Observations from 52 newsletters

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Programming note, I’m changing the publishing schedule of Simple, Not Easy from Friday to Sunday in its second year. Look in your inbox every Sunday for that little bit of motivation to send those Sunday Scaries away.

At the risk of a self-aggrandizing victory lap this newsletter represents 52 consecutive weeks of publishing. I set out a year ago with what I thought would be a fun experiment in discipline and has turned into a creative outlet which shaped my identity, brought new career opportunities, and helped me lead better.

Here are 3 observations on life and leadership I learned from publishing each week for a year.

Consistency can’t be faked

I’ve written a few times about consistency in the last year. I’m a firm believer that over any long enough time horizon consistency > intensity. It’s easy to make goals we keep for a week or a month, but I think true differentiation and learning doesn’t really start to take shape until you start thinking in time horizons of years.

Whether you’re saving for retirement, investing in relationships, or committing to living a healthy life, the longer you’ve kept up a habit the more likely you are to continue.

This phenomenon known as the Lindy Effect posits, “the future life expectancy of some non-perishable things, like a technology or an idea, is proportional to their current age.” In other words, the longer something has been around the less likely it is to go away.

You can use the Lindy Effect to your advantage by simply vowing to outlast others.

I may not always go fast, but I will keep going. Over a long enough time horizon that person is incredibly difficult to beat. So go be that person.

Skill comes through application

It’s easy to fool ourselves into thinking we’ll get better by a bit more planning, enrolling in yet another online course, or cracking the pages of another book.

There’s nothing wrong with planning, learning, or reading but you can’t begin the path toward mastery with anything other than application.

I think much of the resistance to actually doing the thing comes from fear of making mistakes or looking foolish.

Mistakes happen and that’s okay. I published a newsletter this year where I wrote asses 🫏 when I meant to write assess. My Mom caught it and quickly corrected me (there’s another lesson in there about Mom’s being lifelong proofreaders no matter how old you are).

In the moment I realized the mistake I was mortified, now it’s just a funny story.

The path to knowledge can only come with some level of experience. It’s impossible to gain experience without making a few mistakes.

So publish the newsletter, fix your typos, and keep moving.

Writing clarifies thinking

I saw a visual once which had two images. The first was water slipping through open hands trying to grasp it with the caption, “thinking”. The second was water falling into a glass with the caption, “writing”.

This idea of using writing as a tool to capture your thoughts has since stuck with me and perfectly encapsulates the way I feel about this newsletter one year in.

It’s hard to hide behind poor thinking when you write those thoughts down. Nothing is more humbling than being convinced you are the next Albert Einstein in your mind only to write down your ideas and question how your teachers let you progress past finger painting.

But that’s the point.

There’s no better way to pressure test your thinking than to write your ideas down and then read them back to yourself. They’ll be silly and you’ll feel like an imposter at first. But if you keep editing and rewriting your thoughts will get better and you’ll get closer to the truth.

To me, writing not only clarifies my thinking but makes me more articulate in the way I communicate those thoughts to others. This ability to clearly articulate your ideas, recommendations, or approach is invaluable.

It’s an amazing time to be alive

Okay a bonus observation from the year. It’s an amazing time to be alive.

There are many valid reasons to be cynical about the state of society and scrolling through the headlines of any major news outlet will leave you seriously questioning the ability of our species to keep progressing.

Yet, for a few dollars a month I have access to a platform that spreads my ideas to friends, family, and people I’ve never met. Those people (all of you!) then kindly reply telling me when I said something that made you think differently or (one of my favorite types of replies) when you disagree with something I said and offer an alternate take.

That’s an amazing thing and the world is an amazing place. You just have to put in a bit of elbow grease and know where to look.