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For a long time I was very proud of the fact that no girl I had attempted to kiss had given me the cheek. I thought that this meant that I was a precision sniper of dating, finely attuned to the subtleties of the male-female dynamic. I knew when girls wanted that first kiss to happen and had been right every time.
I mentioned this to someone and they said something like, "Well, you're probably playing it way too safe then. You've avoided rejection, but you've probably not kissed a bunch of girls who wanted you to kiss them."
The wind was taken out of my sails immediately. I had been looking at it all wrong this whole time. Something I took as a sign of success was actually a sign of a different sort of failure.
If you never fail, you are leaving success on the table. It's comforting to imagine that you are perfect, but perhaps more likely that you aren't pushing far enough past your comfort zone.
I get called weird a lot. Not usually in a bad way, usually as a term of endearment. Looking at it objectively, I see the argument — I'm definitely a strange person who does unusual things.
The thing is, I don't feel weird. My day to day life feels pretty normal, and the decisions that I make also feel very standard. Take in input, process it, make the best decision possible, move on.
The disconnect, I think, is because of how I make those decisions. When I think about why I often end up doing very different things than most people, it boils down to one key distinction: I completely disregard decisions that others have made in similar scenarios.
Here's why. While everyone obviously has a ton in common with each other, we also have enough differences that decisions can't be made in a one-size-fits-all manner. You and I could be in the exact same scenario, but because we value different things and have different abilities, the correct decision for each of us could be opposite.
I'm going to start writing a little wrap-up about the island every year, partly because I want to chronicle it for my own reading later, but also because there's been a lot of general interest in the island.
If you're late to the party, nine friends and I bought an inexpensive island off the coast of Halifax in 2013. It was untouched forest when we bought it, but we have now built trails as well as structures, the only significant one being a 30' diameter yurt.
This year we got two trips in. The first was a massive trip with twelve different people coming and going, averaging eight to ten at any given time. Five of the owners came on that trip as well as seven guests.
Having so many people here at once was a feat in and of itself. I think the maximum we'd had before was four. But this is the first year that the yurt was up, as we finished it at the tail end of the preceding summer, so we had plenty of space for everyone.
I've been working a lot on marketing recently, as you've hopefully noticed if you subscribe to CruiseSheet's (awesome) newsletter. A basic part of marketing is thinking about the funnel. At the top of the funnel you have people who go to the web site, and at the tiny end of the funnel you have people who actually book a cruise.
Ideally you'd want that funnel to be tube shaped so that every person who visited would also book a cruise, but that's not possible. So while you try to stretch the opening at the bottom of the funnel by increasing conversions, you also try to get more people into the top of the funnel, since some of them will make it all the way down to the bottom.
Over the years I have had some really amazing ideas for blog posts. Hopefully you've read a few of those posts, but the majority of them never got written. That's because I have the exact same thought process every time:
It's been an interesting month so far. Two relevant things happened: first, I got some critical feedback that I needed to hear but sort of stung, and second, CruiseSheet has been doing extremely well.
For the longest time I've run my businesses as I thought they should be run. I'd hear people out and take advice on small things, but even when lots of smart people I love and respect said that I should do something big differently, I wouldn't. I'd listen and feel like I was considering it, but really I knew I wouldn't take the advice.
And then later I'd think to myself about how I had my own way and how great it was and how some day people will see that my way was right!
But that day never really came.
I was encouraged to watch the TV series True Crime, which I was told was excellent. I watched the first couple episodes and found all sorts of things I didn't like about it, which made it easy for me to stop watching the show and write it off.
This happens to me for most TV shows, but it's not an accident. I've cultivated a strong inclination to dislike TV. Usually an optimist, I encourage myself to be very negative when it comes to "low-value" media. I love walking out of movies so much that I'm always looking for a reason to bolt within the first half-hour.
A few days ago I reached a place of disgust with myself. I thought-- "What are you doing? Is this all the effort you're willing to pour into your goals? Are you trying to be mediocre? It's time for a big change!"
That may sound like negative self-talk, but I've developed on purpose an inclination to have those sorts of moments. I see them as fire breaks. If I'm not performing at my best, or near my best, I want to have some level of exasperation towards myself.
Ask anyone what their top priority is, and I bet you get at least three. And if you were to observe their actions, maybe you'd notice that the top priority they're acting on has nothing to do with any of the three they listed.
We all want a lot, and that's because it's easy to want a lot. I want happiness, fulfillment, lots of money, great friends, a great relationship, and just about everything else out there.
It's easy to want a lot. What does it take for me to add something to my wish list? Nothing. I just added a jetpack, and it took me two seconds and felt great. A jetpack! How cool would that be?
But in the same way that great design is defined by negative space, our true wants, those that we will work towards, are defined by those things that we give up.
My sister told me about a date she went on recently. When she very politely said that she didn't think they were a good match, the guy went nuts and said all sorts of rude and outlandish things.
Poor guy. He almost certainly knew that he was digging an even deeper hole by saying the things he said, but his mental state was so bad that he couldn't help it. What would it be like to live in that brain?
He's an extreme example, but I don't think it's all that common for people to really have nice clear minds. The more I talk to people the more it seems like everyone has insecurity, doubt, anger, jealousy, fear, or other negative emotions lurking about a lot of the time.
It's one thing to feel these things occasionally. If a bear suddenly charges at you and you don't feel fear, that would be very strange. But you should not be living daily life with these emotions in your brain.
During a six hour layover in Honolulu, my friend Brian and I went to the Honolulu Museum of Art. The museum is really cool and worth a visit for just about anyone passing through the city. They have the standard sort of stuff, but I was most impressed with their Asian collection. In particular, the Japanese woodblock prints stood out.
Usually I skim over the woodblocks, but their collection was stunning. I went around the room looking at all of them several times before leaving. I took pictures so that I could figure out later who the artist was.
Later, just out of curiousity, I started researching what it would take to buy a Japanese woodblock by a good artist. It was strictly aspirational, not something I intended on buying in the near future.
But I was surprised. Legitimate Japanese woodblocks from the 1800s, when the Shogun was in charge, go for one or two hundred. The ones that captivated me in the museum were by a guy named Ogata Gekko and were printed in the early 1900s, and were even cheaper.
I can't imagine that working at a car rental place is much fun. Especially if you're working in Las Vegas and the line is full of angry customers who have waited an hour only to be barraged with company-managed upsells. I wasn't angry, but I was definitely in line for about an hour waiting to pick up my rental car in Las Vegas.
My friend and I got to the front of the line, and immediately started jokng with the woman behind the desk. We said that we'd like an upgrade to a car with spinning rims, and that it must be good for drive-bys. When she laughed and feigned terror, we invited her into the "business". By the end we were laughing together and she upgraded us to a convertible for free after quietly mumbling "There's a promotion..."
Cruising down the strip in our cherry Sebring Convertible, we talked about the merits of just being friendly and joking around with people.
Fundamentally, people want to get along. My sister went to a plant nursery that was slammed on Yelp for having an unfriendly and sour owner. She made it her mission to be friendly every time in, and eventually they became friends. Few people are really mean and nasty people by nature, rather than by circumstance.