We think we see patterns and causes. Really there are none. We think events are meaningful. Really they’re just coincidence. We’re not used to the logic of probability. Life is more random than it seems.

• Derek Sivers, How to Live

We live in a nonlinear world although we think very linearly. We overestimate our ability to forecast future but never stop from doing it due to the need of sense of security and feeling in control of things. We live our life forward and understand it backwards so that we can rationalize everything happened with cause-effects as if hindsight bias doesn’t exist.

But what does it really look like in reality? Our tracking record tells that we’re inherently bad at foreseeing any rare events and understanding ourself and a complex world around us. Flights can be delayed due to unforeseen weather conditions, Internet can be unavailable due to power outages, doctor appointments can be cancelled and rescheduled without reasons. In software world, uptime is often used as a measure of reliability or stability of online services. To meet the unprecedented customer demand to engage with online activities, many software companies adopted the on-call practice aiming at 99.99% above uptime (i.e. less than an hour downtime per year). The Netflix engineering team even famously invented a tool called Chaos Monkeys that randomly disables their own production instances to make sure they can survive that common type of failure without any customer impact. Not to mention economic or financial bubbles that may burst all of a sudden and cause catastrophic snowball effects.

Last week I went on a trip to Seattle to explore around together with an aim to search for next home as I’m planning to move out of California. Instead of following the conventional “wisdom” to outline a concrete travel plan, I kicked off the trip with a one-way flight from SFO to SEA airport and booked stays through Airbnb in a just in time manner, typically 1/2 days before the current stay ends. That’s I purposefully go with an unplanned schedule for the travel. It may sounds a bit wild at first, but probably not completely irrational if taking my intent to grip an authentic feeling of a new place within a short period of time into account.

There’re a few things that I learned from the trip

• Uber or Lyft drivers are great information sources. Due to their wide exposure to all kinds of passengers and ad-hoc conversations, they tend to form a more comprehensive view of local affairs including food, neighborhoods, culture etc. While talking to friends who live there is another shortcut to build a mental map of the place, the source of information could be narrowed by the social circles you’re in. And since lots of the drivers are immigrants from different countries, it’s a natural opportunity to learn more about cultural diversities. I’ve encountered drivers from all over the world, and many of them are from countries that I never heard about before, it’s fun to listen and learn a bit of new things each time.
• Airbnb would give you more surprises than hotels. Although those two price are already fairly close to each other nowadays, you'll get far more randonimity when staying with airbnb. I had a 2-night stay in an airbnb right next to the Aurora Ave which has a bad name for its prostitution scenes. I had no clue about Aurora Ave before the stay and it could be fair to stay that I won't book the place if I were well aware of its location by following certain popular travel guide. But in reality, the stay was great (average 5 stars by its guests) and Aurora Ave seemed to be just okay, at least not as bad as I had imagined. We can hardly be neutral about things without experiencing them ourselves, a lot of fears are simply caused by unground imaginations. Besides this one, there's another airbnb that comes with an in-house sauna that goes beyond my expectation for an affordable stay (around $100/night excluding tax and platform fees).
• We can get to make new friends when embracing a bit of randomness. A few weeks ago, a fellow colleague who is based in Seattle coming to SF for a company retreat, we haven’t met or worked with each other before besides I have listened to one of her engineering talk organized by the company before. We bumped into each other by accident in the SF office and I vaguely recognized her face. Instead of fear of talking to a stranger, I invited her for a walk around the office. In return, she did the same thing for me when I was visiting Seattle this time. It's completely random and can't be planned, but the experience is great.
• Unplanned trip doesn't cost much more than planned one. When revisiting the trip expenses, I calculated another version of a planned trip with round-trip flights and consecutive hotel stays, the unplanned trip only cost 20 to 25% more as the majority of the costs goes into accommodations which we can't really save much either way. So if you aren't a frequent traveler or budgeting expenditure isn't your primary goal for the trip, the extra costs are actually acceptable, to me at least.

Imagine a planned trip. It might appeal to modern tourism and give you a sense of efficiency. There're an ocean of trip planning templates or travel guides, tourist attractions, restaurants and shopping checklists on the Internet. And they become popular simply because everyone is doing it this way in attempt to squeeze every little room of unpredictability with planned activities and accurate time frames so that everything fits perfectly within a round-trip flight schedule. It's as if it's the only right way of doing things given we're bombarded with commercial news and advertisements persuading us to do so. We fail to notice that so called personalization isn't that personal at all and so called efficiency isn't that effective as well. As a result, we're so attached to a false sense of control that any slight error or randomness may disrupt the entire trip.

Jeff Bezos once said “Wandering is an essential counterbalance to efficiency. The outsized discoveries – the “non-linear” ones – are highly likely to require wandering”. Maybe it’s not a bad choice to break out the planning bubble every once in a while by fusing randomness into our lives in small doses and savoring the little surprises it brings.