Headnet for midges. Zip-on rain gear. Buff for intense sun. This is my packing list for Scotland’s West Highland Way—and it made me wonder if I was in my right mind.
Isn’t this supposed to be a holiday? A getaway with friends?
My thru-hiking son calls this “Type 2” fun.
Type 2 fun refers to activities that are miserable, stressful, and challenging. By design. But in retrospect build character, resilience, a sense of triumph—and great stories.
Misery in the moment. Joy in the memory.
A hike where the packing list requires round-the-clock protection from mozzies is absolutely Type 2 fun … and I’m counting on the retrospective joy, let me tell you.
What I’ve learned? When you’re with your tribe, everything is sweeter—even the disasters.
Like this moment from my book, Quantum Surfing: The Innovator’s Guide to Being Lucky, Aligned, and Unstoppable (LINK), when I acquired Tavola Villa in Fiji:
Rain poured inside the villa. A landslide in the first week demanded tens of thousands in repairs. Taps ran dry without warning. Then came the parade of failures—oven, refrigerator, water pumps, deck timbers caving in. Something new broke every day. A “generator fix” turned out to be nothing more than a blue wire. I remember waking one night, shaking with anxiety, realizing I had actually done this—and there was no easy way to undo it.
We did what we had to. We cooked. We cleaned. We hosted. Lovely families from Australia and New Zealand sat at our tables as my daughter and I rose at dawn, coaxing the coffee to brew, filling the villa with the scent of fresh bread. Tropical lunches served on the veranda. And by evening, we orchestrated multi-course dinners—me in the kitchen, my daughter as sous chef, my youngest son as pastry chef. Somehow, we turned out remarkable meals, inspired by chefs around the world. In those early months, we stumbled into a signature cuisine that, to this day, remains the envy of Fiji.
But the toll was heavy. With the villa full, my daughter and I moved into the one-room caretaker’s cottage. By January, the mold made itself known. I was debilitated by brain fog and bone-deep fatigue. Within months, I was so sick I flew to Australia for treatment.
The undertow of this kind of venture can undo you. I had thought I’d be in Fiji for four months and then back to Silicon Valley, back to startups and advisory boards. The wave laughed.
That wave? 4 years.
It was so confronting at the time that I couldn’t even write about it in my journals. But I did keep a log book filled with daily reports, to-do lists, comings and goings from the villa.
I tell the stories now, and everyone laughs.
And my favorite thing to read today? That dog-eared log book.
Type 2 fun. Disasters of our own making. Treasured bonds, exquisite memories, and classic stories the reward.
To your Type 2 fun—a wry spin on la dolce vita. x