Daring Greatly by Brené Brown is one of those few books that I want to keep multiple copies of, so I can press it into people’s hands and say, “Just read it, trust me.”

Brown, if you’ve never heard of her, is a research professor who studies vulnerability, courage, worthiness, and shame using grounded theory methodology. She’s deeply interested in wholehearted living, which she describes as:

Engaging in our lives from a place of worthiness. It means cultivating the courage, compassion, and connection to wake up in the morning and think, No matter what gets done and how much is left undone, I am enough. It’s going to bed at night thinking, Yes, I am imperfect and vulnerable and sometimes afraid, but that doesn’t change the truth that I am also brave and worthy of love and belonging.

Daring Greatly has nothing and everything to do with money. Nothing, because the research isn’t obviously tied to money; in fact, you won’t find words like “money, financial, debt, or spending” in the index at all. Everything, because the choices we make out of shame and scarcity instead of vulnerability and wholeheartedness are often ones we make with our wallets.

We’re ashamed and afraid: ashamed that we don’t have our sh*t together so we can afford the nice cars, clothes, houses, and kids’ birthday parties like everyone else in our circle can; afraid to be vulnerable with the people who matter about what’s really going on. Afraid to be judged.

Frankly, so many of the people I talk to have been so marked by shame that they’ve lost hope in their ability to recover. Their responses to questions with strictly numerical answers, like “how much does your life cost?” and “do you have any liabilities?” are almost always prefaced with words that indicate they feel shame and guilt about the answer. “I should track my spending” or “I did something stupid” for example.

These are the people who have overcome their shame enough to talk to me! I suspect that for every one person willing to be vulnerable and ask for help, there are a thousand who have been made to feel such shame over their finances - from the personal finance world most of all - that they’d rather chew glass than get financially naked with anyone ever again.

Who should read it?

Every single human should read this book. If you’ve ever let shame make decisions on your behalf (and, spoilers - that’s everyone) this is the book to teach you how to start overcoming it.

If you only have time to read one chapter:

Chapter 3: Understanding and Combating Shame

Everything that follows this chapter builds on the foundation that shame is universal, debilitating, pushes us to make poor decisions, and must be overcome before any of us can lead wholehearted lives and enjoy healthy relationships (including with money).

If you only have time to read one paragraph:

“We live in a world where most people still subscribe to the belief that shame is a good tool for keeping people in line. Not only is this wrong, but it’s dangerous. Shame is highly correlated with addiction, violence, aggression, depression, eating disorders, and bullying. Researchers do not find that shame correlates with positive outcomes at all - there are no data to support that shame is a helpful compass for good behavior. In fact, shame is much more likely to be the cause of destructive and hurtful behaviors than it is to be the solution.”

(Chapter 3: Understanding and Combating Shame, page 73)

If you only have time to read one sentence:

“If we don’t come to terms with our shame, our struggles, we start believing that there’s something wrong with us - that we’re bad, flawed, not good enough - and even worse, we start acting on those beliefs.”

(Chapter 3: Understanding and Combating Shame, page 61.)

By day, John Robertson is a science communicator.

If that sounds like the opening panel of a comic book to you, you’re not wrong. John’s got a superpower, and it’s his unique ability to take big, complex, sometimes messy ideas and make them simple. Here’s the extraordinary part: he does it without reducing those ideas to useless generalizations.

When John writes about a concept (in this case, The Value of Simple: A Practical Guide to Taking the Complexity Out of Investing), he includes all the complex mess that makes personal finance so...well, so personal. He does this with such skill and clarity that you come away knowing what to do about it...a rarity in the world of personal finance writing.

But wait! There’s more! Not only did John write a book about:

• Why you should be investing

• What you should be focusing on

• Why simple index investing is worth pursuing

• How to avoid analysis paralysis and create a good enough personal investment policy and

• How to execute it as simply as possible and maintain it over time

He also created an interactive course - Practical Index Investing for Canadians - to walk you through every step.

Who should read it?

Anyone who has money to invest should read this book, even if you never, ever intend to manage a penny of your own portfolio. It’s a quick read that will enhance your understanding of why you’re investing in the first place. It will also give you baseline knowledge of the value your investment manager has to provide to be worth their fees.

If you only have time to read one chapter:

Taming the Need to Tinker, hands down. I’ve met a lot of would-be index investors in my career, and almost every single one of them needs to tattoo this chapter on both forearms.

If you only have time to read one paragraph:

“Control what you can - keep fees low, save a decent amount of your income, start early, don’t panic - and be prepared to be surprised and make adjustments on the rest. Get started in approximately the right direction, try to keep moving in the right direction in an iterative process of small course corrections, and try not to fear the uncertainty. The future will - at best - only look approximately like how we imagine it will. That uncertainty is just a fact of life.”

The Cone of Probability, page 56 (first edition)

If you only have time to read one sentence:

“Part of setting up an easy-to-follow plan is to make your own life easy and stress-free, but equally important is that the easier a plan is to follow, the more likely it is that you will actually follow it.”

Step 2: Determine Your Risk Tolerance and Asset Allocation, page 73 (first edition)

Worry Free Money: The Guilt-Free Approach to Managing Your Money and Your Life by Shannon Lee Simmons isn’t making empty promises in the title. There’s literally no guilt in it. None.

The revolutionary thing about Worry Free Money is that it doesn’t start with spreadsheets, calculators, or systems. Oh, there are plenty of great tools in here, but you don’t even meet them until the Hard Limit system shows up on page 74; instead, Shannon spends the first quarter of the book identifying and dismantling the reasons money and spending are so entwined with our feelings of adequacy, belonging, and success. Her training as a life coach is evident throughout, but particularly here, where she makes it clear that the tools in the following sections aren’t going to fix your relationship with money if you aren’t willing to look at why it’s broken in the first place.

Anyone who can write 301 pages about personal finance without relying on shaming readers into following “the rules” must be incredibly entertaining or super smart. Shannon is both, and more: she’s empathetic, funny, and so, so practical.

Who should read it?

Almost everyone should read Worry Free Money: Newly independent kids just learning how to adult, singles, couples, families, people with enough money, people with more than enough money, self-employed folks, 9-5 lifers, people thinking about retiring and people who are financially independent, people who love spreadsheets and people who don’t.

If you’re already confident in your ability to happily spend less than you make, however, or consistently save enough to reach your goals, carry no debt, and have never woken up at three in the morning wondering if you’re screwed, Worry Free Money probably isn’t for you (although it might give you valuable insight into how other people think about money). The book also can’t help you much if — for any number of reasons — you aren’t earning a living wage, have to choose between paying for necessities like food, shelter, power, and clean water, or are facing troubles no amount of facility with personal finance can solve.

If you only have time to read one chapter:

Chapter 11: Saying No without Feeling Guilty, hands down. If you have little difficulty saying “no” to spending on yourself but find it incredibly hard to say “no” to friends, family, and community (join the club, btw), you’ll breathe an enormous sigh of relief once you get through Chapter 11. Trust me.

If you only have time to read one paragraph:

“There are bound to be some Life Checklist goals that you have already accomplished and some that you fantasize about achieving, even if they aren’t realistic in terms of what you can actually afford. Those things might include travel, becoming debt-free this year, renting a bigger apartment without roommates, starting a business, putting your kids in Montessori school, buying or renovating a home, rock climbing, a year in Provence — the possibilities are endless. Chances are your people — your Joneses — will have many of the same boxes on their own lists. When you see them ticking off the boxes faster than you are, beware of falling victim to the Inadequacy Influence. You may feel anxious, frustrated and ready to throw money at them, simply to prove that you can have all those things too. When you feel that happening, focus instead on what you have already achieved on your list and what’s truly important going forward. And know that you haven’t failed at life. You’ve just made different choices.”

(from Chapter 2: The Joneses and the Life Checklist)

If you only have time to read one two sentences:

“If budgeting isn’t working for you, it’s not you. It’s the budget”

(from Chapter 5: Why You Need to Stop Budgeting)