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Billionaire Ray Dalio on His Routine-Free Life, What Keeps Him Up at Night and His Next Chapter

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This story is part of the Behind the Desk series, where CNBC Make It gets personal with successful business executives to find out everything from how they got to where they are to what makes them get out of bed in the morning to their daily routines.

Today, Ray Dalio is a finance legend who's been called "the Steve Jobs of investing" because of his tough but innovative management style.

Dalio famously founded Bridgewater Associates out of his two-bedroom apartment in 1975. He hit rock bottom in 1982 when a bad bet wiped him out financially and he had to borrow $4,000 from his dad to rebuild his company from scratch.

Since then, the Queens, New York native has amassed a net worth of $17 billion while building Bridgewater into the world's largest hedge fund, which now manages roughly $150 billion in assets.

Though Dalio stepped down as co-CEO of Bridgewater in 2017, he has remained chairman and co-chief Investment Officer. But Dalio says he will eventually pass along those titles as well, because now, at 71, he is focused on his next phase of life — pursuing his passions and helping others succeed.

And this phase "feels great," Dalio tells CNBC Make It.

Dalio's already started passing along his wisdom with the book "Principles: Life and Work," and now with his new PrinciplesYou assessment (similar to a test he gave Bridgewater employees), which helps people learn about themselves.

He says he wants a legacy beyond Bridgewater as someone who "evolved well" and "contributed to evolution in some small part. And who helped people be all that they could be."

Here, Dalio talks to CNBC Make It about what his days look like, tough love, what keeps him up at night and more.

On his lack of a daily routine: 'I go with the flow'

I usually wake up at about 6 a.m. I meditate. I have breakfast. Then I dive into a variety of things.

I check in on the markets, and then I spend six to eight hours a day, six days a week, digging [into research]. I love digging. I'm basically pursuing my passions now, the markets [and] subjects that interest me — that includes ocean exploration and my family. It's an eclectic mix.

It's pretty intense and it goes probably 'til I have dinner at [around] 7 p.m.

Then I go with the flow. I'll go do walks. I might go kayak or go on a bike. I need to be in nature. I like to be near the water.

[I usually go to bed] around 11 p.m.

But it changes depending on the circumstances. I have no routines.

On his next chapter: 'There's a joy to being free of obligations'

There's an evolution in one's thinking and preferences at each stage in life.

The natural thing I want is to pass along the things that have been valuable to me to help others. It's a joy to see others succeed. I know that will go on for maybe a year or two more and that will end because I will have passed along whatever I think is of value.

There's a joy to being free of obligations.

I'm also very excited because it gives me the freedom to pursue all my passions. Of course, my passions were and always are the markets. I love the markets, but I don't have to manage anymore.

On the biggest misconception about him: I'm 'mean or tough'

I think that I do tough love. Some people find that difficult. Some people wouldn't have it any other way.

There's a culture of meaningful work and meaningful relationships through radical truthfulness and radical transparency and that's not for everyone.

Some people probably look at that and think that I'm mean or tough. Other people probably look at that and find me very loving and different. But I don't really know, I'm just guessing.

On mistakes: If you haven't been successful at something 3 times, 'don't assume you know how to do it'

I thought it would take about two or three years but the transition [out of the role of CEO at Bridgewater] took over the 10 years. Mistakes [were made] in hiring the wrong people [for] jobs that didn't work out.

But I'm very much a fail fast and fail forward type of person.

On the other hand, I have a principle: "If you haven't done something at least three times successfully, don't assume you know how to do it successfully." So, I assumed I wouldn't know how to do it.

I didn't know how to do it for a while and then I learned through my mistakes, the way I normally do, through trial and error, and I learned to get the best advice I could from other people.

On what keeps him up at night: 'The world is becoming a tougher place'

I worry about the U.S.'s declining education, its rising wealth, the resulting irreconcilable internal conflicts and its unsound finances. 

By unsound finances I mean the government creating a lot of debt to finance the spending and monetizing the debt through the printing of money to stimulate the economy that will raise inflation and weaken the dollar. 

I worry that these things are happening when China is becoming comparably strong. [China] is a rising great power that is challenging the leading world power and its world order.

Those conditions look quite like those in the 1930 to 1945 period. In my study of history, I saw this happening repeatedly.  

The world is becoming a tougher place.

The polarity that exists gives people very different lives. For example, if you're in the new technology, venture capital-type world that is flooded with money, things are now fabulous. But if you're in a poor neighborhood, with poor education, things are terrible.

My wife works on trying to help high school students in poor neighborhoods [in Connecticut].  We can see the cycles of poverty, poor parenting, inadequately funded education, unemployable adults, crime and political fighting.

On growing up: 'I really believed I could do anything'

Since I was a kid, I really believed that I could do anything. It was just a matter of testing my character and creativity.

Then, when I discovered that I could also get the best thinking from other people [and] be radically open-minded and take it in, I realized that [anything] was possible.

I also don't mind getting banged around a bit. In other words, if I'm going after something and I get knocked down, I've learned to appreciate that.

On what excites him the most: 'The innovation and bubbling up of ideas'

[NFTs] are a great, interesting concept that I have no idea whether it will work or not. But what I find exciting is the freshness, the innovation [and] the bubbling up of ideas.

It is the same thing from a Steve Jobs and a Bill Gates and an Elon Musk. Just the idea of being able to be an innovative revolutionary and take your ideas [and] make them into realities.

That's happening all over the world. There's a political pressure to put up walls [and] be nationalistic. But if you look at people from all different countries interacting to [innovate], that is really uniquely exciting.

I think, in the end, those who have the best international efforts and exchanges will probably win out.

This interview has been edited for length and clarity.

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