Just another Shutterstock surf picture. Ain’t me. But nice one.

3 Stories of Leadership (from Surf): the Dick, the Gentleman and the Coach

Anecdotes from my second time surfing. Drawing a parallel between surf and management based on 3 stories with different people who volunteered to help me surfing.

Laís de Oliveira
8 min readMar 5, 2017

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I gain a great deal of self awareness from doing physical activities (as per my previous post). Now I’m in the surf mood: I just got started with it.

This time with 3 short stories which gave me a lesson about leadership styles which work (or not) for me. Each story features a main character:

#1: The Dick Without a Board
#2: The Overly-Willing-to-Help Gentleman
#3: The Good One

Each of these instructors represent a different management style and how I work with it. Maybe you relate to it, maybe not (each person works better under different circumstances). Here’s what I learned.

Intro: the sea was beating my hard (as life does, sometimes)…

The sea was pretty rough that day. Strong current. Getting to “the point”, walking and paddling through waves was barely possible. It was also crowded, for it was a long weekend and the forecast was promising.

I could roughly compare myself to others nearby me: more successful and experienced surfers were getting to the point and I could see them, only like 5 meters away, but it seemed impossible to get there and I was being dragged by the current to stay amongst second, third layers of people who would be struggling to catch a wave from the “breaking” area.

I knew I wasn’t the only one having a hard time, but I was getting really tired: each wave I caught got me to the other side of the beach and I had to walk back and in through the current. It was exhausting.

#1: The Dick Without a Board

(AKA the Micromanager)

I was already tired, beaten up, still managing to stay in the water and catch some short waves.

That’s when the “dick without a board” made his first appearance.

He signs that I should follow him and I felt I didn’t want his help. This guy had been at the bar I was at the night before and, from the start, I felt somewhat annoyed by his presence. But at that time, my willpower was getting as tired as my body and I was in no conditions to deny help.

I was trying to understand why did I have to work so hard (why couldn’t I simply navigate it through and get to the right spot?). And I decided to do a free interpretation of my lessons (from the ocean): I needed to learn how to be humble. Important note: I made this idea up. Myself.

And that single idea (the being humble bullshit) defined the next hour of trying to be nice to Mr. Dick Without a Board.

Since I’m often regarded as stubborn, stuck-up, even cocky. And since things weren’t working my way and I was literally swimming against the current, I decided to be humble and listen to him.

He started advising me mostly on things that I already knew and it was not helping; but again, I did my best to follow, for a try. He was the typical boss who’s never been on your shoes, but acts as a know-it-all.

For nearly 45 minutes, this dude was around to “help” by telling me what to do — but that’s what I had been doing anyways.

Like: “you need to paddle, paddle, paddle, then you stand up on the board:” — oh really? Seriously. Or “catch this wave! No not this one, this one. THIS ONE, THIS ONE!”.

And then he’d proceed with the theory of how to stand up and balance on the board using your arms (just theory), demonstrating with his arms on the air with his 2 feet on the ground. Congrats!

But I had my ego depleted and the idea that I had to complete the “being humble” lesson, which got me to insist on the interaction for longer than I should.

But, as the experience with him made me even more more stressed and exhausted, to the point I decided to take a break by the beach.

That’s when he asked me if he could use my board a bit. He’d show me how it’s done. I wasn’t a bitch enough to say no, so, “yes sure”.

He took my board, wrapped the leash around his ankle and went to the sea as who says: “now look and learn”.

Given the fact I was already expecting to be beaten again, I really expected to see him jumping on the board and riding a 3 minutes wave while doing a headstand with an eagle sitting on his butt. Ok exaggeration.

But I expected him to do well.

Next thing I know, I saw my board flipping upside down and the dick was “being rolled” by the waves worst than I had been.

It’s not that he wasn’t catching a wave. He wasn’t even able to stand where I had stood before — he was being dragged by the current until I lost sight of him. He took longer to come back with my board than I would’ve liked .

When he finally came back, he gave me the explanation (aka excuses).

Dick: “Ehm… The problem is with your board, it’s broken…”
Me: “Oh no, so that’s why I’ve been finding it hard too?”
Dick: “Nonono, I mean, for you as a beginner the board is OK. For me it’s not good..”

OK. It’s the board’s fault, of course, but just for him. For me no, for me the board should be fine because I was a beginner.

He was a dick, validated.

But while time he made me wait for my board (which was a good one, by the way), he gave me time to think that I wasn’t there to “learn to be humble”. I was there to learn surfing.

Key Lessons from The Dick Without a Board

  1. To learn surf, you get beaten by the sea sometimes (everybody does). Just keep surfing: one wave at a time.
  2. Stand to your own standards of leadership, partnership or any sort of human interaction. Even when you’re beaten up. Don’t create fake “learning lessons” that get you to endure in an already exhausting interaction: focus on the real learning.
  3. Don’t give up your power, getting the wrong kind of people to help. Getting beaten doesn’t mean you have to stop and listen to any dick who claims to know more — specially after you validated he’s a dick.

Thinking back and connecting the dots, I can recall another moment in life when, while being mercilessly beaten up by my first experience as a founder, by the time my ego was depleted, I thought I had to accept help from anyone who was overly eager to help.

And I did wrong. By that time, I compromised some of my criteria and standards for partnership just because I thought I was learning to “be humble”. Bullshit.

You can be humble while working with the right people. Messy waves will always come around: deal with it first. It takes messy and glassy days to learn surf.

Glassy days are beautiful, but messy days teach you endurance better than any other experience would.

#2: The Overly Willing to Help Gentleman

(AKA the Paternalist)

The “Dick Without a Board” was dense and time consuming, I know.

Worry not. After that experience, it was so easy to deny help from #2 that he didn’t last 30 seconds with me.

What went wrong: he offered to carry my board for me, or to “push me” because I wasn’t paddling hard enough; I said “no, thanks”. Goodbye.

Why? I am here to learn surfing. All of it; I may not have the strength on my shoulders to gain the right speed when paddling, but if I don’t start doing it I never will.

I was there to learn and I wouldn’t with someone doing it for me.

#3: The Good One

(AKA The Coach)

After #1 (Dick) and #2 (Gentleman), I was convinced to try it once again and even more, just one more wave (for a sequence of what would become countless wave). And this time, on my own.

But when #3 came about, he started the conversation with a question.

Unlike #1 (“come here I’ll teach you”) or #2 (“carry your board for you”). He asked me, first: “how is it going?”

Here’s what the Good One did right:

Start from Self-Assessment: “Identify Gaps”

The #3 started the conversation from “how is it going?”. While it seems like a simple question, it was really smart because:

  1. It allowed me to stop and think of how was I doing;
  2. He identified the kind of guidance I needed: it gave him an indicator of my level of self awareness and he could see what I knew.

Giving Perspective and Vision: “Choose your Waves”

Next, he proceeded to check my overall knowledge about surf, but not by telling me how to stand up or paddle (he noticed my struggle was past beyond that, at the time).

He pointed out to the waves and asked me: “which waves would you catch? Why?”

And he made me think of it, even if to see me choosing the wrong waves, but he’d proceed to explain why I should or shouldn’t catch those. He pointed out how to observe, measure the length or roughly the speed of each wave to see how far would I go.

Observation and Pointing Improve:

Then, finally, he proceeded to tell me things he did observe while I was surfing, which could be affecting one thing or the other.

All of his observations were clear and very concrete, no room to subjective shit. And in all the cases, he would never start from an observation without first asking me: “How did it go?”, “Did you catch a green wave or white wash?” , “Where did you look at while surfing?”, etc.

The issue was: I wasn’t riding long enough in a wave and there were many reasons for that. “You stand to straight on the board. You’re a goofy, but you tend to turn to the right, but these waves are on a left hand. You’re slowing down and riding short because of that”

Only at this point would he give me advice on “what to do with my body”, lean forward, move your hips to the left, look to the front, paddle faster, etc.

Finally: Offering Help Where Needed

At the end, did offer to help me catching one wave — when he found I was limited due to other factors than my capacity (such as I was getting exhausted from paddling for the past 3 hours, plus the fact I’m still developing the muscles to paddle tirelessly).

He would only offer to “push me” or take the board once he had already guaranteed that I had got it and could do it again, on my own.

In a Nutshell, the Good One Approach would Always be:

  1. Self assessment: ask me questions, identify what I was/wasn’t aware of;
  2. Give perspective: bringing awareness to blind spots; help solving it.
  3. Observation: offering concrete advice based on his analysis, after self assessment and perspective were given and tested.

And finally, offering help or assistance where needed, if needed, if that would allow me learning or feeling the experience of riding a good wave.

Riding a good wave.

That same day, after 3 hours of exhaustion (my arms could barely push me to stand up) and navigating though an even messier sea (thanks to tides changing), I rode my longest wave t0 that point in life (which felt like almost a minute, but make it 30 seconds).

And once you know how it feels to ride a good wave, you’ll do it again.

You won’t give up because you’ve been beaten enough, but as well you found that you can do it even with the most harsh conditions.

That’s what good leaders do: they give you power. They make you feel like you can do it again, by yourself, with or without them around you.

Satu ombak lagi. 😃 One more wave and way to go. Jumpa lagi!

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Laís de Oliveira

Entrepreneur, Community Builder, Writer | Author of Hacking Communities (2020) | Adventurous learner: I write about life as a constant beginner in anything.