What To Read When Life Gets Tough And A Self-Help Book Just Won’t Do

I got fired…

Security escorted me out. They would send me my box later.

All self-help is bullshit. It’s hard to choose yourself when an iceberg hits the Titanic.

People write books: “How To Not Give A Shit” and it’s supposed to be helpful – to toughen you up, make you stronger.

“The 5 Minute Effective Leader”.

Doesn’t work.

Or then there’s the books not in the psychology section but across the aisle in the self-help section: meditate, think positive, picture positive visualizations.

When the boss asks you to leave and security escorts you out and there’s no severance, there’s also no meditation in the world.

Meditation won’t pay the rent. Thinking of nothing won’t put food on the table.

Visualization is a dream. And the universe owes you nothing.

Sure, if you do it, it might help. But who is doing that?

I’m not doing it.

I can’t. I’m stuck.

When you’re depressed you can’t sleep at night and then you can’t wake up in the morning.

I can’t handle thinking of a future where I might be broke. Or lonely. A shaved head, living in a gutter, abandoned.

I’ve seen it happen.

I’ve been broke…worse than broke, more than once. But I keep coming back.

The truth is that I always go broke when I stop reading.

Before I started my first business I was obsessed with reading everything I could. Fiction (because I wanted to write novels) and non-fiction (because I loved technology and something called “The Internet” was just starting).

And then I started reading books about business because the Internet and entertainment and my life all seemed to be merging with business.

My first business was creating websites for people. My second business was creating “mobile websites” for people, which really didn’t exist then.

In between the first and second business I played poker for 365 days. Even the day my daughter was born. I couldn’t help myself.

My accountant finally said the worst thing he can ever say to me. He said, “you should be starting another business”. I wish I had just kept playing poker.

I lost everything in that second business. Here’s what happened. I stopped reading.

I separated from my wife. I had no clue what my business did. I fell in love. I started drinking a lot. I went broke. Lost my house. Lost my family. Blah blah.

I’m sick of “failure porn”. Ok, we get it.

People fail. Then they come back from it and somehow they turn into Steve Jobs. Steve Jobs is this generation’s mythical “phoenix”.

So now I get to listen to music on my phone and my teenage daughter probably sends nude pictures to boys on her iPhone.

When I was playing poker I read every book ever written about poker. I watched every video. I was still reading a lot.

But something got into my head. Something bad when I started my second business.

I was really unhappy in a lot of ways. I can’t even tell you why I was so unhappy. My dad was always going broke so I thought I was finally going beyond where he went. I thought I was superior to him.

I thought I didn’t need to do what he did.

And since he was a big reader, I no longer needed to read. And since he stayed with his wife, I no longer needed to.

I know now: investing in yourself is the best investment you can make.

Incomes are going down for young people for the first time in forever…

Jobs (a TON of jobs) are being lost to robots, to artificial intelligence

Student loan debt is out of control, nearly impossible to pay back…

And housing keeps getting more expensive…

But forget about failure porn. You don’t have to lose.

Do what I did. Read.

I picked out 20 books to help you. 20 books that will make you smarter (and maybe richer).

Remember I always go broke when I stop reading. So I choose these books as the cure for fear about money.

Some books on this list are the sort of books I call “IQ books”. I read them and I feel like my IQ is going up. “Sapiens”, “Bold”, “Wonderland” are like that and several others.

Other books are about amazingly intelligent people who are sharing their lives and I am just blown away by not only their experiences and their intelligence but also how their playfulness often inspired them to greatness. “A Man for All Markets” and “Moneyball” fall into those categories.

And there’s a third category on this list which includes books I personally used to get myself to be a better investor.

The investing world is constantly changing. But to get good you have to know the foundation and many of these books are foundational, even the one fiction book (a financial thriller from  the 1970s) that snuck it’s way onto this list.

So here it is:

1. ”Tools of Titans” by Tim Ferris
2. ”Bold” by Peter H. Diamandis and Steven Kotler
3. ”Abundance” by Peter H. Diamandis and Steven Kotler
4. ”Unshakeable” by Tony Robbins
5. ”Damn Right!” (biography of Charlie Munger) by Janet Lowe
6. ”Wonderland” by Steven Johnson
7. ”Payoff” by Dan Ariely
8. ”The Billion Dollar Sure Thing” by Paul Erdman
9. ”Sapiens” by Yuval Noah Harari
10. ”Moneyball” by Michael Lewis
11. ”The Undoing Project” by Michael Lewis
12. ”Stealing Fire” by Steven Kotler and Jamie Wheal
13. ”Essays of Warren Buffett” by Warren Buffett and Lawrence  Cunningham
14. ”The Black Swan” by Nassim Taleb
15. ”Fooled By Randomness” by Nassim Taleb
16. ”A Man For All Markets” by Edward O. Thorp and Nassim Nicholas Taleb
17. ”Too Big To Fail” by Andrew Ross Sorkin
18. ”Elon Musk” by Ashlee Vance
19. ”Hedge Fund Market Wizards” by Jack D. Schwager and Ed Seykota
20. ”Reinvent Yourself” by James Altucher