Part-Time Webpreneur

I was privileged to be part of the Harvard Class of 2013 graduation ceremony yesterday where Oprah was the featured keynote speaker.

She stole the show during the morning commencement exercises. Nearly every single faculty Dean wanted to hug her after presenting their candidates for degrees.

It was hilarious.

Her keynote speech was phenomenal. She was very humble and personable (isn’t she always?) and you got the sense that she connected at a very intimate level with the audience.

You can watch her full speech in this video (around 30 minutes long), but I’ve summarized three powerful lessons that I took away from her speech below.

1) You will Fail

Every successful entrepreneur I know of has spoken about the power of failure, and Oprah didn’t skip on that topic:

It doesn’t matter how far you might rise, at some point you are bound to stumble.

You will at some point, fall. And when you do, I want you to know this. Remember this: there is no such thing as failure. Failure is just life trying to move us in another direction.

And here’s what she suggests you do about it:

When you’re down in the hole, when that moment comes, it’s really okay to feel bad for a little while.

Give yourself time to mourn what you think you may have lost, but then, here’s the key: Learn from every mistake, because every experience encounter, and particularly your mistakes, are there to teach you and force you into being more of who you are.

And then, figure out, what is the next right move.

So basically, what she’s saying is: you’re going to fail. And when you do, you can feel bad about it, but then learn from it and move on.

2) We are all Insecure

Oprah didn’t use the word “insecure” in her speech, but this was the word that kept popping in my head when she was talking about the main takeaway from every single one of her 35,000 (!) interviews she’s conducted:

The common denominator that I found in every single interview is [that] we want to be validated. We want to be understood. I’ve done over 35,000 interviews in my career, and as soon as that camera shuts off, everyone always turns to me, and inevitably in their own way ask this question: Was that okay?

I heard it from President Bush. I heard it from President Obama. I’ve heard it from heroes and from housewives. I’ve heard it from victims and perpetrators of crimes. I even heard it from Beyonce and all of her “Beyonceness.”

They all want to know one thing:

Was that okay?

Did you hear me?

Do you see me?

Did what I say mean anything to you?

That’s quite powerful. Realizing that even presidents need some sort of validation made me feel a little bit better about any insecurities I have.

3) Just be Yourself

Earlier in her speech, Oprah talked about how she looked up to Barbara Walters when she was young, and how she wanted to be like her.

As a young girl from rural Mississippi, I learned long ago that being myself was much easier than pretending to be Barbara Walters.

Although when I first started, because I had Barbara in my head, I would try to sit like Barbara, talk like Barbara, move like Barbara, and then one night I was on the news, reading the news, and I called Canada “Ka-na-ta,” and that was the end of me being Barbara. I cracked myself up on TV – couldn’t stop laughing, and my real personality came through.

And I figured out: Oh gee, I can be a much better Oprah than I could be a pretend Barbara.

She then goes on to say:

You will find true success and happiness if you have only one goal. There really is only one, and that is this:

To fulfill the highest, most truthful expression of yourself as a human being.

That last lesson actually reminded me of the first takeaway from the 5 regrets of the dying that I stuck over my desk.

So I think I’m giving that some extra weight.

What a speech.