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Best Books About Life

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Consider the story of Sara Monopoli, a 34-year-old non-smoking mother diagnosed with stage IV lung cancer while pregnant. After delivering a healthy baby, Sara began chemotherapy, hoping for a cure.

Gawande, her physician, recounts the months of wrenching conversations with Sara and her family about her prognosis, side effects, and fears of death and suffering.

Sara avoided frank discussions, clinging to hope, until treatment landed her unconscious in an ICU at the end. Her family, unprepared, had to decide whether to put her on a ventilator. The situation was anguishing for all.

Gawande argues it's a common tragedy. Patients and doctors alike avoid confronting death. Discussions about priorities and the option to forgo treatment remain rare, even when further interventions become more likely to increase suffering than extend meaningful life.

Section: 1, Chapter: 6

Gawande draws on Plato's dialogue Laches to explore the special courage needed to reckon with aging and death well. Fearing debility and demise is natural. But confronting those fears constructively requires two distinct types of bravery:

  1. The courage to confront the reality of mortality - to seek out the truth of what's likely to happen, what choices exist, and what sacrifices they entail.
  2. The courage to act on those truths - to make tough decisions, have difficult conversations, and shape the end of life according to one's priorities.

Section: 1, Chapter: 8

While acknowledging how difficult it is to transform nursing homes, Gawande draws hopeful lessons from innovators like Thomas and others profiled in the chapter:

  • A commitment to learning what makes life worth living for each individual resident - their tastes, history, quirks, needs for autonomy and privacy
  • Constant effort to give residents choices, variety, and spontaneity within the necessary constraints of safety and hygiene
  • Ensuring strong personal relationships between staff and residents, who know each other's stories
  • Creating an environment full of life and reasons to live - living things, children, music, art, projects, social connection

Medical capabilities are only one part of what nursing homes must provide. Equally vital is supporting the residents' ongoing humanity and opportunities to feel meaning and joy.

Section: 1, Chapter: 5

Chapter 2 depicts the inevitable physical and mental decline that comes with aging, as various bodily systems begin failing over time. While medical advances have changed the trajectory of aging, they cannot ultimately prevent the deterioration, frailty and dependence that accompany living into old age for most. People are often unprepared for figuring out how to cope and adapt as their capabilities diminish.

Through the story of Juergen Bludau, chief geriatrician at his hospital, Gawande illustrates a different approach to caring for the elderly. Rather than just trying to fix each health problem, Bludau focuses holistically on helping seniors sustain their capabilities and quality of life as much as possible - being attentive to preventing falls, managing medications, monitoring nutrition, maintaining mobility and social connections. However, this kind of care is underappreciated and undersupported in today's medical system.

Section: 1, Chapter: 2

"Our most cruel failure in how we treat the sick and aged is the failure to recognize that they have priorities beyond merely being safe and living longer."

Section: 1, Chapter: 6

Gawande cites research showing that terminally ill patients tend to care less about survival and other traditional medical priorities than about:

  • Avoiding suffering
  • Strengthening relationships with family and friends
  • Maintaining dignity and control over daily life
  • Having a sense that their life is complete

But these priorities often go unspoken in a system focused on beating disease. Even facing certain death, only a third of terminal cancer patients report end-of-life discussions with doctors. As a result:

  • 40% get chemotherapy in their last two weeks, usually with little benefit
  • Two-thirds never enter hospice care or only in the last few days
  • Half die in hospitals or nursing homes, often tethered to machines, in pain, with family unprepared

Patients need guidance weighing not just medical options but existential ones, while still supporting their need for hope.

Section: 1, Chapter: 6

A key takeaway is that in dealing with the frail elderly, the goal should not just be safety and survival, but enabling them to have a life worth living according to what matters most to them. This requires a fundamental shift in priorities, so that even as health declines, seniors can maintain a sense of autonomy, identity and meaning. Caregiving should center on understanding an individual's definition of well-being and helping them achieve it within the confines of their circumstances.

Section: 1, Chapter: 3

"People die only once. They have no experience to draw on. They need doctors and nurses who are willing to have the hard discussions and say what they have seen."

Section: 1, Chapter: 7

Just like financial investments, experiences can generate compounding returns over time. Perkins calls these "memory dividends." Here's how it works:

  1. You have an experience (the initial investment)
  2. You reflect on the experience over time, gaining intrinsic enjoyment (the dividends)
  3. You share the experience with others, gaining connection and relational equity (compounding the dividends)
  4. The experience becomes part of your identity, paying ongoing existential dividends

Because memory dividends often accrue for decades, long after the upfront cost is paid, experiences can have immense long-term ROI. And the earlier in life you invest in an experience, the longer you have to reap the dividends.

Section: 1, Chapter: 2

Early in his career, Perkins read the book "Your Money or Your Life" by Vicki Robins and Joe Dominguez. It completely transformed his relationship with money and work. The key ideas:

  • Every dollar you earn represents life energy spent to get that dollar
  • So spending money is actually spending precious hours of your one life
  • The goal is to maximize fulfillment from those hours, not to maximize dollars

This means not wasting life energy on meaningless purchases, but also not hoarding life energy (money) so long that you never get to enjoy the fruits of your labor. Perkins started calculating the true hours of life energy each purchase cost and whether it was worth it. This allowed him to better optimize his life energy, not just his money.

Section: 1, Chapter: 1

Just as Perkins' daughter aged out of Heffalumps, we all age out of specific life experiences. Physical activities, family dynamics, hobbies, relationships - each has a lifespan. But unlike food products, these lifespans aren't clearly marked. There's no tag saying "Best By: Age 40" on your running shoes or "Expires: May 2025" on your friendships. Yet the expiration dates exist. Every day, we lose access to experiences we'll never get back. This is what Perkins calls the "many deaths" we die before our final death. To make the most of life, we must become aware of these hidden expiration dates. We must savor each life chapter while it lasts.

Section: 1, Chapter: 7

Once you've hit your net worth peak, your earning and spending patterns should change dramatically. Instead of maximizing your income, your goal becomes maximizing your life enjoyment. This means:

  1. Reducing your working hours (even if it means making less money)
  2. Taking more vacations and sabbaticals
  3. Spending more on experiences, hobbies and relationships
  4. Giving more to family and charity In essence, you're reallocating your life energy from earning to enjoying.

You're transforming net worth into net fulfillment. You're accepting a lower income in exchange for a higher quality of life.

Section: 1, Chapter: 8

"Remember, the goal isn't to maximize net worth, it's to maximize net fulfillment - and that means aggressively investing your life energy in experiences while you still can."

Section: 1, Chapter: 6

One of the biggest obstacles to investing in experiences is lack of free time. Between work, commutes, housework, errands, and family commitments, most adults have very little unallocated time to pursue experiences, hobbies and relationships. Perkins' solution: buy back your time. If you earn $40/hour, paying $20 for a one-hour task (lawncare, housecleaning, etc.) is a great deal. By outsourcing, you free up time for higher-value activities. Of course, this requires having enough money to begin with. But Perkins argues that for most middle-class and above earners, investing money to buy back time will yield significant happiness ROI over the long run. View time, not just money, as a scarce and valuable asset.

Section: 1, Chapter: 6

Ready to start time-bucketing your life? Here's how:

  1. Brainstorm a list of all the experiences you'd like to have in your lifetime. Go wild - include anything that excites you, regardless of cost or difficulty.
  2. Group these experiences into 5 or 10-year "buckets" based on when you'd ideally have them. Be realistic - put physically demanding activities in your younger buckets.
  3. Within each bucket, rank your experiences by priority. Which matter most to you?
  4. Begin pursuing your top-priority experiences in your current bucket. Don't put them off - remember, every bucket has an expiration date!
  5. Repeat the process every 5-10 years.

By time-bucketing, you ensure you're always investing your life energy in the most fulfilling way possible. You live life by design, not default.

Section: 1, Chapter: 7

To avoid deathbed regrets and unfulfilled potential, Perkins offers these suggestions:

  • Calculate how much life energy (working hours) each dollar represents for you
  • For each big financial decision, quantify the hours of life energy at stake
  • Weigh those hours against the life experiences/memories that money could create
  • Lean towards spending now vs. saving excessively for an uncertain future
  • Give yourself permission to enjoy your money guilt-free
  • Aim to die with zero dollars and zero dreams left on the table

Remember, the goal isn't to maximize net worth, it's to maximize net fulfillment - and that means aggressively investing your life energy in experiences while you still can.

Section: 1, Chapter: 3

any of us instinctively avoid risk - we choose the path of least resistance. But playing it safe has a cost. We miss out on growth, adventure and once-in-a-lifetime experiences. We reach old age wondering "what if?" Perkins' antidote is the "would you rather?" test:

  1. Think of a risk you're considering - starting a business, changing careers, moving to a new country
  2. Fast-forward to age 80 and ask "Would I rather have taken this risk and failed, or not taken it at all?"
  3. Pick the choice you'd prefer to live with long-term

More often than not, the bolder path will feel more authentic. You'll value having tried, even if you didn't succeed. Of course, don't be reckless. But err on the side of (calculated) action. Bet on yourself. Regrets of inaction cut the deepest.

Section: 1, Chapter: 9

Perkins shares a poignant story about his daughter outgrowing the beloved "Pooh's Heffalump Movie." For years, watching the movie together was a cherished family tradition. Then one day, his daughter declared she was too old for Heffalumps. The abrupt ending blindsided Perkins. In hindsight, he wishes he'd savored those father-daughter viewings more when he had the chance. The experience crystallized for him the fleeting nature of life's chapters. We often assume our current joys will last forever. In reality, every life stage has an expiration date. By recognizing this, we can be more intentional about savoring experiences before the window closes.

Section: 1, Chapter: 7

The flipside of longevity risk is mortality risk - the possibility that you die much sooner than expected. This risk is why postponing experiences (especially active ones) is dangerous. You never know how much health and time you have left. Perkins argues we should weight mortality risk more heavily than longevity risk when making financial decisions, for three reasons:

  1. You can insure against longevity risk (with annuities, pensions, etc.) but not mortality risk. Once an experience is lost, it's lost forever.
  2. Experiences are often more valuable (provide more fulfillment) when you're younger. Would you rather take that dream trip at 30 or 80?
  3. Pursuing experiences keeps you engaged and active, which can actually increase your lifespan.

Oversaving provides no such benefit. Of course, you shouldn't be reckless. But weighting mortality risk reminds us that the clock is always ticking.

Section: 1, Chapter: 4

"Let's say you're on your deathbed and you're a gazillionaire. You have all the money in the world but you have no ability to enjoy that money. You are no longer a gazillionaire; you are merely a person who is about to die. All that money is now meaningless to you. It has no value because you have no ability to exchange it for positive life experiences. If you find yourself in this position, you have made a huge mistake."

Section: 1, Chapter: 3

Take your biggest risks when you have little to lose. This is often when you're young, single, healthy and flexible. You can afford to go out on a limb, knowing you have plenty of time to recover if things go south. As you age, your ability to bounce back shrinks. You have more responsibilities, more to lose. You can't afford to start over from scratch.

This is why Perkins urges frontloading your biggest risks. When you're low on resources but high on potential, make your boldest bets. As your wealth and commitments grow, shift to more conservative value protection. The goal is to always occupy the risk-reward sweet spot - enough upside to justify the gamble, but not so much downside that failure would be catastrophic.

Section: 1, Chapter: 9

Most people spend their lives toiling away, saving every spare dollar to pass on a large inheritance. Perkins flips this script. What if, instead of saving every spare dollar for your kids' inheritance, you spent some of it giving yourself a "living inheritance" - the gift of once-in-a-lifetime experiences, enjoyed to the fullest while you're still healthy enough? Your kids will likely get more joy from seeing you thrive than from receiving a slightly larger inheritance. And you can still leave them plenty if you give strategically while living. Ultimately, your life energy is too precious to sacrifice entirely. Invest in experiences for both yourself and your loved ones. That's a life well lived.

Section: 1, Chapter: 5

Bonnie Ware, a palliative care nurse, recorded the top 5 regrets of the dying. Three of them relate directly to Perkins' "Die with Zero" philosophy:

  1. I wish I'd had the courage to live a life true to myself, not what others expected of me. (i.e. I wish I'd honored my dreams)
  2. I wish I hadn't worked so hard. (i.e. I wish I'd better balanced work and life)
  3. I wish I had let myself be happier. (i.e. I wish I'd given myself permission to enjoy)

Perkins sees these regrets as tragic wastes of human potential. He argues that by following the "Die with Zero" mindset - aggressively investing in life experiences, optimizing your fulfillment curve, giving yourself permission to enjoy - you can live a life free of these regrets.

Section: 1, Chapter: 3

Many people put off meaningful life experiences until retirement - only to find their health limits their options. To avoid this:

  • Create a "time bucket list" - what experiences do you want to have in each coming decade of life?
  • Be realistic about age restrictions. Aim for physical adventures while you're young and save less active experiences for later.
  • Start investing in experiences ASAP, even if it means going into (responsible) debt like Perkins' friend Jason did. The earlier you start, the more you can improve your fulfillment curve.
  • If you have unfulfilled dreams now, don't put them off. Find a way to pursue them before the window of opportunity closes. Your 80-year-old self will thank you.

Section: 1, Chapter: 2

When Perkins was in his early 20s, making $18,000 a year as a junior trader, he proudly told his boss Joe Farrell that he had managed to save $1,000. Instead of praise, Farrell called him a "f***ing idiot." Farrell pointed out that Perkins was on a high-earning career path, so his future self would be much richer.

By saving so much now, Perkins was depriving his poor current self just to pad the pockets of his wealthy future self. This blew Perkins' mind. He realized the importance of balancing present enjoyment with delayed gratification. Overdoing either one would lead to a life of regret. This lunch conversation set Perkins on the path of trying to optimize his money and time for the most fulfilling life possible.

Section: 1, Chapter: 1

In the experience-maximizing equation, Perkins identifies three key variables:

  1. Time (to have experiences)
  2. Money (to pay for experiences)
  3. Health (to enjoy experiences)

Of these, health is the ultimate amplifier or limiting factor. With great health, you can energetically make the most of your time and money at any age. But poor health limits your options, no matter how much time and money you have. This is why investing in health is so critical. Think of health as an "experiential multiplier" - the better your health, the more experiences you can fully engage in per dollar and hour.

Section: 1, Chapter: 6

To visualize optimizing your life, Perkins introduces the "fulfillment curve." Here's how it works:

  1. Write down the experiences you want to have in life (e.g. traveling, learning an instrument, going back to school).
  2. Assign each experience "fulfillment points" based on how much it would enrich your life. More meaningful experiences get more points.
  3. Chart out the total points you could earn each year/decade of your life.
  4. Optimize your curve. Rearrange your experiences and spending to maximize the area under the curve (your total lifetime fulfillment).

Most people's curves are suboptimal - with too much unfulfilled potential (area above the curve). By shifting spending earlier and converting unspent dollars into experiences, you can create a taller, fuller fulfillment curve.

Section: 1, Chapter: 1

Many people keep a "bucket list" of experiences they want to have before they die. But Perkins argues this approach is flawed:

  1. It treats all experiences as equally feasible at any age (they're not)
  2. It fails to create a sense of urgency (death is decades away)
  3. It can breed complacency (I'll get to it eventually) Instead, Perkins proposes "time-bucketing" your goals and experiences. This means:
  4. Grouping your goals by life stage (e.g. 30s, 40s, 50s)
  5. Pursuing the goals in their appropriate life stage
  6. Regularly updating your buckets as your life evolves

By time-bucketing, you create clarity and urgency around which experiences to prioritize in each life stage. The result: less regret, more fulfillment.

Section: 1, Chapter: 7

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