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⛵️Letter 113: Sail with skin in the game

7 min

A black eye from the boom, Audrey Hepburn, patience, and hammocking

If you are new here or missed last week's edition, you can catch up on the past letters here. This past week I learned about self-care and If you are reading this for the first time, I’d love you to sign up below to join the other learn-it-alls:

Aloha fellow learn-it-all 👋

Greetings from Diamond Head, O'ahu, Hawai'i 🌺

As I mentioned last week, in my reflection on the month of May, yoga is something I started doing daily. It's been a great activity to get my heart rate up with sweating but slowing down my speed. In my annual review of last year, I made a promise to myself that patience is a guiding pillar for me since anything I rush I regret. I found I’ve been lacking in patience.

I need to live up to myself with patience. I grant you all permission to do the same.

Now, let’s dive into letter 113 from a learn-it-all. Enjoy!

❓ Question to think about

Why do I need skin in the game?

🖊 Writing

I'm sick of being opportunistic.

I feel like I live in a world that's always looking for a BBO– a bigger, better offer. (No Google not “bad bitches only” or “being bored online”)

This mindset leaves me feeling ungrateful and lousy.

It's like the internal bully pushing me each day names itself ambition. They tell me their thoughts are the medicine I not only want but need. This pesky lady whispers to me, “you’re short selling and the grass is actually greener over there.” Is this true?

I'm sick of first dates, where I feel indifferent then continue swiping on the silly app instead of changing my approach. I'm sick of having a less than stellar day on the job, and then opening LinkedIn to peruse other jobs out there.

I'm not saying to ignore novel insights when they arise. What I am saying is that I want to get some skin in the game and make up my mind. Having a bunch of open loops drains the RAM speed of my computer in my brain. Probably of my second brain on my Macbook too.

Let’s take this problem off of land…

Come join me aboard a sailboat.

In sailing, there are many directions to navigate but there are still constraints. The main two constraints of no-go zones, in relation to wind direction, are going:

  1. Straight into the wind, or into irons. Your sails will start luffing horrendously out of control. The current will start to make you float backward.
  2. Dead downwind (DDW). If you do this, you will most likely death roll by accident. I learned the hard way with a black eye after the wretched Boom knocked me backward out of my boat the day before my ballet recital.

Boring Beam Reach

Personally, my favorite point of sailing is 90 degrees from the wind at a “Beam Reach”. This is the fastest and easiest point of sail. The wind is on the side of your boat at the beam with the sails out halfway. This makes it a rather boring beam reach.

I have the most opportunity to go either upwind or downwind from this angle. There is also guaranteed speed which can be hard to come by some days. A sailing race, also known as a regatta, will start off with boats zooming across the line whipping around at a beam reach. They’d intimidate each other to get the most favored position to begin with heading upwind.


At age eleven, I remember being at the Bayview regatta in my little single-hand bathtub opti boat on the Detroit channel. I was in the noob green fleet. I was balling tears scared to death of my boat overpowering me with its speed, even with the sails eased out. My attempts to go upwind felt just as scary as going downwind, so I disqualified myself from the race. I continued sailing at the beam reach for that round. I later almost got hit by a freighter in the channel and had my first near-drowning experience. I’ll save that story for another day.

On that windy day racing at a beam reach, I grew rather bored of choosing to sail that way. I didn’t care though because I felt safest that way.

We live in a world with so many people sailing at a boring beam reach for eternity.

The musty middle cruising at full speed doesn’t actually give life much color. Rather it makes it dull. I’m guilty where I find myself here too often on autopilot. It’s what I know too well.  Sure, I always have the choosing power of going up or downwind, but life isn’t about the opportunity.

As author Nassim Nicholas Taleb wrote in Skin in the Game: The Hidden Asymmetries in Daily Life:

“Never trust anyone who doesn’t have skin in the game. Without it, fools and crooks will benefit, and their mistakes will never come back to haunt them.”

How can you get skin in the game?

Four tips to get skin in the game:

  1. Have a timeline. Similar to me with yoga, I'm trying a studio membership for $125 this month. I'm proactively putting skin in the game since I care about healing my spine’s scoliosis and being less injury-prone. I’ll reassess this decision at the end of the month.
  2. Shift your perspective. There's no such thing as failure because you can always learn from every choice you make. Sure you can be losing a bunch of money playing slots in the casino. Be aware of this choice, back out, and learn not to go to the casino next time.
  3. Trust. There are cycles with anything in life. More opportunities will emerge again, but at this moment in time, it is one of convergence for you. Life isn't about maximizing opportunity. It's about converging. Have eagerness and trust the wind is taking you somewhere rich. If it doesn’t refer to #2 above.
  4. See expenses as investments. Time in relationships or learning new skills certainly have a bottom line on the timesheet or expense report. But, they are also investments in your life resume. When they are positioned as hefty expenses you’ll feel guilty or shame about them. These feelings will tempt you to go back to a boring beam reach. Life is about being jovial so reframe that.

Actions speak louder than words.  For Pete's sake, MAKE A STAND.

Closing note

I read in James Clear's 3-2-1 Thursday newsletter yesterday:

Two of the key questions in life: How do I grow? How do I manage risk? You need to do both if you wish to survive and excel.

Putting skin in the game is a way to manage risk and challenge growth. I challenge you to try it as well. Life will certainly be more lively.

📖 Reading

Shoutout to my dad for sending me this text called "The Beauty of a Woman" by Audrey Hepburn. Each time I read this, it gets all that much richer.

Hepburn was the hero of my grandma who was also living in the Netherlands while the Nazis invaded in 1940.

🤗 Fun fact

All three of the influential dutch women I look up to in my life were born in 1929. They were also 7 months apart in age. Audrey Hepburn on May 4, Anne Frank on June 12, and Arnolda Vermet on December 23.

🔎 Word to define

Skin in the game: To have "skin in the game" is to have incurred risk, usually monetary, by being involved in achieving a goal.

In the phrase, "skin" refers to an investment (literal or figurative), and "game" is the metaphor for actions on the field of play under discussion. The aphorism is particularly common in business, finance, and gambling, and is also used in politics.


The origin of the phrase is uncertain but may have originated from golf skins games played at IBM in the 1980s. (Source: Wikipedia)

🌟 Quote to inspire

"To plant a garden is to believe in tomorrow" -Audrey Hepburn

📷 Photo of the Week

Nothing too crazy this week. Hiking that mountain to heaven last week was a doozy. I've been resting more.

I don’t plan to ever get a tattoo in this lifetime, but if I did, it’d say something silly like “When in doubt, hammock.”

🙏 Shoutouts

I appreciate you reading this! If ideas resonated, I’d love you to leave a comment, reply to this email, or send me a message on Twitter @JenVermet. Visit my online home if you forgot who I am. If you want to know what I'm up to right now, check my now page.

Never stop learning 😁

Mahalo 🌺


PS- If you want to read more about sailing, read Why Sailors Sail.

If you’re reading this because someone shared this newsletter with you, welcome! I’d love it if you subscribed:

👣 Footnotes

After writing about this I now have a new addition to my reading list:

Follow your joy and eagerness:


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