The Best Financial Books of 2021

By Jill Schlesinger, Jill on Money | January 11th, 2022

Six picks from Jill on Money

books with $100 bills sticking out Stokato Dreamstime. For article, The Best Financial Books of 2021

Jill Schlesinger, CFP, CBS News business analyst and former options trader and investment advisory fund CIO, recommends her picks for the best financial books of 2021, from tax inequities, a personally sustainable model for success, financial history, gender pay inequality, and more.

The best financial books of 2021

One of the coolest parts of my job is interviewing authors of books that pique my interest – and then compiling my favorites into a “best of” list. Given the chaos of 2020, I skipped this annual ritual last year, but happily, I present Books of the Year, Jill on Money style. In each case, I have interviewed the author on my podcast, so feel to take a listen.

“The Whiteness of Wealth: How the Tax System Impoverishes Black Americans – And How We Can Fix It” by Dorothy A. Brown

“I became a tax lawyer to get away from race,” says professor and author Dorothy A. Brown. But there was no escaping – after helping her parents prepare their tax returns, Brown began a journey to discover how the U.S. tax system is the root of the racial wealth gap. From attending college to getting married to buying a home, Brown argues that Black Americans find themselves at a financial disadvantage compared to their white peers. The results are an ever-increasing wealth gap and more black families shut out of the American dream.

“The Practice of Groundedness” by Brad Stulberg

Spoiler Alert: After early career success, author and career coach Stulberg was blindsided by a difficult diagnosis, which prompted him to make significant changes in his life. The result is a book that highlights the angst, restlessness, frayed relationships, and exhaustion that often accompanies achievement and offers a healthier, more sustainable model for success.

“Trillions: How a Band of Wall Street Renegades Invented the Index Fund and Changed Finance Forever” by Robin Wigglesworth

I wrote about this book when discussing indexing, but if you are a nerd who likes the history of finance (who, moi?), this book is a gem. Wigglesworth brings us back in time to trace the roots of the elegant investment solution that index funds became.

“Machiavelli for Women: Defend Your Worth, Grow Your Ambition and Win the Workplace” by Stacey Vanek Smith

There is nothing more fun than talking to your friend about her book – in this case, NPR host and author Stacey Vanek Smith, who has been covering economics and finance for years. Vanek Smith has an uncanny way of diving deep into a thorny topic like gender pay inequality and coming up with valuable and actionable advice.

“How to Change: The Science of Getting from Where You Are to Where You Want to Be” by Katy Milkman

“If you want to change your behavior or someone else’s, you’re at a huge advantage if you begin with a blank slate,” writes Wharton Professor and author Katy Milkman. Milkman has devoted her career to the study of behavior change and, in this book, she shares ways to identify and overcome common barriers to change, such as impulsivity, procrastination, and forgetfulness. That said, don’t expect a quick fix elixir to cure what ails you, because many of our internal obstacles “are like symptoms of a chronic disease. They won’t just go away once you’ve started treating them. They’re human nature and require constant vigilance.”

“The Premonition: A Pandemic Story” by Michael Lewis

Who else but storied author Michael Lewis could tell the complicated story of a once-in-a-century public health crisis? Lewis’ compelling characters draw us into the narrative, which becomes a sweeping indictment of the Centers for Disease Control and a bureaucratic system that does not allow for brilliant renegades to implement their work – and save lives.

Jill Schlesinger, CFP, is a CBS News business analyst. A former options trader and CIO of an investment advisory firm, she welcomes comments and questions at Check her website at

© 2022 Tribune Content Agency, LLC

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