From Sea to Market: A Captain’s Journey
Let me invite you to join me on a unique voyage—a journey that crisscrosses turbulent markets, the open sea, and lush fairways. I’ve been trading stocks since 2010, but after hanging up my sea boots in 2018—ending 35 years of sailing high seas—I embarked on a new journey into option trading.. That’s when, no longer rolling with the waves but rolling with the market, I turned rookie option trader. The waters were choppy. The learning curve was steep. And, oh, the holes I dug for myself would make any seasoned golfer weep in empathy.
In the early days, I made the rookie mistake of looking at options with the same sailor’s lens I’d used for stock trading. Guilty as charged! It’s like trying to navigate a supertanker with a dinghy’s tiller—or walking onto a golf course thinking all you need to do is swing harder to become Tiger Woods. Captain’s hat, golf cap, or trader’s visor—none protect you from arrogance..
This blog, with its saltwater wisdom and handicap humility, is my attempt to demystify the swirling, mysterious eddies of option trading. And perhaps put a smile on your face if, like me, you once thought all dogs bite because the first one did, or that golf was invented for retiree mobility training. (Yes, that was me.)
Option Trading Fundamentals: It’s a Ship, Not a Dinghy
Reading the Market Weather
If you’ve ever captained a ship, you know every voyage starts with reading the weather and plotting the course. An option trader’s journey isn’t much different—ignore the forecast, and you might end up keelhauled by a margin call. When I first entered the world of options, I treated it like going from deck cadet to Captain overnight (and sometimes forgetting which side was port or starboard). I quickly learned just knowing “buy low, sell high” won’t help if you don’t recognize the trading squalls ahead.
Understanding Market Complexity
Much like sailing a carrier through the monsoons, options demand you respect their complexity. Stocks may be a cruise liner—the steady, slow-moving behemoth—but options? They’re agile frigates, fast as the wind and just as ruthless if mishandled. I learned early: don’t bring an anchor to a sailing regatta.
Granted, my first few option trades resembled attempting to dock a Panamax in a teacup. Slippage, Greeks, and expiration dates blindsided me like rogue waves. One moment, I was sailing free, the next—mayday! “Delta neutral,” I muttered, trying to sound wise, but it felt more like my GPS had jumped coordinates in a fog.
Learning Through Golf: Playing the Market Greens
The Power Swing Fallacy
Much as I once believed golf was about bombing drives like Happy Gilmore, my first foray into options followed the same logic. Bigger trades meant bigger gains, right? Wrong. There’s a reason even seasoned sailors check all their lines. My 4-iron approach to options often ended up with me hacking my trading account out of deep market bunkers.
Finesse Over Force
Option trading, I discovered, is like playing golf in 40-knot crosswinds—you need finesse, strategy, and the humility to yell “BALL!!” and duck when someone else slices. Sometimes, it’s about laying up, not going for the green in two. Sometimes, a prudent iron shot beats swinging for the fences.
After my first blown account, I learned that both golf and option trading share a key lesson: respect the hazard. A bunker on the golf course is like implied volatility in the option market—ignore it, and you’ll spend more time raking sand than putting for birdie. And sometimes, it pays to chip out sideways, live to fight another day.
Risk Management: Batten Down the Hatches
Never Underestimate the Storm
On the open sea, a Captain’s rule number one is never to underestimate a brewing storm. Options, with their intricate array of strikes and expiries, can deliver tempests out of nowhere. I learned to keep tighter stops than a Chief Engineer on a night watch. Position sizing ceased to be an afterthought; just as a Captain never overloads a vessel, a trader should never go all-in on a high-probability “sure thing.” The sea tolerates no arrogance; neither do the markets.
Learning from Market Storms
One memory stands out—a fateful trade where I thought I’d spotted clear skies. Instead, I found my hull breached by theta decay, my precious premiums eroding like barnacles in dry dock. Lesson? The market doesn’t care about your timetable. It’s “hurry up and wait,” sailor.
Golf’s version? That shot you just know you can reach the par 4 in two, only to find the wind shifts and you’re now deep in the woods. Sometimes you need to play smart—chip out, minimize damage, grin at your playing partners, and move on. In both worlds, humility is virtue, not defeat.
Mastering Technical Skills: Navigation vs. Theory
Understanding the Greeks
Learning the ‘Greeks’ in options is akin to mastering shipboard navigation: there’s theory and then there’s doing it on a rolling deck at 3am. Delta, Gamma, Theta, Vega—they may as well be star constellations you’re supposed to steer by. Early on, I confused Gamma with something out of a Marvel comic book. It was all Greek to me—literally.
Practical Application
Like a Captain reading the stars, you have to understand what influences your fate. Delta is the tiller—your trade’s direction. Theta is the slow leak in the hull: time decay doesn’t sleep. Vega, volatility’s tempest, can turn smooth sailing into a hurricane. Once I realized how these interplayed, it became possible to anticipate rather than react.
In golf, it’s no different—you need to know which club to use, how wind and slope affect your shot. If you always swing the driver, you’ll discover sand and water all too frequently. Mastery, in both, is recognizing when to shift gears, adjust your stance, or, sometimes, simply lay-up and watch the chaos go by.
Trading Psychology: From Ship’s Wheel to Trading Desk
The Mental Game
The biggest switch, as with any career at sea, is in mindset. As a sailor, your greatest battles are with weather, equipment, and—let’s admit it—doubting crew. As a trader, your adversary is much closer to home: yourself. I never realized how swiftly “I’ll just hold a bit longer” becomes sinking with the ship.
Discipline and Routine
Discipline at sea means routines, logs, and checklists; discipline at the trading desk is journaling, reviewing trades, and setting alarms—not just to wake up, but to remind you not to trade when too excited, too angry, or, paradoxically, too confident. In golf, there’s a reason players “read” their putts, not just hit and hope.
Here’s a secret I wish someone had shared earlier: sometimes the best trades are the ones you don’t make. Zero action can be a victory, like calling off a difficult approach when the channel markers are off—the ship and your crew (read: trading account) will thank you for prudence.
Learning from Losses: When the Storm Hits
Accepting Setbacks
Let’s be honest. Every Captain logs a few rough passages, every golfer slices into the woods, and every trader chalks up losses that sting. Early on, I lived through days when option premiums eroded faster than my patience, and my trading journal became less logbook, more confessional.
Growth Through Adversity
But mistakes, like wayward drives, are part of the journey. Once, I lost so much on a straddle in earning season, I half-expected to be promoted to “Deck Cadet, Trading Division.” But this too passes. Each loss is a lesson, each hole a chance for par, each failed entry a chart plotted for next time.
I learned to laugh at myself. When the market hands you lemons—or double bogeys—mix a drink, recalibrate, and remember: neither the market nor the fairway carries a grudge. What matters is returning for another voyage, another round, a better trade.
Finding Joy in the Journey
Celebrating the Victories
The sea has its dawns—those moments when the horizon glows, the air tastes of possibility, and the destination feels almost within reach. Option trading has these, too: a perfect call, a winning spread, even simply sticking to your risk plan like a true officer.
And golf also rewards patience—there’s no euphoria like flushing a perfect approach or sinking that unlikely putt. It’s not about winning every time, but about enjoying every round—accepting squalls, celebrating the birdies, and laughing at the bad lies along the way. Be patient when you lose your golf swing for days- it comes back, for sure.
Embracing the Process
So whether you’re venturing into options, Captaining a ship, or hacking your way around the golf course, remember: every mistake is weathered, every victory sweeter after a storm. You’re in command, but you are not in control of the wind. Trim the sails, check your irons, watch your risks—and most importantly, enjoy the ride.
Final Call: Don’t Fear the Water or the Woods
Perhaps you, too, think all dogs bite because the first one did. Maybe you believe life is tough because of one bad storm, or golf is for retirees with titanium hips. Let me offer a Captain’s perspective and a golfer’s smile: the best adventures begin with humility and are sustained with humour. Trade with respect, sail with caution, play with patience—and laugh a little louder at every misadventure.
Fair winds, straight drives, and green trades to you, my friends.
What’s Next: Charting Your Course Forward
In my next blog, I’ll dive deeper into the mysterious world of Greeks, breaking them down through the eyes of both a seasoned sailor and a weekend golfer. We’ll explore how Delta behaves like ocean currents, how Gamma acts like shifting winds on the fairway, and why Theta is every option seller’s faithful first mate. I’ll also share my personal trading strategies—the specific techniques I use to identify profitable opportunities and the systems I’ve developed to track my trades like a ship’s logbook. You’ll discover the simple tools and methods that help me stay organised, monitor my positions, and maintain discipline even when market storms threaten to blow me off course.
In both golf and investing, success is measured over the long term, and consistency beats the occasional lucky shot. Beautifully explained.
In both golf and investing, success is measured over the long term, and consistency beats the occasional lucky shot. Beautifully explained.