100 Books Like Work Optional

Edmonton-based author Ernie Zelinski is probably best known for this self-published international bestseller.

Zelinski semi-retired at 30 after being fired from an engineering job. One of his first books was called The Joy of Not Working, and he later published The Joy of Being Retired: 365 Reasons Why Retirement Rocks—and Work Sucks!. But the one that really struck a nerve for FIRE proponents was How to Retire Happy, Wild and Free, subtitled “Retirement wisdom that you won’t get from your financial advisor”.

Zelinski sugar-coats the content with pull-out quotes and a few cartoons. As the back-cover blurb of my 2014 edition proclaims, “Retirement is the beginning of life, not the end.” It follows that Zelinski believes that the earlier you take Early Retirement, the better, and encourages readers to pluck up the courage to do just that.

To that end, his focus on frugality allows him to… show more.

To me, this book is a classic in the realm of personal finance for a reason. It is the clearest explanation of how money is not actually about money; if you’re actually living by your values and seeking a life that makes you feel truly fulfilled, the point of working is to earn enough money to live on and take care of your future with, while being able to spend the majority of your time doing what you actually enjoy.

I love that this book is centered around finding a purpose without tying that purpose to how you earn a living. It also gives really clear suggestions for long-term investing, and I was happy to see that updated for our current times in the newest edition. 

The late Jack Bogle, founder of Vanguard Group, published this excellent book in 2009.

Consider the following apophyrical tale related in Chapter 10 of Enough: “Too Much Success, Not Enough Character.” It concerns an old greyhound who spent his days at a race track chasing a mechanical rabbit. Over the years, the dog had won over a million dollars for his owner but ultimately decided to quit: not because he was mistreated or had become disabled but because “I found out that the rabbit I was chasing wasn’t even real.”

Those who accumulate more money than they need in life and end up as the richest denizen in the cemetery would do well to reflect on the main premises of Enough. Remember, financial independence is about having income exceed expenses, no matter how modest those expenses might be. It’s about working only because you want to, not because you… show more.

Pensionize Your Nest Egg, or PYNE as some readers call it, is a classic Canadian financial book by famed finance professor Moshe Milevsky and certified financial planner Alexandra Macqueen.

Its audience is primarily anxious would-be retirees who do not have the luxury of having an inflation-indexed, guaranteed-for-life Defined Benefit pension plan offered by an employer. In fact, the headline when I first reviewed the book, was “A Cure for Pension Envy.” Instead, its core reader may have lots of money in group RRSPs, Defined Contribution plans or 401(k)s that rise and fall with financial markets. Hence the subtitle of the second edition, published in 2015, is How to Use Product Allocation to Create a Guaranteed Income for Life.

In practice, this involves using a particular product – the life annuity – to make your nest egg more like a true DB pension. The authors go into some… show more.

Money is the biggest concern for most people thinking about retirement. Suze Orman is the queen of straight-talk about how best to manage your finances during this chapter of your life. She explains practical steps you need to take to make sure you have enough money to last your lifetime. I love that she is ruthless about making readers consider the long-term effects of their purchases and financial decisions.

Wolman and Colmosca, former BusinessWeek writers, were among the early writers to expose just how bad 401(k)s were for workers. They showed how Wall Street interests profited from the plans at the expense of retirement security. They knew a lot about stock market investing and doubted that, even in the best of situations, the stock market would be able to produce enough value to adequately support retirees. They came to the conclusion that the 401(k) system could not be reformed and should be abolished. I liked the book because it was coming from people within the system (BusinessWeek) who realized that it was not working. 

This gem of a book translates the results of Wes Moss’s survey of more than 2,000 happy retirees into ten actionable habits that help you achieve your best “second act.” I love the author’s easy, breezy writing style. Find out how many “core pursuits” are needed to make you a happier retiree!

Harold Evensky and Deanna Katz bring together a collection of experts to explore many different facets of retirement income planning.

This book was ahead of its time in exploring retirement income as a distinct field of financial planning, and it laid important foundations in place. Readers can learn from leading experts about understanding sequence-of-return risk, spending from investments, using annuities, and much more.  

If you could only read one book on retirement planning (other than mine of course!), this is the one I’d recommend. 

It covers a wide range of financial planning and investment topics: life-planning, goal-setting, investment strategy, financial stress-testing, spend-down strategies, tax-management, social security, Medicare, annuities, insurance, reverse mortgages, estate planning, elder abuse, and more

However, while comprehensive, it also does not get too “deep” in the weeds and is filled with wise counsel.  

Yanely’s book is a must-read no matter where you are in your financial journey. She’s engaging throughout the entire book, whether she is sharing an anecdote or a savings strategy. She is a great storyteller and uses her personal experiences to inspire others to make better choices and be financially free.

This easy-to-read book is full of practical information that can be understood by teens and young adults, as well as older consumers who are searching for ways to get ahead financially. She’s practical with her advice and empowering with her knowledge, and she makes you believe your financial goals are achievable with patience and planning.