When Oprah Winfrey gives career advice, she gets me to listen. As a master orator, the media executive, former daytime talk show host and self-made billionaire makes a living out of finding divine meaning in mundane questions, like the difference between a job and a calling, or what you would tell your younger self.
For me personally, though, what has encouraged me through redundancy, career disappointment and unreasonable managers is her advice on how to handle challenging career losses that feel overwhelming.
Oprah Winfrey taught me to reframe career setbacks as learning moments
One grim winter, when I was unemployed and worried I was unemployable, I encountered a YouTube clip from Winfrey’s 2014 lecture to Stanford Graduate School of Business students, in which she shared the one piece of career advice she wanted to leave with them.
As soon as I watched it, I was transfixed by her ability to make the career story of failure I had been telling myself into a much bigger story about life:
There is a supreme moment of destiny calling on your life. Your job is to feel that, to hear that, to know that. And sometimes when you’re not listening, you get taken off track. You get in the wrong marriage, the wrong relationship, you take the wrong job, but it’s all leading to the same path. There are no wrong paths. There are none. There is no such thing as failure really, because failure is just that thing trying to move you in another direction. So you get as much from your losses as you do from your victories, because the losses are there to wake you up.
Her speech gave me the permission I needed to put those hard months into wider perspective. Yes, a layoff was a job loss, but it was not a failure in Winfrey’s eyes ― and shouldn’t be in mine, either. Winfrey said that when you understand that losses are there to wake you up, “you don’t allow yourself to be completely thrown by a grade or by a circumstance, because your life is bigger than any one experience.”
That job I hated? Instead of seeing it as a waste of time, I could be kinder to my younger self and see those draining final months as the push I needed to move toward a role that would energise me. The layoff I experienced? It was a necessary reset after overstaying at a comfortable job out of complacency.
Her speech was a reminder to listen to what my body is telling me. When you are not at ease with yourself, Winfrey said, that’s your cue to move in a different direction. It’s an intuition I listen to more now. “I did the best I could with the knowledge I had at the time, and now I’m going to learn from this moment,” I now think to myself, instead of obsessing over should-haves.
Feelings may not always be facts, but they do carry important messages if you regularly wake up in the morning dreading work. That’s a barometer I have used, and you can, too.
Instead of worrying about one big task, ask yourself: What’s the next right move?
Winfrey’s approach to managing challenges is one I apply all the time when I multitask. As part of her career advice on how to get through hard times, Winfrey tells the Stanford students, “The way through the challenge is to get still and ask yourself, What is the next right move? Not thinking about, ‘Ohh, I got all of this to —.’ What is the next right move?”
It’s a helpful question I use to break down large tasks with many moving parts. Whenever there’s a work project that is starting to overwhelm me, I take a breath, go for a walk, talk to a friend, make a cup of tea, bake a dessert —activities that I know force me to interact with the world outside of my head and outside of my phone. Once I’m in that centered space, I give myself permission to not solve the huge task all at once. That allows me to stay on course with a task instead of going off on detours to my anxiety. Then I think about what the next right move is, and the next right move, and proceed more strategically from there.
Watch Winfrey’s whole talk below: