Young Upstarts

All about entrepreneurship, intrapreneurship, ideas, innovation, and small business.

Why You Should Talk To People

by Jessica Ekstrom, founder and CEO of Headbands of Hope


When I was little, I would get embarrassed because my mom talked to everyone. We’d be standing in line at the grocery store and she’d ask the woman in front of us what kind of peanut butter she’s buying, why she’s buying it and if my mom should switch her peanut butter. Somehow, their conversation in peanut butter would change into what their life’s ambitions are and what their horoscope said that month and how it made them feel. By this time, they’re standing outside with their grocery carts swapping numbers for a coffee date.

Meanwhile, I was waiting ever-so-patiently for the Skittles in the bag my mom promised me.

My mom is never afraid to talk to anyone and has zero concern for what his or her status is. Whether she’s talking to the President of the United States or the mailman, she’s the same person.

Over the years, I became less annoyed by this trait of hers and more admirable of it. The real turning point was when I was interning in Disney World as a photographer. I’d be standing and waving to people all day and it was always so refreshing to have a guest or a family talk to me. People would ask me about my life, my job, my favorite ride, which characters I liked or what they should get for lunch.

I’d always try to do something special for the people that took the time to talk to me. I’d give them fast passes, free stickers, or edit special effects into their photos. You know, stuff that people only dream about.

From then on, I started talking to people. Not really in hopes that I’d get a free sticker, but just because I remembered how good it felt for a random person to even care in the slightest about me. I’d tell the cashier at CVS I thought her earrings were pretty. I’d ask the man working the tollbooth if he was having a good day. I’d ask my cab driver what his craziest cab story is.

One time I told our waitress I thought she was wonderful (she really was) and then she brought me out a free shot of whisky. Even though I’d rather drink gasoline than whisky, it was still a nice gesture.

Another time I was flying out of LaGuardia airport and talking to the guy who was checking by bag. Before I left for my gate he handed me his card and said if I’m ever flying out of LaGuardia and running late or my flight is cancelled, give him a call and he’ll get me where I need to be.

I’m not saying you should talk to people because they might give you a free shot or help you with your flight, but you never know if someone can help you if you don’t speak up and start the conversation. Networking events and social gatherings can be super cliquey. You stick with the people you know and catch up on things you’ve already talked about. Everyone lists off how interesting they are and then you try to reciprocate.

Although it might be uncomfortable, try to get in a conversation with people you don’t know. Even though they might look like they’re all unified, they’re secretly eager for someone fresh to enter the conversation. And if you find yourself in a group chat and you see someone standing by who isn’t involved in a conversation, invite that person into the conversation by asking his or her opinion on the topic you’re discussing.

Everyone has something to share, but it’s up to you to start the conversation.



Jessica Ekstrom is founder and CEO of Headbands of Hope, a socially-responsible, American-made, colorful headwear line. For every headband purchased one is given to a child with cancer and $1 is donated to the St. Baldrick’s Foundation to fund much needed childhood cancer research.




This is an article contributed to Young Upstarts and published or republished here with permission. All rights of this work belong to the authors named in the article above.

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