Quick Question

How Carolyn O’Hara Finds The Most Fascinating Stories On The Internet

"It's a joy for me to see our users connect with really smart stories that enrich their lives."

Carolyn O'Hara from Pocket on connecting readers with impactful stories.

In Bustle’s Quick Question, we ask women leaders all about advice — from the best guidance they’ve ever gotten to what they’re still figuring out. Here, Carolyn O’Hara, the senior director of content discovery at social bookmarking service Pocket, talks about shifting her priorities throughout her career and the power of storytelling.

If you asked Carolyn O’Hara where she thought her career might lead after grad school, she wouldn’t have envisioned anything like Pocket, the app that helps you create your own private corner of the internet. Instead of sending links to yourself, Pocket allows you to bookmark the articles, interviews, and recipes that you want to check out later. You can also use it to peruse a list of all the juiciest must-reads from the web — and that’s where O’Hara comes in.

“When you open the app and you're looking for something to read, we want it to be like your smart, well-read friend who has their finger on the pulse but is only going to send you the things that are worth your time,” she tells Bustle. O’Hara honed her ability to find all the best stories throughout her career, which has taken lots of twists and turns. “I cut my teeth on print magazines, online magazines, blogs, and TV news,” she says. “Ten years ago I don’t think I could have imagined that I’d be doing this type of job today, but it feels like just the right fit for me now.”

As the senior director of content discovery, O’Hara works closely with the machine learning and data products teams at Pocket to figure out algorithms as well as the human curation team to land on the perfect reading recommendations. “It's a joy for me to see our users connect with really smart stories that enrich their lives and that they find really helpful and interesting,” she says. “And even when I open my own Pocket and see an array of stories that I want to save, that's a delight.”

Below, O’Hara discusses the top stories of 2022, who she turns to for advice, and the video she saved to watch before her biggest meetings.

As the head of content discovery, you get to see what’s trending and what types of stories people gravitate towards each year. What was big in 2022?

In 2019, our top story was about managing burnout. In 2020 it was all about, "How are we going to get through this pandemic? What the hell is happening?" Last year, 2021, it was all about, "What is this collective sense of ‘blah’ we’re all feeling?” as the pandemic wore on.

What was so interesting about this year is that we’re starting to see this sense of renewal where people are grappling with changing their perspectives and relationships. Now we’re wondering, “How do I manage my time with technology in a healthier, smarter way?” and “How do I deepen my relationships with people?” or “How do I get joy and excitement out of friendships again?”

These are age-old questions, but people have been grappling with them in new ways in 2022. We used to see a ton of articles on hyper-productivity, but not so much anymore. Everyone’s focus has shifted to redefining happiness instead of being productive. It's about more of a genuine, almost existential contentment that people are seeking.

You started your career in magazines and TV. How has that helped you at Pocket?

I think the skill of taking a lot of info in, distilling it, and being able to communicate it through a compelling story is valuable in every single industry. It's something that I use literally every single day and in almost every meeting I'm in.

Speaking of meetings, how do you pump yourself up before a big one?

I always make sure I know my elevator pitch — that one thing I want people to walk away with burned into their brains. I also have a one-minute clip of Beyoncé from Homecoming that I’ve saved in my Pocket. She does this amazing solo dance right after singing an incredible song. The thought I have when I see it is, "If she could do this dance right after coming off of this song, I can do this meeting. This is a no-brainer." No one's going to beat the queen, but that's how I get my confidence up.

On the flip side, how do you turn your brain off at the end of a busy day?

I feel like my brain whirs at a speed that is not probably healthy all the time, so to slow down I’ll watch TV. I’m in the middle of Better Call Saul right now.

I also love reading physical books. The best version of me is when I'm reading a few pages of a book every day. It’s another thing that helps quiet my brain in a way that a walk doesn’t. I love taking walks — they’re where I have some of my best ideas and I try to take one every day. But when I read a book I go into a meditative state.

Is there a go-to person you’ve turned to for advice throughout your career?

I’ve developed this very informal circle of friends and people I've worked for and with over the years that I can turn to for different kinds of advice. That's proved really invaluable. I've been fortunate in that I've developed really great lasting friendships with a lot of those folks, too.

They give me “full self” advice. If I’m asking for advice about my career, I’m actually looking for an answer bigger and more holistic than that. Because they know many facets of me, these folks can help me understand my shifting priorities.

What’s the best piece of career advice you’ve ever received?

Always read the room so that you can tailor your pitches and strategies to your audience. Don't go into rooms prepared for an hour-long presentation when a five-minute elevator pitch is what will capture everyone’s attention. I think that's something that was drilled into me, too, coming up in media where I was writing, editing, and commissioning pieces for a lot of different audiences. You have to understand what people are interested in.

What’s your advice for someone just getting started in their career?

When I lived in London as a grad student I had this teeny photography hobby on the side. I remember walking around my neighborhood one day when I saw a sign that read “Changed Priorities Ahead.” In the UK that just means the traffic is about to change, but I took a picture because it tickled me and I’ve had it framed in my house ever since. It’s become my mantra.

That’s the advice I’d give to people: Be open to change and be curious about that change because good things will come that way. What success looks like to me now is not what it looked like five or 10 years ago, and I don't expect it to look the same today as it will five years from now — and that’s OK.

This interview has been edited and condensed for clarity.