Expand Your Philosophy: Grief and Regret Are Opportunities to Appreciate

Short principles for long-term clarity—and occasional epiphanies.

How can grief, love, regret, and humility guide us toward healing and self-awareness?

“Fight the tendency to see only darkness in loss; remember the love and passion that once made things worthy of your attention and affection.”

Although at times grief may feel overwhelming and unavoidably impossible to process it is helpful to remember that grief and “having loved” are the same thing viewed from different positions. When you sit in the awareness that the intensity of your grief is directly related to the intensity of the love you once had, transitioning from a place of victimhood (why did this happen to me?) to a place of gratitude and appreciation (wasn’t I lucky to have..?) becomes easier. This is not gratitude served as a platitude, as that is potentially a harmful delusion, but instead it is a connection with our deepest humility and with the experience of having cared intensely for something outside of ourselves. Grief is a contrast point and a truthful reminder of life’s beautiful finiteness, giving definition to the very essence of what it means to love. Although the scars of grief never leave us and are very painful, their connection to the love which birthed them never disappears – reflecting both the light and dark sides of our humanity.

The same is true of regret and “having tried”. The mere presence of regret heralds a risk taken in the attempt to action/avoid something. It is important for humans to have regret as it is the worldly humbling of our presence in the cosmos and a reminder we do not control all outcomes. As the old Yiddish proverb goes “man plans, god laughs”. Regret and the outcomes which birth it are moments to reflect on the things we have tried, what was in/out of our control, and what went wrong and right as no two experiences are the same. Therefore, if someone claims to live without regret, they are likely in denial of the fact that they are responsible for the actions, privileges, or avoidances taken to get to the outcome as this reflective process does not occur. This is especially pernicious in cases where things go wrong. People in this state of denial are missing out as the humility brought about by regret, brings with it opportunities to live in curiosity and appreciation of our humanness. Rather than a life designed to avoid the disappointment of our unmet expectations of reality.  

Grief and regret are not merely negative comparisons of our past state to our current state, they are also an opportunity for us to gain the fullest humility and learning out of any human experience. It helps us to understand our experiences and derive meaning from them. By resonating with the negative feelings and appreciating the loss you endured allows for forgiveness, reconciliation, and empowerment. Although the pain is no flippant thing and is unlikely to be pleasant, the healing process requires us to see the reason behind the pain. To metabolise it into something which can be integrated into our entire being, making us more than we were before.

Take the love you had and lost, and the things you tried and that turned out poorly and allow yourself to derive the meaning of what it meant to you originally. This is the narrative control we have over our lives. We often do not know what we have until it is gone – allow yourself mourning but also allow yourself the deepest gratitude that it graced your life in the first place. Allow both grief and regret to fill you with a sense of humanity and humility as this is the richness of the human experience.

Deepest love and sincerity to all those who have lost or done wrong – your feelings make sense and I believe your pain. Give yourself permission to take as long as you need and arise from its clutches as a more loving human – those are all my prayers for you.

Reflection Questions:

  • Imagine that you already made the incorrect decision and are now regretting not taking another option, what option would that be and how is it different?

  • Imagine you have already lost a family member or friend who is currently alive, what would you miss not doing with them right now?

  • Imagine you have died and the people in your life are now bereft of your presence, what things would they miss doing with you? Remember: There is always someone who will mourn you, and they may not be who you expect.

  • Imagine you are regretting someone else’s decision who made this choice for you, what do you love about it? What do you hate about it?   

Songs That Embody This For Me:

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