I imagine that sailing across an ocean in the time of the Great Explorers (centuries before GPS) must have been a daunting affair. In particular I imagine that the first time one sets sail into a vast ocean with little known about the destination, there is a feeling that you get, in the pit of your stomach, that feels like it's being compressed and melted with burning acid. Sort of like all of your being turning inward on itself and questioning whether you have what it takes, whether you believe in yourself enough, whether you're going to go to within sight of a foreign shore and then crash into the rocks, and, most perniciously, whether you could hide this feeling well enough to get other people to board your boat. That feeling, not unlike "impostor syndrome", I imagine was so profoundly anxiety-inducing that some succumbed just to that. To the fear of a following a path that has not only unknown direction and unknown dangers, but also unknown length.

However, I imagine that the second time one sails across the ocean (if you made it back alive the first time), that feeling is understood, and because it's known, it is familiar and not uncomfortable, even exciting.

Obviously, we don't live in a time where there is much that is geographically unknown, but there is often a lot unknown to us about ourselves. I've been thinking a lot about this process of discovery and the process of knowing thyself and of learning about your boundaries. It takes many forms, "pushing your limits", "leaving your comfort zone", etc, but an important part of life is doing new things, things you haven't done before. And, by definition, you will probably suck at them.

In order to better understand this process, and to see how others think about this, I thought I'd write down some thoughts, realizations, and conclusions and see what happens. This kind of exploration certainly happens during startups, but can also happen learning a foreign language, getting in shape, speaking publicly, writing a blog, going to grad school, starting a new job - anything, I guess, that requires skill.

Specifically, I'd like to understand how a person can best orient themselves when they're doing something new. In particular, how do they observe the world around them and position themselves so that they can make forward progress towards an objective. I'd love to hear how others are thinking about this also, please comment.

I think this is useful, because as the Pablo Picasso quote above tells, in order to do something, you have to do it at least once, and likely suck at it. Managing anxiety that comes from learning something new (or "leaving your comfort zone") can only help you learn.

Understand your commitment

There's no point in venturing across the ocean and being ok with getting halfway. It's important to understand your commitment level and the outcome you want to achieve. Introspection is important so that your motivations and values are clear to yourself and you can explain them to others. In Seth Godin's "The Dip", he advises that you set parameters on why you would quit something ahead of time. This prevents quitting under duress and holding yourself accountable for reaching your goal or not.

Giving up halfway happens a lot in the modern world I think because work has eaten more of our free time. It seems that there is never enough time to advance yourself because life gets in the way. Understanding your priorities is crucial because it makes obvious those things that are costing you time that aren't critical. Want to go to the gym every morning? Quit "The Daily Show" habit at night. It's very easy to take on too much and let time pass without any forward progress.

Start at the beginning

I've gotten comfortable with knowing nothing. When starting, if you check your ego at the door and get ready to eat some humble pie, not only do you not get embarrassed when you make mistakes, but you'll also be a lot more likely to make friends with people and get help. When I started Crossfit I had fallen horribly out of shape, and getting schooled by women (and men) 20 years older than me wasn't a great ego boost, but I was able to focus that into resolve to maintain an exercise habit.

It's important at the start to really understand what the fundamentals are, and how they apply. If you're doing something athletic, it's stuff like keeping your eye on the ball and knees bent. If you're speaking publicly, it's speaking slowly and clearly. If you're starting a business, it's making sure you're earning more than you're spending.

At the beginning, quantity is more important than quality. There's a classic anecdote about pottery here which is relevant, but which I'll only link to second hand. Blindly trying, making mistakes, detecting patterns helps you figure out what's important. In the end as you get better, I've found that it's not what you keep, it's what you take away. This applies in many disciplines: writing, coding, design, etc. "The Master does nothing, yet he leaves nothing undone. The ordinary man is always doing things, yet many more are left to be done." - Lao Tzu.

Learn from others

When I was younger, I thought I was smart enough to do everything myself - or at least, I didn't really like talking to people and I would just deal with the handicap that doing things alone imposed. That was really disingenuous. Going back to the priorities, if you have them clear, then you should do whatever helps you accomplish your objective faster and more certainly. I've learned quite a bit about interpersonal intelligence since starting ReadyForZero from my co-founder. It's important when you know nothing about a topic to look at what other people are doing and how they're connected. Are there groups of people doing similar things? Who is dissimilar? Are everyone's objectives the same? Do people have different skills or opinions that lead them to their viewpoints? This is one of the reasons I think that people who are successful are voracious readers.

And it's not just looking at what they do, but imitating it. I used to be an asshole and thought I could just come up with a better way to do things off the bat. Don't do that. Just start by copying and seeing what marginal changes can be made. Now I think to myself "Can I faithfully reproduce what they're doing?". When I learned to kiteboard, it was a frustrating week of swallowing water while I figured out the mechanics of getting up on the board. All it took was someone to point out that I wasn't moving the kite fast enough, and I was off and running. I could have saved myself a lot of frustration if I had asked or more carefully copied what other people were doing.

A process for progress

One of the most important parts of starting something new (like sailing across the ocean or starting a business) is to setup the process by which you can improve. Most importantly, how can you tell if you're moving forward in the right direction? It's important not only that the oars are moving in the water and the sails are full, but that over time, you're making consistent progress in some direction. If there are quantitative measures, this is somewhat easier, you only need to make sure you're tracking the right ones, and faithfully keep to doing it. If it's something more subjective, or if you're at a point in the error surface that is completely flat (no gradient), then it can be harder. How do you optimize a website with no traffic?

When starting out, there is a certain degree of flailing, and here is where you can feel lost, like you're sailing across the ocean. At that stage it seems like most important to rely on your gut for direction, but have faith in your instruments to measure progress.

Objectively assess failure

Blindly flailing around will certainly lead to some disappointment and failure. It's important to recognize and own up to it. Was it your fault? Really? It probably was. What did you do wrong? If you place blame somewhere else you'll keep getting the same result. This is especially true when trying to develop habits. For example, writing a blog is something new for me, and if I don't post, it doesn't matter that there were a lot of other distractions, that's a failure, and noone's fault but mine.

It's important though that failure drives improvement and not frustration. You will never do things perfectly, and there will always be people that are better, smarter, and more successful. I now try to steal something from how they do things, but use others' success to focus my resolve on putting one foot in front of the other. This can require a lot of faith.

Find the opportunity

When starting something new, don't just start in a random spot, or the spot that's most comfortable. Find where the activity is, where the challenge is. Provide yourself an enriching context where you can make progress and trust that you'll be able to figure it out. In "Outliers", Malcom Gladwell talks about how very successful people are not only exceptional, but their success is greatly influenced by being in the right place at the right time. The problem is that you can't know when that is until afterwards. You have to be willing to venture out into the unknown, and trust that the ability to orient yourself is a skill that can be learned.


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