A couple of quick announcements before I begin today’s post.
1. My new book, Boundless, is now available for ordering: After a wonderful response during the pre-order phase, I finally have the book in my hands and am shipping it out quickly. If you’d like to get your copy, click here to order now at a special discount (available till 10th May). Plus, I’m offering a special combo discount if you order Boundless along with my first book, The Sketchbook of Wisdom. Click here to order your set.
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The Price of Freedom
There’s something uniquely tormenting about looking back at a decision you made years ago, one that you made with good intentions and maybe even a little excitement, and realising that today, you’d choose differently.
I’d been wrestling with that feeling a year ago, every time I entered an apartment I bought in 2018. It was my second apartment in the same building, just a floor below the first one where we lived. At the time, it seemed like a sensible and exciting step. Our kids were growing up, space was always tight in Mumbai’s famously matchbox-sized homes, and I imagined this second apartment as a seamless extension of our current one. It had a beautiful view too: a big garden and a hill in the distance, which is a rare sight of calm in this noisy and cluttered city.
So, I went ahead and bought it. I funded the purchase by selling some of my stocks and mutual funds. That part, in hindsight, stings a little more. But back then, it felt like a meaningful milestone, as I was trying to create a better life for my family.
Then life, as it often does, moved in directions I hadn’t planned for. We lived in that apartment during the pandemic, but in 2022, my next-door neighbour in the original apartment (a floor above) offered to sell his flat. It was a rare opportunity to knock down the wall and combine two flats into a larger one. Still a matchbox, but at least a bigger one, and all on the same floor.
After much thought, I said yes. And just like that, I became the accidental owner of three apartments in the same building.
Anyways, here’s where the mind plays its little games. That second apartment, the one I once saw as an “emotional extension” of our home, quietly changed categories in my head. It was no longer “extra space” or “home office.” It had become an “investment.” And once that mental switch flipped, I couldn’t help but start calculating its returns, as though it had always been a portfolio decision.
The numbers weren’t kind. Seven years later, the expected market price would give me a total return of not more than 15%. Not CAGR or annual return, but 15% cumulative, over the entire period! And that’s before subtracting maintenance costs and property taxes. If I added those in, the return dropped closer to 10%, point to point. Not exactly the kind of return you’d want after locking up a chunk of capital for seven years in India’s commercial capital, and when, in hindsight (ouch!), you realise that you could have doubled or trebled that money by just staying in equities.
So, if you had asked me early last year whether I regretted the decision from 2018, you probably wouldn’t even need a response. My face would have told you everything. I was frustrated at myself.
But some gears shifted in my inner engine in 2024 while I was working on my second book, Boundless. As I researched for the book and dove into ancient philosophies, spiritual texts, and the timeless wisdom of thinkers across cultures and centuries, I began to see “regret” in a new light.
One recurring idea that stood out was that regret is not a flaw of our minds, but a feature of our freedom. That to live a conscious and intentional life is to occasionally look back and wince. And not because we failed, but because we cared enough to choose. We weren’t passive recipients of life but were active participants. And participants, by definition, sometimes stumble.
As Seneca wrote in On the Shortness of Life:
The greatest obstacle to living is expectancy, which hangs upon tomorrow and loses today. You are arranging what lies in Fortune’s control, and abandoning what lies in yours. What are you looking at? To what goal are you straining? The whole future lies in uncertainty: live immediately.
And Ralph Waldo Emerson wrote:
Finish each day and be done with it. You have done what you could. Some blunders and absurdities no doubt crept in; forget them as soon as you can. Tomorrow is a new day. You shall begin it serenely and with too high a spirit to be encumbered with your old nonsense.
The Stoics often said that we cannot control outcomes, only our choices. The Gita speaks of acting without attachment to results. Buddhism teaches the impermanence of all things, that both joy and sorrow pass, and our suffering often comes from clinging to what could have been.
Over the years, I have come to see these as not just lofty spiritual ideas, but practical reminders that regret loses its sting when we stop treating life like a formula that can be perfected and start honouring it as a process or a journey filled with learning, detours, and redirections.
And so, the apartment? Yes, it didn’t work out the way I imagined. I am now looking to sell it off, but I have stopped looking at it with regret. Instead, it has become part of my curriculum. It taught me humility. It reminds me that even with experience, we never graduate from the school of decision-making.
Every phase of life asks new questions. Every decision brings its own unknowns. Regret, then, isn’t a verdict, but a signal…that we lived, that we learned, and that we’re still evolving.
Isn’t that the strange and beautiful thing about freedom? That it allows you to rewrite your understanding of the past. And you don’t do this to change the facts (you can’t), but to change the meaning you assign to them. And in that reimagining, regret can soften. It shifts from being a tormentor to becoming a teacher.
I’ve also learned that even the most carefully made decisions come with risk. The best plans still encounter surprise detours. We don’t get to rewind the tape. All we can do is forgive the version of ourselves that acted with sincerity, and understand that wisdom often arrives late, usually after it’s no longer useful for that specific decision.
The challenge is not to live a life without regret. That’s impossible. The real challenge is to not let regret harden into cynicism or self-blame. To see it, instead, as part of the price of living a life with agency. A life where we get to choose, to act, and to risk being wrong.
I won’t pretend the sting is gone entirely. It still surfaces, especially when I see the opportunity cost in numbers. But I try to meet it now with less self-judgement and more curiosity. I remind myself that the very ability to reflect, to feel, to learn, and to grow is its own kind of wealth.
So, if you’re living with a regret of your own, maybe about money or a career move, a relationship or a risk you took that didn’t work out, I hope you take a lesson from my lesson.
The very fact that you could choose means you were alive to the moment. You were engaged and not sleepwalking through life.
Regret may stay with us, but it doesn’t have to define us. It’s simply part of the landscape we cross when we choose to live freely. It’s like a quiet companion on the road we walk when we decide, again and again, to live life on our own terms.
And I’d rather have my bruises and all, than a life where I never got to choose at all.
The Sketchbook of Wisdom: A Hand-Crafted Manual on the Pursuit of Wealth and Good Life.
This is a masterpiece.
– Morgan Housel, Author, The Psychology of Money
That’s all from me for today.
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Thank you for your time.
—Vishal