Since moving to the Caribbean, learning how to sail became part of my bucket list.

I’m prone to motion sickness for as long as I can remember. As a kid, I was the only one in my family that’d throw up by simply being in the backseat on a highway. It is quite odd that I took on the challenge of being in a 30-feet, single haul racing boat for hours at a time.

There were several days after coming home sun stroked, line scratched, and seasick, I questioned myself why I continued to pay and torture myself. I wouldn’t say that I find most of the tasks enjoyable. It took a lot of energy to remember all the terms, follow directions while disoriented, and remain confident so I don’t just burst out crying.

I want to know how to control a boat at sea. For some reason that is enough to keep me going.

This past weekend was the culmination of my effort. As part of the bareboat skipper course, we were doing our first ocean crossing from our island to the next. It’s a pretty short journey, around 22 miles, or 4 hours with the right sailing conditions.

I dreaded it.

Sailing Across Open Ocean

You see, in order to sail this particular course, we have to go through a particular section of the channel where the current from the Atlantic hits shallower shore. Adding on the gusts of trade wind, the waves can be high and irregular.

Even on a large ferry, I could barely function when I went through that particular stretch. I could not imagine how I was supposed to operate a sailboat through it.

It is not absolutely necessary for me to do this crossing.. I could easily choose to finish my course in the calmer water on the Caribbean coast.

But I know I’d regret not doing it when I had the chance to. Who knows when I’ll ever muster the courage to do an ocean crossing like this again when no one is pushing me?


Suddenly, I think I can relate more to people who are afraid of the volatility in the market.

Stock market can be volatile. We know that for a fact, like I knew the sea can be rough. There is no telling the actual volatility we will experience before we embark on the journey.

Before we went on this trip, I asked our instructor whether there is a chance we won’t go due to weather. She thought about it and said, “Of course if I feel if there is danger, I won’t put myself in that danger. If it’s like the past few days, (which in my opinion were high winds, random gusts, and unexpected showers), I’d say it’s normal and I’ll definitely do the trip.”

It sounds so much like when I tell my clients, “Yes, the market might drop and exhibit a lot of ups and downs. It’s normal. I’m in it too and I’ll continue investing.”

We cannot make the volatility go away. We can only decide to continue on knowing there is volatility, or not go on this trip at all.


When we were discussing about the trip, another instructor sensed my hesitation. He wanted to know whether I actually feared going into open ocean with no land in sight on a tiny boat.

When he put it that way, it was cleared to me that vomiting on a boat isn’t a true risk in his mind. The real risks are something serious happens to the boat or the crew in the middle of the open ocean.

In fact, this is why as a skipper, before every sailing trip, we go through all the safety equipment, first aid, provisions, radio checks, and mechanical run down. There is a tiny but real chance that the weather might turn, the boat might malfunction, and the crew might do stupid things.

Those are the risks, the bad things that might happen that we can be prepared for, which is different from the volatility of the seas.

Skippering as a skill is in part knowing what to do when facing these risks. Being able to take control in various condition is what makes you a captain.

Isn’t it so very similar to dealing with the markets?

The risks of investing in the market is not necessarily the volatility along the way, but losing part of what you put in right when you need to withdraw it. The best way to prepare for the risks is not scrambling only when the crash comes, but making adjustments knowing the crash will come (and go.) That means for those close to needing to withdraw, investing less in more volatile markets and keeping enough liquid cash to weather the storm.

The Journey

Two hours before we planned to set sail, I got a phone call from our instructor who was making the trip with us.

“So the forecast says the wind may be gusting up to 25-30 m/h. I’m giving you an option not to go today, but we don’t really have any time in the schedule to go until later in the year.”

That didn’t help with my confidence, but I took a leap of faith. Apparently, it is still sailable condition. Otherwise we won’t be able to go at all, right?

The sea was every bit as rough as I expected when we departed. Leaving one shore without being able to see the other, all I can focus on was the horizon, or my head started spinning as the waves crashing against the hull. The wind is making whistling noises the whole way. Only one person was strong enough to go down and check our location on the charts to make sure we were still on course. And one hour before we arrived, I threw up.

They say vomiting is seaman’s cure, and I experienced it firsthand. As soon as that happened, the knot in my stomach was gone. We could see our destination now.

To tell the truth, that night when I revisited my day, I didn’t feel pleasure or satisfaction. I accomplished my first ocean crossing, but it wasn’t an enjoyable journey for me. The experience makes me think I’ll never enjoying sailing again.

Fortunately, or unfortunately, we still needed to sail back across the same channel. We built in a day to sail along the southern coast of the island before bracing open ocean one more time.

Even the easier course didn’t make our second day of sailing better. There was constant risk of jibing when sailing downwind, numerous fish pods to avoid, and intermittent heavy showers the entire day. To cap the day off, our anchor got tangled over an old metal chain on the seabed and we almost lost it; and in the process, we realized the foot that fixed the boat’s propeller to the hull was gone. A decision was made to not use the engine at all except when we entered the marina at our destination.

Who would have thought, at that point, that the third day brought one of the most enjoyable sailing day that I’ve ever had?

It was breezy from the right direction, blue sky with dotted clouds, and uniform waves gently crossing the channel. We were sailing close to the wind, with a lot of heeling but high speed. I was on the helm, capturing the exact moments where I was in control, and not being taken by the force of wind or the current. I was even able to eat while the boat was cutting through waves!

Continue so you can arrive

All of us will encounter different investment journeys in our lives. Not all of them will be pleasant. Depending on when you entered the workforce and started investing, you might have experienced a 10-year bull run, or very little growth with a lot of volatility.

How we began our investment journey often shapes what we interact with the market. For me, the stock market crashed 2 years after I began working full-time (and in the industry that was hit the most.) I saw my stock award dropped from thousands of dollars to a few cents.

I’m glad in hindsight that this experience didn’t deter me from continuing to invest. In fact, it taught me early on that the worst could happen, but we recover.

What is important with all of our investment journeys is that we get to our destinations. There will be risks of loss and short-term volatility, and much of it are dependent on the macro environment. We might not even enjoy the process that much. But eventually we will get where we need to be as long as we stay on the boat.

Have faith, keep sailing, and don’t jump.


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