As I was working on my daily content, it struck me that October is full of significant milestones and memories for me. Some are joyful, some bittersweet, and some a mix of both.

• 1994 – Moved into my first home with my first husband.
• 1998 – Met my second husband.
• 1999 – Held our commitment ceremony.
• 2004 – Adopted our children.
• 2008 – Legally married.
• 2011 – Experienced the first blizzard of my life after moving to New England.

It’s quite the list. And as I approach 59 years old, I’m reminded that the older we get, the more our calendars fill with these moments. Some months, especially around the holiday season, can feel so heavy with memories (happy, sad, or simply tender) that it can be hard to stay grounded in the present.

And the question becomes: What do we do with those dates?

When the Calendar Becomes Heavy

Grief and memory make us more aware of time than most. A single date on the calendar can carry an entire weight of memory: the birthday of someone no longer here, the day you said “I do,” or the anniversary of a loss.

Sometimes, those days ambush us. You wake up, realize the date, and feel the heaviness hit your chest. Other times, you see the date coming weeks in advance and dread builds like a storm on the horizon.

But here’s what I’ve learned after decades of living with both joy and loss: the day doesn’t get to decide how you feel. You do.

Shifting from Dread to Choice

I don’t mean forcing yourself to feel happy, or denying the sadness that comes. What I mean is this: if you want to stay under the covers and shut the world out, then let that be your choice, not the calendar’s. If you want to honor the memory with a ritual, plan for it. If you want to reclaim the day with something joyful, you can do that too.

The difference is intention. When we decide ahead of time how we want to approach a milestone, we give ourselves a semblance of control. We’re not at the mercy of the date; we’re guiding our response — and that’s powerful.

Practical Ways to Take Back Milestone Days

Here are a few practices that have worked for me and for others. There’s no right or wrong way; there’s only YOUR way.

• Plan a Ritual – Light a candle. Write in your journal. Visit a place that holds meaning. Rituals give structure to feelings that otherwise feel overwhelming.
• Choose Connection – Spend the day with someone who understands, or create a gathering in memory of the person or event. Grief is heavy when carried alone.
• Flip the Script  – Reclaim a hard anniversary by adding something new: a hike, a day trip, a meal at a favorite restaurant. Doing something different changes the way the day feels.
• Give Yourself Permission for Self-Care – Stay in bed, binge-watch a show, order takeout. If that’s what you need, honor it. Rest is a valid choice.
• Declutter the Emotional Weight – If the day still feels heavy, try a symbolic release—write down the feelings and tear them up, or let a leaf or flower float down a stream.
• Plant Something New – Start a class, pick up a hobby, or set a small goal. Just like a tree sheds leaves in fall to make way for spring growth, creating something new reminds us life continues.

Life’s Expanding Calendar

As we age, more and more of our days are marked by moments—good, bad, and in-between. Some months feel like an endless series of anniversaries and reminders. But here’s the truth: while the calendar may grow crowded, our capacity to shape how we experience those days also grows.

We’ve survived. We’ve endured. And with that comes the ability to decide—not perfectly, not every time—but more often than not, how we will carry the weight of memory into the present.

Your Challenge This Week

Take a look at your calendar. Notice one upcoming date that holds meaning to you, be it joyful or painful, light or heavy. Instead of waiting for the day to ambush you, decide now: How do I want to feel on that day?

Make a plan, however small, to honor that intention. Write it down, mark it on the calendar, tell someone if it helps.

Because the truth is this: more than 80% of the things we worry about never happen, yet we expend time and energy (emotional and physical) doing so. But when we choose how we want to face the days that matter, we reclaim some of the power grief and memory try to take from us, and it allows us to focus our energy on what’s real to us.

The date may stay the same every year. But how you live it? Well, that can be different.

What’s one milestone date on your calendar that you want to reclaim with intention this year?