Twenty years ago I moved to New Zealand knowing exactly no one.

I was fresh out of college, it was 2005, and I'd landed in a country where I had no family, no old classmates, no fallback plan if it didn't work out. What I didn't expect was how many wonderful friends I'd make there. One of them was Richard.

Richard and I ended up at the base of the Auckland Sky Tower together. At the time I think it was the tallest building in the Southern Hemisphere (or that’s how I remember it). We were there for the opportunity to take a 630 foot plunge off the side of a perfectly good building.

I negotiated with the guy at the counter for a discount. He said “No, but…” for the same price, I could jump twice. I am, for the record, genuinely terrified of heights. I am also, apparently, cheaper than I am afraid of heights. So, we jumped twice.

We rode the elevator up, got harnessed in, and walked out onto a plank hanging off the side of the building. The guy helping me was kind but said one of the wildest things to me anyone has ever said: "I'm going to count you down from three. When I say go, just step off the building." I stepped off.

About a hundred feet down, the rope yanked me to a dead stop. No explanation. I was just hanging there, spinning slowly, with no idea why I'd stopped or what happened next. My rotation brought me level with the observation deck, where a crowd of strangers was pressed against the glass, watching a guy in a harness dangling in midair — and taking his picture. I remember feeling so much fear that I was numb.

A few seconds later the rope released and I dropped again, this time all the way to the ground, braking before I touched the Landing Zone.

Turns out there's a countdown clock on that observation deck. The whole thing — the drop, the stop, the second drop — was timed and planned from the start. Someone up there was tracking exactly where I was and when to release me, the entire way down. Nobody told me any of that beforehand. From where I was standing, I'd just fallen off a building and stopped for no reason, in front of an audience.

I don’t remember if Richard or I jumped first, but I do remember riding the elevator back to the top and laughing about our experience. It was my turn again — the second jump I'd talked my way into.

The second time was almost boring by comparison, and I mean that as a compliment. I still felt the fear — that part doesn't go away — but I knew the stop was coming, and I knew why, and I knew it would end fine. So instead of spiraling, I looked around. I actually saw Auckland from up there. When the rope caught me outside the observation deck the second time, I made faces at the crowd — the running man, mock terror, the whole bit — instead of composing what I thought might be my last thoughts. Same rope. Same drop. Same exact stop. Completely different jump.

I've thought about that difference more than I've thought about the jump itself. The first time was a genuine crisis, entirely because I didn't know what was coming. The second time, the exact same event was almost fun, because I did. Nothing about the mechanism changed. What changed was whether I was the only one who didn't know what was about to happen.

I do ServiceNow and Anthropic implementations for a living now, and I've caught myself thinking about that second jump more than once mid-project. For a customer going through a platform rollout for the first time, the drop feels exactly like my first jump — sudden, disorienting, no clear reason yet for the parts that don't make sense, an audience watching. For the person running the project who's done it fifty times, it's the second jump. Same events. Completely different experience, because one of you has the information and the other doesn't.

Stepping into the unknown is always like that. But I think the job — my job — is to make sure the first-timer's version looks more like my second jump than my first, knowing exactly what is coming and when. No unexplained stops. More warning about what's coming and why. It won't stop being scary. It just doesn't have to feel like a disaster.

Richard and I lost touch somewhere over the last twenty years, the way you do with people you're closest to for one specific season of life. If he ever reads this — hey, Richard. Thanks for jumping twice with me!