I’ve been away the past few days drowning in saltwater trying to learn a new sport–kitesurfing.

How did this all start?

My younger brother lives a tragic life and has been living in a kitesurfing mecca known as La Ventana, Mexico (2.5hrs North of Cabo San Lucas on the Sea of Cortez).

My bro told me that I didn’t have the skill or ability to kitesurf. Of course, being the oldest brother, this sort of banter needs to be met with a swift and definitive reaction. I was heading down to Mexico to learn this crazy sport.

How did it turn out?

Well, after 3 days on the water I managed to learn how to fly the kite and get up on the board–still need a lot more practice, but my brother says my progress is about as fast as one can expect for in the challenging world of kiting. If any readers get some time, you should try this sport out–very frustrating, but truly awesome.

How is this relevant for Investing?

Of course, in order to write-off my kiteboarding trip as a business expense, and therefore make it 100% tax-deductible, I needed a valid business reason. My case to the IRS is that learning how to kite helps me learn the skills necessary to manage a portfolio.***

A laundry list of similarities for your review:

• Learning how to kite surf, first requires that you learn how to fly a kite (duh).
  • Investment realm: you need to know accounting, basic finance, and how to use a calculator before investing.
• After learning how to fly the kite, you need to drown a few times.
  • Investment realm: start investing with small amounts and take your lumps early. I’d rather invest with someone who’s suffered a 50% drawdown than someone who has always made money.
• Never go full throttle on your kite–and NEVER panic when you crash and burn–or otherwise you’ll really be fu$%ed.
  • Investment realm: stay away from leverage and “hanging at the margin’s edge”; when the market is blowing up, don’t panic…just release the throttle, swallow your pride, and drift to a soft landing.
• Flying downwind is easy, fun, and builds confidence, but you also need to learn how to fly upwind, which is hard and frustrating, but it may save your life.
  • Investment realm: Going with the flow of a bull market is easy and not really skill, but may give an investor the mirage of skill. The real skill comes in learning how to make money in a bear market, when the investing winds are carrying you out to sea!
• Focus on the basics and learn safety techniques–this stuff is boring, but may save your life in the future.
  • Investment realm: see a whiz-bang investment strategy that requires a math PhD to understand? Skipping buy-and-hold equity and jumping immediately into barrier options on wheat futures? …think again.
• Life is about overcoming challenges and getting better.
  • Investment realm: investing is about overcoming challenges and getting better.

See, learning how to kitesurf in a way to make you a better investor. So set up your next trip, tell your boss you’ll put it on the company tab, and have some fun.

***disclaimer: if you are an IRS agent reading this, I am joking, of course.