Grief Doesn’t Care About Your Plan
Why certainty makes grief harder than it needs to be
In the three years since my daughter died, I’ve spent countless hours trying to force certainty into a world where it no longer exists.
My thinking swings between the philosophical, where I ask myself who the hell am I now, what do I believe, where am I even headed, and the deeply physical urge to punch a wall when clarity once again refuses to show up.
Then there are the moments that aren’t abstract at all, when I’m simply flailing around for something solid to grab onto so I don’t get swept away in the storms that only grief can conjure up.
I guess in some ways, this story is about the stories we’re told.
Grief as the Great Disruptor
My wife is German and has regaled me with the terrifying fairy tales of her youth. I grew up on Cinderella, where if you just hang on long enough, life will make things right. She grew up, on her dad’s knee, learning that life will hurt you whether you deserve it or not. Often, survival is the victory.
I’ve joked with her that the Germans, being typically efficient, are killing two birds with one stone by combining a little child abuse with teaching important life lessons. Of course, what they’re really doing is showing their love by teaching their young the importance of resilience.
Continuing with the theme of horrifying fairy tales, experiencing a devastating loss can feel like being trapped as the main characters in Hansel & Gretel.
One day, life is hard, but at least it’s understood. The next day, the people and structures you relied on are gone. Grief feels like being abandoned by a world you trusted. Even if it sucked, it was familiar. And now?
I don’t know if I’m the parent of one kid or two. What I thought was my life’s work doesn’t seem important at all. My stamina and ability to produce work are nowhere near what it once was and I’m starting to wonder if it’s ever coming back. The sense that I can protect the people I love, my primary job as a man, has been kneecapped.
So many of the things I thought I could count on are gone. I’m living in a level of uncertainty that can feel intolerable. Life looks a hell of a lot more unpleasant when you’re worried about a boogeyman around every corner.
Why We Seek It
Our brains aren’t built to make us happy and comfortable. They’re built to keep us alive. And the biggest threat to our survival is…uncertainty. There’s that fucking word again.
Not having a clue what to expect activates the same systems in our brain as a physical threat. Our lizard brain takes over and we shift into fight, flight, or freeze. We react by doing things that make sense in the moment but that often cause us, and the people we love, long-term harm.
The most destabilizing uncertainty is realizing what’s never coming back and having no idea what will replace it.
Grief shatters your sense of order. Grieving is everything we do in response, whether it’s healthy or destructive, to try to restore it.
Welcome to the Pain Factory
I entered the latter part of 2023 as the Warden of Fucking Upsidedownville, a prison of my own construction. There was only one inmate, who happened to be me. It’s the place where no one comes to visit and the place I couldn’t leave.
I obsessed, like Rain Man with a box of matches, about how in one, nightmarish six-week period, I was going to experience a whole lot of unwanted firsts. What would have been Chloe’s twentieth birthday, our first Christmas without her and then the first anniversary of her violent death.
I knew they were all going to be terrible because…I needed them to be. If I could predict the pain, it couldn’t ambush me. It was something I could count on when I felt like I couldn’t count on anything else. I picked up a stake, walked into the future, drove it into the ground and then held on for dear life.
As the days clicked over, my dread grew like I predicted it would. And in some perverse way I craved it. At least it made sense when nothing else did.
When the days finally arrived, I felt absolutely nothing. I’d spent months stockpiling dread, and somehow even that ran out. The days that were supposed to hurt couldn’t even be relied on to do their job.
That was year one. Year two, turned out to be…exactly the same. Can a grieving dad not catch a break? Just one? All I was asking for was to be able to predict something. Anything.
I’m writing this five days after the third birthday without my daughter and once again, I’ve narrated myself into believing I could outsmart grief. And once again I’ve been proven wrong.
I’d been feeling good the weeks leading up to her twenty-second birthday. My wife and daughter were home from their trip to Australia. The work I’m meant to do and the impact I’m now meant to have is becoming clearer to me, and I’d just gotten back from a trip to Louisiana with some truly wonderful men.
When my wife asked me how I was thinking and feeling about Chloe’s birthday I replied with, “I think it’s going to be Ok. I feel like I’m in a really good place.” I actually meant it.
What happened next? Chloe’s birthday was the hardest, most painful one yet. It figures.
I could handle the grief. I did. What made it worse was the frustration, disappointment, and anger that came with being wrong again.
The grief hurt. But the expectation that it wouldn’t multiplied the impact.
There are so many ways to make grief more difficult than it already is. I’ve done them all and somehow keep discovering others.
What I’ve learned, for the fiftieth time is that grief doesn’t much care about your plans. It doesn’t respond to dread, doesn’t reward optimism, and doesn’t follow the script you write for it.
Healing won’t come from getting better at forecasting pain. It’ll come from stopping the forecast altogether. It’ll continue to arrive unannounced, and I’ll continue to do my best to let it hurt when it hurts.
And I’ll keep reminding myself that I can handle whatever shows up, without narrating it into something worse.
If this piece resonated, I’ve put together a short guide on how unacknowledged loss shows up inside change, and how to respond when things feel harder than they should.
You can download it here:



I’ve been grieving 2 deaths and the loss of a traumatic relationship for 2 1/2 months now. The pain is so bad and completely unpredictable. I can’t outsmart it either. Thank you. This helps. I am always grateful and relieved when I can write. It is kind of like, good, that’s done for this week. Post is set. Because this shit is impacting everything that matters to me.
I relate so much to the "Upsidedownville" of it all. My husband and I just lost our second child earlier this year. I feel like I'm walking around in an invisible horror movie while everyone else's life is "up and to the right." I think the people who exist outside of grief have more certainty about my grief than I do and that can be so painful. The people that say "It will get better" but they said that after I lost my first and it honestly has only gotten worse. I just have to breathe and get through the next 10 minutes and then the next 10 minutes...