Two Roads Diverged in a Wood: Gifts for a New Direction

Many of our memorable Mileposts occur when we set off in a new direction: we choose the road less traveled.

Once we step out, we’re in new territory. Everything is about to change. We can’t go back.

It’s thrilling and terrifying in equal parts.

The most obvious life event in this category is a wedding. It’s also true of starting a new job or company, purchasing a new house, or bringing a baby into your family.

For the most part, we gather as much information as possible before we begin a new stage in our journey. We’re nervous, but reasonably confident.

After we take that first step, we’ll realize that we’re in way over our heads. We don’t know what we don’t know. We’ll panic and flounder. We’ll probably experience spectacular failure. And enjoy sweet successes, too.

But that’s all ahead of us.

The Milepost moment marks the transition point when we’re looking forward with giddy optimism. The friends that are a few steps ahead of us in their own journeys are going to approach these Mileposts with a mixture of humor and wisdom.

They wish us luck.


Across history and cultures, transitional Mileposts are associated with symbolic gifts, tangible expressions of intangible sentiments. I can’t help but notice that gifts of luck are offered at the Mileposts where we aren’t as open to advice. It isn’t exactly because we think we know it all; it just marks a moment where we don’t yet have any experience to apply the advice to.

Luck is very much appreciated.

It’s why we give the cobalt stand mixer to the newly married couple that has not yet, to anyone’s knowledge, demonstrated any interest whatsoever in baking. Good luck with that! The giver knows that it’s only a matter of time before the couple will realize that baking can be therapeutic and healthy, and they’ll pull out the instructions. In the meanwhile, it’s going to look fabulous on their counter, assuming they have counter space to spare.

The Romans presented good luck tokens before a battle. The modern-day equivalent is the swag bag given to athletes before a competition. Most bags predictably include the event t-shirt, a water bottle, and granola bars. Perhaps a gift specific to the sport is added, such as a chalk bag at a climbing comp.

My favorite comp gifts are the unexpected surprises. Once, my daughter received a yoga mat, paired with yoga classes offered during the event; the coordinators were deliberate about crafting the swag bags to communicate care to the athletes.

My favorite comp gifts are the unexpected surprises. Once, my daughter received a yoga mat, paired with yoga classes offered during the event; the coordinators were deliberate about crafting the swag bags to communicate care to the athletes.

Lucky gifts come in all shapes and sizes. We’ve figured out how to express luck with practicality, by putting a modern twist on the traditional symbols: horseshoes, four-leaf clovers, bluebirds, bamboo.
For example, after closing on a new home, our real estate agent gave us a personalized embosser set (for our new address) and a letter opener with a horseshoe on its handle. It was her custom to give each of her clients this housewarming gift.

Any step in a new direction is cause for celebration. As leaders or loved ones, we want to show up and be intentional about supporting the journey.

Sometimes, the harder we work, the luckier we get.

Sometimes, the path ahead might get a little rough. Regardless of what happens, the gift expresses our support. We believe it’s going to work out. We’re right there with them.

It’s going to make all the difference.

Here’s to good luck!

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Let us help you create a Milepost Moment!

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