Could Have, Would Have, Should Have: Why Conversations Can’t Wait
Article by K. Wong
Illustration by Gwen Kethnon
My father’s final weeks were marked by silence. Seizures had placed him in a medically induced coma, cutting off his ability to communicate. At the same time, my father-in-law, battling Multiple Systems Atrophy, was losing control of his throat muscles, making speech increasingly difficult. Both were slipping away, leaving us navigating a space filled with memories of their voices and the awareness that further exchanges were no longer possible.
Even if I had more to ask or say, it wouldn’t have mattered—those moments were gone. What remains is a permanent void where conversation and connection once lived, a silence that cannot be filled. And while memories and past conversations bring comfort, they can never replicate the richness of direct interaction or the immediacy of a shared moment.
Regret often arises in these times, the “could have, would have, should have” creeping in to remind us of missed opportunities. But these experiences also reveal an important truth: this isn’t just about end-of-life moments or life-threatening illnesses. It’s about the everyday—the times when we carry good or bad news, when choices need to be made, or when a simple check-in could make all the difference. Communication matters at every stage of life, and the opportunity to connect meaningfully is fleeting.
Why We Delay: The Myth of “Later”
It’s human nature to assume there will always be more time. Life pulls us in countless directions, and we tell ourselves that tomorrow will be the day we have that important conversation or share that untold story. But tomorrows are never guaranteed.
Perhaps these conversations are postponed because they feel difficult or inconvenient. We might think, What’s the urgency? They already know how I feel, or, This isn’t the right time. The truth is, there is rarely a “perfect” moment to speak. Waiting for one often means the opportunity is lost altogether.
The Weight of Regret: Lessons from Missed Conversations
Regret from missed communication is among the most universal and profound human experiences. Whether it’s the friend we never reached out to, the parent whose advice we never sought, or the sibling we didn’t reconcile with, these moments add up.
Studies consistently show that poor communication—whether it’s a lack of clarity, suppressed emotions, or unspoken thoughts—can weigh heavily on our emotional well-being. The “could have, would have, should have” moments linger, often louder than the memories of what was actually said.
The Power of Urgency: Why Communication Matters Now
So how do we break the cycle of hesitation? By recognising that every conversation is an opportunity. Sharing your thoughts, asking meaningful questions, or simply taking the time to connect—even in small, everyday ways—builds a legacy of open communication.
This isn’t just about recording monumental life stories or preparing for end-of-life moments. It’s about making choices now to capture the seemingly ordinary moments that shape relationships:
Telling someone why they’ve made a difference in your life.
Sharing a family recipe while recalling the story behind it.
Asking a loved one about a time they overcame a challenge.
Clarifying misunderstandings or addressing conflicts with honesty and empathy, creating space for resolution and growth.
Small actions like these deepen connections and create a sense of presence and understanding that lives on, even if the person isn’t physically there. Taking the time to clarify, apologize, or simply listen can bridge gaps in relationships, fostering trust and a shared sense of value. It reminds us that open communication is not only about joyful moments but also about navigating difficulties together.
Preserving What Matters: A Legacy for the Future
Beyond spoken conversations, documenting what matters ensures that these moments endure. Journaling, recording audio or video, or even writing letters are all ways to create a record of thoughts, stories, and wisdom.
In the age of technology, tools like video biographies can elevate this effort, capturing not just words but the essence of someone’s presence—their voice, expressions, and gestures. These records are more than keepsakes; they’re bridges between generations, offering future family members an opportunity to connect with the past in a way that feels immediate and personal.
A Call to Action: Make the Choice Today
The choice to communicate—urgently, intentionally, and meaningfully—is one we make every day. It’s a choice to prioritise connection over convenience, to preserve what matters instead of leaving it to chance.
Regret is powerful, but it doesn’t have to define your story. The familiar refrain of could have, would have, should have often follows missed opportunities and unspoken words. By making the decision today to speak, to listen, and to record what’s important, we can sidestep those lingering doubts. Whether it’s a difficult conversation, a treasured story, or a simple “thank you,” these moments form a legacy that will one day speak for us when we can no longer do so ourselves.
Time moves forward, and the choices we make—no matter how small—shape the memories and connections that endure. Don’t let the could have, would have, should have become part of your reflections. Take the opportunity now to make your connections meaningful. Let’s make them count.
Further Reading
Elias, A., & Brown, A.D. (2022). The Role of Intergenerational Family Stories in Mental Health and Wellbeing. This study explores how sharing family stories across generations can positively impact mental health and emotional connections.
Galvin, K. M., Braithwaite, D. O., Schrodt, P., & Bylund, C. L. (2018). Family Communication: Cohesion and Change (10th Edition). A comprehensive guide to how families communicate, adapt, and grow through life’s challenges.
Zeelenberg, M., van de Bos, K., van Dijk, E., & Pieters, R. (2002). The Inaction Effect in the Psychology of Regret. A fascinating look at how missed opportunities and inaction contribute to feelings of regret.