It’s Not How Many Times You Lose, It’s This

It’s Not How Many Times You Lose, It’s This

This post was originally shared in my DT Email Newsletter here.

I love this from Rocky VI: 

“It ain’t about how hard you hit. It’s about how hard you can get hit and keep moving forward. How much you can take and keep moving forward.”

The late Charlie Munger didn’t spend his 99 years pretending life was easy. 

In fact, at 31 years old, the young Munger’s life looked like it was a dead end. He was divorced, deep in debt and watched his nine year old son battle with cancer. 

By 69 years old, Charlie Munger became one of the richest people in the world, achieved his billionaire status, rebuilt his family, and stayed married to his second wife for over three decades. 

He raised eight children, had countless wonderful grandchildren and became one of the most respected business thinkers in history.

He eventually achieved his dream of life:

  • financial freedom,
  • a house full of books,
  • and a large, loving family. 

Like Warren Buffett, he did what he loved and had forged a life-long companion building one of the world’s best performing investment funds – Berkshire Hathaway. 

Yet, it wasn’t all like this. 

In 1949, at 25 years old, Munger was earning only a modest salary at a law firm. He was hired at the law firm, Wright & Garrett for $3,300 per year and had just $1,500 in savings.

There were no obvious signs of a great life ahead of him. 

By 29 years old, his marriage crumbled, Charlie Munger lost nearly everything in the divorce. His ex-wife kept the family home in Pasadena, California. 

Munger moved into temporary housing where condition was so bad, and had to drive a worn-out car his children complained it being so unattractive. His response? “This helped discourage gold diggers.” 

Then came the hardest blow. 

Not long after his divorce, Charlie Munger learned his young son Teddy had leukemia. 

By then, Charlie was 31 years old, divorced and watched his nine year old son leave him. 

Munger’s friend, Rick Guerin, later recalled seeing Munger visit the hospital, hold his son, then wander the streets alone afterward, overwhelmed by grief.

Years later, a medical condition left Charlie Munger one eye blind, leaving him in unbearable pain – forcing doctors to remove it entirely. 

From the outside, he wasn’t just facing a low point. He was completely wiped out. 

And yet he simply went back to work the next day.  

Charlie Munger never treated his suffering as an excuse to give up. He said: “The iron rule of life is: Everybody struggles.” 

As the year draws to a close and I write my final Sunday Weekly Newsletter for 2025, I can’t help but feel a mix of nostalgia and quiet reflection. 

While it’s easy to look around and see festive celebrations, year-end parties and highlight reels, the truth is not everyone ends the year on a high note. 

Charlie Munger’s Cinderella story reminds me about his entire life philosophy: bad things can happen. 

We get stuck in the same spot, we stew and vacillate, we procrastinate, we blame the weather, fate, the government. But sometimes, all you need to believe is to take the next step.

My favourite comment from Charlie Munger is this: 

“I’ve had my Berkshire stock decline by 50% three times. It doesn’t bother me that much. That’s just a natural consequence of an adult life.” I just love this. 

With that, I wish you and your family a Happy New Year 2026. May the year ahead bring you clarity, resilience and the quiet strength to keep on keeping on. 🙂 


For now, I love to share some of my favourite articles for 2025:

Sometimes, investing can be simple. 

Willie Keng, CFA

Founder, Dividend Titan

Author

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