Hunting Discomfort

Success comes when you can embrace fear and anxiety.

Hunting Discomfort

September 2023   minute read

When Sterling Hawkins takes the stage at Atlanta’s Georgia World Congress Center in October, don’t let his calm self-assurance and seemingly effortless conversational manner fool you. In his heart, the keynote speaker addressing attendees at the NACS Show will be a fifth-grade boy about to embarrass himself in front of the whole class. But that’s just how he likes it.

Hawkins, now 41, is at ease with that discomfort. He’s made a career out of not just living with it but seeking and embracing it. In fact, he’s built his business philosophy around the concept of hunting discomfort, like that terror he felt as a 10-year-old.

It all goes back to Harry Houdini. The young Hawkins had prepared what he was sure would be the grand finale for a fifth-grade project. He had a pair of handcuffs as a prop, and the camcorder was running. He had practiced his presentation many times before his big day and was confident about his classmates’ reception of his show. But then he froze. The words would not come.

His soaring enthusiasm collided with fear once he had to perform in front of his peers. This was the moment he met his life partner: discomfort. It would walk hand in hand with him for decades to come, reminding him to feel it but then conquer it. Like any good partnership, his discomfort supports him and pushes him to meet his goals. And that’s exactly what Hawkins wants to share with people. Being uncomfortable is an unconventional tool that will yield incredible results.

Building Momentum

Hawkins rode a roller coaster of successes and setbacks for the next couple of decades. Between starting and selling a tech company, surviving the recession of ’08, finding a love of public speaking (at an event in Singapore) and pausing and pivoting during the pandemic, Hawkins settled into discomfort.

The impetus for his first metamorphosis came about after Hawkins and his father, Gary, found backers for their budding tech company in Silicon Valley. The idea was revolutionary at the time—enable customers to make purchases by placing their finger on a biometric reader.

This was Apple Pay before Apple Pay, and Hawkins had begun to imagine himself as the new Steve Jobs. He was living in a San Francisco penthouse, and a life of private jets and Hollywood parties beckoned. And then the housing market collapsed, the financial backing dried up and bankruptcy followed.

“We hit the valley of despair,” Hawkins explained, the pain still close to the surface. “The next day, I’m moving to my parents’ house.” His girlfriend broke up with him and he felt that his life had become a sad country music song. “It was easily the darkest moment of my life—and it was actually years long.”

The turning point came when he received a mass email about a large conference in Singapore. The thing that scared him most was speaking in public, a fear of everyone seeing him for what he really was—a business failure. The stakes were higher than in fifth grade.

Something told him to confront the fear. He remembered his mother, quoting the poet Robert Frost, telling him, “The way out is through.” Then he found himself typing out a reply proposing that he speak at the conference. Before he could change his mind, he hit Send.

To his surprise, the conference organizers hired him to speak on his business acumen. Hawkins had signed a contract and couldn’t back out. So he spoke at the conference, and he was a hit. He realized two things: He could succeed as a public speaker, and his commitment to speak was stronger than his fear of doing so. Perhaps most importantly of all, the discomfort he had felt had prompted him to do something transformative.

“We live lives, and by extension run our businesses, avoiding, denying and surviving discomfort, and we don’t even know it, because we’ve made these decisions, likely from when we were kids. We go about our day avoiding the things that don’t feel good.” But denying discomfort, he decided, was a way we hold ourselves back.

Hawkins hunts discomfort through adventure sports—ultramarathons, extreme cycling, skydiving, trekking the Sahara, mountain climbing and shark diving. “It’s not like I’m some kind of thrill-seeker or adventure junkie,” he maintained. “I’m doing it because it throws me into that unknown space and builds that discomfort muscle. It helps me grow on the other side of it.”

He now speaks 70 to 80 times a year, which equates to 200 days or more on the road. He’s taken his experience of launching, investing in and growing over 50 companies and built an inspiring message that he delivers on stages across the world.

At the NACS Show in Atlanta, he will outline his compelling five-point #NoMatterWhat system aimed at teaching entrepreneurs and businesspeople how to grow their resilience and drive forward through discomfort to achieve results no matter what obstacles are in their way.

But Hawkins never allows himself to think that his life is all smooth sailing. During the pandemic, his speaking engagements were suddenly canceled en masse.

“Dude, it was a disaster,” he laughed. “You know, having been through that big company crash [in ’08] and having built some real success in the speaking business, it felt like, ‘Oh, my God, it’s happening to me again. No matter what I do, I just can’t win.’ Right?

“I sank into that for a while. For several weeks, I sat on the couch and ordered pizza. It got so bad that the pizza company was checking in on me to see if I was alright.”

Referencing his budding friendship with his local pizza place, he said, “It became this really kind of vulnerable moment where we connected at a human level beyond any business that we were doing together. In part, it was actually that phone call [from the pizza place] that made me think, ‘Wait a minute. I know how to do this. This is just the unknown again.’”

That weekend, he got off the couch and ran 50 miles.

Succeeding No Matter What

Like many in business during the pandemic, he had to adapt to survive and, ultimately, to thrive again. “I retooled what I was talking about because we had to address the pandemic in that moment,” he explained.

“So we built out a whole virtual studio where we could deliver that message in a way that was beautiful, reliable and meaningful. It was still different from in person, but it was the best we could do at that point.”

He also used the pandemic to write that book he’d been meaning to for years while always finding reasons not to. “I was too busy, which is, I think, one of the best excuses, right? Because most people can’t poke holes in that. So when the pandemic happened, I caught myself.”

Hawkins went through a similar process to the Singapore speech, making a commitment by finding a publisher and signing a deal that forced him to deliver. The result was “Hunting Discomfort: How to Get Breakthrough Results in Life and Business No Matter What,” published by Wonderwell last year.

Despite his success, Hawkins remains grounded, often drawing on his family legacy. A particular influence is his grandmother, who died from cancer when he was 13. He remembers how she dealt with knowing she had little time to live.

“She looked into the face of the ultimate unknown—death,” he related. “And she said, ‘I’m going to confront this.’ The doctors offered her some kind of numbing agent, so she wouldn’t really be conscious going through the end.

“And she said ‘No, I’m going to feel it. I’m going to go through the messiness. I’m going to go through the pain, I’m going to go through the fear. And I’m going to look into the eyes of my daughter, my mom, I’m going to look into the eyes of my grandkids. And I’m going to say that I love them in the face of that fear.’ I think to me that that’s courage.”

Hawkins has four nieces under six and lives in Denver in part to be able to spend time with them. “I’m close to my parents and siblings. I spend a good amount of time adventuring. I love traveling. The cities that I’m in, I take a chance not just to give the keynote and spend time with the businesses, but to explore.”

And that fear of public speaking, once his most acute discomfort? “I’ve got a capacity to deal with it now and sit in it,” he said, “and I feel the fear, the embarrassment, whatever it is, and then allow it to pass through me.