Optionality gives you room to breathe. You can take it easy. Wait, wait, wait—and then swing for the fat pitches with all your might, using the resources you've gathered so patiently. Optionality is the power to say “no”. You can maintain integrity. Walk away from a bum deal, blow the whistle, refuse to do anything that conflicts with your values. Choose to fail on your own terms, rather than succeed on someone else's. (Location 118)

Tags: optionality

Note: .optionality optionality gives you the space to say no to opportunities and to explore freely

There's no need to fret about exactly what the future holds. If you have optionality, volatility is your friend. Instead of struggling against the chaotic randomness of the universe, you can harness it to work in your favour. (Location 123)

Tags: optionality

Note: .optionality when you have options then volatility is your friend

Optionality = the right, but not the obligation, to take action. (Location 126)

Tags: optionality

Note: .optionality

what we're looking for is trades that offer large, unlimited upside with small, fixed costs. (Location 140)

Tags: upside

Note: .upside look for high upside and low downside

Thales used his knowledge of astronomy—an informational edge over his detractors—to observe that there was going to be a large crop of olives. So he raised a little money, and bought advance rights to every olive press in Miletus, at a large discount. When the season arrived, the bumper crop triggered a rush of demand. Thales let out the presses on his own terms, getting good and rich, (Location 149)

Tags: options

Note: knew there would be a big harvest so boughts options on the olive presses

The optionality approach to getting lucky starts with identifying and capping the risks which might ruin your life. This gets you into the position of 'not losing', which is a major victory in and of itself: all you have to do is consistently not-lose, and you’ll come out well ahead of the pack. (Location 164)

Note: Cap your risk and consistently not lose

The single most powerful way to open up your options in life is to a) have more money, or b) require less of it in the first place. (Location 291)

Tags: money

Note: .money

Frugality isn’t about hoarding money indefinitely, or being an ascetic, or trying to escape from reality. That’s acting dead, and great-grandpa will beat you every single time. Frugality is about opening your options. (Location 438)

Tags: frugality

Note: .frugality being frugal provides you with more options

Money is much better thought of as an option on the good life: it can be used to buy back freedom, to spend time with loved ones, to lever us into more fulfilling work, to eliminate stress and negative influences, to broaden our skills and interests, and to change the lives of the less fortunate. (Location 1239)

Tags: money

Note: .money

It's impossible to know exactly what your future self will want, but you can predict with near 100 per cent certainty they’ll be grateful you’ve set them up with high-quality options: - financial capital - good health - valuable relationships - useful skills and experiences With broad capabilities and resources at their disposal, they can execute on whatever makes sense at any given moment. (Location 1456)

'better to be vaguely right than exactly wrong’. (Location 1471)

Tags: optionality

Note: .optionality

Microsoft minted more than 10,000 millionaires among early employees—but (Location 4305)

Tags: microsoft

Note: .microsoft

Here are the main predictors of job satisfaction: - Working with good people - Having autonomy over your work - Feeling like you’re making an impact - Finding something you’re half-way good at, and Sticking at it long enough to develop mastery (Location 4872)

Tags: career

Note: .career

The key to success lies in knowing how to both strive for a lot and fail well. Ray Dalio (Location 4937)

Tags: failure, success

Note: .success .failure

Taleb describes the perfect barbell strategy job as having “few intellectual demands and high job security, the kind of low risk job that ceases to exist when you leave the office”. Ideally, it should be non-political, low-profile and won’t force you to bastardise your other work. You do your 9 to 5, and then you check out. All your evenings, weekends and vacation time are free for working on your speculative side-gigs. (Location 4982)

Tags: career

Note: .career have a safe job that lets you also spend time on speculative bets

Have a well-paying job. Seriously pursue your art for love, not money. Sivers says this is the lifestyle followed by the happiest people he knows: “How nice to not expect your job to fulfil all your emotional needs. How nice to not taint something you love with the need to make money from it.” (Location 5032)

Tags: career

Note: .career have a well paying job and do your hobby for fun

Our life is frittered away by detail. Simplify, simplify! A man is rich in proportion to the number of things which he can afford to let alone. Thoreau (Location 5784)

Tags: simplify

Note: .simplify

Why does wearing a chunky gold chain look rich to poor people, and poor to rich people? The signal is simple: "I have enough resources that I can waste $500 on this shiny metal ornament." But rich people are not worried about being confused with people who don't have $500. They have to distinguish themselves from the insecure middle classes, and the way they do so is through countersignalling: by refraining from obvious displays of wealth, they demonstrate that they're so secure in their position that they don't need to broadcast it. (Location 5801)

Tags: status, wealth

Note: .wealth .status

Barbell Strategy: A bimodal distribution between two extremes, avoiding the middle ground. One end of the barbell is hyper-conservative, or ‘cheap’; the other is hyper-aggressive, or ‘expensive’. (Location 6184)

Tags: strategy, barbell

Note: .barbell .strategy