Recently, I wrote two blog posts that were two parts of a letter to my younger self. All in the name of figuring out what I would advise him had I the chance to travel back in time to help him navigate an often-bewildering life that had no mentors or guides.
I think it’ll be good practice for me to write one now to my older self too.
It’ll give me a chance to pause, ponder, and predict what I might be like in the next 30 years or so before I’m six feet under.
So here goes:
What I’ll Say To “Senior Me”

Hey K
How’s life? I know it’s crazy for me to write this cos likely you, the older me, would already know the contents of this letter. After all, you’ve lived this life I’m now in already no?
Still, I wanted right off the bat to tell you that you’ve done good and you’re exactly where you are supposed to be now. Of course, I’m making many assumptions here, given I’ve no visibility on what’s going on right now in your life.
You could be enjoying it with good health. Or not.
You could be actively participating in family life and community living. Or not.
I’m hoping you are a happy grandpa now. Or maybe not.
So many possibilities. So many unknowns from my point of view. Heck, it’s probably better if you write to me instead! Or better yet, pay me a visit! Surely technology after 2050 should allow for time travel of humans, not just letters.
Right now though, that’s all I can do in my timeline. Which is why I decided to write a letter to my younger self and another one to you.
Regrets? I’ve Had A Few

As you well know, I’ve regrets and failures in my life. Nearing my mid-50s now, how can I not? How can anyone not? (Other than the delusional narcissists among us. Which reminds me — did Donald Trump win the 2024 Presidential Elections? I know I’m just three months away from finding out, but I can’t wait!)
I think of regrets from different decades of our lives. From school and curriculum choices, to where we live, to career choices, friends, and experiences I had or hadn’t.
The list goes on, with regrets big and small.
But the burning question in my mind now is what about the “senior me”? What about you? What regrets do you still harbor?
Of course, the hopeful me now wants to believe you didn’t accumulate new ones but have learned to make peace with all our regrets.
But I’ve recently learned that regrets should not simply be seen as something we need to put to rest.
Regrets Shape Who We Are Too

In his 2022 book “The Power of Regret” the writer Daniel Pink argues that regret is an unavoidable fact of life and that it should be embraced as a useful and instructive emotion. What we regret, he says, can teach us about who we are. It helps to reveal what we want, what we fear, what truly matters to us, and what doesn’t. It is a tool that can help tune our moral compasses, strengthen our values, and keep us from repeating the same mistakes over and over.
Of late, I’ve been reading stuff from retirees who lament how they didn’t prepare well for retirement, an oft-quoted regret. I’ve even responded in a forum letter published three months ago, cautioning more to prepare ahead for retirement in ways that go beyond the purely financial.
But in light of what Pink said, I’m thinking now that the regrets we have also shape who we are, and how we view the world around us. Of course, being upset and rueful over something we wish we did or didn’t do is to be expected.
However, we should go further, after the dust settles, to see that regrets often mold our perspectives for the better. If taken in the right spirit, it can sharpen our resolve as well as deepen our convictions and values.
For example, I’ve always regretted not pursuing the Humanities in my teenage and young adult years of tertiary education, choosing instead the “safe” route of courses in Science and Business. Yet that regret eventually drove me to put aside my disappointment and recognize how my love for the Humanities needn’t be quenched forever.
Look at me now, blogging consistently for the last five years, and growing in my reading and writing on any and every subject — books, movies, music, special needs, parenting, and life in general. Can anyone say I’m still the (struggling) Science and Business student that I was before? Can anyone ignore the Humanities side of me springing forth with each essay and poetry blog post I dish out weekly?
Cherish Your Regrets, “Senior Me”

If struggling with regrets is putting you down and keeping you up at night now my “Senior Me”, would you hear me out, please?
It’s not worth it!
Those negative feelings sap away too much energy you’re not likely to have now in your twilight years.
If your younger me now is struggling at 50+ to have the energy to do stuff I did in my 30s and 40s, all the while nursing a chronic backache, I can only imagine what state your physical and mental conditions must be! (Though I pray hard of course to be proven wrong)
Instead, hold fast to these words of encouragement and assurance.
You are right now where you were always meant to be. You’ve done more than your fair share and no longer have anything to prove. Rather than wishing you could turn back the clock and do, redo or un-do stuff in your past, savor the fact that every decision, every milestone, every success or failure has nevertheless still brought you to this point in your existence.
Enjoy every moment, even if it flies against every evidence to the contrary. Even the real world in your time with all the knowledge it has, still won’t have life figured out yet I’m certain. So don’t bother looking to the world, or external validations by strangers and friends to decide that you matter or have value.
Doing all that was an exercise in futility when I was a teen. It is still an exercise in futility in my time now. And I have no doubt it will continue to be so in yours.
All to say this: You were, you are, and you have always been enough. Regrets and all.
So take care Senior Me and live each moment you have now to the fullest!
Your Younger Self
