Road trip with Oprah Winfrey and friends

I took a little road trip with Oprah Winfrey this weekend and we had some good, deep talks about life.

“You do not get what you want in life,” she told me. “You get what you intend.”

I listened, fascinated, as she told me all about her own journey — how she saw her grandfather’s red brick house when she was a little girl and said, “Some day I am going to live in a brick house.”; how she counted six trees in the front yard of a colleague she considered successful and vowed that some day she would have a front yard and six trees; how she got all dressed up for her first appearance on the Tonight Show and had to endure the unkind ambush of guest host Joan Rivers, who asked her how she got so fat. “I like food,” she answered gamely, but the question stung; how she built an abiding friendship with Gayle King because each was genuinely happy for the other’s success; how she never missed a single show — and she taped 4,561 of them — because she valued all of us. “Because you were showing up, I showed up,” she said.

Like all good road trips, ours included some revelations. I learned, for instance, that I needed to find some time in my day to focus. Just that. I need to figure out what I’m aiming for, then head that way.

I really enjoyed our time together, as did the other 17,999 people who also joined the conversation Saturday at the Xcel Energy Center in Saint Paul. Oprah has a rare ability to connect with people on a personal level even in a room that big and full of fans all pumped up because they had not seen her in years.

I think we all felt like we were sitting on her gorgeous front porch at her home in Santa Barbara (where she said she encourages all her guests to dance after they toss back a tequila shot. We danced too, along with another guest, Julianne Hough, and that was fun and inspiring.)

That is Ms. Winfrey’s gift. With her wit, genuine interest and sage advice, she seems like she is talking directly to you.

I listened. I filled out my workbook and made plans to find my focus. Encouraged by her guest Jesse Israel, author of the Big Quiet, I set a timer on my phone to practice five minutes of meditation every day.

I paid attention when Suzy Orman told me to live below my means but within my needs, and I appreciated Angela Manuel Davis’ call to take the gift of today.

Then, we all sat down with Tina Fey, who made us laugh and think, because she had mastered the art of “making comedy without hurting anyone” and I felt like I had made another friend (albeit one who had already achieved all her career goals and was currently enjoying her hiatus).

Oprah’s 2020 Vision Tour continues this weekend in Charlotte and will land in Atlanta, Brooklyn, Dallas, San Francisco, Los Angeles and Denver in the coming weeks.

I highly recommend you take advantage of this life affirming opportunity to catch up with an influential friend.

My sister Jenny, pictured here on Oprah’s left, is executive producing this tour. As I’ve written about before, Jenny is an Emmy-winning producer who has worked for Oprah for 25 years. Pictured on Oprah’s right is our mom Peggy, who saw the show when it opened in Fort Lauderdale. My mom was thrilled and impressed to see her daughter in action. “They call Jenny a unicorn,” she told me. “You have to see her. She’s amazing.”
I did see her the following week in Minnesota, along with her godson Vinnie and his new bride Danni (and my friend Jill) and I have to agree with my mom that our Jenny is amazing.
So generous was Oprah in her presentation that she shared actual journal entries with us.
She also shared her friends and we all got to dance with Julianne Hough.
And chat with Tina Fey.
Oprah and Tina share a love of Mary Tyler Moore and it was fun to see them reenact the famous hat toss.
These two ladies were so intent on seeing their idol that, when they found themselves locked out of their hotel room early Saturday morning after slipping down to the lobby for coffee, they showed up anyway, all jammied up and wearing blankets against the below zero Minnesota chill. I love that.
It was really nice to catch up with my old friend.