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The Money Trap: Chase Millions, Find Emptiness


A quick announcement before I begin today’s post – 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. You can also enjoy lower prices on multiple-copy orders.

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.


There’s a cruel joke about money that no one tells you until it’s too late:

If you don’t have enough, it controls your life. If you have too much, it can do the same.

We’re sold this idea from childhood—study hard, work smart, climb the ladder, and one day, you’ll have enough money to be free. 

Free from stress, free from obligations, free from anything that feels like work.

But what happens when you reach that point and still feel empty?

You see, the problem with money is that “enough” is an illusion. Ask someone making ₹50,000 a month what number would make them truly happy, and they might say ₹100,000. Ask someone making ₹100,000, and they’ll say ₹500,000. Push that further, and you’ll hear ₹1 crore, ₹5 crore, ₹10 crore.

Worse, in today’s world, people are openly flaunting their income and net worth on social media, which, I’m sure, leads to many people watching them feeling inadequate and not having enough, sometimes even when they do.

It never ends.

There’s a reason why some of the wealthiest people in the world keep working—because the game is never over. The finish line keeps moving.

If money alone could buy happiness, billionaires would be the most joyful people on earth. Instead, they are often some of the most restless. They make bigger houses (one in my city cost $2 billion to make), take grander vacations, arrange lavish weddings, and chase the next high—only to realise that every new milestone feels just like the last one.

It’s the hedonic treadmill at its finest.

Don’t get me wrong here. Money is freedom. It can help you buy security, relieve stress, and open doors. 

But beyond a certain point, money can start to isolate.

It creates a distance between you and the real world. I have seen it personally in my extended family—how wealth, instead of bringing people together, builds invisible walls. Some don’t break for generations.

Also, when you can afford anything, little has real value. Food doesn’t taste as good when every meal is a luxury. Travel feels dull when every destination is accessible.

Another way money becomes a trap is when it removes the struggle that makes achievements meaningful. If you can buy your way out of every inconvenience, you lose the satisfaction of overcoming. Life becomes easier but not necessarily richer.

This is my biggest worry with this entire idea of building “generational wealth.” Too much of it can leave the next generation with financial richness, but also with the poverty of imagination, courage, and enterprise.

Another trap money creates is that it makes you question what to do next. Imagine if work was only about making money, then what happens when you don’t need to work anymore? What drives you? What makes you wake up in the morning?

At a certain level of wealth, people stop playing for money and start playing for meaning. The ones who don’t? They keep chasing zeros, hoping that somewhere along the way, happiness will catch up to them. Sadly, it doesn’t always happen.

Like, read this letter from Jake Kassan, the founder of watch, eyewear, and accessories company MVMT, who sold it for $100 million in August 2018 to watchmaker Movado and then vented his emotions on Reddit—

Some eye-opening lessons, right?

Kassan is now 33 and, in an interview recently, said, “I can’t buy more peace of mind. That’s my relationship with money. I’m grateful for it, I appreciate it, and I’d rather have it than not… but it won’t make me a happier person.”

Now, you don’t have to have a high net worth or be ultra-rich to experience this paradox of luxury, just like Kassan. Even small upgrades in lifestyle can reveal the trap.

For example, when I bought a Honda City in 2015, suddenly, my Maruti Alto (my original dream car) felt inadequate.

When I moved into a bigger house in 2018, suddenly, I needed more things to fill it.

When I started travelling 2AC on the train, suddenly, 3AC felt unbearable (though I still prefer train travel to flight travel any day!).

Every level of financial success brings new expectations, new comparisons, and new dissatisfactions. The more you have, the more it takes to feel excited again.


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


So, what’s the solution to avoid the money trap?

To each his own, but I think one probable solution is to redefine wealth beyond money. 

True wealth is health, relationships, freedom, and purpose. Use money just as a tool; don’t make it the goal.

Another solution is to find meaning outside of accumulation. If the only reason you’re working is to make more money (and so you can talk about it), you’ll never know when to stop. So, find work that matters beyond the money it can earn you.

A third solution is to embrace your financial limitations and constraints. Sometimes, the happiest moments come from not having everything at your fingertips. If you are in your mid-forties like me, look back to your growing-up years in the India of 1990s, and you’ll understand what I’m trying to say here.

Remember when having a single bicycle in the neighbourhood meant every kid took turns riding it? Or when Sunday’s episode of Mahabharat or Shaktimaan was the most exciting event of the week? Birthdays meant homemade cake, and a new comic book—Tinkle, Champak, or Chacha Chaudhary—felt like a treasure. Ice cream was a special outing, not a daily indulgence. Family vacations weren’t international getaways but road trips to a relative’s house, packed in an Ambassador or a Maruti 800, where the journey was half the fun.

We didn’t have everything, but we had enough. And somehow, that made everything more special.

Lesson? Scarcity creates appreciation. Struggle makes achievements meaningful.

If there’s one big lesson I have learned about money in my life, it is that it’s powerful but a terrible master. 

If you don’t decide how much is enough, the world will decide for you—and the answer will always be more.

Your real win? Knowing when to stop chasing and start living.


P.S. Want to leave you with a passage from my book Boundless, from the chapter on Joseph Heller’s lesson on what it means to have “enough”—

Click here to check out Boundless. It contains 52 lessons across themes like self-discovery, dealing with adversity, mindful living, personal growth, and societal virtues—each designed to guide you toward a life of meaning, growth, and fulfilment. Thank you!

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