Ep. 26: Caroline Page – Taking a Risk for your Dreams

Following your dreams doesn’t come without risks. Like most dream chasers, when Caroline Page decided to go after her dreams, she faced a lot of uncertainty about the future. But she knew it was worth the risk. In her chat with Aimee J., Caroline shares the process of dream-chasing and how – in the end – she found her way to happiness. After spending many years in theater and believing this was the life for her, Caroline faced the reality that entertainment simply wasn’t the lifestyle she wanted. So she set out to chase her dreams and follow the passion she knew in her heart was her purpose.

TWEET: “Every man dies. Not every man really lives.” #Braveheart. Find out more on this episode of #ChasingDreams.

The decision to follow your dreams is the most important one you’ll ever make.

Caroline first faced her life’s passion in high school during a mock trial. It was then that she found the path that would eventually lead her to happiness. Getting there, however, would mean she had to take some risks, face some fears, and fight to find her way. After deciding to pursue entertainment law, she found her way to sports law and discovered her true calling. Her desire to distance herself from the entertainment industry encouraged Caroline to search for a better legal speciality to secure a happier future. Once she found sports law, Caroline knew this was where she belonged.

How did Caroline end up in New York City?

After attending law school in California, most of Caroline’s friends assumed she was planning to take the California state bar exam and practice law there. But Caroline had other plans. LA wasn’t the life for her, so she decided to make her home in New York. After passing the New York state bar, Caroline made a life in New York City with no friends, no job, and not a lot of money. It was worth the risk though, because she knew this would lead her to the life she dreamed of. After doing acting jobs to get by, she was able to land a legal assistant job at CAA Sports, which paved the way for a bright future in sports law.

TWEET: When you find your #passion, go after it with everything you’ve got. On this week’s episode of #ChasingDreams

Why it’s important to keep searching for your dream job.

Even though Caroline liked her job at CAA Sports, she knew there weren’t enough challenges for her. She was ready to practice law as an attorney and leave legal assistant status behind. After a colleague recommended she apply for an opening at NFL Players Association, Caroline was able to secure the job of her dreams. She relocated to Washington, DC and now reaps the fruits of her labor in chasing her dreams all these years. Caroline shares the importance of following your dreams, no matter what, and how taking risks can truly create a life without regret.

Caroline’s belief that anyone can live a life without regret.

Caroline shares her story of risk-taking and following the road less travelled in order to chase her dreams. Even though she faced a lot of uncertainty about the future, she always knew she had to fight to get what she wanted out of life. Caroline shares her favorite movie quote, which is the perfect way to sum up her approach to life. Her inspiring story of perseverance will surely give hope to dream chasers everywhere. Caroline is now living the life of her dreams. She travels, has a career she is passionate about, and is happy. That’s what dream chasing is all about.

TWEET: Chasing dreams means taking risks. Why it’s all worth it on this week’s episode of #ChasingDreams


  • [0:59] Introduction of Caroline Page of the NFL Players Association.
  • [2:22] Discussing Caroline’s background in acting, and how that evolved into a career in sports law.
  • [4:51] How Caroline shifted gears from entertainment law to sports law.
  • [6:36] Why Caroline took the bar exam in New York state rather than California, where she went to law school.
  • [9:24] Caroline discusses her “back-up plan” when she decided to go to New York to take the bar exam.
  • [11:06] The chance Caroline took in going to New York and how she dealt with the transition.
  • [13:26] The path that led to Caroline’s first job as a legal assistant at CAA Sports.
  • [15:07] Caroline’s search for a job and how she narrowed the focus to make sure she found her way into sports law.
  • [17:13] The reaction of friends and family when Caroline shared the risk she was taking by moving to New York.
  • [19:36] Starting the job with CAA.
  • [21:40] Why Caroline decided it was time to move on to a new opportunity.
  • [23:58] How Caroline found the opportunity at NFL Players Association.
  • [29:23] Starting out in DC with a new job at NFLPA.
  • [30:58] How Caroline found her way to happiness by following her dreams.
  • [34:48] Caroline shares her love of travel and how she’s created a life that allows her to travel.
  • [36:28] The most memorable travel experience Caroline has had thus far.
  • [38:14] Caroline’s favorite movie quote and how it has meaning in her life.
  • [39:04] Caroline shares her advice to fellow dream chasers.
  • [40:59] Aimee discusses Caroline’s achievements and how she’s created a life without regret.


If you know in your heart what you want to do, you have to go after it.



NFL Players, Inc.


TWEET: The decision to follow your dreams is the most important one you’ll ever make. #ChasingDreams

TWEET: Creating the life you’ve always dreamed of with Caroline Page. Find out more on #ChasingDreams

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