If Not This Then What? When Every Asset Feels Like Polished Garbage
May 29, 2025
Regret doesn’t ring a bell. It echoes.
It hums quietly in the background while you scroll past a stock you didn’t buy. It sits beside you in the driver’s seat while you sell the one winner that was finally working. It’s the ghost trader you argue with—the one who bought Bitcoin at $300, sold Tesla at $1,200, and never touched the Chinese internet names.
That voice is the chorus of a portfolio built on maybes.
“If not this, then what?”—the most dangerous question in investing. Because it feels rational. It sounds like analysis. But under the hood, it’s pure psychological paralysis dressed up as optionality. And optionality is only useful if you exercise it.
Let’s unpack how this cognitive mirage forms—and why it traps even seasoned traders in loops of hesitation, crowd mimicry, and long-tail regret.
The Burro at the Crossroads
Picture a burro standing at a fork. One road looks promising but unproven. The other has footprints—thousands of them—but they lead off a cliff. The burro hesitates. “If not this, then what?” it thinks. Time passes. It stares at both paths until night falls and wolves circle.
That’s most investors. Paralysis by analysis.
But the burro’s mistake wasn’t in the hesitation. It was in not choosing at all.
Market decisions are rarely between “right and wrong.” They’re between “right now and maybe later.” And indecision, in volatile conditions, is a decision. It’s a passive form of loss—death by omission.
The Portfolio of Maybes
Go look at the average investor’s portfolio. Not the performance-chasing Reddit threads or Instagram screenshot gains. I mean the real stuff. The brokerage account that hasn’t been opened in weeks. The forgotten holdings, the broken SPACs, the biotech hail marys that never hit.
You’ll see a museum of hesitation:
- Stocks held too long hoping they “come back”
- Cash waiting for the “right time”
- ETFs are bought because they’re safe, but unloved
- Trades entered with half conviction and full fear
This isn’t a portfolio—it’s a graveyard of “maybe.”
Maybe it’ll turn around.
Maybe the Fed pivots.
Maybe China reopens.
Maybe AI stocks aren’t overbought.
But here’s the catch: “Maybe” doesn’t compound. Only clarity does.
Cognitive Bias: The Illusion of the Better Option
“If not this, then what?” feels smart because it forces comparison. But psychologically, it’s often a mask for loss aversion and regret minimisation. Behavioural finance has long shown that humans fear losses twice as much as they enjoy gains.
So what do we do?
We delay action to avoid the sting of being wrong.
We anchor to prices that are no longer relevant.
We watch the market like a roulette wheel instead of participating like it’s chess.
This is decision paralysis disguised as analysis. And it infects your entire trading ecosystem.
The problem isn’t a bad decision—it’s no decision, driven by the fear of future regret.
The Technical Trap: Chasing Perfect Entries
Technicians aren’t immune either. In fact, they’re often the worst offenders.
You spot a breakout. You hesitate. Volume’s not quite perfect. RSI is extended. There’s a divergence forming—maybe. You wait. The stock gaps up 8% the next day. Now you’re chasing. You tell yourself, “I’ll wait for the retest.” It never comes. It’s 30% higher a week later.
“If not now, then when?”
By the time you get confirmation, the market’s already re-priced the risk. You bought certainty—but at a cost. That cost is called alpha leakage.
The crowd waited with you. The crowd got in late. The crowd rode the last 20% and took the 40% drawdown. Again. That’s not trading. That’s mimicry with a time delay.
Mass Psychology and the Myth of the Clean Entry
Most traders are waiting for a setup that feels good.
But good feelings in markets are dangerous. If it feels comfortable, you’re likely not early. And if you’re not early, you’re the product, not the buyer.
Markets are psychological battlefields. The edge goes to those who act before the narrative is clear. That’s where your Burro Theory breaks free: the stubborn investor who doesn’t follow the crowd into comfort zones. Who sizes smaller but moves earlier? Who’s not asking “If not this, then what?” but “Why not now?”
Emotional Liquidity and Regret Cycles
Regret is more than a feeling. It’s a form of emotional liquidity.
Every time you don’t pull the trigger, you store energy. That energy builds until it becomes reactive—not strategic. You panic-buy tops, revenge-trade breakdowns, and sell lows for “mental relief.”
It’s not just volatility in price. It’s volatility in your psychology.
Here’s the loop:
- You hesitate on a setup you liked
- It runs without you
- You buy the next setup early, trying to compensate
- That one fails
- You stop trusting your system
- You hesitate again
And now you’re back in the Maybe Loop. This is portfolio decay via emotional oscillation.
Case Study: The 2020-2023 Delayed Entry Trap
Let’s go tactical.
In 2020, tech stocks roared post-COVID. Many retail traders hesitated—too much uncertainty, valuations too high, “if not this, then what else?”
By mid-2021, they gave in and bought the top. What were they doing in between?
Regretting the gains. Watching Tesla, Shopify, ARKK, Square double and triple.
Their eventual entry was not strategic—it was emotionally coerced.
That’s what happens when you confuse “rational caution” with “fear-based inertia.”
And it’s repeating now. AI names. Bitcoin. Commodities. The same whisper: “If not this, then what?” That’s not due diligence—it’s passive anxiety.
The Edge Isn’t Certainty—It’s Conviction Under Uncertainty
So what’s the antidote?
It’s not FOMO trading. It’s not blind contrarianism either. It’s building a conviction framework:
- Know your levels
- Know your narrative edge
- Know your risk
- Pull the damn trigger
That’s where technicals meet psychology. The chart doesn’t care how you feel. The market doesn’t reward maybes. And time doesn’t refund indecision.
Tactical Reset: Build a Portfolio of Yes or No
Here’s how to kill the maybe cycle:
- Run a Regret Audit: List your positions “just in case.” Ask: Would you buy this now? If not, why are you still holding it?
- Preload Decision Trees: If X happens, I buy. If Y happens, I cut. Set it, forget it, execute it, and remove the gray zone.
- Track Psychological Drawdowns: Not just financial ones. What trades drain your confidence? What setups leave emotional residue? Cut them out like cancer.
- Rewire “If Not This…” Thinking: Flip the script. “If not now, when?” “If not this price, what signal?” Turn analysis into action paths.
- Size for Uncertainty: You don’t need to go all-in. You just need to go in. A small position beats zero exposure.
Final Word: Choose, Act, Move
“If not this, then what?” sounds sophisticated. But it’s often the mask of fear. The market doesn’t wait for your comfort. It rewards preparation married to action.
The investor with an edge isn’t the one who knows everything. It’s the one who acts despite not knowing. Who accepts that regret is inevitable—but missing the whole move because of hesitation is not.
Kill the maybes. Fire the ghost trader in your head. Build conviction, take the trade, and own the outcome.
Because regret doesn’t come from being wrong.
It comes from never stepping in the ring at all.
