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3 Books I Wish I Read in My 20s


Books I wish I read in my 20sA while back, I did an interview and one of the questions was – what 3 books do you recommend. This question came up a few times now so I thought I’d write up a good answer here so I can refer to it at anytime. BTW, this is a good tip for new bloggers. If you have to do something a few times, then just write up a good response which you can use over and over again. I really should be better at this by now and have a canned response ready for most questions.

Also, I recently read two really great books in quick succession. These two made it to the top of my list (#2 and #3) and I wish I read them a long time ago. They would have helped tremendously when I was in my 20s. Anyway, here are my recommendations.

Disclosure: We may receive a referral fee if you purchase a book through the links in this post.

1. Your Money or Your Life

Your Money or Your Life by Vicki Robin and Joe Dominguez is a classic guide to financial independence. It was originally published in 1992 and updated in 2008.

The main thing I got out of this book is how to look at money differently. Most of us work for money and that means trading your limited time for money. When you buy something, think about how much time it took to earn that amount. An unnecessary pair of shoes might take 5 hours of work. An expensive car might take a whole year of work. It’s easier for me to avoid spending money when I look at it this way. Previously, I didn’t really make that connection. Money is just money, not time.

This book is not perfect because some numbers are outdated and they recommended investing only in bonds. This was okay when the interest rate was high, but I think it’s better to invest in a good mix of stock and bonds now.

YMOYL is a great book to get you started on your Financial Independence journey.

2. How to Fail at Almost Everything and Still Win Big

This book is written by Scott Adams, the creator of Dilbert. I just read this book and it made a huge impression on me.

I’m sure you know this concept – it’s good to fail because you learn from your mistakes. I agree, but I never liked failing. Failures are discouraging and it’s tough to learn in that situation. This book gave some great examples of how to fail forward. You can fail often, but learn a lot in the process and still become successful in life.

I think this book is a must read for young entrepreneurs, independent thinkers, and people who dislike the traditional career track. There are a ton of great concepts here that can change your life. I don’t agree with every theory he has, but the good points outweigh a few unusual ones that probably wouldn’t work for me.

I was so impressed with this book that I purchased one after I finished the copy from the library. Now, that’s an endorsement from a cheap guy like me! You have to support the author if a book is worth the price. Lastly, the book was engrossing and easy to read. It was one of the most enjoyable non-fiction books I’ve read in a long time.

3. Common Sense on Mutual Funds

I really wish I had read Jack Bogle’s Common Sense on Mutual Funds when I was in my 20s. Our net worth would be bigger if we just followed his simple investment advice instead of fumbling around. If you invest in the stock market or have any kind of retirement account, you really should read this book.

This book is a little dry, but the first half was very informative. I skipped through most of the 2nd half so don’t let the 600 page count intimidate you.


So those are my top 3 recommendations. I really wish I read these books when I was young. They would have helped me in various facets of life. I’m still glad I read them, though. It’s never too late to learn. I still have many years in front of me to put these ideas to good use.

Other great books

Here are some other great books that I like.

The Millionaire Next Door: The Surprising Secrets of America’s Wealthy

This book showed me that anyone can become a millionaire. Actually, we’re one of those millionaires next door now! I consider that a great accomplishment.

The Joy of Not Working and How to Retire Happy, Wild, and Free by Ernie J. Zelinski.

Ernie Zelinski is my hero. If you’re thinking about early retirement, you need to read his books.

How to Engineer Your Layoff by Financial Samurai: Negotiate A Severance and Be Free!

Unfortunately, Financial Samurai’s book came out after I quit my job. I could have easily gotten a severance if I stayed just one more year. Oh well, I can’t complain too much because everything is going great. If you’re thinking about quitting, then you need to read this book and negotiate a severance instead.

Millionaire Teacher: The Nine Rules of Wealth You Should Have Learned in School by Andrew Hallam

Andrew Hallam retired early on a teacher’s salary. It’s not impossible. He has an awesome story and you should read his book. Currently, he is traveling around the world with his wife and public speaking to teachers. He doesn’t charge for these speeches and I think that’s a great way to give back.

Books on my reading list

The Intelligent Investor by Benjamin Graham – I tried to read this book about 10 years ago and couldn’t get through it. Maybe I’m patient enough to do it now.

What are some of the books that you wish you read in your 20s? I’m in my 40s now, but I still love to read and learn. Let me know what I should put on my reading list.

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Joe started Retire by 40 in 2010 to figure out how to retire early. He spent 16 years working in computer design and enjoyed the technical work immensely. However, he hated the corporate BS. He left his engineering career behind to become a stay-at-home dad/blogger at 38. At Retire by 40, Joe focuses on financial independence, early retirement, investing, saving, and passive income.

For 2018, Joe plans to diversify his passive income by investing in US heartland real estate through RealtyShares. He has 3 rental units in Portland and he believes the local market is getting overpriced.

Joe highly recommends Personal Capital for DIY investors. He logs on to Personal Capital almost daily to check his cash flow and net worth. They have many useful tools that will help every investor analyze their portfolio and plan for retirement.
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{ 60 comments… add one }
  • Michael @ Financially Alert April 27, 2017, 12:39 am

    Thanks for sharing, Joe! I’ve read a lot of books, but there are always so many more to consume.

    The Millionaire Next Door really opened my eyes when I was younger to never make assumptions about how people look. Millionaires are some of the bummiest looking people I know!

    The Intelligent Investor is a great read, though you may consider the revised version with updated commentary.

    • FinancePatriot April 27, 2017, 10:06 am

      Those are all great books Joe. I also like Affluenza as well. It’s more of a minimalism type book. Have you ever read Jacob’s book, Early retirement extreme? I am thinking about purchasing it.

      As for the layoff book, I DID buy it and am in the process of negotiating severance. I will write about it after I am done, but needless to say, this is an ideal profitable way to early retire.

  • Anthony April 27, 2017, 2:33 am

    Andrew Tobias, “The Only Investment Guide You’ll Ever Need.”

    • retirebyforty April 27, 2017, 6:45 am

      I’ll put this one on my list. Thanks!

    • Ms. Frugal Asian Finance April 29, 2017, 4:36 am

      I also like Dave Ramsey’s “The Money Makeover.” I think it’s the best book I’ve read in years. I even bought a copy for my sister. I’m a big fan of his philosophy and business model!

  • Jan Basson April 27, 2017, 2:35 am

    Thanks for this gr8 article and for sharing the books that inspired/helped you. Really appreciate it.
    Keep up the good work!

  • Al April 27, 2017, 2:59 am

    Interesting. First book about time, my favorite dimension that helps recognize or ascertain your position. Second book on attitide towards failing. Funny thing is that always told my kids that if they were going to fall, fall fowards. Third book about technique or how to.

    Three very imporgant things to know in life. Your time and position, mindset or attitide, and strategy or approach. All three are about a direction or trajectory.

    Had read the same books but one that influence most was a writing by Plato, Message to a young men. These writings change me and literally forged my direction in life.

    In my 20’s, I was such a different person forging a path forward. Napoleon Hill, How to win Friends and influence People would be my first choice then Strauss Generations then Jack’s book about indexing.

    Dealing with people was, is, and will be the number one skill needed in life. Generations explains group perspectives and why we think or act a certain way. Jack’s book in a simplification of very complex problem about investing.

    The Essance of Happiness by Dali Lama changed me or confimed my core believes. Two things to find out in life. Who you are and what you believe. This book does both.

    Four Pillars of Imvesting by Berstein is an eye opener in how things really work. Winning the Loser’s Game by Ellis is extraordinary and at the same level as Jack’s book. Easier reading.

    • retirebyforty April 27, 2017, 6:48 am

      I’ll put these book on my list. I read How to win Friends before, but it didn’t really connect with me. I’ll probably need to read it again.
      Thank you for the recommendation.

  • Buy, Hold Long April 27, 2017, 3:00 am

    Excellent thanks for these, I am 25 now so I may take your advice and read these books. Cheers

    • Ramona from PFtoday April 30, 2017, 9:01 am

      These are indeed great books. I read them in my 30 and wished I did it earlier. The fist proper ‘money’ book I read was the Millionaire Next Door and it blew my mind. I realized trying to keep up with the Joneses is such a bad idea and you don’t need to ‘show’ you have more money than others.

  • Mustard Seed Money April 27, 2017, 3:24 am

    I definitely wish I jumped on the Bogel bandwagon a lot earlier in life and read more of his books when I was in my 20s. I was a little overconfident in my ability to pick stocks and I’m sure if I had picked passive index funds that I would have done a lot better. Oh well.

    • retirebyforty April 27, 2017, 6:50 am

      I took way too much risk in my younger days. Most of the risky investment didn’t pay off and the one that did, weren’t big wins. Passive index fund would have been much better for sure.

  • Dave in Sunny FL April 27, 2017, 3:43 am

    I am so glad that I read The Richest Man In Babylon when I was that age. It has made a tremendous difference in my life. Thanks!

    • retirebyforty April 27, 2017, 6:49 am

      I’ll put this on muy list. Thanks!

  • [email protected] April 27, 2017, 3:54 am

    I am working on compiling a list of these types of books for my son and daughter. My son is headed to college in the fall and wants to major in finance. Your Money or Your Life and Rich Dad, Poor Dad are books I want him to read – just to learn to look at money and people in different ways. The other book I would add is Jim (JL) Collins recent book, The Simple Path to Wealth. It is a quick and witty read – and it explains things in pretty simple terms. A simple path would have been very easy to follow in my 20’s. I lost gobs of money to huge fees in my investments for the first twenty years of work. It’s scary to think about that now… I need to check out Adams book and The Richest Man in Babylon. They are now on the summer read list.

    • retirebyforty April 27, 2017, 6:53 am

      I like Rich Dad, Poor Dad, but I think there are too many bad concepts mixed in with the good stuff. A lot of people think Kiyosaki is a fraud.
      I’ll put JL’s book on my list.

      • Monica Paslawski April 28, 2017, 7:44 am

        I like Kiyosaki’s perspective in many ways, and his work can change your mindset – but I do have a problem with cavalier use of OPM. I am a firm believer, that when I invest with OPM – I need to have skin in the game myself, and I only invest with similar thinking businesses.

  • Apathy Ends April 27, 2017, 4:47 am

    Been off my reading game over the last few months, something about a having a baby takes a lot of reading time away.

    I am in the middle of A Random Walk Down Wall Street and the 4 hour work week.

    Both are pretty good (half way through each one)

    The Automatic Millionaire was one of the first PF books I read – highly recommended

    • retirebyforty April 27, 2017, 6:54 am

      I read 4 hour work week, but it didn’t connect with it. I probably need to read it again.
      I’ll put Automatic Millionaire on my list. Thanks!

  • The Tepid Tamale April 27, 2017, 4:47 am

    Joe, thanks, I am adding How To Fail at Everything and Still Win Big to my list. I only wish there was more time to read! The book list grows instead of shrinks. A couple of books I wish I had read in my 20s.
    – Rich Dad, Poor Dad – Does a good job on the income side, but nothing on the expense side.
    – The Millionaire Next Door – Great overall view of money and strategies.

    I think these 2 were great, but for me the missing piece was something that really showed me how little I needed to spend. I haven’t found a book for this yet. I have finally learned this missing piece from blogs such as this one, Mr. Money Mustache, Early Retirement Extreme, etc.

    • retirebyforty April 27, 2017, 6:55 am

      Your Money or Your Life is pretty good for living frugally.
      The blogs are great resources that are easily accessible. The internet is great! 🙂

  • Nicoleandmaggie April 27, 2017, 5:04 am

    I do not think I would want to support Scott Adams. I prefer my advice from people who aren’t proud (racist fascist) misogynists. Ugh. He’s not even pretending not to be. He is proud of it.

    • retirebyforty April 27, 2017, 6:57 am

      In the book, he was resentful about not getting promoted due to diversity issue.
      I dropped by his blog and saw some strange ideas there too.
      The book is still really good, though.

      • SpreadsheetMan April 28, 2017, 8:33 am

        I agree about the book. The “systems vs goals” thing resonated with me – I’ve been doing that with exercise (via cycling) for the last 10 years and it has worked big-time. I’m massively fitter and thinner in my mid-50s than I was in my mid-40s and none of it relies on willpower or any kind of conscious thought now.

        Some of his other ideas are rather …strange, but I’ll take the message on-board even if I don’t endorse the messenger 😉

  • Jim @ Route To Retire April 27, 2017, 5:05 am

    I really loved “The Millionaire Next Door”, but I would also add the “Richest Man in Babylon” – very old, but explains the fundamentals of getting wealthy that we still preach today. I also loved Robert Kiyosaki’s books (“Cashflow Quadrant” and “Rich Dad Poor Dad”) – very motivational for me.

    I’m going to have to get one of Ernie’s books. Funny thing is, I was actually just checking them out yesterday.

    — Jim

    • retirebyforty April 27, 2017, 7:00 am

      I think you’ll like Ernie’s book at this point in your FI journey.
      I like Rich Dad Poor Dad, too. But there are too many issues with it.

      • Jim @ Route To Retire April 27, 2017, 9:15 am

        I like the Kiyosaki books because they were definitely a wake-up for me on how to make money work for you. But they’re definitely not a step-by-step guide on how to do things. His book though was the reason I decided to start going down the rental property side of things.

        Which one of Ernie’s books would you recommend I start with?

        — Jim

        • retirebyforty April 27, 2017, 9:52 am

          I think you probably should start with How to Retire Happy, Wild, and Free. There are some overlap with the other book.

  • The Magic Bean Counter April 27, 2017, 5:17 am

    I’m with you on the Jack Bogle book. Man if I could go back it would make a HUGE difference to my bottom line. Thanks for sharing

  • The Grounded Engineer April 27, 2017, 5:28 am

    Thanks for sharing the reviews. I recently listened to the Mad Fientist’s podcast interview with Vicki Robin. Her story is fascinating. I want to check out the Financial Samurais book for one of my next reads in potential preparation for early retirement!!

  • Justin April 27, 2017, 6:00 am

    I remember reading Bogle’s Common Sense on Mutual Funds while on a business trip to some random destination (probably for a 2-5 day training seminar). Great to get paid by your employer to sit on a plane learning how to save and invest smarter so you no longer rely on that employer. 🙂

    This was 10+ years ago but I assume they have updated the book since. If not, probably no big deal since the underlying principles are still relevant. As I recall it, no real way to beat the market and index funds are the best way to guarantee you’ll be well above average compared to the universe of mutual funds out there. Not too much new knowledge for those already well versed in the low-cost-is-best field of thought but a great resource for those starting out investing (and one I wish I read in college BEFORE starting FT work and spending way too much on commissions on actively managed funds).

    • retirebyforty April 27, 2017, 7:04 am

      There is a 10 year update in 2009. Everyone think they can beat the market, but the truth is they can’t do it consistently. The more fee you pay, the less you get. He illustrate this concept very well in this book. I wish I read it way earlier.

  • Mrs. Picky Pincher April 27, 2017, 6:02 am

    Oooh, thanks for sharing these! I just hit my mid-twenties, so it seems like a perfect time to read these. 🙂 I’ve read YMOYL and it was awesome. I wish I’d read it before college, to be honest.

  • Dividend Growth Investor April 27, 2017, 6:17 am

    I have read book one and three in my 20s nonetheless. May need check out Adams’ book – many people have recommended it.

    I would like to add the book : “Cashing in on the American Dream: How to Retire at 35” by Paul Terrhorst. He is a CPA who retired at age of 35 in the 1980s, and has been retired and travelling the world with his wife for the past 30 years.

    For whatever reason I found the Millionaire Next Door too repetitive, though I knew the lessons prior to that. The Intelligent Investor is pretty interesting, but Security Analysis is tougher to read.

    • retirebyforty April 27, 2017, 7:05 am

      I’ll see if I can find Paul Terrhorst’s book. I admire them a lot.

  • Insourcelife April 27, 2017, 6:24 am

    Very nice! I needed an actual book to read. It seems that most of my reading is done on the phone and I miss flipping the pages. Just placed a hold on Scott Adams’ book at the local library. Also placed a hold on “How to retire happy, wild and free”. All copies were checked out… Looks like a lot of people are thinking about this stuff around here!

    • retirebyforty April 27, 2017, 7:06 am

      I like real book so much better. It is so much easier on my eyes.

  • Jen April 27, 2017, 8:30 am

    I wish I would have read Your Money or Your Life in my 20’s too! It’s one of the best personal finance / self-improvement books out there and totally puts life (and work) into perspective. Work, and how you spend your money, can truly suck the life energy out of you.

    I love your book recommendations – I will definitely put some of those on my ‘to read’ list. Thanks for sharing!

  • Mr. Tako April 27, 2017, 12:15 pm

    Great book list Joe! I *did* actually read some of these in my 20’s. 🙂

    I haven’t read the Scott Adams book yet, but I’ve seen multiple recommendations for it. I’m going to have to add this one to my reading list.

    Anything by Jeremy Siegel is a fantastic read btw.

  • Our Frugal Escapades April 27, 2017, 1:01 pm

    The very first book I’ve ever read on finance was “Your Money or Your Life” and still use it as a reference today. The lessons the book teaches are invaluable and still highly relevant in today’s world.
    I read “The Intelligent Investor” many years ago when I became obsessed with reading up on Warren Buffett, and find it well worth the read. Understanding Benjamin Graham’s philosophy on value investing only reaffirms the notion of having low-cost, low fee index funds as the mainstay in our portfolio. Well worth taking the time to read!

  • Done by Forty April 27, 2017, 3:20 pm

    I’ve only read one of the three. Looks like I have to make a trip to the library!

  • susan April 27, 2017, 10:19 pm

    Bogleheads Guide to Investing

  • Jonathan April 28, 2017, 4:38 am

    I have a newbie question here.

    Can anyone recommend a good site where I can download historical stock/index data without any restrictions on how far back you can go?

    Many sites are quite limited in their ability to provide long-term quotes. As an example, on Yahoo Finance, a search for DJIA shows that it only goes back to 1985. TD Ameritrade only allows you to go back 20 years. I really want the data to cover the *ENTIRE* history of any stock, any fund, any index I am looking for.

    Thanks for your suggestions.

  • Your First Million April 28, 2017, 7:27 am

    Those are 3 great books that I would agree with. I think my top 3 book recommendations for anyone in their 20’s would be these 3 however:

    1) Rich Dad Poor Dad by Robert Kiyosaki
    2) The Richest Man in Babylon by George S. Classon
    3) The Millionaire Real Estate Investor by Gary Keller

  • Benjamin Davis April 28, 2017, 12:47 pm

    I personally like to recommend (and woulda had read earlier) Rich Dad Poor Dad by Robert Kiyosaki and Millionaire Real Estate Investor by Gary Keller, but those are still excellent recommendations Joe!

  • Allen April 28, 2017, 1:55 pm

    The Rational Male – experiences men can expect from women. It can save you thousands!

  • Project2035 April 29, 2017, 3:51 am

    Nice list 🙂 I would add Jasons or dividendmatra book. Sadly he sold his blog 🙁 That blog and book was my main inspiration to join dividend investments 🙂

  • Jay April 29, 2017, 6:52 am

    Thanks for sharing your reading list! I think these are some great books, and I recently purchased the Scott Adams book and just waiting for it to arrive from Amazon, so glad to hear that one is highly recommended

  • K.P April 30, 2017, 1:31 pm

    Thanks for the post. As someone in my 20’s it’s of great value. What recommendations do you have for self awareness at an early age?

    • retirebyforty May 1, 2017, 8:39 am

      I don’t know… You should try reading a bunch of books from the library to see what clicks. It really depends on your personality.

  • Iuri Q May 2, 2017, 3:10 pm

    I recommend reading ‘The Most Important Thing-Uncommon Sense for the Thoughtful Investor’ by Howard Marks. Though I should have acknowledged, it surprised me how similar his ideas was with Graham’s (The Intelligent Investor). I read Mark first, it was nice to read and really opened my mind, with very practical advises. Graham’s TIE seemed hard to read, and not much more useful than Marks application of his ideas. By the way, I’m lucky guy: In my 20s.

  • Work Life Moolah May 3, 2017, 12:37 pm

    Great list Joe. There is a reason why The Millionaire Next Door is on about every must read list. I read it in my early 30s and it formed the foundation of my PF philosophy.

    Rich Habits by Thomas Corley is a book I read last year that I would recommend to a 20 something. Excellent habits to develop when one is starting out in the world.

  • Amy @ Life Zemplified May 3, 2017, 2:33 pm

    I second Rich Habits. Also, liked Napoleon Hill, How to Win Friends and Influence People, as well as Think and Grow Rich.

  • Rob Typher May 6, 2017, 6:25 pm

    Frugal is cool. Better for our world, and as YMOYL (which everyone should read) pointed out, we appreciate our needs being satisfied more than our wants, and certainly more than our wishes.

    It would be interesting to hear how you give back. Volunteer at school? Coach? As Dave Ramsey points out, giving back is an important part of our relationship with money. And his “Baby Steps” recommendations are excellent!

    Dave and I part ways when it comes to investing, i.e. he thinks it’s a slam dunk to earn 12% a year in stocks, and he has quite an ego. But if you can get past that there are some very good concepts, particularly dealing with debt.

    I was also blessed to have the opportunity to be a stay at home dad, which allowed me to start my own business. Raising our children to be good people is the most important job of all, don’t you think?

  • Lisa Hong May 15, 2017, 9:19 pm

    I absolutely agree with the book Your Money or Your Life regarding being cost conscious when spending. For me, I use a site called Whoppered that calculates how many hours you have to work to buy something. My experience is that if you simply become aware of how much things cost relevant to your income, you can make good financial decisions. If I realize that I have to work four or five hours to afford a nice dinner, I might cook at home instead.

  • Big Mountain June 11, 2017, 1:42 pm

    438 days by Jonathan Franklin. Not a financial book at all other than the fact that he lived for over a year at sea with zero expenditures. When living frugally and buying only the necessities, this book brings into perspective how blessed we are. Will require/encourage my kids to read before leaving the house.

    • retirebyforty June 12, 2017, 8:44 am

      Thanks for letting me know about 438 days. I just put it on my list.

  • jz July 11, 2017, 11:20 am

    I wish I would have read Thomas Sowell’s Basic Economics. It doesn’t exactly fit in with your other recs but kind of gives you a bigger picture of how the world really works which I think can help with individual decisions.

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