Derek Sivers

Wild Problems - by Russ Roberts

Wild Problems - by Russ Roberts

ISBN: 0593418255
Date read: 2022-09-12
How strongly I recommend it: 9/10
(See my list of 320+ books, for more.)

Go to the Amazon page for details and reviews.

How to improve your HUGE major life decisions, like whether/who to marry, whether to have kids, where to live, career paths, and such — where you can’t use the usual checklist/data approach. This economist addresses self-identity, “deepest self”, and “something I was meant to do”. You can’t use a pro/con checklist with an item that says “lose respect for myself”.

my notes

A “wild problem”:
a big decision where the right path isn’t obvious,
where the pleasure and pain from choosing one path over another are ultimately hidden from us,
where the path we choose defines who we are and who we might become.

Whether to marry,
who to marry,
whether to have children,
what career path to follow,
how much time to devote to friends and family,
how to resolve daily ethical dilemmas...
These big decisions can’t be made with data, or science, or the usual rational approaches.

When you focus on what you know and can imagine, you ignore your full range of choices.

Important things are hard to measure.
Measurable things are misleading.
So what kind of decision framework is left?
This book is my answer to that question.

Face these problems without forgetting what’s at stake.

Imagine the decision to become a vampire.
Once you’ve made the leap into vampire world, and find you don’t care for it, you can’t go back.
Once you become a vampire, your tastes will change.
Which “you” should you consider when deciding what’s best for you?
The current you or the you you will become?
Many decisions involve burning bridges, crossing into a new experience that will change you in ways you can’t imagine.

Leading decision expert said,
I was trying to decide whether or not to move to Harvard from Stanford.
I had bored my friends silly with endless discussion.
Finally, one of them said, “You’re a leading decision theorist. Make a list of the costs and benefits and try to calculate your expected utility.”
Without thinking, I blurted out, “Come on, Sandy, this is serious.”

Make a list of costs and benefits to figure out what you’re “really after.”
«I get half way through my balance sheet and say: Oh, hell, it’s not coming out right! Have to find a way to get some pluses over on the other side!»
Flip a penny in the air. Not as the way to make the decision, but as the way to discover “what you’re hoping.”
Where your heart lies.

Why evoke an emotional reaction?
To know how that choice is going to make us feel, not just physically but emotionally.

Eudaemonia = “Flourishing”
Becoming something beautiful and worthy of admiration.
Fulfilling our human potential.
To live life fully.

Big decisions produce more than a stream of costs and benefits.
Those choices define who you are, and affect your life’s meaning.
The challenge of facing them when they don’t work out well is part of living as a human being.

What would you give up to have a more meaningful life?
What pleasure or consolation would compensate for failing to become the person you think you’re meant to become?

Nothing cancels out betraying who you are or who you aspire to be.
So you can’t add “losing respect for myself” as one of the costs on either side of the ledger.

When thinking of pros and cons:
Don’t mix flourishing with narrow utilitarianism.
Think of each separately.
Consider their relative pull in how you want to live.
Bring the role of flourishing into the light.

Flourishing is both quantitatively and qualitatively different from our day-to-day pleasures and pains.

Purpose, meaning, dignity, and our sense of self:
These are more important to our overall well-being than small and fleeting pleasures and pains.
A fulfilling life, a life well lived, is about more than adding up pleasure and pain and trying to make the former greater than the latter.
Well-being and flourishing persist and overlay your daily experiences.
Who you are is more than what you experience.

You gladly endure some suffering to achieve something you value deeply,
even if the suffering lasts longer than the achievement's joy.
You volunteer for heartache and unease. You like a challenge.
Pain, especially when it’s in service of an ideal, can be a source of meaning.

What kind of hiking trip do you want?
Type 1 = nice the whole time. Nothing too stressful. You enjoy it while you’re in it and after. A day at the beach. A walk in the park.
Type 2 = hard. Endure moments of pain, difficult days with steep climbs, crossing freezing streams, carrying heavy gear.
But a Type 2 experience you never forget, makes you stronger, and when you overcome the obstacles you’ve accomplished something more than pleasant.
You might not enjoy it (much) while you’re in the middle of it. But you enjoy it after it’s over.
Marriage and parenting are much more Type 2 than Type 1.

Invited to a job in Jerusalem. On narrow utilitarian grounds, this was a no-brainer. Only a fool would take the job. A number of friends and family told me to turn it down. But when it came to who I am and who I want to be, it was a no-brainer in the other direction.
I took the job because I felt like it was something I was meant to do, a calling.
To turn down the opportunity would have felt like a betrayal of the deepest parts of me.
(But if my wife had opposed the decision, I would have turned it down.)

Where we live is about who we are and not just what we experience.
We became Israeli citizens, not to save some money on taxes, but for a change in our identity - our sense of self.

You can spend all day in the pool having as much pleasure as possible and ignoring flourishing.
Maybe it doesn’t matter to you.
It’s easy to ignore the parts of life that are not easily imagined,
things you might enjoy once you’ve made a leap,
things that yield more pain than pleasure, day to day, but give your life purpose and meaning.

A sunny pool and margarita are pleasures easily imagined.
It’s harder to imagine a more meaningful life if you spent less time at the pool.

Two ways to earn the praise, appreciation, admiration, and respect of the people around you.
One way is to be rich, powerful, and famous.
That gaudy and glittering path is easily noticed by many. It is seductive.
The other is to be wise and virtuous.
That path is not in the spotlight, and not as popular.
It attracts those who themselves are wise and virtuous.
If you care about flourishing, you have to work hard to keep the better path front and center.

The secretary hiring algorithm. To maximize chance of marrying the best man among many suitors (hiring among applicants). Interview 37% of them. Don’t marry any of these. These interviews are a way to learn about the quality of what is available. Note the best one of the these, and use him as a measuring stick - the benchmark - for the remaining 63%. As soon as you reach someone better than that one, marry/hire him.
In real life, this is more of an anti-lesson. The mathematical version of the question of who to marry is elegant, but not so good for living.

With wild problems, the quest for the best is a mistake.
The perfect is the enemy of the good. But the almost-perfect can be just as dangerous.
The best spouse/partner/career/city doesn’t exist — not just because they’re hard to find. It’s not a meaningful concept.

Satisficing is the best strategy.
Realizing that it is time to make a decision and there is no reason to think there is a better option? That’s not settling. That’s deciding.

Flaneurs wander not aimlessly, but thoughtfully.

Life is like trying to plan a trip to Rome without a guidebook.
Start by facing your ignorance.
Some of us would love for someone to give us an itinerary to go with our trip to Rome - a tour bus where all the stops are preplanned because they’re the popular ones.
But most of us would prefer to discover for ourselves what we love about Rome and what we might come to love.
Wouldn’t you rather be surprised than have it all mapped out for you?
Might travel with someone who can help you discover what Rome has to offer.
Who might make a good traveling companion? No guidebook can tell you who to travel with.

Unmarried friends create extraordinary friendships.

How we treat those around us, defines us.
Every day, we can see those around us as a way to flourish, or as a way to achieve a more utilitarian pleasure.
Often these two forces compete.

Allow another human being the chance to open their heart.

Marriage turns love into loyalty.

Privilege your principles.
Put your principles above the day-to-day costs and benefits.
Your decisions define who you are.
Don’t make trade-offs when it comes to your essence.
Live with integrity.
Do the right thing and respect yourself.

Have a rule. Try to follow the rule.
You spend less time deliberating and suffering.
You don’t agonize over whether following the rule is too costly or not in this particular case. You just follow the rule.

My lesser self, the one I am rather than the one I want to be, will find a way to justify and rationalize.
Rules prevent us from fooling ourselves.
Rules maintain who we are, our sense of self.
Rules help us become who we might want to become.

Life isn’t just about who we are, but who we aspire to be.
Right now, I may not care for opera. But I might aspire to appreciate it.
Aspire to be a better person.
Aspire to be a more reliable friend.

Human beings are aspiring rather than desiring beings.
We aspire more than we desire.

Max Beerbohm story: “The Happy Hypocrite.”
The face beneath the mask now matches what the mask displayed to the world.
The inner man now matches the outer one.
How is that possible? The answer is practice.
Through changed behavior, he changes who he actually is.
To get to where he wants to go, he wears the mask.
He becomes that better person by actingj
By performing the actions of a good person, he becomes that person.

Practice at what you want to become.
You can change your preferences.
What once appealed to you can become unappealing.
What you once found unappealing can potentially give you pleasure if you try it and persist at it.

You have conflicting parts inside of you.
Which one wins?
The one you feed the most.

The future is shrouded from us.
Because we crave control and certainty, we want more information and better strategies.
We’re better off trying to get used to the darkness.
This goes against our nature. Uncertainty makes us anxious.

Optionality is when you have the freedom to do something but not the obligation.
Being able to change your mind, reverse your decisions, is optionality.

Don’t agonize over whether anything is the right choice. Don’t waste time trying to get more information.
Look for strategies to cope with the inevitable uncertainty.
You can’t know in advance what will work.

Widen your options.
Have more experiences than fewer.
Try stuff.
Stop doing the stuff that isn’t for you.
Admit that a decision you made didn’t work out.
Embrace opportunities that make your heart sing.
Spend less time trying to figure out in advance what those might be and more time taking chances as long as you can opt out at a low enough cost.
Exploring can turn out much better than a planned itinerary.

Life choices that turn out differently from what we hoped aren’t mistakes.
They’re just choices that turned out differently than we hoped.
We shouldn’t call those mistakes.
They’re more like adventures.

Go on an adventure that you can end without great cost.
It turns out badly, cut it short.
If it turns out well, enjoy the ride.
This beats trying to figure out in advance which adventures are the best ones.

Grit and persistence are overrated.
Take advantage of optionality when you can.
Visit a place before you move there.
Don’t finish every book you start.

The specter of regret makes us fear making any decision at all.

More information is just a form of procrastination.

The only way to understand whether a certain career path is right for you is to actually try it for an extended period.
Those who hover on the edge of a commitment, reluctant to make a decision until all the facts are in, will eventually find that life has passed them by.
The only way to understand a way of life is to take the risk of living it.

Poets, sculptors, novelists, and composers learn about what they are crafting in the process of crafting it.

If you always or too often say no, you’ll miss a chance to connect with someone - you’ll reduce the amount of serendipity in your life.
Taking advantage of optionality means:
Say yes to things that are not obviously worth doing but have the chance to expand your horizons, your experiences, your connections.