How This Southwest Airlines Exec Views “Scary Meetings” At Work

In Bustle’s Quick Question, we ask women leaders all about career advice, from the best guidance they’ve ever gotten to what they’re still figuring out. Here, Sabrina Callahan, Southwest Airlines’ senior vice president and chief digital and marketing officer, talks about her career journey and what she’s excited to bring to the skies.

Sabrina Callahan grew up in Iola, a small Kansas town of just 5,000 people. Fast forward to today, and she’s leading digital strategy at one of America’s largest airlines — but getting there meant taking risks and learning how to say “yes” to everything.

After studying journalism and public relations at the University of Kansas, Callahan landed in Dallas, Texas in 2010 where she began her career in marketing. She got her start at Hilton and then moved on to roles at Walmart and AT&T. She quickly learned that each time a new company came knocking, even if she wasn’t jazzed about leaving her current role, pivoting and staying open to new opportunities always served her well.

As she made moves, one company stayed in the back of her mind throughout the years: Southwest Airlines. “For anyone who's ever studied brands, or marketing, or culture, Southwest is a dream job,” she tells Bustle.

The airline is known for its friendly atmosphere, funny flight attendants, and, of course, those colorful airplanes. Now, 90 days into her new role as chief digital and marketing officer, Callahan is excited to carry the torch. “We’re looking at what makes Southwest fun and dialing that up,” she says. “There’s so much that customers and employees hope to see from us, and we want to deliver.”

Callahan is looking forward to flexing her creative muscles. “At Southwest, there’s no such thing as a crazy idea,” she says.

Below, Callahan talks about her morning podcast ritual, the cleaning routine that centers her, and her view on multitasking.

Walk me through your morning routine.

On an ideal day, I get up at 6 a.m. and get some type of workout in. Sometimes I’ll do a Peloton ride — just something to clear my head. I enjoy the quiet, because I don’t get a lot of it. I wake up my three kids and then it’s coffee, shower, and I get to the office by 8:20. I’ll listen to a podcast on the way.

Which podcasts do you like?

Every single day I listen to The Best One Yet, because it gives you the top three business trends to know about. Then I’ll hit up On with Kara Swisher and The Pivot. If I have a big meeting, I’ll do Smartless, Good Hang, or Call Her Daddy — anything lighthearted that gives me a break from business.

Do you get nervous before big meetings?

The further I’ve gone in my career, the fewer “scary meetings” I have. There are important ones with a lot riding on the alignment in the room, but I go in prepared. By the time I walk into a room, I’ve done the heavy lifting and the meeting is the final bow.

How do you cope with work-related stress?

I let it all out with a workout or cleaning. If there's a day where my husband sees me on the Peloton for an hour and then I'm running around cleaning, he’ll ask, "Are you OK?" And I’ll be like, "I don't know. You've got to give me at least an hour." Cleaning gives me back a sense of control.

What’s the best career advice you’ve ever heard?

I once heard someone say that work can feel a lot like juggling 30 glass balls. The busier the day, the more balls you have in the air. You can’t catch all 30 before they hit the ground — but you can likely snag two or three. Every morning, I identify which three I want to catch. It reminds me to do important things really well, and I forgive myself for the rest.

What’s one of your glass balls today?

Making it to my daughter’s last volleyball game of the season tonight. It doesn’t matter who comes into the office or what happens, I will make it to that game.

I have to know, where do you love to travel?

I got married in Breckenridge, Colorado, so I love going back there to the mountains. I obviously love flying back to Kansas to see my family, too. And I’m excited to try Cabo, Cancun, and our newest destination, St. Thomas.

This interview has been edited and condensed for clarity.