By Katy Steinmetz
October 31, 2014

On Nov. 2, Nik Wallenda will try to outdo the feats that seven generations of his daredevil family have done: the scion of the Flying Wallendas will walk a tightrope across the Chicago skyline, up an incline for half of the stunt and wearing a blindfold for the other.

This is the Discovery Channel’s latest bid to capture the world’s attention with live broadcasts of life-or-death events (like April’s planned ascent and wing-suit jump off Mount Everest that was derailed by a tragic avalanche). And this is Wallenda’s follow-up to dramatic tightrope crossings over Niagara Falls and the Grand Canyon in recent years. Doing something ever-more daring, he says, is the way to be successful in the daredevilry business.

Wallenda will start his walk on a wire 588 feet above the Chicago River. First, he’ll traverse an incline the length of about two city blocks from one skyscraper to another, ending at a height of 671 feet—making it the highest balancing act in his family’s history and his steepest walk ever. From the second skyscraper, Wallenda will don a blindfold and walk a level wire 543 feet above the ground to his third and final pillar of safety.

TIME spoke with Wallenda about why he chose Chicago, what makes him risk his life and what he hopes viewers get out of watching him on TV or Discovery’s live stream.

TIME: Growing up in the Wallenda family, did you feel you had a choice about whether to join the act?

Wallenda: I actually felt like my parents did everything they could to get me out of the business. In fact, I know they did. I was going to study to become a pediatrician, because the business had struggled financially and my parents were having trouble making ends meet. And they wanted me to have nothing to do with it.

Why did you decide to do it anyway?

I started at such a young age. My uncle called me when I was getting ready to go away to college and asked if I wanted to be part of recreating the seven-person pyramid in Detroit, Mich. And I talked my parents into allowing me to do it, and when I got there, I realized there was an amazing opportunity. We just needed to change the direction of our business and we could be successful in it. I had struggled with going to college because I had so much passion for what I did, performing. I started walking a wire when I was 2. So that was really a turning point, the revelation that we just needed to change our business model.

Is that business model now centered on record-breaking?

It’s centered on continuing to keep the name in the spotlight. My great-grandfather did an incredible job of that, creating the seven-person pyramid and doing many amazing walks around the world. And continuing to keep his name in the spotlight. Really, that’s what it was about, never being complacent but continuing to push on and move forward.

And how will this feat be pushing yourself in a new way than all the feats you’ve done before?

In two ways. One is I’ve never walked up an inclined cable. I’ll be walking up a 15-degree incline for this event, which is extremely strenuous. It changes your center of gravity and how you balance and everything in that sense. In the second portion, doing it blindfolded, which is something I didn’t even realize was possible until a few years back when I started training, taking away that most important sense, which is vision as a wire-walker. It is definitely the most challenging walk I’ve ever done.

Once you have that blindfold on, how do you mentally and physically change your approach to staying on the wire?

Mentally, it’s the biggest challenge of all. I’ve done this so long, muscle memory sets in. That’s why I can do it. But mentally, overcoming those fears is my biggest challenge in life, for sure. Putting myself in a place of confidence, knowing that I can do it. Training in really tough conditions makes me confident that I’ll be able to do it over the city of Chicago.

Why did you choose Chicago, rather than, say, New York or San Francisco?

All of those are on my radar, for sure. Chicago’s something I’ve worked on for a while. My sister lived there for 13 or 14 years. I spent a lot of time in that city. I was absolutely attracted to the name the title the “Windy City.” And it worked out where Chicago was able to give us approval. We were able to get the buildings to approve and all of that. So that’s why Chicago’s next. I’m working on many more.

When you’re getting these approvals, whether it’s the mayor of the city or the owner of a building, what are their hesitations?

For the most part, there’s not a lot of hesitation. Of course they’re all worried about my safety. But I think I have an amazing track record of eight world records, as well as walking over Niagara Falls and the Grand Canyon. And of course that builds confidence in them. In the end, the media attention from around the world is only positive for the city. This special will air live in over 220 countries around the world. The visitors’ bureau can’t afford a commercial like that, for two hours long. I don’t think anyone in this world can afford to pay for a commercial like that. So it’s definitely great for them, just like it was for Niagara Falls … Of course, as a building owner, they’re concerned with liability. What if something happens? And really more than anything concerned about the safety of their building, which is where [all the] engineers come in.

As you said in the beginning, they’re concerned about your safety. Is there a scenario in which you fall and it’s not a good commercial for them?

I don’t know. You look at NASCAR, and people dying on occasion, and it doesn’t hurt their sport. That’s for sure. They still have every endorsee you could ever imagine. I don’t know for sure if it would be good or bad. My great-grandfather lost his life in Puerto Rico. And it surely didn’t hurt tourism in Puerto Rico. Would you say I’m never going to go to Chicago because Nik Wallenda fell there? I don’t think you would. So no, I don’t think it is a bad for them. Of course, I’m all about staying on top of that wire.

Obviously the commercial value is not the important factor if that terrible outcome happens. As much as you can imagine what you might be thinking if you did fall, would you have any regrets?

I don’t think so. I’ve lived an amazing life, and continue to live every day like it’s my last. And I think everybody should live that way. Of course, some of my training is about staying on that wire, and catching that wire, and holding on for 20 minutes. I’ve got redundant rescue plans within 90 seconds. It’s not as though I get up there carelessly. There’s a lot more science and engineering that goes into it than you could ever imagine.

Why do you want to do this and what do hope people get out of watching it?

Everything I do I hope inspires–actually, I know inspires many people. Maybe not all of them. But I hope to inspire people to continue to push themselves to become better at what they do. This walk is all about continuing to push myself to not become complacent but continue to work harder, move forward and become better at what I do. And I hope to inspire people that no matter what their challenges are, if they’re willing to work hard enough, they’ll be able to accomplish whatever their dreams are in life. Mine just happens to be a little more unique than most.

Is there an element of this, like soldiers going back into battle or thrill-seekers, that you just can’t live without, an energy from performing daredevil feats like this?

I’m not your average daredevil. I’m definitely not an adrenaline junkie. I certainly love my wife and my three kids more than anything in life. And if they asked me to stop tomorrow, I would. If they asked me not to do the Chicago walk today, I would not do it. So that’s not my life. My family’s done this for over 200 years. I’ve done it since before I was born. My mom was six months pregnant with me on the wire. I’ve walked the wire my whole life. And it may be hard to comprehend, but this is life to me. It’s not an occupation. It is not a job. Very seldom in my career do I get a rush out of what I do. It’s about the love and passion for what I do.

Write to Katy Steinmetz at katy.steinmetz@time.com.

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