FORTUNE — James Barrese grew up in the San Francisco Bay Area, and so it was not unusual — expected, really, given the Silicon Valley stereotype — for him to start teaching himself computer programming. It served him well: He went on to study mechanical engineering at Stanford University and eventually become a programmer for the university.

E-commerce systems were of great interest to Barrese, and he worked on them for large companies and nonprofit organizations alike. His goal? Figure out a way to automate payments. The experience helped him land a position at eBay EBAY , where he built and scaled the company’s core operating system.

Two and half years ago, Barrese moved to eBay’s PayPal subsidiary and became the company’s chief technology officer. The role, he says, is a way to help people around the world participate in e-commerce and earn money in a global market.

Barrese, 45, spoke with Fortune.

1. Who in technology do you admire most? Why?

I really admire Larry Page and Sergey Brin at Google. Back in the very early days of Google, they set a vision for what they wanted to do, and ever since then, they have been pushing the envelope.

2. Which companies do you admire? Why?

I admire what Apple has accomplished. The craftsmanship, and simple integration of their products, has been groundbreaking for the consumer adoption of technology.

3. Which area of technology excites you most?

I’m really excited with what’s happening in wearables and the “Internet of Things.” The Internet of Things work will be creating breakthroughs and useful innovation in small computing devices. There are some great opportunities with identity and security here.

4. What advice would you give to someone who wants to do what you do?

Always be learning. Try to solve the hardest problems. Never be satisfied with the status quo. Surround yourself with great people.

5. What is the best advice you ever received?

The best advice I ever received is “to become comfortable with the uncomfortable.” Throughout my career, I’ve been thrown into many difficult and ambiguous situations, and there isn’t always a lot of data to help figure out exactly what’s going on. You have to learn how to make hard and tough decisions with the limited data you have, your experience, and your gut.

6. What’s the next big project you want to tackle?

I think the shift to alternative forms of authentication is a really interesting space and has a lot of opportunity. It’s the “death of the password,” and it’s becoming feasible.

7. What challenges are facing your business right now?

What we have is the opportunity to converge and simplify payments and commerce. Through mobile technologies and devices, consumers will have new ways of paying. Looking back through history, first we had barter system, then currencies, and then we developed broader forms of credit. We’re in the middle of another historic shift in the way people pay. Our challenge is in making something relevant, simple, and global.

Many companies recognize the fundamental shift that’s happening and have been working to take advantage of the opportunity. We’ve held this vision for a long time and have been investing in new modes of payment. We’re not worried about competition, but more so about, “How fast can we make this happen?” Whether it’s on mobile, online, or in-store, we’re tackling a new end-to-end payments experience.

8. If you could have done anything differently in your career, what would it have been?

I wish I had learned to speak the language of business a bit earlier in my career. Technology and business both use different vocabularies, but often are saying the same things. It’s phenomenal when you have alignment on a mission and strategy with an entire team charging in the same direction.

9. What was the most important thing you learned in school?

At Stanford, it was emphasized that you’re there “to learn how to learn.” You’re going to be learning your entire life, so you need to figure out how to optimize that skill. Everyone should make lifelong learning a habit.

10. What is one unique or quirky habit that you have?

I’m a gadget freak. I love electronic gadgets. I’m always trying them out. Nine times out of 10, they wind up on the shelf after a couple of weeks. Recently, I tried to improve my posture with a device that straps on to your back and will buzz if you’re sitting improperly. Unfortunately, the first day I tried it I wound up sitting onstage at a company all-hands meeting, and it was buzzing constantly as I was talking. Let’s just say that gadget experiment lasted for just a few hours.

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