When Every Season Hurts: Surviving Grief Anniversaries and Death Dates All Year Long
There was a time in my life when I thought grief only lived in December.
My mom died the day after Christmas in 2013. That first holiday season without her was devastating. Counting down the days to her death anniversary was like a subscription to pain I couldn’t unsubscribe from. The years that followed felt pretty much the same.
I expected December to hurt. I braced myself for holiday songs in stores, for tangled lights in neighbors’ yards, and for the unbearable silence around the Christmas tree. Grief lived there. And in some ways, I could prepare for it.
But what no one told me about grieving multiple losses—what I didn’t expect—is that when you’ve lost enough people, no part of the calendar feels safe anymore.
Now May hurts, too.
Of course, Mother’s Day has always carried a sting, but in recent years, that grief expanded. My best friend died from COVID on May 13, 2022. Then, in the same week in 2024, my cat died. Suddenly, the tulips blooming and the days getting longer didn’t bring comfort. They marked loss. Again.
This is what cumulative grief looks like: season after season, date after date, gathering weight.
You start to realize grief is not a one-time disruption confined to a death anniversary or a certain time of year. It’s a constant presence. And as your number of losses rack up, so does the sense that you’re grieving continually—that you’ve got your own subscription to pain that you can’t unsubscribe from.
In this blog, I’ll talk about grieving multiple losses and navigating a year filled with grief reminders. I’ll also share four tips for honoring your grief dates so you feel more prepared to face them when they unavoidably arrive.
Grieving Multiple Losses Means Losing More Than People
When I sat down with illustrator and author Tyler Feder on a recent episode of Grief Grower, we talked about what it’s like when loss stops being isolated to one person, one event, one season of the year—and starts touching every corner of your calendar.
Tyler’s mom died when she was 19 and she recently lost her dad to cancer in 2024. As she told me: “Before my dad was sick this last time... my mom got sick over the summer, so that was bad. Then she was really into a lot of the Jewish holidays that are in fall... and she died in spring. So every single season was related to her in some way.”
That idea landed hard. Because when you're grieving multiple losses, you’re not just grieving people—you’re grieving time itself. Holidays. Weekends. Their birthday. Your birthday. All of it can be marked by absence.
While many of my clients and students talk about the death anniversary of their person being the hardest time of the year (and that was definitely true for me too at first), other days can be difficult too—and those days can take place not just in the season that your person died, but all year round.
The Calendar Becomes a Minefield
Grief anniversaries, death anniversaries, or “griefiversaries” as I like to call them don’t just show up as a sad date circled on the calendar. They creep in through your body, your dreams, your energy levels. They’re sneaky. Even if you forget the date, your body often remembers.
Even the way our people die can dictate how the calendar feels. A drawn-out illness brings reminders of their decline everywhere. Quick, shocking deaths freeze time. Either way, the result is the same: grief becomes a shadow stitched to the seasons.
Some grievers, like my wife, can’t help but notice dates and numbers.
Some grievers, like one of my Life After Loss Academy students, feels impending grief seasons as illnesses in her body.
I personally tend to pair losses with nature. If the spirea is blooming, I feel the ache of my best friend’s death. If the ground is frozen, I remember watching my mom die in our home during Christmastime.
The reminders and the sense that something awful (or the anniversary of something awful) is just around the corner can feel neverending.
And for many of us—especially after multiple losses—we start to wonder, Is there any time of the year that’s actually safe?
One of Tyler’s wonderful grief illustrations, about how springtime changed after her mother’s death | Credit: @tylerfeder
The Grief Tipping Point: When Dates Stack Up
Tyler and I both spoke to the moment when grief crosses a threshold. One death turns into two. Then three. Then more. And suddenly, you’re not just grieving a person—you’re grieving your old relationship to the calendar.
In our podcast episode I said, “You go from having pockets or times in the calendar that feel safe from grief to suddenly having what feels like your entire calendar overrun by things that remind you of the people you’ve lost.”
For me, it was the shift from “December is hard” to “Oh, May is hard now, too.” For Tyler, it was discovering that her dad died two weeks before her mom’s birthday, and her mom died two weeks before her dad’s birthday. The eerie symmetry of it led her and her sisters to create “Spirit Week,” a two-week period where they’re extra gentle with themselves.
She said: “So much of grief sort of feels like when you're up really late and everything is just like surreal and funny and you can just laugh or cry at any moment... So right now, we're just treating them as like during these two two-week periods, we're gonna be real gentle with ourselves.”
She’s right. There reaches a point where you’re carrying so many losses that mechanisms like humor feel like one of the only ways to cope. It’s very reminiscent of the famous “This is fine.” meme that circulates in times when an awful world event is happening—like a genocide, natural disaster, or scandal—yet you’re expected to work, communicate, show up, and be a human as if everything is normal.
You’re saying, “This is fine,” when absolutely nothing about what you’re living through is, in fact, fine.
The famous “This is fine” meme, featuring a dog in a small hat drinking a cup of coffee saying “This is fine.” while his house burns around him. | Credit: KC Green
Cumulative Grief Is Not a Personal Failing
Here’s what I want you to know: if your grief feels heavier over time, if every new loss feels like yet another hard thing to carry, if the calendar feels like it’s closing in on you, you are not broken.
You are experiencing cumulative grief.
This isn’t something people warn you about when you experience your first major loss. Even if they do, you’re already overwhelmed, and it’s likely that the concept of cumulative grief won’t feel completely real until you actually live through it. But if you happen to live long enough, it’s almost guaranteed that you’ll experience another loss—whether a death, breakup, diagnosis, or other major loss.
It’s a natural part of life—to experience loss. But it’s also one of life’s great challenges—to figure out how to keep going when every season holds reminder of who and what is no longer here.
See if you resonate with Tyler’s words: “At some point you rack up so many losses that you're like, ‘It feels like my life is not even real.’ And I tell [my loss story] to other people and they think I'm making it all up.”
This is the invisible weight that people who haven’t experienced major loss just don’t understand. We’re not just sad because we lost someone once. We’re sad because we keep losing. And the grief keeps piling up.
Our calendars are full of landmines and potholes and tender spots. And with the turning of each new year, we stare our date books down again, wondering what fresh, new losses will eventually be added to our growing collection. This is the ever-present reality of cumulative grief.
How to Cope When There Are No “Safe” Seasons Left
So what do you do when you’ve got multiple losses to grieve and it feels like loss has taken over your calendar?
Here’s what I’ve learned, and what I teach inside Life After Loss Academy:
1. Make a grief calendar.
Make a list of all the days that hold grief weight: death anniversaries, birthdays, diagnosis days, breakups, “dates of knowing,” holidays your person loved, and so on. Look at your year. See the clusters. This isn’t about tallying all of your grief; it’s about preparing to care for yourself. Consider not only specific dates, but seasons too, such as the holiday season, graduation season, and harvest season.
2. Create helpful rituals in advance.
One of the biggest things my clients and students struggle with is anxiety about upcoming grief dates. But you can reduce anxiety by having a plan—or even a semblance of a plan. Ask yourself: What small thing could I do on this day to help me feel like my grief is honored?
Rituals don’t have to be grand. You can light a candle, make a recipe your person loved, visit their favorite spot, or do something meaningful on their behalf. For instance, Tyler and her sisters invented Spirit Week to remember their parents. Every year on May 13, my friends and I meet for bubble tea at my best friend’s memorial bench.
If you want to make a big production about the day, do it. But small rituals or actions have an impact too. Consider making a list of rituals or actions—from low energy to high energy—and then choose closer to the day, or even on the day.
3. Make room for grief to show up.
Instead of resisting or trying to power through grief during hard times, make space for it. If you can, schedule fewer commitments. Give yourself permission to cry, to cancel plans, or to rest. Grief demands energy. Respect its needs. Don’t fight its presence on the calendar; let it expand to fill the day or week where you anticipate things will be heavier than usual.
If you’re able to take off work or school, fantastic. If you can’t, there are still things you can do to take care of yourself. Consider ordering prepared meals so you don’t have to cook, picking an outfit “uniform” to wear in advance, asking a friend or a babysitter to look after your kids for an hour or two, or scheduling a flower bouquet or gift basket for delivery so you can enjoy it on your grief day. Dedicating time to meditate, take a bath, go for a walk, pet an animal friend, or grab coffee with a good friend can be ways to offer yourself kindness.
4. Gather your grief allies.
Whether it’s friends, family, or online spaces like mine or Tyler’s, having people who “get it” makes grief less isolating. Consider who has been supportive in the past and invite them to continue to support you in the present. A simple script like, “I’m having a hard time as my best friend’s death anniversary approaches. Can you recommend a favorite restaurant to order carryout from so I don’t have to cook this week?” can be helpful.
If you want to download my Printable Grief Dates Calendar, complete with a list of potentially difficult seasons + 13 ritual ideas for honoring grief throughout the year, join us in Life After Loss Academy. You’ll get on-demand mini lessons for navigating grief plus weekly grief coaching with me where you can ask questions and get customized guidance for your unique loss (or losses!). Learn more and become a student today.
Closing Thoughts: Grief Is a Constant Companion, Not a Calendar Event
In our conversation, Tyler said something that stuck with me: “[Cumulative] grief is like mosquito bites. It's not necessarily like you're getting bit by a snake, but no one likes getting mosquito bites constantly.”
Cumulative grief—or the grief of multiple losses—is just that: low-grade, constant, sometimes invisible, but impossible to ignore. And living with cumulative grief changes how you move through the world. It changes how you feel in spring, in summer, in December, on your birthday, and even on a random Tuesday at 3pm.
But cumulative grief also invites you—demands you—to care for yourself in a deeper, more honest way. To not just endure grief dates, but protect them. To honor them. To see them as sacred. To live a life with grief, not against it.
If it seems like every season hurts right now, you’re not alone in that reality. No matter who or what you’ve lost, you deserve compassion, tenderness, and space—366 days a year.
If you’d like to listen to my full conversation with Tyler, you can do that here.
And again, if you’d like to access compassion, tenderness, space, AND tools for living with multiple losses, I hope you’ll join us in Life After Loss Academy. Find out more and join here. (Pay special attention to the Establish module, where I talk about making a grief calendar!)
