Never Normal Newsletter

Climbing Hills, Setting Goals, and Learning to Read

Last week I wrote about finding yourself and whether it’s a “success killer” to travel in your youth (instead of going all-in on career early on).

Reader Lukas replied to say:

This is great! Thanks for writing it!

I also enjoyed the McAskill quote about “spending 5% of your time deciding how to spend the 95%”.

I’m now wondering about the different ways on where to place those 5% … most of it at the beginning of your career (= the travel and finding yourself) or sprinkled throughout your life (= short sabbaticals)? I assume the latter is better because plans and goals keep changing.

Here’s my take:

I wouldn’t treat “5%” as an exact number — at least, not as an upper limit. I read it more like a suggestion to “make sure you do enough experimentation early on to figure out how you should be spending your career”.

Climbing the wrong hill

Start-up founder and investor Chris Dixon compares searching for the right career to a classic computer science problem, hill climbing.

Imagine you are dropped at a random spot on a hilly terrain, where you can only see a few feet in each direction (assume it’s foggy or something). The goal is to get to the highest hill.

While it’s tempting to simply “go up” from wherever you are standing, that’s a sub-optimal strategy. You’ll end up at the top of the nearest hill, instead of finding the biggest hill.

People early in their career should learn from computer science: meander some in your walk (especially early on), randomly drop yourself into new parts of the terrain, and when you find the highest hill, don’t waste any more time on the current hill no matter how much better the next step up might appear.

Hugging the X-Axis

David Perell’s latest essay also touches on this topic, but he comes at it from the other side.

Our parents and grandparents may have gotten married in their 20’s and spent 30 years working in one company, but our generation struggles with commitment (to anything — career, relationship, home, etc).

Instead, we want optionality, as David points out:

In a world as grand as ours, shouldn’t we try to experience it all? Change it up. Visit every country. Try a bunch of careers. The menu of life is vast, and it’d be a shame to only order a single entrée.

I can certainly relate to that, having spent years on the road, living in Airbnbs and hopping to new cities and countries every few weeks or months.

So what’s the problem?

The problem is that a life without commitment is a life spent hugging the X-Axis.

Doing anything meaningful starts with a long time horizon.

Long time horizons change our incentives, usually in good ways. This is one of the core findings of game theory: people treat each other better when they intend to interact repeatedly in the future.

Putting these two ideas together: You want to spend enough time exploring and experimenting to find your “biggest hill”. Once you find it, you should commit and go all-in.

Think of it like watching TV. If you just turn on the TV and start watching the first show that happens to be on, chances are slim that it’s going to be something you actually want to watch.

So, it’s worth flicking through the channels to see what else is on. But if you just keep flicking forever, you won’t get to enjoy a single show or movie or sports match or whatever.

Lukas also asked about exploring later on, not only in the beginning.

To stretch the TV analogy a bit — you don’t want to just sit there staring at the same channel forever. Especially if the program you were watching already finished.

So how do you know when you should “change the channel” in life?

I don’t think there’s a set frequency for how often we should be experimenting, but the end of the year / start of the new year is as good a time as any to take stock of how things are going and to set some goals for the year ahead.

Big Scary Goals!

As Nat Eliason writes in his latest Medley, the point of setting goals is not simply to achieve the goals:

To me the point is to give yourself an exciting challenge, where completing the challenge requires you to become a better version of yourself…

So one thing I’m thinking about with my yearly round of goal setting is: what large goals can I set that will force me to change my life in an interesting way?

Once you reach a basic level of income and comfort, I believe you need to intentionally increase the difficulty on your life to stay motivated. Setting sufficiently large goals is a great way to do that, and can make work much more interesting.

​Nat’s point about goals being a vehicle for bettering yourself echoes one of the most profound lessons I’ve learned so far in life. It came not from my personal experience, but from a book:

Sharing What I Read

I highlight interesting passages as I read online and on my Kindle, then I review my highlights each morning. I recently started sharing highlighted passages (like the one above) every day on Twitter. You can find them all here.

I tend to read a lot of non-fiction, especially biographies/memoirs, history, and “self improvement” books. These books have had a huge impact on my beliefs and choices in life (they’re also the source of many Quality Questions).

But sometimes it’s nice to switch things up and read a traditional book on paper, especially a novel. No screen. No highlighting. It’s a good way to unplug and get out of my head at the end of the day.

I just started reading Momo. It was recommended to me by Katerina from the Quality Questions community. She wrote, “It’s a book written for kids but should be mandatory reading for adults.”

I only realized after getting my copy that it’s written by the same author (Michael Ende) who wrote The Neverending Story. That was my favorite movie as a little kid. I nearly drove my sister insane singing the theme song over and over and over when I first saw it.

Lifelong Learning – It’s Never too Late

Speaking of reading, this woman in India just fulfilled a long standing ambition by learning to read at the age of 104!

That’s all for this week. More soon…

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I write occasional emails to share what I’m thinking, learning, and doing. It’s all related to the idea of breaking free from the “default plan” in life.

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