Time to lean in

Facing the Fear, showing up like a pro, and hitting publish

There comes a point where the only thing left to do is to sit down and do the work, and I have arrived.

Over the past year I’ve experienced a growing desire to write. The universe blessed me with endless topics to explore. So I wrote often. I wrote about money. I wrote about modern work. I wrote about meaning. I wrote about great books, podcasts, and movies. I wrote about simple ideas that changed my life.

There was just one massive problem. Most of the time, I couldn’t hit publish. I had the Fear. Fear that I’m not a “writer”. Fear that it wouldn’t resonate. Fear that I need to choose a lane. Fear that I’ll write something today and disagree with it a few months from now.

It turns out that there are only two things standing in the way of me being a writer: writing and hitting publish.

Turning Pro

In some areas of my life I am a pro (to use some Steven Pressfield verbiage).

For the past ~10 years I’ve (mostly) worked on growing software companies, and when I show up at work I am a pro. When I’m investing and researching businesses, I am a pro. When I look at my bookshelf, it’s clear that when it comes to reading I am a pro. From the moment I put my wetsuit on until the moment I get back to the car after a surf, I am a pro.

To clarify, I do not mean pro in the traditional sense. Despite my fancy Excel sheets and thousands (?) of hours spent researching and investing, I am not a “professional” investor. I haven’t gotten through a Dostoyevsky novel (yet). I’ll drive 4 hours in the middle of winter to go surfing and catch one good wave if I’m lucky. But I show up, and I show up like a pro.

A professional shows up every day.

A professional does not fear failure.

A professional pursues excellence but is not shackled by perfection.

A professional writes and hits publish.

And therein lies my issue. When it comes to writing, I’ve been acting like an amateur.

Leaning in is the only way forward. I must do the work. I can’t be sure anyone will care, or that it will find the right eyes. The only thing I can be sure of is that I will write about what energizes me and it will be great work, because I will show up like a pro.

Thinking and Feeling

Welcome to Thinking and Feeling, a Substack that actually gets published :)

If the past year of writing journaling (shout out to my friend Ian for this post that has been living in my head rent-free) is any indication, I suspect I will write mostly about money, meaning, and modern life. I also suspect that I will go off script and explore new frontiers.

I will write often, I will write authentically, and I will hit publish.

I’d love to have you along for the ride (to the 40 of you who aren’t my Mom).

Time to lean in.

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Shout out to Adam, a pro, who used a skillful combination of knife and feather to help me see more clearly that which was right in front of me.