notes #8: on chasing your dreams and making bets

In the past week I read my first fiction book in a long time. I’ve been wanting to read more fiction to expand my horizons and peak into the brilliant minds of these authors — having heard great things about this genre.

I used to think that non-fiction books are the way to go, but lately I feel that I’m missing out on a lot…

The Old Man and the Sea by Ernest Hemingway

I first heard about this book from the movie The Equalizer starring Denzel Washington. If you did a quick Google search, you’d realise that it’s a classic that won the Pulitzer Price for Fiction and the Nobel Prize for Literature.

It’s a rather short and simple story of an old man’s struggle to catch a big fish despite the difficulty and criticism of his peers. But in that slightly over 100 pages of words, I came to learn about the nature (and beauty) of struggle, the perseverance of a man chasing his dreams, and the role of luck in our uncertain world.

Making a Bet

The big fish we are chasing today may have morphed into different forms, but the struggle remains unchanged. In some ways, those of us chasing unconventional paths or seeking to do something bigger than ourselves know that the journey is like being in the middle of the sea — uncharted, dangerous, and with no guarantee.

Regardless of what we choose to do, as Annie Duke writes in Thinking in Bets, everything that we do is a bet — not a guarantee — no matter how obvious they seem.

• Going to university is a bet that you will be able to do well and find a job.

• Crossing the road is a bet that you will not be hit by a car.

For the most part, we make most bets without thought, because experience has shown us that we’re right most / all of the time. But the possibility of being wrong remains.

When we are so used to these kinds of bets, the moment something goes wrong, we struggle to accept it. And it creates a big problem, especially if we invested a lot of time and effort into it.

On the flip side, there are some things we know that have inherently high risk like starting a business. Yet, sometimes our confidence (or our past luck) makes us downplay that risk. It doesn’t mean we shouldn’t make such decisions, but that we should be prepared mentally — so we can stick it out if required, or leave more amicably.

In mathematical circles, this is known as probability. As Warren Buffett shares in some of his writings, we should strive to think about the world in probabilities — something I still struggle with.

The moment you start seeing things in a probabilistic way, your perspective changes. You stop worrying about the little things and see the big picture; you stop being misled by news designed to trigger you and focus on real numbers; you start embracing the role of luck in both your success and your failures.

Decision vs Outcome

Thinking in bets also brings to light another perspective: the gap between our decisions and the outcome. Because of the inherent uncertainty that exists, making a good decision may not always lead to a good outcome and vice versa.

Understanding this is crucial to developing the right mindset:

• Focusing on things within your control, and equally importantly, ignoring those outside your control

• If you did something dumb, you did something dumb — a good outcome doesn’t negate it

• You can make a good decision and get a terrible result, so don’t be too hard on yourself

And so to end off today’s newsletter, here’s the takeaway: the world is designed in probabilities — and while your dreams may have an infinitely small chance of success, take that bet — focus on making good decisions regardless of the outcome — and be proud of yourself for that.

Cheers,
Joesurf

💡 Inspiration of the Week

From The Old Man and the Sea by Ernest Hemingway:

• "A man can be destroyed but not defeated."

• "Every day is a new day. It is better to be lucky. But I would rather be exact. Then when luck comes you are ready."

• "Now is no time to think of what you do not have. Think of what you can do with what there is."

From Thinking in Bets by Annie Duke:

• "What makes a decision great is not that it has a great outcome. A great decision is the result of a good process."

• "In most of our decisions, we are not betting against another person. Rather, we are betting against all the future versions of ourselves that we are not choosing."

• "Improving decision quality is about increasing our chances of good outcomes, not guaranteeing them."

🧠 Weekly Notes

📖 Book [8/10] — The Old Man and the Sea by Ernest Hemingway:

• The dignity of struggle: True strength isn’t just in winning, but in fighting a worthy battle, even when the odds are stacked against you. ⭐

• Isolation & Companionship: The journey may feel lonely at times so find good companions, whether physically or in spirit.

• Man vs. Nature: The novel explores our deep connection with nature—how we respect, battle, and coexist with forces larger than ourselves.

📖 Book [8/10] — Thinking in Bets by Annie Duke:

• Decisions vs. Outcomes: A good decision doesn’t always lead to a good outcome. Separating the two helps you improve long-term thinking. ⭐

• Embrace uncertainty: Life is more like poker than chess—there are unknown variables, and the best approach is to play the odds, not seek certainty.

• The power of “I’m not sure”: Instead of clinging to certainty, acknowledge when you don’t know. Being open to probabilities leads to better decision-making.