the timeless advice of Dr. Seuss.

Quitting a job: Sometimes two milestones happen at once: you quit a dissatisfying job and pursue a passion (i.e., start a new job or dive in to the world of entrepreneurship). Pauley says the very best thing you can give such an adventurer is a care package: “Think: boxes you got at sleep-away camp: comfort foods and loving sentiments.” I suggest you make a book of quotes, poems, and photos or, like the graduates above, send them to Postgradolesence for support straight from the expert.

Retiring: A search on Pinterest will reveal that “retire” really means “Relax Entertain Travel Indulge Read Enjoy.” I love the idea of an arty, typographical reminder that the time has come to revel in one’s free time. I’m also partial to gift baskets filled with objects that say “retirement!” without actually spelling it out. Imagine a swanky arrangement of pajamas, wine, a travel journal, and books about the new loafer’s favorite hobbies.

Life By the Mile: Gifts to Mark Major Milestones


Pick out something from the couple’s registry, then put their stamp on it. Literally. They don’t call it personalization for nothing! Monograms elevate any present to the status of personal, heartfelt gift. Plus, if the couple gets a duplicate, you know yours won’t be the one they return!

Here’s a short guide to the type of personalization for different materials:

  • Cloth items such as bedding, bath towels, table linens, and tea towels can be embroidered or silk-screened.
  • Glass and metals will be etched or engraved.
  • Wood burning is used on — duh — wood such as serving bowls, objets d’art, and cutting boards.

Bonus points if you use the same font the couple chose for their wedding invitations.

Life By the Mile: Gifts to Mark Major Milestones

New Home

Buy the homeowner some stock! I’m not talking Wall Street, I’m talking about filling shelves! When moving, especially to a bigger place, there are about a million things people forget they’ll want. Or they’ll have what they want but no clue which box it is in. Pick one of the following and fill ‘er up: pantry, liquor cabinet/bar cart, or cleaning supply closet.

Life By the Mile: Gifts to Mark Major Milestones


Whether the new child was procured via DIY or adoption, she is about to turn your favorite couple’s world upside down. Forget about getting something for the little bundle of joy — leave that to the elated grandparents. Instead, focus on her parents.Help them battle sleep deprivation and overwhelm by providing freezer meals, springing for a few weeks of house-keeping services, or designing a set of vouchers they can trade in for errand-running and babysitting.

Life goes on for miles and miles, so this only covers about a fourth of the journey. Don’t be sad if you see the perfect gift listed above, but none of these milestones are on the horizon. For Plum Deluxers, every minute is worth celebrating and gifts are always welcome. But, if you really need an excuse consider some of these other bends in the road:

  • The ubiquitous 21st birthday
  • Every birthday after the 21st ending in 0
  • Silver and Golden anniversaries
  • An empty nest
  • Completing a marathon, iron-man, mud run, etc.

Photo Credits: Nickolai Kashirin, Diane Pauley, See Jane Work, GreySkiesBlue, Krista, and Kathleen Franklin.

Life By the Mile: Gifts to Mark Major Milestones

Janice Bear

Janice Bear is still a girl despite her 30-something years. She laughs too loud, talks too much, and is certain her hair has a mind of its own. While unsure of what she wants to be when she grows up, she's positive the search will be a 5-star dramedy. Catch her when you can at Never a Plain Jane.

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