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Advice / Succeeding at Work / Getting Ahead

Here’s What Oprah Wants You to Know About Waiting for That One Big Break

Oprah Winfrey delivering a commencement speech at Colorado College on May 19, 2019

Oprah Winfrey is practically synonymous with success. As a media icon, a philanthropist, a billionaire, and a household name who needs no surname, she knows a thing or two about it. And she often shares her wisdom with willing audiences, as she did when she spoke to the graduating class of 2019 at Colorado College on May 19.

“The truth is success is—it’s a process,” she said. “I’m here to tell you that your life isn’t some big break like everybody thinks it is. They’re waiting on the big break. It’s actually about taking one significant life-transforming step at a time,” she explained. “Small steps lead to big accomplishments.”

In other words, every action every day builds on those from yesterday and the day before, and it’s the slow accumulation of actions and choices that carves out paths to success in your life and career, the way a steady stream of water can sculpt a smooth route through even the roughest stone over time.

Winfrey recognized that many of the graduates sitting before her harbored a great deal of anxiety about what those paths could and would look like for them. The same was probably true of some of their parents and siblings and others there to celebrate their commencement, and those watching online anywhere in the world. No matter where they are in their lives and careers, people still get anxious about what their futures hold.

From her perch at the podium and decades into a successful career, Winfrey admitted that the money is “fabulous” and all the attention is “also good sometimes,” but the real reason she believes she now has a beautiful life is neither of those things.

“It’s because I had [an] appreciation for the small steps, the seeds that were planted, the map and flow of my life that unfolded because I was paying attention,” she said. “You have to pay attention to your life because it is speaking to you all the time and the bumps in the road and the failures...pointed me in a new direction and led me to a path made clear. That is what I’m wishing for you today: Your own path made clear.”

That clarity doesn’t come without failure. It’s an inevitable feature of any path toward success—one that not only humbles you, but also teaches you about the fleeting nature of success as it’s traditionally measured. So instead of looking only at objectives achieved and visions manifested to account for your self-esteem, she said, think about how all the steps and actions you take every single day impact the people and the world around you.

Your path isn’t about one decision taken at graduation or any other point. Your career isn’t about one big break. Your purpose “gets revealed to you daily. It is not just one thing. It is the thread that is connecting the dots of everything that you do,” she explains.

Winfrey said that her friend and mentor Maya Angelou impressed upon her that “you have no idea what your legacy will be.” She repeats that idea everywhere—in this case nearly five years after Angelou’s death—because your legacy “[is] not one thing. It’s everything,” she said. “The most important thing is how you touch other people’s lives. Every day you’re carving out the path. Even when it looks like you’re not.”

So don’t get so wrapped up in waiting for the one big break. Instead, consider the choices and actions and obstacles right in front of you. They will define your path and your success and the mark you leave, regardless of the job you do or the field you work in.

Being anxious about uncertainty is normal, to an extent. But “I’m here to tell you that you’re going to be more than okay. So take a deep breath with me right now and repeat this: Everything is always working out for me,” Winfrey said. “That’s my mantra. Make it yours. Everything is always working out for me because it is, and it has, and it will continue to be as you forge and discover your own path.”