the wisdom of insecurity book summary

Actionable Book Summary: The Wisdom of Insecurity by Alan Watts

The Book In Three Or More Sentences:

Although clever, we’re quite insecure and unable to enjoy life. Incapable of appreciating the current moment. We’re always preparing to live, but we’re not actually living – only looking forward to having “good times” in the future, which leads to a melancholy-like lifestyle. In The Wisdom of Insecurity, Alan Watts explains how our constant desire for more things is instilling anxiety in our lives and preventing us from truly digging life.

The Core Idea:

If the only thing you’re after is enjoyable moments and more things, you’ll be stuck in a vicious circle where you’ll be forever seeking more and more. Accept pain in your life. Because the only way you can grow professionally and even spiritually is by increasing your willingness to suffer. The more you suffer, the more you’ll mature and therefore cherish what you currently have.


  • The harsh reality is this: We constantly expect new things to happen that’s why we’re never truly happy.
  • Obsession over possessions and securing your wealth is time-wasteful.
  • While pleasure is what we seek, pain, and change, are the only thing constant in life.

5 Key Lessons from The Wisdom of Insecurity:

Lesson #1: We’re Happy Only When We Have A Future To Which We Can Look Forward To

Or as the author states in the book, “Human beings appear to be happy just so long as they have a future to which they can look forward—whether it be a “good time” tomorrow or an everlasting life beyond the grave.”

Our happiness always depends on something expected in the near future. Whether this will be a wedding party or a salary raise. We’re constantly looking forward to distant events that have the power to make our lives feel carnival crazy – at least that’s what we think. But say it’s finally your wedding day, or your salary do get increased, will you be finally happy? Most probably not.

Even when the expected “good times” arrive, we can’t truly enjoy them unless there is a sign, a promise that there is more to come in the future. Put another way, we are always chasing something that will lead to our ultimate happiness but when we get it we start chasing something else.

It’s like a vicious cycle: We expect something in the future > This thing happens > We expect something else in the future > This thing happens… That’s why we’re constantly scrolling online looking for things to buy or things to like. Our desire for a future event that will make our lives oh-so-good always seems right around the corner and never actually here.

Lesson #2: Pain and Pleasure are Interlinked

Pain and pleasure are an integral part of our lives. You can’t separate them. They complement each other. They are like the two sides of a coin. If pleasure is clearly visible in a current situation this also means that pain it’s somewhere out there, waiting to sabotage how we feel.

For instance, the average person hates his job. He complains all the time. Secretly steals print paper. Calls his boss names behind his back. Yet, he needs the job so he can pay the bills and go on vacations every once in a while. To this person, work is pain and what he does after that is the pleasure.

However, if he increases his pain threshold, he’ll probably also increase his pleasure cap. What do I mean? Well, if you do more work, regardless of how you feel about it, you might get a juicy raise, thus get more pleasures in the long run. Yes, the example is a bit shallow but this is how everything in the world works. We need to experience more pain in order to get more pleasures. It’s like a universal law.

An entrepreneur will hustle and grind (experience pain) for quite some time until he reaches a state where his product is making enough money so he can live the life he wants (pleasure). The same happens when you want to lose weight and get in shape. You’ll push yourself in the gym, eat salads and say no to alcohol for the greater good – your new ripped body.

So, what Alan Watts wants to say is basically this: Accept pain in your life so you can experience more pleasures. Still, keep in mind that there is no getting rid of the pain.

Lesson #3: The More We Get Involved In Life, The More We Get Frustrated

Yeah. It might sound strange but the author explains it really well: “We seem to be like flies caught in honey. Because life is sweet we do not want to give it up, and yet the more we become involved in it, the more we are trapped, limited, and frustrated. We love it and hate it at the same time. We fall in love with people and possessions only to be tortured by anxiety for them.”

The more we get and own the more we have to lose. Therefore, the more time we spend protecting our gains. That’s why rich people are really sensitive about their businesses and possessions. They buy expensive vaults and security to protect them. They invest heavily in order to maintain their wealth. Of course, this is something logical. You don’t want to lose what you’ve worked so hard for, right? The problem occurs when this becomes an obsession.

When we become overprotective and constantly worry about our money, about the things we own and even about what other people think about us.

A possible way to stop freaking out about whether or not you’ll keep your possessions is to simply have fewer of those. Accept the fact that fewer things and fewer relationships – but more meaningful – is far better than constantly pursuing more things.

Lesson #4: There is No Real Safety and Security

The notion of security is based on the feeling that there is something within us which is permanent, something which endures through all the days and changes of life.” Alan Watts

There is nothing permanent in life. Except for those two things: pain and change. Existing means handling pain and overcoming change. Nothing lasts indefinitely and pain will surely catch up with you at some point.

Understanding that there is no security and nothing permanent in life gives you a sense of freedom. Since we’re all constantly trying to secure our future by saving money and building businesses, realizing that permanence is an impossible state will allow you to enjoy more the current moment.

But this understanding can come to you only through awareness. By observing and reflecting. Seeing that things move, change, evolve over time will calm you down and you’ll start acknowledging more your daily experiences. Helping you to become more pleased with yourself and with what’s happening in the present moment.

Lesson #5: We live to Protect Our bodies From Pain And to Experience Pleasure

Since we can only feel with our bodies we have little interest in the feelings of other bodies. Thank God some of the pleasures we seek involve other people: talking, singing, dancing, having sex, building something together. Otherwise, the world would have become a bloody arena of selfish pricks who are trying to dominate and to secure their own asses.

A lot of people are consumed by selfish thoughts. All they want is to get their hands on pleasurable activities and move away from pain. This is the ultimate mission for a lot of people. However, when you think about it, I mean, really think about it, you’ll see that this type of behavior won’t make you happier, the opposite is likely to happen.

When we only care about ourselves we’ll alienate ourselves from the rest of the world. Making us worthless assholes no one wants to hang around with. But if we focus on the opposite – help other people to feel good – we’ll find more friendships and more fulfillment in the long run.

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Actionable Notes:

  • Backward law: A brief example of the backward law is this: “The more you try to stay on the surface of the water, the faster you’ll sink; but when you try to sink, you float.” The same applies today. The more we pursue happiness, the more miserable we feel. Try the reverse: Don’t focus so much on being happy all the time, find joy in the difficult to handle tasks. Soon you’ll be much happier.
  • Think more like animals: Our high-expectations spoil the current moment. We dread about the future and moan about the past. This leads to an extremely miserable present. Be more like the follow animals. For the animal, happiness narrows down to enjoying life in the immediate present – not in the assurance that there is a whole future of joys ahead of him.
  • Create your own standard of living: We crave distractions – strange sounds, romantic pleasures, new gadgets, more things. All of this, as fast as possible. And to keep up with this standard most of us are willing to put up with things they absolutely loathe – fake relationships and jobs they hate. But true joy rarely comes from pursuing what everyone else is chasing. In most cases, joy comes from doing something completely different from what everyone else is doing. Something you don’t want to share because you fear being judged. But since we only live once, do you really think that you should care what other people think about your hobbies? Find what you love and make it your unique standard. You don’t necessarily have to do what everyone else is doing to feel good.

Commentary And My Personal Takeaway

The main mission of Alan Watts is to help us know ourselves better. To smash our current understandings about happiness and pain so we can find meaning in this, at first, meaningless world.

The book was published in 1954 but the whole concept is timeless, also, quite true even today. We’re living in a pleasure-seeking age. We want to feel good all the time which, unfortunately, is making us unable to cope with pain. Intolerable to the daily struggles which result in depression.

The concept I liked most in the book is the following: The thing we desire more than anything else in life is to feel good. But since this is not possible we’re in agony when even the slightest sign of pain appears. Or in other words, to really feel good, we need to make “painful” things seem more desirable. Tasks that will lead to future gains more appealing. This way, you can finally start exercising even though you don’t quite like doing physical activities.

Notable Quotes:

Human beings appear to be happy just so long as they have a future to which they can look forward—whether it be a “good time” tomorrow or an everlasting life beyond the grave. For various reasons, more and more people find it hard to believe in the latter.” Alan Watts

If we are to have intense pleasures, we must also be liable to intense pains. The pleasure we love, and the pain we hate, but it seems impossible to have the former without the latter.” Alan Watts

We crave distraction—a panorama of sights, sounds, thrills, and titillations into which as much as possible must be crowded in the shortest possible time.” Alan Watts

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