Career Lessons from the Appalachian Trail with Curt Smith, Ep #21

In this episode of Tech Talent Today, I’m delighted to be joined by Curt Smith, a Senior Technology Executive with over 25 years of experience. Curt was the Chief Technology Officer at E-Trade for over 13 years, SVP Global Technology Operations at InterContinental Hotel Group, and SVP Global Chief Technology at Manulife. He currently runs his own partnership as a trusted and strategic advisor to firms specializing in infrastructure, internet, and cloud. Listen to learn more about his journey!

You will want to hear this episode if you are interested in…

  • Trekking for Trevor [03:27]
  • Career advice on the trail [13:50]
  • The transition from Wall Street to E-Trade [15:57]
  • Journey to C-level [20:29]
  • The changing culture of working locations [30:07]
  • The future of the tech hiring market [36:24]

Trekking for a purpose

Curt is from North Georgia and has visited the mountains in Georgia and North Carolina for years. Back in his E-Trade days, he and a group of friends would have weekend trips where they’d hike for a few days, and on the last night, they’d go to their base camp and play poker all night. All of that was on the Appalachian Trail, which caused Curt to become interested in the history and the idea of a six-month hike through the whole trail. But with his family responsibilities and a job, even if he had six months, there would be something else to utilize his time better.

Midway through the pandemic, Curt had the opportunity to retire from his corporate life. Suddenly, six months didn’t seem like such a long time. His family was settled and supportive of his adventure, so he started preparing mentally to go. The most challenging aspect of such an endeavor is the mental game. He needed to have a purpose.

Curt’s youngest son, Trevor, has special needs. The family has been involved with an organization in Georgia called Families of Children Under Stress (FOCUS). FOCUS helps thousands of families through challenging situations, and Curt has worked with them to help run a golf tournament and raise funds. To have community support, Curt told the organization that he was planning on doing the six-month hike. That’s when he came up with the idea of Trekking for Trevor. The trek would become a fundraiser for the organization that has meant so much to Curt’s family.

Career and passion

Along the trail, Curt found himself giving career advice to other trekkers in their 20s and 30s, though he tried to keep it light and not take away from the experience. One woman was a recent computer science graduate. Throughout their conversations, the woman mentioned not wanting to sit in an office all day. Curt’s advice was to find her passion and then match that passion to her skills as a computer scientist.

Curt’s career went through a couple of phases before he was able to match it to his passion. He decided early in his career that he didn’t want to be on the selling side of a business. After having worked in sales, he moved to an advertising agency. But in the late 80s and early 90s, there wasn’t much tech being used. Also, the tech budget would be the first cut if the company lost a customer. That’s when Curt landed at Lehman Brothers on Wall Street. Tech then became mission-critical to stay ahead in the business. Curt did well there for years when he decided to have a family and move from New York. He then had the opportunity to move to E-Trade, which he loved.

Curt’s journey to C-level

Most of Curt’s jobs were just above his skill level. While he had to scrabble, he wasn’t afraid to take risks. Many roles he had the opportunity to take were offered because the other person saw something in him. He found the offers confusing because he didn’t see those things and knew that the position he was offered wasn’t his specialty. When he started at E-Trade, his role was in operations. He quickly picked up engineering. Then slowly, architecture was layered on top of that. Then he learned quality assurance and data warehousing. Eventually, one of his coworkers asked his boss why Curt wasn’t the CTO.

Through that process, Curt didn’t aspire to be CTO, but he enjoyed everything he was doing. The opposite can be true as well. If people jump into industries they’re not passionate about, they will become dissatisfied with their work, no matter the title. The notion of having the title will feel good at first, but that wears off quickly. People need to figure out what makes them tick and makes work enjoyable. If the only reason to take a job is money, then it might be best to skip it and find a better match of career and passion.

Resources & People Mentioned

Connect with Curt Smith

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