Grieving the ‘What Ifs’?

Finding Peace with the Life You Have

A lot of people have been there: staring into the middle distance and playing the mental montage of the life we could have had. It's the ghost of the roads not taken, the echo of the person we might have become had we been bolder, dreamed bigger, or just once, stepped firmly outside the comfortable fence of our familiar routines.

In later life, as the decades stack up, these 'what ifs' can become heavy, triggering a unique and profound type of emotional pain: grieving the life you didn’t live. 

It can feel as real and consuming as mourning the loss of a person, because in a way, you are mourning a potential self and a potential future.

The Pain of the Unlived Life

When we talk about regret, it’s often tied to specific decisions—the job we turned down, the person we let go of. But grieving the unlived life is broader and more existential. It’s a deep, persistent ache born from the sense that you fell short of your potential, that you played it safe when you should have been radical.

This grief can manifest as:

• The Loss of Potential: You mourn the vibrant, globe-trotting entrepreneur you could have been, or the talented artist whose portfolio remains largely in their head. It’s the mourning of a "better" version of yourself.

• A Lack of Adventure: The crushing realisation that you prioritised security over excitement, and now the energy, the money, or the opportunity for those grand adventures seems to have passed you by.

• The Shame of Comfort: Feeling embarrassed that you chose the easier path, leading to the painful feeling that your life narrative lacks the compelling risks and triumphs you believe others possess.

  
  

This emotional process is valid. It is a form of loss. You are losing the potential future you had pinned your hopes on, and giving yourself permission to acknowledge that sorrow is the first, crucial step toward moving forward.

The Comparison Trap: The Illusions We Chase

It is almost instinctual to look over the fence at your neighbour's or friend's life. However, comparison is ultimately a futile and damaging exercise that helps no one.

When you look at Susan from the book club who is always on a cruise, or David from the golf course with his seemingly perfect family, you may be comparing your messy, complex internal reality with a carefully curated external performance.

Here's the harsh truth about the comparison trap:

• We Only See the Surface: Susan's expensive cruises might be masking profound loneliness, or she might have complex health issues she never discusses. David's success could be built on decades of stressful, unhappy work, and his perfect family might be struggling with hidden conflicts. No one's life is a highlights reel.

• They Have Regrets Too: Just because someone is financially comfortable doesn't mean they don't have their own 'what ifs.' Perhaps Susan regrets not having children, or David regrets missing his kids' formative years while he was building his empire. Every human who reaches later life carries a burden of choices they would undo. Their perfect exterior does not equal internal peace.

• It Steals Your Joy: Focusing on what others have actively prevents you from appreciating what you possess. Comparison is the ultimate thief of joy, convincing you that your own hard-won contentment is worthless unless it meets an external, often fake, standard.

You simply cannot know the reality of another person's heart or mind. Giving up the comparison game is one of the most powerful steps you can take toward self-acceptance.

Therapy and The Path to Self-Compassion

While it’s vital to acknowledge this grief, we cannot remain trapped in the past. The goal isn't to erase the regret, but to integrate it—to accept that your life is a complex mosaic of good and bad decisions, and that is perfectly human.

A therapist helps you find self-compassion by asking a vital question: "What was my past self trying to protect?"

You may have played it safe because you valued stability. You perhaps didn't take the risk because you were worried about your family or worried about failing publicly. 

You made those choices with the best information, resources, and emotional capacity you had at the time. Cultivating self-compassion means acknowledging that your past choices were often acts of self-preservation or love for others, not acts of failure. You deserve forgiveness for not knowing what you know now.

Two Truths to Anchor Your Acceptance

1. The Best Things Are Often Free

When you truly pause and assess your well-being, the greatest sources of comfort and joy are usually non-monetary, and they are accessible right now:

• Genuine Connection: A deep, honest conversation with a friend; the unconditional love of a grandchild. The wealth of your relationships is your true legacy.

• The Natural World: The simple pleasure of a walk in the park or along a beach, or a glorious sunset. These moments of stillness and beauty cost nothing.

• Personal Growth: Taking time to read, meditate, learn a small new skill, or finally dedicate time to a dormant creative pursuit.

  
  

These are the elements that create true, lasting richness in life, and they are available to everyone, regardless of their pension pot.

2. It Is NOT Too Late to Make Changes

Perhaps the most damaging element of regret is the accompanying lie that the game is over. It feels like the door to change has closed, but that simply isn't true. You have more agency now than you think, and it’s never too late to improve your life.

Change in later life isn't usually about becoming a millionaire; it's about making small, deliberate adjustments that create a profound shift in your daily experience and outlook:

• Challenge Your Narrative: Work on actively changing the inner story you tell yourself. Instead of, "I missed my chance," try, "I have valuable experience, and I will use the time I have wisely."

• Micro-Adventures: You can explore a neighbouring town, take a bus route you've never taken, or join a club that meets people outside your usual circle. Small acts of low-risk boldness reignite a sense of adventure.

• Set Intentional Goals: Focus on something achievable that is driven purely by your values, like volunteering for a cause you believe in or mastering a new skill.

True acceptance is not passive surrender; it's active reconciliation. It means fully accepting the reality of your past choices and the imperfect person who made them. And from that place of peace, you gain the clarity and the power to make the most of the years ahead. The person you are today is the sum of every one of those choices, big and small, brave and cautious. And that person, right here, right now, deserves kindness and a chance to live well in the time that remains.

What is one small, free, and accessible change you could commit to making this week to honour the person you are right now?

Need help in this area, or any other? Get in touch here or via email here.

Kirsten

Freedom Therapy