Why Start Writing Again?

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Why We Are Here

Writing is hard.

No medium forces you to reconcile with your true thoughts quite like writing. It is, in a word, a terrifying process. 

You begin with a blank page. The cursor beats in what can sometimes feel like an accelerating fashion. It knows you don't know what to do. The quickening pace mirrors your heartbeat as you become increasingly uncomfortable with the blank page staring back at you. 

It is daunting. You can almost hear the sound of the cursor pounding — highlighting the fact you are unable to convert the jumbled mess in your head into words on a page. That’s writing. 

And like I said, writing is hard. 

Diagnosing The Problem

But what is it that makes it so hard to do this “introspective” form of writing? 

After all, don’t we spend a large majority of our collective days communicating through the written word? Emails, texts, comments on twitter or instagram, reddit posts, or even the occasional Facebook post (no judging here…but come on, it’s 2024). 

Yet when we sit down in front of a blank page and look to craft something unique and coherent (dare I say original?) it becomes something that almost seems foreign. Why is that?

My two cents.

We really spend so little time actually thinking deeply about...well anything. 

In order to clearly articulate an idea through the written word you really need to know what you are talking about, and more-so than editing or drafting, that requires thinking. 

As I sit here writing this blog, I realize that I have spent a great deal thinking over the past several months, thinking about a lot of things.

• How have my decisions led me to where I am today?

• Why do I care about the things I do?

• Why am I surrounded by the people in my life?

• What am I doing?

• Where am I going?

These are questions we all ask ourselves, and usually with increasing velocity as we leave our blissful adolescence and enter into adulthood. 

From the countless conversations I have had over the past several months, they are questions that don’t go away. 

But interestingly enough, they are questions that often go unanswered. They linger in our minds like a tick that has nestled itself into our subconscious and latched on for the long haul. We barely notice it, but over time those unanswered questions continuously take and take and take. 

These lingering questions, they eat away at our confidence. They take away from our sanity. And most importantly, they take away from our identity.

I hate that idea. I hate the thought of unanswered questions having some irrevocable power over my subconscious. I want to be in control of my mind. And most importantly, I want to be in control of my decisions.

Harnessing Power over Your Own Decisions

Unanswered questions allow the outside world to dictate your actions. 

When you don’t answer important questions for yourself, you subconsciously seek answers from others without ever internally vetting the information. You fill gaps with the ideas of those who don’t know you, your ideas, your motivations. You pattern match to patterns that don't exist in your own life. 

Unanswered questions inevitably transform into what is known as “open loops”, but what does that mean?

An open loop can most broadly be defined as “a system of the process where there is no feedback controlling the system’s operation”. 

This can mean different things in different contexts, but for our purposes, it can boil down to the following: 

This is kind of how your brain works with unmade decisions. There is a bunch of energy being used up, in the background, that can and will ultimately drain your internal battery. In this case, however, the implications of a drained battery can be a little bit more severe. 

Anxiety, depression, self-doubt, all of these can be the result of open loops, of unmade decisions. The cognitive load they impose can cripple even the strongest minds. None of us are immune — I know I certainly am not. 

So, how does this relate to writing?

So far, we have established the fact that unanswered questions are probably a bad thing and that leaving them unanswered can be even worse. So how do we avoid being crushed under the cognitive load of unmade decisions?

You guessed it, the written word. 

Now, I would not necessarily say that I am predisposed to being a writer, for those who know me well I can be a bit of a talker. 

I talk through my thoughts, ideas, and problems incessantly. But it has become clear to me over time that this is not necessarily the “right” way to solve my current issue. 

The more I seek others’ input, the more I see the loop I am trying to close becomes recursive — meaning the wheel just keeps on spinning until something ultimately breaks (with the thing breaking being my sanity).

Writing, on the other hand, closes that loop. 

It is nearly impossible to write a coherent essay or blog without taking the time to answer the question you set out to answer -- or at least valiantly attempt to. 

You sit in silence, you writhe in intellectual discomfort, and you continue to watch the cursor. Tick. Tick. Tick. Until the blank page becomes so unbearable to look at that you are forced to the hardest part - try. 

Here is the important part. 

Trying matters — a lot. You are not always going to be able to come up with an answer to these open-ended questions. And that is ok. But the painstaking process of battling your psychology, your preconceived notions, and your ideas both loosely and strongly held, is the process you need to begin to get the clarity you need. 

Thinking leads to writing, writing leads to understanding, and understanding leads to more writing which ultimately leads to knowing. 

MY Struggles with Open Loops

Some might not know, but I have technically been a writer my whole life. 

I “published” a 300-page fiction novel in 5th grade modeled after The Chronicles of Narnia. When I was in college I wrote a 50 page dissertation on the role journalism played in the Iraq War. At Goldman Sachs I was responsible for a 50,000+ client “Renewables Update”. And as recently as 2022, I was a professional writer employed by Front Office Sports. 

But after leaving my professional writing job I lost all desire to write. Something in me just wasn’t prepared to put in the work required to decide “what” it was I “should” write about. 

For months, I wondered what would be the best (or maybe most interesting?) way for me to spend my time writing. I had just taken over portfolio management responsibilities for my Family Office. There was plenty of interesting stuff to write about. 

• Biotech industry analysis

• Renewable energy markets

• Business building

• Systems optimization

• Running a family office

To me, the content opportunities were endless. 

Each having its own “commercial” opportunities to write about. 

Yet, for some reason, I never opened a Google Doc. I could never bring myself to put the (metaphorical) pen to paper — and it was driving me fucking insane. 

It turns out that when you have neither a carrot nor a stick, it becomes increasingly difficult to find the motivation, or more importantly, the inertia to start. 

For two years, I sat idle and frustrated. I texted friends and family ideas I had about starting newsletters or blogs but they all fell flat. I never launched any of them. I never actually really worked on any of them. 

Why? Because none of them actually solved a problem for me. 

Meanwhile, as I searched for a writing project that seemed like it would never come, real-life questions were starting to pile up and they were going unanswered. 

I reached a point, in February of 2024 where I no longer felt like I knew why I was doing anything. It was abject depression which felt pathetic. I was more than financially stable, in a happy relationship, living in the coolest city in the world, helping grow my family’s legacy while also literally working to help cure cancer…and somehow I STILL felt like I wasn’t doing the right thing. I still felt lost. 

It was then that I FINALLY borrowed some printing paper from my apartment building's front doorman, sat down at my kitchen counter, and just wrote down the list of questions swirling around in my head. 

The list was long, it was intense (at least to me) and I knew for a fact it was incomplete. 

My life had become a wasteland of tactical and emotional open loops that I had allowed to drain my battery for months and probably years without ever even realizing it. 

I was lost. 

Today

Today is a new day. I have found my reason to start writing again. 

One of the first open loops on the list above was figuring out why the fuck I couldn’t get started writing again. So, I said fuck it and just started writing.

The exercise took several weeks but I finally came to realize what I have been outlining for you this entire post. I need to write to answer the questions leaving burning holes of doubt and discomfort in my brain. 

I need to write to have the conviction to make decisions that reflect my true beliefs. 

This post is an ode to closing loops, answering questions, and doing the one thing that we should all probably get moving on.

Start Writing.