Deep Thinking: 14 Books That Will Change Your Perspective on Work, Life, and Money

It’s a story I’ve told quite often. When I first realized the extent of my personal finance troubles several years ago, my first reaction was to go to the library and grab a giant pile of personal finance books. Some of those books were utterly forgettable. Others offered really good practical advice. One of those initial books changed my life completely.

Since then, reading about personal finance and self improvement has been a constant part of my life, both because it’s a passion of mine and because I do so to continue writing interesting articles for The Simple Dollar.

As with that initial batch from the library, some books are forgettable, others offered really good practical advice.

A few changed the way I behaved in a fundamental way. They changed how I thought about the world. They altered my relationship with my money, my work, and my overall life.

This article is a list of 14 of those books.

These books are not intended to provide easy fixes for your current financial predicament. While some of them do provide some degree of advice on how to directly change your financial standing, the primary focus of this list is something different entirely. The focus is on cultivating a mindset and relationship with your money, career, and the people around you that will lead directly to abundance in every sense of the word.

As you’ll learn, quite often that abundance is found by subtraction, not by addition. You’ll also find that solutions to one type of problem in your life are often found in completely different areas of your life.

I challenge you to read these 14 books. Make this list your reading list for the next year. Don’t just skim through these books, either. Think about the ideas they’re spelling out and how those ideas really connect to your life.

Your Money or Your Life by Joe Dominguez and Vicki Robin

This book singlehandedly transformed the way I viewed the connection between the choices I make every day and the greater decisions I make about my life. It opened my eyes to the value of frugality and day-to-day personal responsibility about my financial bottom line and that of my family.

Every dollar that I earn is representative of some portion of my life’s energy. If I’m making 15 dollars an hour, for example, that 15 dollars represents an hour’s worth of my life. If I then spend $150 on something, that means I just sacrificed 10 hours of my life to have that item. Is it really worth it?

The tradeoff is actually even worse than that, because that $15 an hour rate doesn’t include factors like the cost of transportation to get there, the taxes and other money taken out of my pay, the time invested in going to and from work that I’m not paid for, and so on. If I look at the total number of hours invested in work and work-related tasks and the total amount of money I actually bring in, that rate goes even lower.

Those insights – and many more – came from this book, and they transformed not just how I was spending my money, but how I was spending my life. It was a heady change, to say the least, and it was that change that eventually gave birth to this very website that you’re reading right now.

Early Retirement Extreme by Jacob Lund Fisker

The subtitle of this book is “A philosophical and practical guide to financial independence,” and that description is pretty accurate. Rather than providing easy answers and recipes for retiring early, this book is all about the path to thinking differently about your money, your professional and life choices, and how those things connect to having personal freedom.

Many people have visions about making major changes to their life, but they feel “locked in” by most aspects of their life – their education, their career, their accumulated possessions, their debt load, their social circle and social standing, and so on. It is that internally perceived sense of “lock in” that keep people from making major changes to their life – and it is that discomfort that they feel about the distance between the life they truly want to lead and the life that they’re leading that convinces them to surround themselves with creature comforts to blur out that discomfort and forget about it.

Fisker’s solution to this is becoming a lifelong learner and having lots of goals that are strongly bent toward leading you to financial independence as quickly as possible. Ideally, you should be able to take actions that move you forward toward multiple goals in your life, such as taking up a free hobby that encourages physical fitness or engaging in fixing up a very inexpensive house.

Another part of his solution is to recognize that there is no difference between needs and wants and most of our spending is directed by self-imposed “lines in the sand” dictating how we choose to spend our lives. Perhaps the biggest breakthrough we can make for financial independence is recognizing those artificial “lines in the sand” and simply wiping them away.

Shop Class as Soulcraft’ by Matthew Crawford

The core premise of “Shop Class as Soulcraft” is that the manual trades (repair work, carpentry, and so on) offer intellectual, personal, and physical challenges and pleasures that the information-based economy and lifestyle simply cannot match. This is why many people choose to spend their free time on hobbies that engage manual effort, such as gardening, woodworking, home improvement, and so on. They provide challenges and pleasures that can’t be found in front of a screen.

At the same time, manual trades provide a lot of skills that are often lacking in other career paths today – and those skills end up being invaluable in almost everything you do in life.

They teach that the material world is not inherently a disposable one and that many of the elements you throw away often have a use. They teach that complex tasks aren’t something to be afraid of and are usually just made up of a series of smaller tasks that can continually be broken down until the individual steps are practically trivial.

As a parent, manual tasks provide infinite opportunities for teachable moments. Perhaps most of all, manual tasks often encourage the practice of a large repertoire of individually simple skills that combine together incredibly well and also apply individually to other larger tasks.

There is something intellectually beautiful in making and building and repairing and doing things yourself, with your own hands, and that process builds the person into something more as well.

I discussed “Shop Class as Soulcraft” at length in an earlier article discussing

seven things I’ve learned by doing it myself. You can also read Crawford’s original essay upon which the book was based.

Voluntary Simplicity by Duane Elgin

voluntary simplicityOn one level, “Voluntary Simplicity” seems to be an argument regarding the connection between individual choices and the environment. When you make an individual choice to throw away some trash, for example, you are making a choice that has a small but detrimental long-term effect on the environment.

That’s just the surface level of the book, however. Where “Voluntary Simplicity” really shines and makes you think is when you dig down to the deeper ideas. “Voluntary Simplicity” actually shares a key core with some of the books listed above – you don’t have to overconsume (or consume at all) in areas that aren’t key to the big picture of your life.

The thing is, all of us do that very thing. We consume resources in areas that amount to very little in terms of the key areas of our lives. We buy things and burn energy on stuff that is essentially useless to us, and we do it every single day. We do it when we toss something in the trash or leave a light switch on. Even ignoring the environmental impact, those things cost us financially and separate us from the life we want to live.

Self-Reliance and Other Essays by Ralph Waldo Emerson

Ralph Waldo Emerson might just be my favorite American writer of all. His essays, of which “Self-Reliance” is an incredibly powerful and relatively long example, virtually always leave me thinking about my own life, my own choices, and my own place in the world.

In “Self-Reliance,” Emerson hammers home a few key points, the first of which is that you really shouldn’t care what other people think of you, especially those you don’t know and will never interact with. Those people do not matter and they often scarcely notice you anyway. They don’t notice and don’t care what car you drive or what clothes you wear or where you live.

The ones that actually do matter and notice you are usually far more impressed by your character and your willingness to listen and thoughtfully converse with them than anything else. If you take that as true, what does that imply about how you spend your money and time?

The further point that Emerson makes – and remember that I am compressing a long and very thoughtful essay down here – is that having a set of skills that can serve you well no matter what life deals to you can help you survive challenging times, but it can also open the door to tremendous personal freedom.

If you have built in yourself the skills necessary to take care of your basic needs and to learn new things quickly, you don’t really need much else from life. You have the capacity to choose your own path in radical ways, whether it’s simply walking away from the rat race or choosing a completely different path for your life. The more self-reliant you are, the less control society’s structures have over you and how you live your life.

You can read “Self-Reliance and Other Essays” in a very inexpensive Dover Thrift edition.

The Millionaire Next Door by Thomas Stanley and William Danko

The core idea behind “The Millionaire Next Door” is that millionaires in the real world live a drastically different existence that what you might expect given the popular culture impression of what a millionaire is like. The evidence the authors have for this is a robust study of people who are millionaires in the United States.

Most millionaires are frugal and are quiet pillars of their community. They typically do not live in big ostentatious houses. They are usually very direct about what they want and what they have to offer you. This book digs deeply into the behaviors and relationships of the “average” millionaire and, often, those truths run counter to what you might expect from a millionaire.

Yet, beneath that, the even deeper lesson that this book teaches is that you can’t judge a book by its cover. If your initial impressions of a person’s financial state aren’t always accurate, who’s to say that your other initial impressions are accurate?

A Random Walk Down Wall Street by Burton Malkiel

The core idea behind “A Random Walk Down Wall Street” is that the stock market, over the long run, is basically efficient. Although there may be short periods where the stock market jumps a lot higher and a lot lower, it will, within a fairly short time, return to the long-term average of growth and continue more or less along that path.

The idea of the “random walk” is that the stock market doesn’t stick precisely to that line of long-term growth, but varies back and forth around it in an essentially random fashion, and from that observation (and others), Malkiel draws several conclusions about investing.

To me, there are two types of books on investing. The vast majority of them fall into what I view as a lesser class of them. They just tell you what to invest in or give you simple rules to follow.

The better class of books, of which this is one, focus on the reasons behind those rules and actually create an investment philosophy. That’s why this book is on my list – it puts forward an investment strategy and explains, in detail, the philosophy behind that strategy.

Mindset by Carol Dweck

The core concept behind “Mindset” is that people subscribe to one of two distinct worldviews. They either view the world as “fixed” – in other words, the person they are is already defined and that their failure is indicative of a personal flaw – or from a “growth” perspective – in other words, that the person they are is malleable and that failure is an opportunity for growth.

A person can have all of the natural talent in the world, but without a “growth” mindset, they will never use that talent to push themselves toward greater things. They will stop when they fail for the first time, limit themselves, and never go further.

Meanwhile, a person with relatively little talent paired with a “growth” mindset actually has great opportunity to succeed because they see failure as a teachable moment that shows them what they specifically need to work on and improve so they won’t fail next time.

Most of this book runs through the implications of that core idea, but when you start examining your own life through the lens of that core idea, you start to come to some interesting conclusions.

Walden: Or, Life in the Woods‘ by Henry David Thoreau

The core idea of “Walden” is familiar to most of us. The author, Thoreau, chose to live as deliberately as possible for two years on the shores of Walden Pond. He spent most of those two years living in incredible minimalism, growing his own food, writing in his journal, and so forth. Yet he didn’t live a solitary life, as he walked into the nearby town of Concord almost every day.

The profound message that this book hammers home throughout isn’t that you should live in complete minimalism (though that’s a theme as well), but that you should live with complete self-honesty.

We often tell ourselves stories to make up for the poor choices we make or the ways in which we live that are in contrast with the things that we believe. Self-honesty means cutting through all of that and truly thinking about those conflicts and trying to resolve them.

In my eyes, that kind of self-honesty is an essential ingredient for independent and self-directed living today. If you are not honest with yourself about the consequences (and benefits) of how you spend your time, your money, and your effort, you’re going to constantly make poor choices that take you further and further from where you want to be.

I haven’t discussed this book in the past on The Simple Dollar, but it’s still quite worth reading. It’s available in an inexpensive Dover Thrift edition.

The Complete Tightwad Gazette by Amy Dacyczyn

This book is a collection of articles published by Amy Dacyczyn in her Tightwad Gazette newsletter in the 1990s. The book itself is a rather large tome, numbering 900 pages in length. The individual articles, of which the book contains hundreds upon hundreds, mostly focus on specific tactics for saving money, though some have a philosophical bent.

So what’s thought-provoking here? What’s thought-provoking is how the author just tears into every single aspect of life, breaking all of it down into simpler and less expensive chunks.

There is nothing sacred here. There is no “line in the sand” that shouldn’t be crossed. Every single expense is something to mine, to tear down, to make smaller and more efficient and less wasteful and more minimal.

It is really easy for people to “wall off” certain portions of our lives and deem them untouchable, but if you take down those walls and look at everything and start rethinking everything, your life begins to change in profound ways.

The Bogleheads’ Guide to Investing by Taylor Larimore, Michael LeBoeuf, and Mel Lindauer

“The Bogleheads’ Guide to Investing” provides an interesting pairing with the other investing-oriented book on this list, “A Random Walk Down Wall Street,” in that they both present an investing strategy but rather than focusing solely on how to implement that strategy and the rules to follow with it, they dig into the ideas behind that strategy and why it works. Both books connect the practical and the philosophical in a way that brings about deeper understanding of how to invest your money.

Here, the writers focus on a strategy that’s oriented toward index funds, which are very low-cost mutual funds that are broadly-based by design. Index funds simply invest in small fractions of lots of different things with very simple rules to guide those investments, which means that little active management is needed to run them, which thus means that they don’t have many costs to be passed along to the investor. This book runs deep into the reasons behind investing in index funds.

The Shallows’ by Nicholas Carr

This book offers a fascinating perspective on the pervasive Internet use of the modern world and how it encourages us to think in a very shallow way about information because it is available to us in a nonstop flood. Rather than drinking deeply from specific sources of information, the Internet encourages us to dig into brief articles and sound bites on a lot of topics, leaving us with a shallow understanding of a lot of things rather than a deep understanding of anything, which leaves us open to manipulation and poor understanding.

Even worse, this kind of information flood eats away at our ability to focus, which makes it harder for us to accomplish bigger things. It becomes harder to study, to save, to build relationships, and it all comes down to losing the ability to focus because of the constant flood of information that the Internet provides. This book really makes you consider the impact of that change in human thinking in the modern world and whether it makes sense to intentionally cultivate and retain the ability to focus more deeply.

I discussed this book at length in a recent article I posted here entitled ”

The Plastic Mind,” which you may find worthwhile if you find this brief summary of the book interesting.

born to buy

Born to Buy’ by Juliet Schor

“Born to Buy” provides a fascinating deep look at how marketers reach out to children with marketing messages, shaping their desires and thoughts before they’ve even had the chance to reach the level of self-actualization that many adults reach.

As a parent, it’s easy to see the impact that this book discusses. There is perhaps more marketing directed toward my children than marketing directed toward me, and they don’t yet have the years of experience to deal with it. How is that marketing shaping them? How can I help channel it as a parent?

Not only does it provide a profound guide for parents in terms of helping their children navigate a challenging media world, it also provides much insight for adults as you can begin to see how marketing has shaped your thinking and choices from your earliest days, setting down patterns from childhood that continue on to your current life.

Bowling Alone‘ by Robert Putnam

I haven’t previously mentioned this book on The Simple Dollar, but I’ve come to realize that it has had a deep and profound impact on my perspectives on life, money, and work over the last several years.

The premise behind “Bowling Alone” is that one of the most powerful elements that has altered our spending patterns and financial choices in the past few decades is the gradual decline in community. Community organizations have been on a long decline in the past several decades, leaving people without structures to plug themselves into for social contact and social support on a local level. This is where the title “Bowling Alone” comes from, as things like bowling leagues and teams have become less and less popular as people turn to individual activities in their homes (like watching television, for instance, or using the Internet).

We’ve lost a lot in that transition. Social groups provide a strong social outlet, sure, but they often provide support and advice and direct help in other aspects of life, often creating a sense of well-being that’s hard to replicate elsewhere.

The key message? Get involved in some things in your community, both with people you know well and people you don’t know so well. If you don’t have a group to join, look for one using tools like Meetup or your local library.

Too long, didn’t read?

Read these 14 books. Make these your reading list over the next year or so. As you read them, don’t just flip from page to page. Instead, think about the books and how they apply to your life and how they change your understanding of how you work, how you spend your money, and how you live.

I will virtually guarantee that if you read through these 14 books and give each of them the time and thought they deserve, your thoughts and perspectives on money, work, and life will radically shift in interesting and vital ways.

Good luck.

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Trent Hamm

Founder & Columnist

Trent Hamm founded The Simple Dollar in 2006 and still writes a daily column on personal finance. He’s the author of three books published by Simon & Schuster and Financial Times Press, has contributed to Business Insider, US News & World Report, Yahoo Finance, and Lifehacker, and his financial advice has been featured in The New York Times, TIME, Forbes, The Guardian, and elsewhere.