Why I Invest From 5,000 Miles Away
I live in northern Japan.
The NYSE opens at 10:30 PM my time. Earnings calls happen while I'm asleep. My broker's customer service is never awake when I need them.
Early on, this felt like a disadvantage.
Now I see it as the best thing that has ever happened to my investing.
-I can't watch the market all day. I can't react to every tick.
-I can't panic sell in real time.
-I have to make good decisions in advance and trust them while I sleep.
That constraint forced me to build a process that doesn't depend on being there every minute.
Turns out, that's what good investing looks like anyway.
There's a strategy called The Wheel.
Step 1: Sell a cash-secured put on a stock you want to own.
Step 2: If assigned, you buy the stock at a price you chose.
Step 3: Sell a covered call against your shares.
Step 4: Collect premium. Repeat.
No prediction required. No price target needed. No market timing.
Just disciplined, mechanical income generation on companies you already believe in.
It won't make you rich overnight. It will make you consistently less wrong and consistently more paid.
When a put I sold is heading toward assignment, I don't try to avoid it by rolling down and out just to dodge owning the shares.
I go back to the original question I asked before I ever sold the put: was I comfortable owning this company at this price? If the answer is still yes, I let assignment happen and take the shares.
If the answer has changed, that's a sign my thesis broke, not a sign the trade needs defending.
Assignment isn't the risk. Owning something I no longer believe in is the risk.
You can love a company and still overpay.
Margin of Safety means: what is this business actually worth, and am I paying significantly less?
It's not a magic formula. It's a discipline.
It protects you when you're wrong about growth, amplifies returns when you're right, and lets you hold through volatility without panic.
Price is what you pay. Value is what you get. The gap between those two numbers is where generational wealth is built.
Think of options as insurance policies.
When you sell an option, you are acting as the insurer, collecting a premium to take on an obligation.
If you already want to buy shares at a lower price or exit at a higher target, selling options pays you for doing what you planned anyway.
You get paid for being clear on your numbers.
A trade that is up on paper isn't a win yet. It is just an unrealized possibility that looks good right now.
Feeling pleased the moment a position moves your way tends to make you less careful, tempting you to ease up on risk controls.
A win is only real once the position is closed and the cash has settled. Until then, it's still an active trade with all the risk that word carries.
The most durable investors do almost nothing day to day.
They don't react to every Fed announcement, refresh quotes every hour, or chase earnings volatility.
Their entire process comes down to three steps:
1. Buy wonderful businesses when they are on sale
2. Sell options to steadily lower their cost basis
3. Wait
Most people struggle with this not because it is difficult, but because it feels boring. But in long-term investing, boring is the real edge.
What if every share you owned had a job?
Not just to appreciate in value, but to generate income while you wait.
Every time you sell a covered call or a cash-secured put, the collected premium lowers your effective cost basis in that position.
Do it consistently and you reduce your downside with every cycle. The dividends become pure profit, appreciation is a bonus, and your capital works continuously.
Most investors wait for the market to do all the work. Sourced options put the position to work while you wait.
Before deciding whether to sell a put or a call, decide how much risk capital the trade deserves based on your conviction level.
Deciding size after picking a direction anchors the trade to excitement in the moment. That is the wrong input to size from.
Deciding size first forces an honest conversation about how sure you actually are, separate from how tempting the trade sounds right now.
Conviction earns size. Excitement doesn't.
How I screen for a margin of safety:
I compare a company's current price to a conservative estimate of what the business is actually worth, then require a real gap before acting.
Conservative is the operative word. I don't use best-case assumptions or assume growth continues uninterrupted forever. I use numbers that hold up even if a few things go wrong.
If the price only makes sense assuming everything goes right, there's no margin of safety. That's just optimism with a spreadsheet attached.
The gap is what protects you from being right about the business and still losing money on the price.
The weeks that feel like nothing happened are usually the ones I'm proudest of afterward.
No panic, no chasing, no changing my mind three times. Just the plan, running exactly as written.
The memorable weeks make good stories. The quiet ones build the account.
I used to chase. A stock I liked would move away, and I'd pay to catch it.
Now I name the price I'm willing to pay and wait. Sometimes it comes. Sometimes it doesn't, and I move on without regret.
Waiting at a price I picked has a lower hit rate than chasing. The trades I do get are much better ones.
The best investor I know does almost nothing.
He doesn't check his portfolio daily. He doesn't react to Fed announcements. He doesn't have a hot take on earnings.
What he does:
โข Buys great companies when they're on sale
โข Sells options to lower his cost basis
โข Waits
Most people can't do this because it feels too boring. But boring is the edge.
The three core tenets of durable investing:
1. Never invest in a business you cannot clearly understand.
2. Only buy shares you would be comfortable holding if the market shut down for a decade.
3. Keep cash ready so that when real opportunities appear, you put out a bucket, not a thimble.
Patience is the real edge.
Most days in a good plan, nothing happens. No trades, no adjustments, no decisions.
That used to make me nervous. I assumed that if I wasn't acting, I wasn't working.
Now I read a quiet week as evidence the plan is doing its job. The positions are sized right, the prices are set, and nothing needs me.
If a plan demands constant attention, it probably wasn't finished.
A cash-secured put is a commitment to buy a business, not a way to collect premium and hope.
If I wouldn't genuinely want to own the company at that price in an account drawdown, I skip it every time.
The premium is never worth owning a stock you lack conviction to hold.
Price is what you pay. Value is what you get.
Protecting capital isn't about avoiding the marketโit's about refusing to overpay for mediocrity.
When you focus on acquiring wonderful businesses at fair prices and letting time do the work, volatility stops being a threat and becomes an entry point.
If a position would be uncomfortably large after assignment, size it down before selling the put, not after getting assigned.
The premium is the reward for a decision you've already made peace with. It's never the reason to make the decision.
A trade that's up on paper isn't a win yet. It's a possibility that looks good right now.
I used to feel pleased the moment a position moved my way, and I made worse decisions because of it. The good feeling made me less careful.
Now I treat the win as real once it's closed and the cash is settled. Until then, it's still a trade, with all the risk that word carries.
Predicting market rain doesn't count. Building arks does.
Real investing edge isn't guessing next week's headlines. It's holding quality businesses with capable management, keeping cash ready for rare opportunities, and letting time compound value.
When the plan is clear, volatility becomes an ally rather than an emergency.
Three ways selling options changes portfolio management:
โข Turns waiting into income: your capital generates premium while waiting for your price
โข Reduces downside risk: collected premiums lower your net purchase price
โข Creates structural flexibility: cash-secured puts and covered calls adapt as prices move
You don't need to predict daily volatility when your strategy benefits from time passing.