365 Squarey Monsters: Why One Day Isn’t Enough for Valentine’s

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Step into a store this time of year and you can't miss the changeover — roses, candy, and heart-adorned cards arrived as quickly as the Christmas sales disappeared. That timing isn't accidental. Valentine's has grown from a single day into a full-blown season.

It's also widened in ambition. What began as a holiday centered on romance has become a moment to acknowledge love in all its forms. Sometimes that means gathering friends for a Galentine's Day lunch. Other times, it's as simple as wishing a stranger "Happy Valentine's" the same way we casually offer a "Happy New Year."

I'll admit, I'm a fan of the extended season (no surprise there!). When Valentine's rituals stretch beyond a single day, they create more chances to reach out and deepen relationships that might otherwise go unmarked.

That widening scope is what gives the season its staying power beyond its square on the calendar. It creates space for gratitude, reconnection, and small gestures that carry an outsized weight.

The roots of modern Valentine's

Rumor has it that Valentine's Day traces back to a secret meeting between the flower, candy, and card industries. Years ago, we — I mean, they — got together and devised a plan to convince the population that love must be proven with flowers and a card.

Jokes aside, traditions don't last unless they tap into something real. Valentine's took hold because it gave people a simple way to express care and signal affection. Long before greeting cards and candy aisles, people were already looking for ways to say, you matter to me.

That instinct turns out to be well grounded. As Arthur Brooks recently reminded me, one of the most reliable paths to happiness isn't spending on ourselves, but spending on others. When we give, we're not just making someone else feel seen but also reinforcing our own sense of purpose and belonging. The act of choosing someone else, even in a small way, shifts our attention outward and strengthens the bonds that make life feel meaningful.

That's why Valentine's works. It gives us permission — and a prompt — to practice generosity in the service of connection. The result is stronger relationships and, often, a lasting lift in our own well-being.

Valentine's love lessons

The rituals around Valentine's have offered early lessons in why relationships matter for generations. They've taught us how to express ourselves, how to read one another, and how to take the small social risks that connection requires.

I still remember the Valentine's days of my childhood. In the days leading up to Feb. 14, we carefully cut heart shapes from red construction paper and wrote messages for classmates. After exchanging them, we read and reread what we received, searching for meaning between the lines.

Then came the school dance, complete with decorations, anticipation, and the nervous courage it took to ask someone to dance. It turned out to be excellent preparation for the years that followed.

At home, my mom had her own ritual. Every year, she greeted us with hugs and a box of chocolates. The gesture made the day feel special, but it mattered most because it reflected the care and attention that shaped our family all year long.

As a grandfather, I've adapted my mother's tradition and added a twist of my own. Each year, I send Cheryl's Cookies to my seven grandchildren, making sure they arrive early so the treats can be enjoyed in the days leading up to Feb. 14. The only requirement is that their parents send back a photo of the kids.

It's a small ritual, but it carries a big message: You're loved, and you're always on my mind. Plus, I get a photo, too!

A nudge in the right direction

I've spent a lifetime in the flower-and-candy business, which has given me a close view of how small gestures influence the way people relate to one another. I believe these moments carry more weight than we realize, reaching beyond individual relationships and into the fabric of public life.

That's the opportunity of the Valentine's season. It encourages us to notice the people in our lives, to act on the impulse to reach out, and to say the things we've been holding onto.

In times like these, that kind of attention can go a long way.

All the best,

In this episode of Celebrate Your Story, I sit down with Ed Mitzen, founder and CEO of FingerPaint Group, for a conversation about what it takes to build a company that lasts.

Ed walked away from a stable career at 30, with young children at home and no guarantees ahead. He started his business in a basement, pushed through years of uncertainty, burnout, and personal loss, and ultimately built FingerPaint into an 800-employee company serving some of the largest healthcare organizations in the country.

Along the way, he learned lessons many entrepreneurs discover the hard way — that the work never truly shuts off and that success often comes at a personal cost.

We talk about the parts of entrepreneurship people don't always share: starting over after divorce, carrying the weight of payroll and responsibility, and finding perspective after years of effort. Ed also shares how advances in AI are reshaping healthcare and the workforce, and why those changes have made questions of access, opportunity, and dignity even more urgent.

That urgency led Ed and his wife to create the Business for Good Foundation, using their business skills and resources to invest in workforce development, housing, and entrepreneurship in underserved communities. It's a reminder that while business can be demanding, it can also be a powerful tool for lifting others.

What do you think? Share your thoughts and stories with me here.

In this week's Power & Impact, I spoke with entrepreneur and investor Slava Rubin — founder of Indiegogo and a leading voice in alternative investments — about how big changes take shape and how to recognize them early.

Throughout his career, Slava has developed a habit of paying attention, looking for early signals rather than waiting for change to become obvious. We talked about how new technologies may gradually open access to assets that once felt out of reach, and why shifts like these tend to unfold without many people noticing. As Slava put it, big changes and opportunities rarely announce themselves.

We ended by talking about young people entering the workforce at an uncertain moment. Slava's advice was straightforward: Don't wait for the perfect job. Get your foot in the door, keep learning, and keep moving. As I've said before, treat your resume like a verb.

If you're curious about where money, technology, and opportunity are headed — and how to stay ahead of the curve — this is a conversation you don't want to miss.

When a moment becomes a lasting memory

Last week, I wrote about the events and milestones that serve as speed bumps in time and force us to reflect on where we've been and where we're going. As 1-800-Flowers.com marks its 50th anniversary this year, I've been experiencing a lot of those moments.

When I started the company in 1976, I believed that if we did our work right, we would touch people's lives in ways big and small — and help them create memories. A letter I received last week from a reader named Linda brought that belief into sharp focus.

Here's Linda's email about her daughter Ashley:

Dear Jim,

Approximately 35 years ago, my 7-year-old daughter came to me crying. "What's wrong?" Tears flowing, she said, "I called 1-800-Flowers to get you a flower — they said I couldn't get one flower!"

It was the sweetest, saddest thing. I told her it was just like she sent it to me because she tried!

My sweet daughter had a car accident in Japan on July 16, 2023, and left us July 28, 2023. I always connect her with lilies and roses.

Thank you for being a part of my memories of my girl. I know the person on the phone must have thought it was the cutest call all those years ago.

Many memories,

Linda

There's nothing I can add. I'm grateful to Linda for trusting me with her story, and my heart goes out to her for the loss of her daughter. I feel honored to have played even a small part in Ashley's life and in the memories that keep her close.

A different kind of Valentine

Valentine's Day has traditionally put romance front and center, but that's only part of the picture. For many of us, Feb. 14 also reminds us to be grateful for the people whose presence has shaped our lives in other ways.

It might be the friend who never made a speech but always picked up the phone, or a relative who set an example you didn't fully appreciate until years later. It could also be someone who stepped in at just the right moment and helped you see yourself — or a situation — more clearly.

If someone like that comes to mind, I'd love to hear your story. I'm gathering reflections from our community for an upcoming Celebrations Pulse, and your words may be exactly what another reader needs to read right now. As a small thank-you, I'll randomly select five submissions to receive a surprise from our family of brands.

Sunday, February 1, 2026

Why One Day Isn’t Enough for Valentine’s

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