20 People Who Got To Live Their Dream Life

19. Matthew Berry

For most of his career, Matthew Berry was a Hollywood screenwriter on TV shows like “Married With Children”. Even though a lot of people would consider that to be a dream life, he hated it, and spent a lot of his free time playing fantasy football on a website he created. At 35 years old, he decided to make his passion project into his new career. Through his TV connections, he contacted a producer from ESPN, and that agreed to let him run a fantasy sports league section for their website. Now, he gets to have full as a full-time job.

18. Brock Pierce

Brock Pierce was a child actor best known for his role in the Disney movie The Mighty Ducks. As an adult, he started to learn about Bitcoin, and became an early investor in cryptocurrency. Because of his forward thinking, he was able to become a multi-millionaire. Now, he has a vision of how blockchain is going to change the world. He moved to Puerto Rico to try to help revive the island after being devastated by a hurricane. He also wants to make it a new cryptocurrency tax haven. Almost every day, new people are moving to Puerto Rico to help him live his dream.

17. Brian Kelly

As a young man, Brian Kelly and his dad were into a hobby of collecting airline miles and calculating how they could get the best deals on flights. He went to college and got a job working on Wallstreet, but he did not enjoy it very much. As an adult, Brian started a website called “The Points Guy”, and made sure to keep up with blog posts every single day. He started out charging clients a $50 service fee to help them get the best deal on a trip using their airline miles. As time went on, he started making money from credit card referral bonuses and ad revenue. Today, he has several employees, and he gets to travel around the world in first-class accommodations for free.

16. Richard Branson

As a young man, Richard Branson loved taking international flights, and he even bragged about joining “the mile high club” as a teenager. When he grew up, he established Virgin Records in the 1970’s and signed some of the most famous rock bands in history, like The Rolling Stones and The Sex Pistols. When he started making a lot of money in the music business, he took some of his earnings to establish Virgin Airlines in the 1980’s. He has five different companies that are valued at over a billion dollars, so his life is mostly working on his passion projects and traveling the world. He even plans to go into space with his newest project, Virgin Galactic.

15. Adam Savage

You may recognize Adam Savage from the TV show “Mythbusters”, and anyone who has seen any episode of the series knows just how much he genuinely loves his job. Getting to test out crazy things for a living is already fun enough, but in his spare time, Adam Savage is also apart of a YouTube channel called Tested, where he gets to build his dream movie props and costumes in his massive workshop in San Francisco. He enjoys making elaborate costumes and visiting fans in disguise.

14. Georgia Hardstark and Karen Kilgariff

As the hosts of the “My Favorite Murder” podcast, Georgia Hardstark and Karen Kilgariff are constantly in awe that they get to do the thing they love for a living, which is to tell stories to each other about true crime while hanging out with cats. They are so popular, they get to tour around the world and tell their stories live in front of thousands of people.

To someone who has never heard of this show before, it might sound pretty morbid, but in reality, it’s very funny, and it also educates and empowers women to be strong and protect themselves. Women have written in to say that the tips on safety have actually saved their lives, and police officers write in to say that the stories helped them solve crimes.

Georgia is a former hostess of a Food Network TV series, and Karen is a standup comedian and screenwriter. Both women were working and living in Los Angeles, and they met each other at a party. They were both just going from gig to gig, until they decided to sit down and make a show together. Now, this is their full-time living, and they make enough to support themselves (and a few employees!) from their podcast alone.

13. Hugh Hefner

As a young man, Hugh Hefner was inspired to change his image after a girl rejected him in High School. He started to dress better, and ask his friends to call him “Hef”. He joined the army, and began working in journalism afterwards. He realized that men’s magazines were a lot of outdoor and adventure topics, but that men really wanted to see more pinup. With a $1,000 loan from his mom, Hugh Hefner started the Playboy magazine, and he eventually ended up making a TV series, as well. As time went on, the brand became more and more popular, and Playboy clubs opened up in Las Vegas and Atlantic City. He could eventually afford a mansion where gorgeous models lived with him full-time. He was said to be one of the most envied men in the world. During an interview with The New York Times, Hugh Hefner said, “I am the luckiest cat in the world, and I know it.”

12. Bob Ross

As a young man, Bob Ross worked as a carpenter and joined the air force. All his life, he had to experience being surrounded by a lot of macho energy, and he had commanding officers screaming at him all the time. He rose to the rank of sergeant, and had to become the person yelling at lower-ranking officers. Bob Ross swore to himself that one day, he was going to live a much calmer life that was not so high-strung. The air force base was stationed in Alaska, and he thought the mountains were so beautiful, he decided to learn how to paint landscapes in his spare time. However, he only had 30-minute breaks, so he had to teach himself to complete a painting within that amount of time.

Even after moving back to his home town in Florida, he still painted the snowy mountains of Alaska, and he continued to finish an entire painting at record speeds of 30 minutes each.

After meeting his mentor, William Alexander, Bob Ross decided that he wanted to pursue painting on TV. He retired from his military career in order to pursue art full-time, so he was very short on money. He decided he might save money on haircuts by getting a perm and giving himself an afro, which is how he got his unique look. Bob Ross filled in for one episode of William Alexander’s TV show. An artist and producer named Annette Kowalski came to visit Alexander, and when she heard he was not on set that day, she was disappointed at first. But when she watched Bob Ross paint and talk in such a soothing voice, she found herself mesmerized by him, and knew that other people would love him, too. From then on, Bob Ross got to live his dream life by painting “happy little trees” and getting paid for it.

11. Louis Cole aka “FunForLouis”

As a young man, Louis Cole was a Christian youth outreach worker, and he also worked for Sky TV. He decided to give that all up and start traveling around in a school bus. As time went on, he started posting videos on YouTube about eating gross things called “FoodForLouis”, which helped him earn some popularity online. As time went on, though, he focused on travel vlogs, instead. Now, he produces full-length films of his adventures, and essentially gets to travel the globe as a job. He has recently expanded his brand to multiple businesses under the umbrella of the “Live the Adventure” brand, which includes unique experience AirBnB rentals, travel tours, and more.

10. Steve Irwin

When he was still alive, Steve Irwin’s happiness about being around animals all day, every day was easy to see through the screen. He had a real passion for wildlife, and his infectious love for animals helped to spread that appreciation all over the world. He grew up in his parent’s wildlife park, which is probably why he felt such a deep bond with animals, like they were part of his family. He ultimately died by being stung by a stingray, but that has not stopped his daughter, Bindi, from having the same passion that her father had.

9. Neil deGrasse Tyson

There are few people in the world who seem to love talking about science as much as Neil deGrasse Tyson. Tyson grew up in New York City, and he studied at Harvard, Columbia, and Princeton. He began working at the Hayden Planetarium, where he explained the universe to students and guests with a huge amount of excitement. He also has the special gift of taking a very complicated subject and explaining it in a way that normal people can understand. He was one of the scientists who declared that Pluto should be classified as a “dwarf planet”, so we have him to thank for giving the little guy the boot. Today, he is best known as being the new host of the TV series called COSMOS.

8. Hayao Miyazaki

Growing up, Hayao Miyazaki’s father was the designer and owner of Miyazaki Airlines. So he was surrounded by airplanes, and his dad was always sketching them. This inspired Hayao’s love of drawing, but while he was great at drawing planes just like his dad, he focused on drawing anime characters, instead. He got a degree in economics, but ended up in a very unrelated job at Toei Animation as an artist.

His first manga (comic) that he published on his own was called Nausicaä of the Valley of the Wind, which became his first full-length movie. It was so successful, it lead to opening his own animation company called Studio Ghibli. They made some world-wide hits like Spirited Away, Kiki’s Delivery Service, and Howl’s Moving Castle.

Making a movie is very hard work, and it often requires living on very little sleep. Miyazaki has retired from directing films more than once, claiming that he will never go back to the job again. However, after taking some time off, he goes back to making movies, because deep down, he just loves it that much.

7. Erik Salitan

Erik Salitan is one of the stars of the National Geographic TV series “Life Below Zero”, and he is the perfect example that one person’s dream might be another person’s nightmare.

When he was 18 years old, he moved to Alaska to attend college. He wanted to be near the arctic circle, because he loved hunting, fishing, and the outdoors. It was his dream to be a wilderness man and live off of the land. He got married, and had children at a young age. When he became famous for his TV show, he used some of that money to help make investments in the small businesses around his town. Just like generations of men hundreds of years ago, Erik Salitan supports his family through subsistence hunting. “There is no other true wilderness left than right here, in the heart of Alaska”.

6. Tyra Banks

Tyra Banks became a professional model when she was just 15 years old, and she became the first African American woman to appear on the cover of GQ and Sports Illustrated. For years, she was a Victoria’s Secret “angel” model, but she also branched out with an acting career.

Unlike other models, Tyra refused to let her modeling define the rest of her career. Even as she got older, she branched out to create her own businesses, and was the host of America’s Next Top Model and her talk show called “Tyra”.

5. Guy Fieri

For years, Guy Fieri was an unknown restaurant owner in California. He auditioned to be on a TV series called “The Next Food Network Star”, and the audience loved his personality. Now, he gets to go around the country eating food, saying silly catchphrases, and meeting new people on a daily basis. He has published several cook books, appeared on multiple TV shows, and he has a chain of restaurants.

4. John Tarrow

Fiction writer John Tarrow grew up in London dreaming of living in a castle or a stately home in the English countryside. But just like most people, he could only afford to buy a 3-bedroom semi-detached house (we call those a “duplex” in the US). Even though his house looks relatively normal from the outside, he was able to transform the interior to look like you have stepped back in time, with each room having a different theme. His house is called “Talliston”, and he has even gone as far as to write a fantasy series inspired by his house. (Or maybe it’s the other way around?)

3. Riley Whitelum and Elayna Carausu

In his 20’s, Australian-born Riley Whitelum worked on an oil barge, and saved up the vast majority of his paychecks with plans to use it to buy a house some day. He broke his neck while he was on the job, and spent months laying in a hospital bed. He was very lucky that he was not paralyzed, but he still questioned why he was living his life slaving away at work and ultimately not living the life he truly wanted. This near-death experience inspired him to use his nest egg to buy a yacht that he called “La Vagabonde”.

Riley sailed to Greece, where he met a fellow Australian, Elayna Carausu. She was already living a dream life as a scuba instructor and musician. The two fell in love and started sailing around the world together. Elayna started a YouTube channel called “Sailing La Vagabonde”, and audiences around the world in the “boat life” community loved watching them live out their dream. They now make a full-time living online from their yacht.

2. Kylie Jenner

As the daughter of Bruce and Kris Jenner, Kylie Jenner grew up in the spotlight on the reality series Keeping Up With The Kardashians. As she grew older, Kylie branched out to work on her own passion project by starting a makeup company called Kylie Cosmetics. She also has her own clothing brand together with her sister called Kendall & Kylie that is sold in PacSun and TopShop. She is now the youngest female billionaire in history, and she recently gave birth to her first daughter, Stormi, so now she is a busy mom who gets to “have it all”.

1. Gordon Ramsay

Born in Scotland, Gordon Ramsay was actually a professional soccer player when he was only 15 years old. In 1985, he injured his knee, and his sports career was over. He went to college to earn a degree in hotel management and also became a professional chef. His restaurant was so successful, he earned three Michelin stars in the 1990’s.

In the 2000’s, he ended up going on TV with reality series like Hotel Hell, MasterChef, Hell’s Kitchen, and Boiling Point. He moved to the United States to film American versions of his most popular series, and he is known all over the world. He is known for his tough love, but at the end of the day, he is having the time of his life helping aspiring chefs and hotel owners find success in their businesses.