The Extra Mile is Never Crowded
When you combine surprise with delight, it's easy to stand out
I’m still talking about my visit to The Ivens, the hotel I stayed in for last year’s Web Summit in Lisbon. Why? Because I found an experience entirely different, in the most delightful of ways. Given its price point, I expected the usual luxury touches: pressed linens, marble bathrooms, maybe a chocolate on my pillow at turndown. I found all three, but I also found something entirely different. Next to my sunglasses on the night stand, the staff had placed a note that read, “Your future looks bright,” accompanied by a small cloth in a beautifully printed package to clean my lenses. On an embroidered linen towel at the foot of my bed weren’t the typical throwaway slippers, but instead plush, cozy ones that I still use today. Each night, beautifully designed stationery listed can’t miss sites of Lisbon next to the evening’s signature cocktail on my table.
It was a series of tiny gestures, each of which surprised me. These weren’t some throwaway perks; they were thoughtful, personal, and, most importantly, unexpected. They didn’t just deliver the basics—they went the extra mile. And guess what? I’m still singing their praises today.
Mediocrity is the Norm, & Nobody Praises Normal
It’s no secret that brands like Amazon dominate by exceeding customer expectations. But what about the rest of us? As entrepreneurs, managers, and superconnectors, we all have a unique opportunity to create meaningful moments by doing what most won’t—going the extra mile.
Here’s a story for you: as the CEO of Hello Alice, I regularly shout out small businesses I love. Mostly I get a ❤️ and sometimes a “thank you for sharing” comment, but one entrepreneur, George Joseph, surprised and delighted me, so here I am four years later bragging about his business, Common Bond, one of my favorite breakfast/brunch/lunch spots in Houston. After reading my small biz shoutout in the Houston Business Journal, George took the time to look up my email, sent me a thank you note, and when I responded with how much I loved his restaurant’s egg scrambles, he asked if his bakery could send a cake to our company to show his gratitude. The thought alone surprised me, and our entire team, but what arrived was beyond a delight:
It was such a beautiful work of art that I ended up posting it on our company Instagram, and have probably told a hundred friends in various contexts (and now all of you) how much I love this local Houston bakery and what an amazing culture George has built there. That, my friends, is how to craft a surprise and delight moment.
Consider this: According to a Gladly report, 68% of customers said they’d pay more for a product if the experience felt special. I would agree, and will definitely forego my usual Hotel Tonight (a brand I am also regularly delighted by) last minute deal for a stay at The Ivens next time I’m in Lisbon, and whenever possible, I choose Common Bond as my morning meetup spot. Yet, a staggering 80% of businesses admitted they rarely, if ever, focus on creating "delightful" experiences.
So why is no one doing this? Because going the extra mile requires pushing beyond society’s limits—and that's exactly why it's so powerful.
The Simple Art of Surprise & Delight
Big brands may grab headlines, but small businesses are the true MVPs of surprise and delight because the distance between stakeholder and customer is so small. And it doesn’t always have to cost money. Here are a few ideas to spark your creativity:
Put something other than bills in the mail when people least expect it. My friend Kristen always sends the most creative Valentine’s Day crafts to her friends. It comes at a time when I’m rarely expecting something in the mail, and the homemade touch reminds me of how incredibly innovative she is.
Share memorable photos. Whether it’s a picture of a pet, child, friendship or meaningful location, memories bring us back to delightful moments, and the unexpected thought never fails to surprise.
Build a sensory experience. L’Occitane always spritzes their tissue paper with fragrance in my shopping bag. They turn buying shampoo into an experience I look forward to.
Pick up the phone or knock on someone’s door. In an age where everyone texts and emails, an old-fashioned conversation with words of appreciation directly communicated makes all the difference in the world.
Fix or upgrade something. A colleague recently told me how impressed he was because his bike repair shop discreetly attached a free LED light to his repaired bike. How’s that for a glowing review?
Bring the Delight to Work
Perk up the Monday blues by prioritizing small, unexpected experiences. The result is happier, more loyal—and more productive—teams.
A manager at a tech startup leaves a small gift, like artisanal coffee beans or a vinyl record, on employees’ desks after they hit a personal milestone, like completing a marathon.
A restaurant owner surprises their staff with mental health days when they notice burnout. The kicker? These are paid.
At a small design firm, employees celebrate their birthdays by choosing a charity for the company to donate to in their name.
A marketing agency in Denver holds impromptu Lego challenges every month. The winning team gets a quirky prize (like a custom bobblehead).
A boutique accounting firm surprises new employees with personalized welcome kits, including their favorite snacks, books, and even dog treats if they have pets.
Why the Extra Mile Is So Empty
There’s a simple reason why most businesses and managers don’t embrace these strategies: effort. It’s easier to check boxes than to go beyond them. But going the extra mile doesn’t have to be expensive, and a little thought goes a long way. They show customers, employees and friends that someone took the time to think about them. When we feel appreciated, we tend to share it, and in a digital age dominated by word-of-mouth and reviews, stories are currency.
A Surprise & Delight Moment for You
Speaking of surprise and delight, here’s one for you. Did you know that the phrase “going the extra mile” comes from an ancient Roman law? Soldiers could force civilians to carry their gear for exactly one mile—but no more. The rare person who volunteered to carry it farther didn’t just help out; they stood out. That’s where the phrase was born.
As I write this, I’m still using the slippers The Ivens gave me—lush, cozy, and worlds apart from the usual paper-thin hotel freebies. It’s a daily reminder that excellence doesn’t have to mean extravagance.
The extra mile is lonely for a reason. Most people quit before they get there. But for those who venture into this uncrowded space, there’s one thing waiting: an unforgettable experience, whether you’re delivering it or receiving it. So, whether you’re running a business, managing a team, or just trying to make someone’s day, here’s your challenge: don’t just meet expectations. Exceed them—because the empty road is where all the best stories begin.
To going the Extra Mile,🥂!