26 books like How to Retire Happy, Wild, and Free

I actually believe the Alexander technique should be taught in schools from the start, to become a lifelong habit to improve lifelong health, but it’s never too late to start. While there’s no denying it is best taught hands-on, there aren’t enough teachers out there. There are many books but this one has a lovely holistic approach. Even better, if you’re lucky enough to have a practitioner within reach, the book adds to your understanding and to the benefit of your sessions. Win, win.  

This book is a collection of small, powerful but sentimental stories around serious and personal themes that will tug at your heartstrings. Each story left me wanting more as the characters are forced to wrap up their quick journey into the past before their coffee gets cold. The sense of longing, loss, nostalgia, and community are central themes of this book, and it certainly made me reminisce about people and memories dear to my heart. 

It’s a little book of quotes, the sort of book you could keep in the guest loo (if you don’t mind losing your guests for half an hour), but it is stuffed full of oomph and I’ve carted it with me through three migrations because it has been giving me quotes, when I needed something pithy and to the point, for thirty years. I really hope it is still in print because nobody’s getting their hands on my copy. Relevance to my theme? Picked at random – “the first forty years of life gives us the text, the next thirty years supply the commentary” (Arthur Schopenhauer). “If I had my life to live again, I’d make the same mistakes – only sooner”. (Tallulah Bankhead)   

We’ve outgrown vaulting over five-barred gates, running up mountains, drinking all night, and springing bright-eyed from our beds, and so what? For anyone in denial, or clinging stubbornly to youth, Dave is the Baby Boomer to point out the stark realities. He’s funny but he’s ruthless. Fifty’s not the new thirty. It’s fifty. The reason I recommend it is that it can be hard to let go and you’ll waste precious autumn if you don’t accept the inevitable, and move on with a spring in your step into what I have found to be the best period of all. Laughing helps. Laughing always helps.  

Your Money or Your Life is like a cheat code for living. The authors cut through all the “shoulds” we place on money to ask this simple question: What do you really want from life? 

Once you have pinpointed the specific things that make you feel satisfied, alive, connected, contented, and energetic, you can easily let everything else go–and then your money decisions easily fall into place. You simply need to ask yourself if a financial decision supports the things you want most.

The lessons of this book are simple to understand, but not easy to implement. But getting into the habit of thinking more about your life energy than about money means you’re on your way.

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.

I’ve always like the phrase “Work Optional” to describe the state of being financially independent enough that you don’t have to work for money anymore, but nevertheless choose to for reasons like having a purpose, or structure.

Work Optional is also the title of another fine American book on Financial Independence, bearing the subtitle Retire Early the Non-Penny-Pinching Way. The author is an American woman, Tanja Hester, who “retired” early at age 38, along with her husband Mark, who was then 41. I put the word “retired” in quotes because, as is usually the case with advocates of the so-called FIRE movement (Financial Independence, Retire Early), Hester didn’t actually retire to do nothing.

Generally, I find that when FIRE proponents say they “retired” at 30 or 40, what they really mean is they quit working as salaried employees for a corporation, to launch what amounts to an encore career built… show more.

The Simple Path to Wealth is hard to beat as an introduction to investing.

This book has a singular message; invest in a U.S. stock market index fund and call it a day. Every page in the book, brings the reader back to that conclusion. While I have small quibbles with some issues (such as international diversification being glossed over,) if you find investing confusing or overwhelming this book is a fantastic place to start as it simplifies investing. 

Dana Anspach’s book on retirement planning is an accessible exploration of how to put together a retirement income plan.

She is a financial planner and well-respected retirement planning expert who was picked to create the retirement planning course for the Great Courses series. This book will help readers prepare their own retirement plans with confidence.