Over the years, I’ve written about many personal finance books that have been incredibly valuable to me and to many others in terms of helping them figure out their finances and build a path to a strong retirement or even to financial independence / early retirement. Perhaps the most in-depth list was this one, where I outlined fifteen essential personal finance and career books.
As time as gone on, though, I’ve come to realize that many of the best lessons I’ve ever learned about the mindset and other life choices needed to get you to a state of financial independence have come from books that aren’t strictly about finances or careers. They’ve come from a wide variety of other fields – philosophy, psychology, time management, personal growth, and so on.
Today, I want to share twelve of those books with you. These books won’t directly provide financial advice, but what they will do is help you to figure out what you want out of life and how to prioritize the many different demands that you face so that you can begin to make better decisions – financial and otherwise – that will lead you to the kind of life you want to live. These books are packed with ideas, so expect thoughtful reading where you pause a lot to think about the ideas presented, whether you agree with them, and how they impact your life.
A Guide to the Good Life: The Ancient Art of Stoic Joy by William Irvine
A Guide to the Good Life focuses on applying the principles of the philosophy of Stoicism to modern life, redirecting them to help with navigating such modern difficulties as achieving one’s life dreams and ambitions, staying under emotional control, and avoiding distraction.
The core idea of the book is that the only thing you can really control are the thoughts in your head and the actions you take and that by practicing control over those things and evaluate your impulses and emotional responses and whether they make sense, you can discard less helpful thoughts and impulses and cultivate more helpful thoughts and impulses.
I have found incredible value in the ideas of Stoic philosophy over the years. In fact, I would attribute many of the good things I have in my life to using those ideas in my day-to-day living. In fact, at least two other books on this list at least touch on Stoicism.
Three Lessons from A Guide to the Good Life
Practice negative visualization on occasion. Imagine losing the things in life that you value the most: the loss of loved ones, the loss of our own faculties, the loss of our career, the loss of our most valuable possessions. We often take all of those things for granted, and spending real time visualizing and thinking about life without those valuable things helps us appreciate them and the bounty that we really do have in life.
Focus on internal rather than external goals. Internal goals are ones entirely governed by your own thoughts or actions, while external goals are affected by what others can do and have control over. Make it your goal to, say, study ten hours a week rather than earning an A in a class, because earning a good grade is an inevitable outcome of the studying, whereas the grade itself is outside of your control.
Practice daily reflection. Spend some time each day reflecting on your behavior and your life choices. What could you have done better? Consider those situations and conceive of better ways of handling those kinds of situations. Journaling is a great way of doing this, because writing down thoughts forces you to slow down, deeply consider what you’re thinking about, and really hammer the solutions you conceive of into your head.
Voluntary Simplicity: Toward a Way of Life That Is Outwardly Simple and Inwardly Rich by Duane Elgin
The idea behind this book is that choosing a simple life – one free from a lot of distractions and redundant physical possessions – is incredibly life-affirming, though he is very clear to separate the idea of voluntary simplicity from forced simplicity (i.e., poverty). Choosing simplicity means you get to choose how to simplify and in doing so you’re able to let go of the things that are a net negative to you. Rather than being a prison of limited means, it’s incredibly freeing.
To me, Elgin’s message ties in closely with the idea of minimalism, in that it’s a noble goal to reach a point where every possession of yours has a purpose that’s meaningful to you, as does every bit of time you spend. If your possessions and uses of time don’t have purpose and aren’t contributing value to your life or contributing to your greater purpose, then they’re a distraction and ought to be cut away.
I’ve written about Voluntary Simplicity in the past, if you want a more in-depth summary.
Three Lessons from Voluntary Simplicity
Choosing simplicity is exerting decision-making power over your life. It’s a pure embodiment of the fact that you control the realities of your life. Quite often, the time we waste and the things we own but do not use are examples of how we allow our own impulses to run the show, and those impulses often run counter to our true life goals and dreams and desires. Choosing simplicity is centered around exerting control over those impulses and putting our big life dreams and ambitions front and center.
More income does not equal more happiness once you’re above a certain level of basic income. There comes a point – and it’s a surprisingly low point – where additional income does not contribute to additional happiness. Additional income might unlock access to some pleasures that aren’t otherwise accessible, but you pay a high cost in terms of stress and time to unlock those things, a cost that often counterbalances the unlocked pleasure. Finding happiness and joy in things that do not have a financial cost to unlock tends to be an incredibly powerful source of lasting joy and happiness in life.
Actions and purchases that promote passivity and dependence are usually mistakes. When you start buying things that require you to maintain a certain level of income, you become dependent upon the safety of your job and career. When you start relying on others to take care of your basic needs because you’re just too busy, you become passive and struggle to maintain your life on your own. Both are mistakes because they put you at a tremendous disadvantage if anything in your life doesn’t go perfectly.
Meditations by Marcus Aurelius
Marcus Aurelius was a second century Roman emperor; Meditations is simply a collection of his personal notes that he wrote for himself. Marcus Aurelius is considered to be the last of the “Five Good Emperors,” in that he was a part of a succession of Roman emperors who led the Empire at the height of its strength and good governance. Many consider Rome’s decline to have begun shortly after Marcus Aurelius left the throne.
So, what’s the value in the notebooks of a Roman emperor? The notebooks trace the internal thinking of Marcus Aurelius as he attempted to both be a good person and a good emperor, so he internally sought out principles by which he could achieve both aims. He was heavily influenced by stoicism (see the first book on this list for more on that) but sometimes branches out into other useful schools of thought.
More than anything, it’s about his struggle to maintain good values and judgment in a world of distraction, something that many modern people can identify with.
Three Lessons from Meditations
Don’t waste your time worrying about people who have no positive impact on others; save your time and attention for those who do. Make an effort to fill your life with people who have a positive impact on you and on others and slowly divest yourself of relationships with people who do not. There are always negative people in life; don’t spend your time or energy on them unless absolutely forced to.
Seek peace within yourself, because you will never find it outside of yourself. The only way to find true peace and happiness in the world is finding it within yourself. You must be the source of your own contentment and joy, because the world will not consistently provide it for you.
Don’t resent people for their character; instead, treat their character as simply who they are, accept it, and make choices accordingly. Don’t get caught up in negative feelings toward other people because of their character flaws. Accept those flaws, then take action to minimize the negative impact of those flaws upon you. You cannot change the flaws of others; you can only work to change your own flaws.
How I Found Freedom in an Unfree World by Harry Browne
Although this book is somewhat couched in libertarian political principles, the focus of the book is really on being radically honest with ourselves as well as others (noting, of course, that “radical honesty” doesn’t mean negativity).
Browne’s core argument is that a sense of freedom comes from within and we choose within ourselves how much power that we allow the outside world and the prevailing culture to have over our lives. We have a great deal of control over our own choices, but we often let outside forces steer those choices into a comfortable channel for them but not necessarily for us.
The solution, then, is to have a strong understanding of ourselves, first and foremost. What do we value? How do we wish to be treated? Those types of questions are internal, but the answers help bring us to how we act in the world.
Three Lessons from How I Found Freedom in an Unfree World
Every second trying to pretend to be something you’re not is a second of your life wasted. Whenever you bend your core values in order to accommodate the desires of others and what they want you to be, you become a weaker version of yourself. Don’t bend your core values, but instead reflect and observe the world to strengthen the ones that continue to resonate.
Understand your emotions, but don’t act on them when they are surging. This is a bit of stoicism, but it’s incredibly important and valuable advice. Sometimes in life, our emotions get the better of us and we become impulsive, driven by desires in that moment without any thought as to the long term. Don’t let that happen. When you feel a surge of desire within you, recognize it and remember it but don’t act on it. Reflect on it later when you’re calm and outside of that emotional flood, then figure out what to do about it with a cool mind.
Don’t make decisions today based on what you’ve invested in the past. Many times in life, we sink time and money and effort into things only to find that they don’t produce any real fruit for us. When it comes time to make a decision, always choose the one with the best outcome, not the one you’ve invested the most in to this point. Consider that investment to be a sunk cost, one that brought you to the point where this decision was available, but don’t let it make your decision for you. Don’t walk away from a friend in need just because you spend $50 on tickets for a concert tonight unless you value $50 more than that friendship.
Making It All Work: Winning the Game of Work and the Business of Life by David Allen
This is David Allen’s lesser-known book; he’s generally better known for his book on personal productivity, Getting Things Done (which I’ve written about extensively).
I view Making It All Work as something of a bird’s eye view of Getting Things Done, in that it shares most of the key ideas of GTD, but then backs off and looks at it from a broader perspective. Yes, you have tools for getting things done in your daily life, but what does that really mean in terms of your life as a whole? That’s what Making It All Work really tackles. It provides some great productivity tips, but then it puts them in context of a broader life.
I’ve written an extensive review of Making It All Work if you’d like more details on it.
Three Lessons from Making It All Work
Trying to remember things for later breaks your focus, so you should record the thoughts you want to visit (or do) later in some external way that you’ll review often. This is a good principle to use no matter what it is that you happen to be doing in that moment. You’re going to do your best at that task if you give it as much of your focus as you can and things that pop into your head or things that you are trying to remember for later are mere distractions that eat away at that focus, so get them out of your head. Write them down somewhere, in a place that you’ll look at again soon. I like to use a pocket notebook for this. Then, when you do review that space where you jotted down that note, you can take appropriate action on it. This keeps you having things slip through your mental fingers and maximizes your focus on the moment.
Organizing without perspective is useless and generally causes more problems than it solves. You can make endless lists of tasks, but if those tasks aren’t broadly pointing you toward big goals in life, those lists really aren’t very meaningful. The tasks you add to that list should be things that are of genuine importance to what you want to achieve in life, not busywork foisted on you by others and by unwanted responsibilities dumped on you.
A good life connects the “meaning of life” to the little things you do every day. All of the things you do in a given day should be tied to the big things you want in life. Discovering those connections – or recognizing that some things don’t have a connection – is deeply valuable, as is the time spent figuring out how to divest yourself of the things dumped on you that don’t have any connection to your broader life’s purpose.
Self-Reliance and Other Essays by Ralph Waldo Emerson
Self-Reliance is probably the most impactful essay I’ve ever read, and it’s one I re-read quite often. It spells out the importance of being able to rely on yourself, your thoughts, and your judgment outside of others, because when push comes to shove, it’s your thoughts and your judgments that define the path you’re going to be taking in life.
Emerson’s other writings are similarly powerful; though they perhaps don’t resonate quite as strongly as Self-Reliance does for me, very few things do in life. I consider a healthy collection of Emerson’s essays to be some of the best reading a person can take on if they’re reflecting on their life and their life’s choices.
A while back, I wrote a three-part essay on Self-Reliance that you may find valuable: part one, part two, and part three.
Three Lessons from Self-Reliance and Other Essays
Save your energies for the things you truly care about and don’t waste your time, money, and energy giving only a token appearance or a token effort toward some thing you think you’re supposed to care about. If something you don’t care about is eating any significant part of your life in terms of time or effort, it’s well worth your time to find some way to minimize the impact of that thing. A life full of things that matter to you is the best life.
Contradictions between our true values and our behaviors are a huge part of why we don’t succeed. We often fail because we didn’t give our best effort, and we often don’t give our best effort because the thing we’re doing isn’t in line with what we really value or care about in life. When we try to exhibit behaviors that aren’t in line with our true values, those behaviors are usually weak and clumsy and we end up undermining ourselves with them. You’re better off behaving in line with a less popular value that you hold dear than you are faking a behavior in line with someone else’s more popular value.
Try something new. The worst thing that can happen is that it doesn’t go perfectly, in which case you’re usually right back where you started. Failure at something new rarely puts you in a significantly worse place than you started, and success at something new almost always improves your standing. The only “risk” in many such new things are false risks that we invent when we’re afraid of change or of something new.
The Wisdom of Frugality: Why Less Is More – More or Less by Emrys Westacott
This is a philosophical approach to the idea of frugality; it’s perhaps more in the normal area of a book I might write about on The Simple Dollar than almost anything else on this list, but it doesn’t get into practical frugality tips at all.
instead, the focus of the book is on the why of frugality, not the how. Why would a person choose to be frugal beyond the straightforward financial benefits? This book provides a thorough coverage of those questions and brings up some interesting points.
Honestly, I will probably do a thorough review of this book in the coming months on the site, but it will definitely merit a re-read first.
Three Lessons from The Wisdom of Frugality
Frugality is an act of appreciation for the bounty you have in life, not a denial of what you do not have. Many people think of frugality as denying yourself things that you might want. The focus is on the things that you do not have. Westacott argues that the reverse is true, that thoughtful frugality places the focus of your life on the things that you actually do have and encourages appreciation of them. Rather than accumulating more stuff, it’s all about appreciating the untapped bounty that you already have in your life.
Frugal living makes the world better for everyone by minimizing the use of nonrenewable resources. Frugal living typically centers around having fewer possessions and finding lots of uses and extending the lifespan of the things that you do have. That results in less waste, which means less junk in landfills and less pollutants in our land, our air, and our water. This creates a better natural world for all living things.
Using frugal principles frees your mind from decision stress, enabling you to make better decisions in other areas of your life. If you use frugality as a guiding principle in your life, you’re often diverting yourself away from unnecessary purchases and thus away from thinking about where to put things and what to do with things. Given that people only have so much mental energy for decisions in a given day, frugality frees up that mental energy for other uses, such as living a fuller life.
The Art of Learning: An Inner Journey to Optimal Performance by Josh Waitzkin
Josh Waitzkin is a former chess champion and was the subject of the film Searching for Bobby Fischer. Later in life, he chose to step away from competitive chess and instead became a world champion level practitioner of tai chi.
In doing so, he realized that there was a great deal of overlap in the process of learning and thinking about both chess and tai chi, enabling him to use many similar principles in two very disparate fields.
The Art of Learning is a distillation of those shared principles. It looks at how people learn: how similar techniques can be used to learn very different things and how knowledge and experience from other areas can be applied to your new area of focus.
Three Lessons from The Art of Learning
Transferring knowledge and experience from different spheres of your life is the biggest key to deeper understanding. Waitzkin’s core argument is that the process of learning a new subject is made much easier when you recognize that you are able to draw on other areas to enhance and speed up your learning. Looking for familiar patterns in a new subject that allows you to pull in ideas from other subjects you already know about enables you to unlock a great deal of knowledge and understanding fairly quickly when approaching something new.
Developing and strengthening basic skills, such as reading ability, basic mathematical ability, reasoning ability, and so on, makes everything in life easier to tackle. These are effectively transferable skills in that they’re useful in almost everything that you want to do and learn in life. Being able to process and retain what you read, being able to handle basic mathematical principles, being able to reason effectively, and many other fundamental skills are the foundation for learning almost anything, and the stronger those basic skills are, the easier it becomes to tackle something new and the more effective your time and focus will be.
Invest in loss when learning a new skill by learning from mistakes and resisting old habits. Failure is the best teacher of all because it tells you that you’re clearly doing something that isn’t working and needs to be corrected. Success never shows you what you are doing wrong. When you fail, you can take that information, evaluate where you went wrong, and try again, resulting in better performance.
The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph by Ryan Holliday
Most of the time, we view life’s obstacles purely as something in the way of where we want to go, but the reality is that quite often, the obstacle itself is the key part of the path and it is through overcoming that obstacle that we actually reach our destination.
For instance, you might view a difficult person as an obstacle to completing a team project, but often it is handling that person that is the true value in the project, not the project itself. You might view the pain of exercise as a giant obstacle for fitness, but it is actually that pain that is building your fitness.
In other words, don’t view obstacles as things that are preventing you from achieving. Instead, view obstacles as the things that are the fundamental building blocks of achievement.
Three Lessons from The Obstacle Is the Way
Pushing yourself through difficult things – building willpower, in other words – is a fundamental skill that will help you in virtually everything that you do. It is much easier to give up on a goal than it is to keep pushing forward when success isn’t coming easily. Often, it is that obstacle that keeps other people from easily finding success and it is through cracking that obstacle that you’ll find what you’re looking for.
Failure is more valuable than success if you pick yourself up when you fail, figure out where your misstep occurred, and move forward with that in mind. You’re going to try things. You’re going to fail. The question that matters is what you do next. Do you give up? Or do you reassess, figure out what went wrong, and try again?
Bad moments are painful, but the biggest positives in life often come out of the ashes. You’re going to fail. You’re going to hurt. You’re going to sometimes feel like there is no path forward. The thing is, it’s often in those lowest moments when the most unexpected good things happen. Never give up.
Shop Class as Soulcraft: An Inquiry into the Value of Work by Matthew Crawford
I don’t think this list would be complete if I didn’t include Matthew Crawford’s two books. This was his first.
The focus of this book was on how thinking is relatively valueless unless it leads to doing. You can theoretically think out everything you want, but until you do it, you won’t know if it’s practical. You can daydream about goals all you want, but until you start working on them, they won’t come true.
That core principle – that actual work is central to a joyful life and to any real success – is expanded upon throughout the book in countless ways, from the usefulness of sustained work in achieving something meaningful to the peacefulness that comes from focusing on a task at hand.
Three Lessons from Shop Class as Soulcraft
The most meaningful things in life are the ones you have invested a lot of yourself into in the form of consistent work and effort. The feeling you get from having achieved something of true quality on the back of your sustained skill and effort over a period of time is almost unmatched in the world. It’s not easy to attain, but it provides a peak like little else in life. The process of actually investing yourself in your work has inherent value, too, and also feels good. I identify with this greatly, as I’ve come to recognize that a “flow” state, where you lose track of time because you’re so mentally and physically engaged in the task before you, is perhaps one of the most enjoyable states a person can be in.
Separating “thinking” from “doing” is a trap that causes people to develop and enforce ideas that don’t really work. You can have lots of great ideas, but they really don’t matter too much until you put them to the test and see if they work. Separating thought from work often leads people down paths that simply don’t function in the real world.
Put your ideas into actual practice as frequently as you can and revise from there using the feedback from that practice. If you have an idea, do it and see if it works. If it does, then you can use that going forward; if it doesn’t, learn from what went wrong and formulate new ideas. It’s that constant cycle between ideas and action that makes great things happen.
The World Beyond Your Head: On Becoming an Individual in an Age of Distraction by Matthew Crawford
Crawford’s second book extends his thoughts on the value of translating thought into effort and work to the idea of focus and distraction. His core argument here is that it is focus that allows us to create successful and unique things and it is distraction that causes us to become less distinct in our thoughts and actions.
Creating things of value requires doing things in a way that’s different than everyone else, and that takes a lot of effort and focus. Distraction breaks that focus and stuffs us with ideas and concepts of others. That can be good in small amounts, but consistent distraction tears down our ability to focus on the reality of the world around us and damages our ability to have unique thoughts and translate those thoughts into the real world.
In other words, focus is an absolutely essential tool for anyone who wants to create something meaningful and great.
Three Lessons from The World Beyond Your Head
Intense focus on a task anchors you to the real world and is the foundation of lasting success. Focus is a bridge between your mind and soul and the real world, and it is the expression of our mind and soul that is the source of the creation of truly worthwhile things. When we allow ourselves to deeply focus, we put ourselves in position to use all of our abilities and unique talents to create great things. (Again, this ties into the idea of a “flow” state, which I talked about above.)
Modern culture steers us all toward being very similar, but there is little value in being similar. Most of modern culture is distracting and serves to break our focus and fill us with ideas and thoughts that are very similar to everyone else. We’re left with a reduced ability to focus and a reduced set of our own ideas to draw upon, which means a much smaller window to create things of value.
Applying intense focus to the world often reveals other options that aren’t readily apparent. Another challenge of distraction is that it cuts out opportunities and options by either filling our minds with thoughts of only certain options or by harming our ability to focus intensely enough to see other options. Eliminating distractions takes care of both things at once.
Man’s Search for Meaning by Victor Frankl
This book tells Frankl’s story as the survivor of the concentration camp at Auschwitz during World War II and what psychological tools he and others used to survive that kind of intense trauma. In the end, Frankl’s main conclusion is that what helped him and others survive was a central sense of purpose and meaning that they were striving for.
Thus, Frankl’s argument is that the most powerful thing we can have for ourselves in terms of surviving the challenges of life is a central purpose, one that drives our actions and convinces us to push through whatever challenges may fall in that path.
Different people may have vastly different central purposes and meanings for their lives, but it is the mere presence of that central purpose that can provide a central drive for our life.
Three Lessons from Man’s Search for Meaning
Man’s deepest desire is to find meaning and purpose for themselves and the world around them, but life does not owe us an answer. That’s the key thing – we are not owed an answer to the key question of what our life purpose and meaning is. We must put in the effort to seek it out for ourselves, and it is the discovery of that meaning that gives us a driving sense of purpose and a will to overcome great challenge and hardship. It is a journey, not an answer merely given to us.
The world is a mixture of good and bad and seeing elements of it as strictly good or strictly bad leads us down a path of failure. It’s often easy to fall back on a sense that the world is made up of things that are good and things that are bad. The truth is that almost everything in the world is a mix of the two and when we choose to see things as only good or only bad, we are intentionally not seeing the whole picture, and when we stop seeing things as they actually are, we tend to start making large judgmental mistakes which lead us down negative paths.
The most effective way to overcome pain and suffering is to figure out a purpose for pushing through the suffering. Everyone deals with some kind of pain and suffering – emotional, physical, mental, or otherwise. Frankl argues that the most effective way for people to deal with their own pain and suffering is to be on that journey to figuring out their meaning and purpose, because knowing that purpose or even being well on the journey to it can provide a deep motivation to overcome pain and suffering and challenge in life.
Final Thoughts
If you spend the next twelve months reading these twelve books, you’ll find yourself with a much more powerful understanding of the world, your place in it, and the personal, financial, professional, social, and spiritual choices you’ll make in your daily life.
If I had to pull one message out of all of these books, it’s this: spending reasonable time reflecting on your own life, particularly in reviewing your mistakes and how you could improve upon them so that they’re not repeated, is perhaps the most valuable thing you can do. It is perhaps the most profound thing I’ve come to understand about myself in my adult life and it’s the one lesson I desperately want to pass along to my children as they grow and to every reader of The Simple Dollar. Such reflections form a vital backdrop to every financial decision that you make, as well as the other choices you make in every part of your life.
Good luck.
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