Most human beings fantasize about having a big reward: winning a large contract, securing a million-dollar contract or winning a big prize. Others even speculate on what they would do in case they were to become filthy rich overnight or won the lottery jackpot. Would you leave a job? Change your location to a beach town? See the world? Or instead, open up a new business?
Most of us could only imagine such a moment that has been experienced in life by some celebrities. Being surprised, a lot of them did not quit their careers immediately. Now, we will see how certain celebrities dealt with their major wins and what they did for the first time.
1. Oprah Winfrey – Invested in Herself and Others
Oprah may not have been a “winner” in the traditional sense, but her rise was swift once The Oprah Winfrey Show hit the air. She became a media mogul, who was once a local news anchor. Did she give it all up and relax?
Nope.
Oprah tried to double her success instead of quitting. She started her own production business, Harpo studios. She felt she has to have complete ownership to her content and her brand. She also learned to invest in people-she would give away scholarships, construct schools among other things and supporting communities also.
Lesson: Even when you win big, investing in your future can be more rewarding than just walking away.
2. Rihanna – From Pop Star to Businesswoman
Rihanna was among the world most selling artists. She proceeded into the business world instead of just limiting her career to singing only. In 2017, she started Fenty Beauty that turned out to be a massive success. She also left music not because it was forced to but because it was something that did not bring as much thrill and wealth to her.
Not only does Rihanna earn as a billionaire today due to music. Most of her wealth comes from her business ventures.
Lesson: A big win can open new doors. You don’t have to quit—you can pivot.
3. Daniel Radcliffe – Kept Working After ‘Harry Potter’
Daniel Radcliffe became the top famous actor when he played the role of “Harry Potter”. He has gained millions in the series. He could have easily retired in his teen.
However, he did not. Rather, Daniel decided to continue to act in smaller and more demanding roles. He made it to Broadway productions, independent films, and even to comedy series.
When he was interviewed he said he doesn’t want to be a celebrity only because of just one role or movie. He wants to develop and do himself good in other aspects aswell.
Lesson: Passion for your craft can be stronger than a big paycheck.
4. Keanu Reeves – Gave Away Millions But Stayed Humble
After The Matrix turned into a huge success, Keanu Reeves earned millions. However, instead of being superstar, he simply shared much of his income with the film crew and behind-the-scene employees. He also did not quit acting. He continued to accept new roles and put extra efforts.
Keanu is still living a modest lifestyle despite his abundant wealth. He uses subway to work, gives a lot to charity, and continues to do what he likes.
Lesson: Winning big doesn’t have to change your core values.
5. Lady Gaga – Used Her Success to Support Causes
Lady Gaga gained popularity along with a rapid success and collected millions through her music. However, she did not just stop there, but instead, she utilized her popularity to make a change. She started up the Born This Way Foundation, which is all about mental health and empowering young people.
She also did not stop acting, singing, and even performing, giving the support to the causes close to her heart.
Lesson: You can use your big win as a platform to help others.
6. Jay-Z – Turned Music into an Empire
Jay-Z became a businessman worth a billion dollars. He did not stop once his music career became successful. Rather, he launched his clothing brands, tech investments, even joining as a part-owner of a basketball team.
He kept working, not because he had to, but because he wanted to build something bigger.
Lesson: Winning big can be just the beginning—not the end—of your journey.
So, Should You Quit Your Job?
The above stories indicate that the big win does not necessarily require quitting your job. Actually, Some of the most famous people in the world didn’t slow down at all. They may change direction, slow down, or focus on something new—but they don’t just walk away.
Naturally, the case is unique to each and every one. Having a no-good job, or a dream you always wanted to chase, a big win might be your ticket out. But it’s also worth asking:
- What truly makes you happy?
- Is there something else you want to build or create?
- Would quitting now help you grow, or hold you back?
Final Thoughts
Should you ever come into such a situation where you have won big (in this case, it can be due to your talents, or it can be through a business deal or even luck), then it is always acceptable to dream. And there is nothing wrong with continuing doing the job that you love.
Like Oprah, Rihanna, Keanu Reeves and other celebrities, they did not just use their money and run away. They have used their success to expand their wealth, assist others, and venture into a new direction. That is probably the finest sort of win of all.
