There are few sports more applicable to markets than sailing.

As I age, sailing becomes a sport I cherish more and more. It is a fascinating sport not only from its skill level and uniqueness, but also its ability to demonstrate one of the first great achievements of humankind, after fire and the wheel, we mastered the water.

A small sailing ship has immense power in the way it travels, harnesses the energy around it to move, and never expels an ounce of emissions, making it totally natural in the way it traverses the water. Quite literally, you are caught in the wind, moving at nature’s speed and emotion at any given point.

The more I sail, the more I realize how many things stand out to me in terms of relatability within my own life. One of those things being how it relates to markets, of which I’ve spent many years of my life doing whether it’s building communication apps for traders or next level tech for investors to perform better research.

Here are some similarities that I’ve come to realize:

– In sailing, you literally have to ride the trend (wind).

– You cannot fight the trend (wind), as you will not going anywhere.

– You must always be observing your surroundings for risks.

– You cannot ever predict the wind or water so all you can do is position yourself in the best place to succeed.

– When the facts (wind or water) change, you change your mind.

– It’s good to know the basics and not overcomplicate things. For example, you don’t need to know advanced weather stats or data like atmospheric pressure, but knowing which way north is helps and is totally applicable.

– Related to the above bullet point, in markets, the over complication of any strategy or style, too many tools and inputs, becomes far too noisy and it becomes harder and harder to be rational. Stick to the simple things.

– Overconfidence will get you tipped and down into the water you’ll go. One will never over power the wind or elements around you. Be humble around nature.

– Working your way upwind is 100x harder than the downwind ride you took to get there. So don’t ever fall for the too-good-to-be-true schemes! You’ll just find yourself in an even more difficult place than before.

– Related to the above, there’s a stat in financial markets whereby if you lose 10% on a trade, you need to make 11% to get back to even and so forth. The number needed to break even only increases. This kind of mindset is true for sailing as well. If you fly downwind in 30 seconds, you’ll only find yourself in place whereby you now need to work upwind for the next 20 minutes.

– 90% of sailing is preparation, planning and organization. For example, prepping a boat and getting it ready is truly time consuming and takes days of practice. This is similar to markets as well.

– Always wear a life vest! I’m a great swimming and don’t believe I need one, but for the rare chance the boat tips in an aggressive way or something happens that seriously hurts you, the vest will keep you afloat. These types of risks can’t be ignored. Similar to markets, one can lose everything very easily without proper precautions.

I’ll add more to this list when I get time! Thanks for reading and hope you enjoyed it.

I had a great day of sailing just the other day as the weather changes, fall comes in, and weather begins these moments need to be cherished!