Published on August 13, 2020

Most impactful things in life take time for their significance to become apparent.  For me, surfing is one of those things. Now, to put all my cards on the table, I am NOT a good surfer by any objective assessment, but learning to surf has vastly enhanced my perspective on investing. 

While it initially started out as an excuse to hit the beach on random summer weekends, surfing has become an integral part of our vacation planning and necessary for periodic relaxation and reflection.  Lessons learned from the sport, and some surfing trips themselves, have also led to some life-changing investments.  

The interplay between hobbies and day jobs is a well-trodden path by bloggers, and it’s not hard to find a half-dozen articles that compare surfing to various forms of investing. 

So I’ll make it quick. 

Here are my main investment takeaways from surfing.

There will always be another wave.

Richard Branson, the founder of Virgin, put it this way: “Business opportunities are like buses; there’s always another one coming.”  Short of an asteroid removing the moon from the Earth’s orbit, there will always be tides, and therefore waves to surf.  Never let the fear of missing an opportunity be an excuse to make a rushed decision.  

Your preferred waves at your favorite spot may not always be there when you need them (more on this below), but there’s always a good wave to surf somewhere.  There will always be investment opportunities, but one needs to prepare and go after those where you have conviction.  In surfing, if you try to catch every wave, you won’t catch a single one. 

Pick your spots.

The North Shore of Oahu, Rincon, and Bali are all very famous but very different surfing destinations.  Some are sand breaks, some are prone to different wave shapes, and others require different ambient conditions to produce the best waves.   

When planning your next surf session, there are two important questions to ask:  

  1. What kind of wave are you looking for?
  2. What conditions are most likely to bring about those waves?

Investing is the same.  What style of investing do you prefer: value investing, growth investing, or momentum investing?  What is the time horizon for your investing? Certain asset classes, sectors, and even countries make better investments under different conditions.  Are we coming out of/going into a recession, are there secular technological changes, and what is the posture of the current government?

These are all questions investors need to ask when they “pick their spots”.  And just like surfers sitting on their boards, bobbing before the break, ready for the next perfect wave, patience is a necessity.

Even when you find the right beach at the right time, do you go to the spot with the best waves?  Maybe, but what if there’s a huge crowd?  The Castaway is not one for crowds and often finds he has better luck and more fun picking the overlooked waves with few people.

This idea can be drilled further down but the key point is this: Know your investing sweet spot and what conditions are most conducive to it.

Enjoy the Process

Whether it is deciding between different surf locals, surveying an individual beach for the best breaks or simply shooting the breeze as you wait for the next wave, many aspects of surfing can be as rewarding as the limited yet exhilarating time one spends actually riding a wave.  

You should feel the same with investing: Hitting the buy and sell buttons are only the tip of the iceberg.  Whether you follow fundamentals, technicals or a combination of both, if you don’t enjoy the process of finding your investment style, improving, and doing the legwork, it will be difficult to stick to it.

I have seen beautiful things and met wonderful people that I would have not otherwise met during my surfing and investing journeys.  The journey of surfing, in fact, led to my discovery of an up-and-coming surf town, where I purchased property that constitutes one of the biggest investments in my portfolio.  

The rush that comes from riding a wave and having an investment go according to plan are two of my favorite experiences.  Both require a lot of prep work, which I have also learned to love over time.  Whether it be surfing or another activity, hopefully, there is something in your life that gives you perspective and improves your investing the way surfing does for me. 

To your investing adventure,


The Castaway Capitalist

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