The Grief of Realizing You Don't Know Where You Are Going In Life
How do you keep walking when you no longer know the destination?
The Encyclopedia of Grief is an archive where we talk about the kinds of grief that shape our lives quietly, often without anyone noticing. This season is focused on the grief that follows the broken promises of modern day life. We’re not here to fix anything. Take what you need and leave the rest.
There is a form of grief that arrives when you realize you no longer have the answers. When your knowledge, your confidence, and your well-built plans all begin to dissolve beneath you. This is a grief of losing certainty, not because you were wrong, but because life outgrew the neat containers you once used to understand it. What rises in its place is not a new solution, but a frustrating form of humility.
For me, this grief arrived slowly like fog rolling in. I believed that I had to have everything figured out from a young age. Which isn’t surprising, considering most of us had that message forced onto us throughout our time at school. I still cringe thinking about my college major that was completely wrong for me looking back. But I truly believed that if I just read enough, worked hard enough, stayed alert enough, I could stay ahead of life.
Slowly, things started to unravel. I no longer aligned with my past definitions of success. My driving forcedMore questions were arising than the answers. The systems that didn’t work for me no matter how well I played the game, questions that refused easy answers, and a sinking feeling that it was time to finally turn toward the abyss and accept that I had no idea what I wanted to do with my one wild and precious life. It was crushing.
Of course, all things travel in cycles. Six months later and I have a completely new and unexpected path I’m excited to travel. But damn, was it frustrating to have no answer to the question “what’s next for you?” that every single family member asked me during that period.
✾ What This Grief Looks & Feels Like
This grief often shows up quietly. At first, it might feel like doubt or a sense that something no longer fits. What used to feel solid begins to feel slippery. You might recognize it in moments like these:
Realizing the path you worked is hard to build no longer feels right
Losing confidence in a spiritual belief or tradition that once gave you meaning
Questioning everything after a diagnosis, job loss, or unexpected betrayal
Feeling like the advice and mentors that once guided you no longer apply
This grief doesn’t always look like heartbreak. Sometimes it looks like silence or standing in a room full of people and wondering how you ever felt sure of anything at all.
It often lives in the upper body, where thought, voice, and breath intersect. You might feel mental fog, confusion, or spinning thoughts. You may be caught between intuition and doubt, your through tight, and chest heavy. Even if no one else can see it, your body knows something has shifted.
“Be patient toward all that is unsolved in your heart and try to love the questions themselves.” —Rainer Maria Rilke, Letters to a Young Poet
✾ Where This Grief Comes From
This grief is everywhere. When I was experiencing this grief earlier this year, I started to search out to my friends and family to see if any of them had experienced this. And boy, was I surprised to find out that they’d all been through this phase.
You see it in the burnout of overachievers, in the therapist who no longer trust her own tools, in the spiritual seeker who questions whether the rituals ever really worked We live n a world that praises certainty and quietly punishes the ones who lose it. We are taught to trust the expert, the five-step plan, the algorithm. It’s what we were conditioned to do since we first entered school. But when our questions get too big for those frameworks, there is little room to unravel.
In a society that worships certainty, not knowing can feel like failure. But this isn’t new! Throughout history, people have entered what mystics call the “cloud of unknowing” or the “dark night of the soul”. Losing certainty wasn’t a crisis—it was a rite of passage for any person taking full responsibility for their lives.
After realizing that everyone around me had gone through this phase, I started to realize that knowing how things are going to unfold is not the goal. The goal is figuring out what brought me joy and excitement, and going toward that thing without clinging to the outcome.
✾ Mythic Mirror: The Fool’s First Step
In the tarot, The Fool is the first card of the Major Arcana. Numbered zero, it represents both nothing and everything, a beginning that hasn’t yet become defined. The Fool stands at the edge of a cliff, eyes lifted, heart open, belongings light.
There is no plan. Only the invitation to step forward.
This is not the recklessness of someone unaware. It is the quiet bravery of someone who knows they no longer belong to the story they were living. The old truths dissolve. And still, the next step calls.
This is the grief of The Fool: the ache of leaving behind a former self without knowing who will take their place. And sometimes, the most sacred journeys begin not with knowing, but with trust and surrender.
“The truth you believe and cling to makes you unavailable to hear anything new.” — Pema Chödrön, When Things Fall Apart
✾ Three Ways to Work With This Grief
Read: The Surrender Experiment by Michael Singer. A powerful companion if you're exploring how to live without control. It offers a real-life story of what becomes possible when you start learning to trust.
Create: A note in your phone where you can collect the big, unanswered questions you have about your future. Don’t rush to solve them. Just let them live there. Over time, come back and jot down how each one unfolds. You may be surprised by how often the answers arrive in ways you never could have imagined.
Challenge Yourself: Each day for one week, reach out to someone in your life and ask them how they dealt with uncertainty or confusion over their future plans. You’ll be surprised how many others have gone through this and have advice on how to navigate it with care.
If you stop needing to be certain, who might you become?
I asked myself that question six months ago when I was desperately begging for clarity on where I was meant to go next in my life. I let the question linger, allowing it to echo through the places where my old beliefs once lived. I kept a note of all of my unanswered questions, and updated it weekly when things seemed to magically work themselves out.
And without much input from me, the questions started to answer themselves. I eventually stumbled onto my new path, with all the unexpected and glorious projects popping up in my future. This Substack is no exception! I never could’ve imagined writing a column on modern day grief and how our unwillingness to discuss them is keeping us isolated and disconnected. But here we are, and I’m so glad that I found you here.
If this grief resonated with you and you’d like to contribute to future seasons of the project, you’re invited to take our Share Your Story of Grief Survey. The goal is turning this into a community-led project, and I’d love for you to get involved.
Thank you for spending some time with this grief. Each entry in this library is a small act of remembrance for the parts of us that were never given space to feel, question, or break apart.
We are here to sit beside grief, not tell it what to become. Before commenting, check out our Community Guidelines. If you need more support, the Grief Resource Hub is here for you.