Get On the Path

You can get out smarted, but don’t get out hustled.original-windsurfer1

My dad used to tell me that there are three ways you get beat. He said, “you can get out smarted, you can get out spent, or you can get out worked.”

Think about it in the context of your sailing. If your competitor out smarts you with forecasting, strategy, compass numbers, playbooks, clever rules situations, better tuning then how do you compete against someone with more information?

If your competitor out spends you with new equipment, travel, coaching, fitness, nutrition, spa-days, tutors, private jets you’re getting outspent. How do you win against the deepest pockets? Against people who can buy almost every component of a winning campaign?

If you are getting out trained, by someone with more on-water hours, more boat work hours, more class-room, or sailing hours then you need to step up your hustle.

We say, there are three ways to win a sailboat race: speed, leverage, and rules. Well, I think there are three ways to win a campaign:

  • Out Smart Them
  • Out Work Them
  • Out Spend Them

An athlete with this combination is the triple-threat of competition. A three pronged dagger into the heart of your hopes, dreams, and aspirations.

My dad would go on to say, “you can’t get beat by one of these things alone, but you can by two of them.”

He would also say to me, “and there’s always someone who is richer and smarter than you.” Don’t let anyone out work you.”

And I don’t. I never will.

How do I have the confidence to know that I can out work and out hustle any hustler? Because I’ve been tested. Because I see every day as a test, and I methodically use a personal feedback loop to: 1) identify my priorities, 2) strategize an action, 3) do the work, and 4) analyze the success or failure of my plan.

This is all about discipline.

Discipline is doing the things you should do, rather than the things you want to do.

Sometimes it’s difficult to define the things you “should” do. To figure this out, you need to spend time identifying your priorities. In business we do this with a few steps. First we decide who we are, and we do this by outlining our core values. What is important to us? What defines us? What gives us joy, purpose, passion?

Humans are dynamic individuals, capable of change, growth, recession, anger, joy, compassion, and competition. Your goals will change. Your targets will change. But your core values, the things that define you will not. Your core values are your guiding light.

whyThe second step is to establish the mission. What is your “why?” What is it you want to accomplish that you haven’t yet? Ask yourself, “what’s the mission?” The most important aspect of this step is honesty. You must be honest with yourself on what is achievable.

You are not a professional athlete. You aren’t getting paid to sail full time. You aren’t on an Olympic or America’s Cup campaign (yet). Right now, at this point in your life you are a full time student, family member, friend, and a part time sailor.

Which means you need to learn the skills to balance all these responsibilities you have and be the best in in each area. How can one person do so much? The short answer to that question is to maximize the potential of every situation by staying mindfully present in each moment. Everything you do, you must “Do It 100.”

You must know yourself, what you’re capable of, and your ability to execute.

You must become aware of your time management, tasking, capacity for work, and efficiency.

Know Thyself

Multitasking is bullshit. Multi-tasking should be called multi-failing because human beings can’t do it. You cannot study for test, while hanging out with friends, and work out at the gym at the same time. But we often try to do these things, often times without knowing it.


Example: You are at home, at the dining room table studying. You are working on a math problem but you’re also getting thirsty when your phone buzzes. So you swipe it open, check the snap, send a selfie, close the phone and look back at your math work. You read for two seconds, but since you already paused working, your brain sends a message that overrides your thinking and you walk to the kitchen for a drink.

You aren’t multitasking, you are multi-failing.

In the wise, mustachioed words of Parks & Recreation’s Ron Swanson, “you should never half ass anything. You should only whole ass one thing.”

What is your capacity for work?

Consider this, you need to be a good friend, sibling, child, student, athlete, and the list goes on. So you need to learn to balance all these responsibilities.

Often times what dictates our schedule are deadlines rather than priorities. Studying happens for the next test scheduled for Monday rather than the one on Wednesday. The friend who is cranky gets more attention than the one is less demanding. You go to tennis practice rather than sailing because the coach is meaner.

“The squeaky wheel gets the grease.” And that wheel is about to fall of the axle and ruin your chances at college, friends, happiness, etc, etc. And the metaphoric grease here in this example is your time.

This is not a sustainable system. This is not a system you own or have control over. You are slave to an unhappy overlord who tortures you with deadlines and emotional manipulation. To be a victim of time is to, as Hamlet lamented, “to suffer the slings and arrows of outrageous fortune…”

You are living in the monkey house. Get Out

That is an expression my wife uses when she’s trying to tell me to get some perspective on something. Let me paint the picture for you. Imagine you’ve gone to the zoo and you walk into the monkey house exhibit. An indoor space with trees, ropes, ponds and of course monkeys. The first thing you notice when you walk in is 1) it’s loud, and 2) it smells like crap.

An enclosed space where monkeys jump, play, eat, sleep…..ummmmmm, yeah that place wreaks of poo. There’s poo everywhere. And of course it’s loud. They’re monkeys.

After a while watching the monkeys cuddle one another, or swing on the ropes and jump limb to limb, you become acclimated to the noise and the smell. They don’t bother you anymore because you’ve lost perspective. You’re distracted by the cute monkeys and forgotten the real world outside.

But once you leave you realize: “Wow, it smells way better out here and I can hear myself think!”

Life has a way of putting us inside the monkey house. The monkey house is a snare trap of deadlines, decorated with stress, anxiety, guilt, and unmet expectations.

Get the hell out of the monkey house. Have some self-respect for your time, energy, and goals.


Discipline is doing the things you should do, rather than the things you want to do.

Now, you need to figure out what it is you should do. Hold yourself to your core values and your why. To figure this out is hard work. You must work at it every day. Some days you will miss the mark. But that’s okay, “kaizan” keep learning.

This part is not just for reading and thinking. It requires action.

Here’s what I recommend, after you’ve done some work and laid out your core values, your why, and now have some clarity on your goals, consider the most powerful phenomenon in the universe: TIME.

Your time is precious, valuable, and sacred. You must treat it as such.

  1. Make a list of all the things you need to do today.
  2. Cross off all the ones that don’t speak to your core values
  3. Make a new list of the remaining tasks
  4. Rank them in order of priority from highest to lowest
  5. Make a new list of only items labeled 1-3
  6. Start on number one, and once completed move down the list sequentially.

What you’ve just done is identified your priorities and put yourself into action. Make a spreadsheet calendar for the next two weeks and plan your execution of tasks out. For example:

  Saturday Sunday Monday
Morning Priority 1: repair boat Priority 2: study to chemistry test School: Chem. test
Afternoon Sailing Sailing School
Evening Rest Priority 2: study more Priority 3: Go to gym


Try this and tell me how it goes. Another way to go about doing this type of planning, is to use this format of scoring your activity:

GOAL: Get A’s at all classes, Maximize Sailing Time, Be Better Friend

VALUES: School first | Sailing & Friends equally important

  Perfect Score Mon Tues Wed Thu Fri Sa Sun Actual


School 5 1 0 1 1 0 0 0 3
Friends 3 1 0 0 1 1 1 0 4
Sailing 3 X 0 1 0 0 1 0 2


In this format, I scored a 1 if you achieved your goal in each area and a 0 is you did not. Above, you can track and see that the scores reflect missing the mark in school, prioritizing friends and not sailing.

Don’t miss the most important part of this process. Learning more about yourself and making a new plan for the next week.

“You are only as good as your next step.”iceberg

You are not a machine

If you were a machine, you could work 24 hours a day, 7 days a week for as long as possible until your system failed or you ran out of power. Because you aren’t a machine, but a living breathing human being you need a few things to perform: Nutrition and rest.

I love CrossFit, it has changed my life. To give you some context and describe the significance of the education I have received while learning to become a CrossFitter, I need to explain a few things to you. I have been a sailor since I was nine. A competitor since 10. I was the youngest member of the US Sailing Team at 15. I won a National Championship, and I have competed in three Olympic trials. I thought I was an athletic person, but I didn’t know what it meant to be an athlete until I started CrossFit.

CrossFit values ten qualities in fitness: Cardio Endurance, Stamina, Strength, Flexibility, Power, Speed, Coordination, Balance, Agility, Accuracy. You must be a balanced and well-rounded athlete to be a good CrossFitter. You can’t just lift heavy stuff or run fast at length. You must do both. You must be fit in all of these areas.

How can you become both the strongest and the fastest, at short sprints or at long distances? How can you have the explosive dexterity of a gymnast and the power of a weightlifter? The answer is practice in all areas, focusing on weaknesses, and honing strengths. But to be the best athlete you must also be the best at recovery.

How can you Out Smart and Out Work the competition as an amateur athlete? You must find balance in your life to be happy.

The answer is to learn to value rest and recovery. You must value the times when you “switch off” and prepare for the next challenge ahead.


My brother Luke is a professional athlete. He is both pursuing an Olympic campaign & America’s Cup campaign. I recently went to see Luke while he was staying at my sister’s house before Sailing World Cup Miami. It was about 6pm and Luke was playing Xbox and eating a rotisserie chicken from Publix.

I sat down on the couch, and asked him, “what are you doing?” And he set the controller down, leaned back on the couch put his hands behind his head and said, “I’m winning.”

We laughed. And I asked,” what are you talking about? No you aren’t, you’re doing nothing.”

“Exactly,” he said.

He explained to me, “I woke up early and ate breakfast and meditated. Then I went to the gym, after that I ate again and went to the boat park, I fixed a broken part, rigged and went sailing. And I crushed it. Then I ate when we got in and I went to the physio for stretching. We have another big training day tomorrow and so I’m eating, playing this game, then I’ll read and go to sleep. Right now, my job is to rest. Right now, I’m am doing “work” to rest, relax, recover so I’m ready to Do It 100 tomorrow. Right now, I’m winning.”

He was right.

You are not a machine. And your brain is a muscle that needs time off to relax and recover. When you sleep it gets to slow down and recharge. When you sleep your muscles heal themselves. You prepare for what’s next. You must prioritize recovery.

Recovery optimizes performance.

Love the Routine

How can you manage this intense level of self-discipline to do the things you should do, rather than the things you want to do?

You want to eat ice cream. You want to stay out late with friends and go to that guy’s house party. You want to have fun. You also want to achieve the highest level of success you can in sailing. You also want to get into a good college.

The only way to maintain your motivation and to stay on the path when you’re tired of working so hard is to be confident knowing two things: 1) you are in control 2) you love the routine.


They say, “variety is the spice of life.” Bull shit. You must love your own routine, and you will because you are in control of it. You are not tied down to the giant bullseye that gets impaled by the “slings and arrows of outrageous fortune.” You will own your daily process. You will win while you’re studying, eating, sleeping, training, with friends, or reading a book.

You will be present in each moment and learn the expanse of the eternal space that exists within each second if you are paying attention. You will watch yourself grow, and fail, and recover, and grow again.

You’re only as good as your next step, so get moving.

Leave a Reply

%d bloggers like this: