If you’ve ever stared at your brokerage account wondering,
“Should I just wait for a dip?”
then you’re not alone.
We love to believe we’ll make the smartest, most rational choice.
But investing isn’t just money and maths.
It’s fear, regret, impatience, FOMO, doubt, hope, and that eternal whisper:
“What if I waited? What if I bought more? What if I bought earlier?”
So I want to introduce you to three fictional investors - Arun, Dev and Ravi and how each chose a different path over 30 years. For this analysis, let’s assume it’s a same level playing field with Same income. Same investment product. Same market returns.
The only thing that differed was their behaviour.
And as you’ll see, behaviour is the real portfolio driver.
Let’s step into their stories.
Investor 1: Arun - The DCA Loyalist
Arun started his investing journey the way he does everything in life:
quietly, consistently, without fuss.
Every month - regardless of market noise, Trump tantrums, elections, recessions, optimism, or doom - Arun put in his fixed amount.
At first, he doubted himself.
His colleague, Dev, kept boasting:
“Mate, why are you buying at the top? I’m waiting for the crash.”
Arun hated the idea of overpaying. But he also hated the idea of overthinking.
So he shrugged and kept investing anyway.
His emotional rollercoaster looked like this:
He felt foolish during market highs
He felt foolish during market crashes (“Why didn’t I wait?!”)
He felt foolish when others bragged
He felt foolish when others panicked
But - and this is key - he never stopped.
Over 30 years, it doesn’t matter whether he bought it at high, low or somewhere in between - given that he has sticked to it - he is still well above because he simply didn’t miss compounding cycles.
Investor 2: Dev - The Dip Hunter
Dev was confident, analytical, and… suspicious.
He hated the idea of buying when things “look expensive.”
His rule:
“I’ll only invest when the market dips. That’s how smart people do it.”
So Dev saved every month — but deployed funds only when he saw a “real dip.”
The problem?
Markets rarely give us clean, obvious dips.
And when the dip does come, it rarely feels safe.
His emotional battles:
Saved cash for months and felt like a genius
Market kept rising… he felt stupid
Finally a dip came… he hesitated
Then a BIGGER dip came… he froze
News headlines screamed doom… he delayed
By the time he invested, markets had either recovered — or he deployed too little
His portfolio grew - but slowly.
The simulation reflects this: because Dev missed too many compounding cycles while waiting to “feel confident.”
Waiting sounds smart. Feeling ready almost never happens.
Investor 3: Ravi - The Hybrid Strategist
Ravi didn’t want to be like Arun (“too boring”)
or like Dev (“too stressful”).
So he invented a hybrid system:
Every month he invests 70% (to stay in the game)
He saves 30% as dry powder for dips
When the dip comes, he deploys the accumulated cash
Sounds perfect, right?
Well… kind of.
Ravi’s emotional maze looked like this:
Scenario 1 - Dip comes early (e.g., Feb):
He deployed too early.
Then the market dipped further.
He felt regret.
Scenario 2 - Dip comes late (e.g., Sep):
He sat on cash for eight months.
Market kept going up.
He felt regret.
Scenario 3 - Dip was only 5%, then market recovered:
He deployed and felt brilliant for 3 days.
Then felt regret wondering if he should’ve waited for a “bigger dip.”
Scenario 4 - Dip never came:
He carried cash for months.
Felt regret about “cash drag.”
Scenario 5 - Dip came, but headlines were scary:
He doubted everything.
He deployed half.
Market went up - regret again.
Yet despite all the psychological friction, Ravi still performed better than Dev, because at least part of his money always stayed invested.
The simulation places him right between the two.
So who wins?
Depends on how you define “winning.”
Arun wins on performance.
His simplicity beats optimisation attempts.
Ravi wins on emotional comfort.
He feels somewhat in control.
Dev wins on feeling intellectually superior…
…but not financially.
Why this happens (the simple truth)
Markets don’t reward intelligence. They reward consistency. Markets don’t have emotions.
They don’t care how clever you are at predicting dips. They care how long you stay invested.
Trying to buy dips feels rational - but it requires:
timing
courage
discipline
luck
emotional detachment
Most investors have… none of these. Because we are humans and humans are emotional creature.
The saddest part?
Dip investors often believe they’re being strategic - but feel worse because they always think they could’ve done better.
Meanwhile DCA investors feel foolish often - but end up wealthier.
The real story isn’t about returns. It’s about psychology.
The Optimist (DCA)
“I don’t know the future, so I’ll just participate.”
Feels occasional embarrassment.
Ends up ahead.
The Analyst (Dip Hunter)
“I want maximum efficiency.”
Feels constant doubt.
Ends up missing the train repeatedly.
The Pragmatist (Hybrid)
“I’ll play both sides.”
Feels regret in both directions.
Ends up somewhere in the middle.
None of them are wrong.
They’re just human.
A final emotional takeaway
Whether we are Arun, a Ravi or a Dev, I think:
No strategy works unless we stay with it for decades.
And the strategy we can stay with - is the one that fits our psychology.
There is no perfect. There is only “what we can live with.”
That’s the real secret of long-term investing.