The Problem
Two people live inside my account.
One sells insurance: sells Puts, sells Calls, collects premium, and gets paid for time. The other bets on direction: buys stock, waits for it to rise, and holds on when it falls.
Nine months later, the insurer made $2,048. The gambler lost $4,064.
That’s not a metaphor. Those are the real numbers from my IBKR settlement reports, January through September 2026. Today I’m publishing the verdict — and answering the question that keeps circling back: for the stock still stuck underwater, do I keep holding, or sell it and turn the capital into a cash-flow machine?
My Thinking
First, the scorecard (settlement basis, through 2026-09-30):
| Engine | Trades | P&L | Avg per trade | Record |
|---|---|---|---|---|
| Option selling (CSP/CC/PMCC) | 143 | +$2,048.22 | +$14.32 | 6 of 8 tickers positive |
| Stock direction | 48 | -$4,063.80 | -$84.66 | 7 of 8 tickers negative |
The monthly track makes it even clearer: May through July, before the rules were enforced, the account bled -$1,807. August and September, after “seller-only” became the constitution, the account turned +$27. Same hands, same account — the only variable that changed was discipline.
And the most painful part is the same-ticker ledger:
| Ticker | Options P&L | Stock P&L | Net |
|---|---|---|---|
| TRON | +$584 | -$851 | -$267 |
| RGTI | +$482 | -$712 | -$230 |
| QUBT | +$241 | -$382 | -$141 |
| NVTS | +$202 | -$492 | -$290 |
Four tickers, options profitable on every one, stock losing on every one. The rent never covered the house.
The Insight
On the same ticker, selling its volatility pays better than betting on its direction — not because selling options is smarter, but because “waiting to break even” is a wound that keeps bleeding.
TRON is the most expensive footnote to that sentence: the stock once showed a +$2,000 unrealized gain I didn’t take. It ended as a -$2,838 unrealized loss — a $4,800 round trip. Nine months of lock-up, and not just the money: the opportunity cost. That same capital in the seller engine has run at roughly 2.4% a month.
The math of “holding on” was never “once it recovers I win”. It’s: by the day it recovers, you’ve already lost every dollar of cash flow that capital could have produced — plus nine months of sleepless nights.
Practical Advice
If the stock must go, it should still leave with discipline. Three rules:
- Sell by plan, not by emotion. No panic-selling on crash days, no greed on rally days. The correct way to “find a good price” is to place an order — not to stare at the tape.
- Use GTC ladder orders. Split the exit into limit orders at a couple of price rungs. If they fill, you’re out; if not, you wait. No watching, no betting on highs — let the system do the waiting.
- Sell first, repair second, deploy last. No new positions the night you liquidate. Recovered capital first turns cash positive and brings leverage back under 1.5x. Only after those gates pass do new positions enter the review pipeline.
Where does the money go afterwards? Back where it belongs: cash-secured Puts, and CCs/PMCCs backed by shares or LEAPS. Selling “nominal CSPs” while holding underwater stock was really renting with borrowed money; after the stock is gone, the same strategy becomes genuinely cash-secured — a better risk structure, not a worse one. Core tickers still follow the old standard: under fifty dollars, long-term uptrend, thick liquidity, fat premium.
Trading Insights #007 · To be continued
Addendum (2026-10-13): Ledger figures re-verified against broker trade-level settlement records (through Sep 30): options corrected from 121 trades / +$1,825.77 to 143 trades / +$2,048.22; stock direction corrected from 41 trades / -$2,874.83 to 48 trades / -$4,063.80 (assignments and expiries now fully included). Monthly track re-aggregated: May–July revised from -$1,875 to -$1,807; August–September (full months) revised from the old snapshot +$923 (Aug 15–Sep 15) to +$27 (the full months include the late-September TRON liquidation of -$864; the Aug 1–Sep 17 window alone was +$903). The conclusion stands: the rent never covered the house.