I'm Afraid of the Choices I've Made

Exploring Why I'm Doing All This Work

Photo by Jonathan Pease on Unsplash

“Tim, you need a guard dog!” 

I was sitting in a Barnes & Noble Bookstore Saturday night and had just texted the cover of a Seth Godin book called The Practice: Shipping Creative Work, to my friend

Rick Lewis

. 

“Have you seen this book before?” I asked him, anticipating a text back of wholehearted approval, that I should not only buy this book, but also affirmation that another book would help me solve my silent insecurity about being able to ship quality creative work consistently. 

“No, but I certainly have a high regard for Seth Godin,” Rick replied. 

“It’s what I needed…I have been faltering and questioning myself on producing my 52 essays and 52 podcast episodes.” 

No response. 

I breathed in the smell of new books, and walked to another section of the bookstore to find answers.

Then the phone rang. 

Incoming Call from Rick Lewis. 

I immediately picked up and walked over to the coffee shop stationed at the front of the store. 

“Hey Rick,” I answered. 

Rick didn’t hesitate. 

“Tim, you don’t need any more books. You need a guard dog. You're already shipping work right, left and center, week after week, and high quality work to boot. Why in the world are you buying something about shipping work?"

I was quickly reminded of my previous confession of my tendencies towards avoiding real work. I sat in a small corner at a scratched and bruised wooden table, and tried to process with Rick what in the world I was doing. 

“Why are you writing? What’s all this work and production for?” 

Rick and I talked for over 25 minutes, chipping away at my purpose, my goals, and my desired outcomes. Beyond many epiphanies and answers to questions that Rick helped me tease out, I realized I had never shared with anyone here that I’ve been doing something pretty intense: attempting to write 52 essays and publish 52 podcast episodes this year. 

This decision has created an internal struggle. One, between my intense desire for quality over my mission for quantity and consistency. Secondly, what am I doing all of this work for?

What I realized after my conversation with Rick is that I picked up that book from Seth because I’m uncertain if I can keep up both the consistency and the quality over the long term — and without clarity on what outcomes I desired, I definitely won’t be able to sustain the effort.

More than that, deep down in the darkest crevices of my soul, I’m afraid the choices I’ve made in life won’t ever allow me to accomplish the dreams I have.

Why would I pursue this journey of writing? 

In 2008 I was 18 years old and got paid to write. It was exhilarating to get that check in the mail, especially after years of writing and publishing my thoughts and ideas online for free.

For the first year of college I continued to write and get paid, but at some point around 19 years old the writing faltered, faded, and suddenly was finished. Frankly, there’s a lot to unpack about 19 year old Tim we don’t have time for now, but it seemed the flame had gone out.

As I went off to college, I was convinced my life would include writing. I had both the passion and the gifting. I imagined being published in The Wall Street Journal, The New Yorker, The Atlantic, Christianity Today, or many of the other publications I was reading and still read today. I imagined writing award-winning books, speaking about interesting topics to crowds, and regularly contributing quality essays on a personal blog.

But, it didn’t happen.

The writing flame tried to return many times in spurts and sputters, but it always got snuffed out.

The dream vanished into the air like the cloud of steam over my morning cup of coffee.

But then, when it seemed most dark, there was light again. A belief that maybe that dream wasn’t gone forever. That being a writer wasn’t just something I thought, but something I could be. With consistent effort, here I am today.

A writer.

But what are the outcomes of my current writing I hope to achieve? If I’m honest, I want to see my work in places like The New Yorker or The New York Times. I dream of seeing a book on the wall at that same Barnes & Noble I like to frequent.

I want to see my work in publications like the ones I’ve listed above, I want to write and publish a book, and I want to utilize any skills I have around thinking and telling stories to speak and motivate those who will listen. I’ve always regretted not pursuing that dream.

I’m so often afraid that the choices I’ve made to pursue business “success” has made being published something that will always just be a dream, never the truth.

This Substack and the podcast stands as a weekly battle to prove that thought and that fear wrong.

So, I’m honing my craft here on Substack every single week, and have found many unforeseen benefits to writing even beyond these desired outcomes.

1. Writing and podcasting clarifies my thinking. 

“Writing is thinking,” says David McCullough, “To write well is to think clearly. That’s why it’s so hard.”

Since my time in the Write of Passage cohort, I’ve realized one of the most incredible truths about writing is how it clarifies what I’m thinking and what I believe. There’s a reason that Jeff Bezos has said “I like a crisp document and a messy meeting.” This document forces the Amazon team to write before they have conversation, to ensure immense clarity for discussion. 

I’m often taking something I’m thinking about and writing for personal and professional clarity. The essays sitting in my drafts folder are all based around helping myself think more clearly about some particular topics. 

2. Writing (and having conversations) is something I can’t help but do 

Seth Godin shares a short story in the book I didn’t buy about putting yourself “on the hook”:

“Askıda ekmek: there is bread on the hook. It’s an ancient tradition in Turkey. When buying a loaf at the local bakery, you can choose to pay for an extra loaf and, after bagging your purchase, the owner will hang the second loaf on a hook on the wall. If a person in need comes by, he or she can ask if there’s anything on the hook. If so, the bread is shared, and the hunger is relieved. Perhaps as important, community is built.”

Seth’s point is that in the same way when you create something for others to consume, you put yourself “on the hook” and you serve and feed the hungry.

This is the creative act and the creative work I feel compelled and called to do, regardless of any outcome. 

I am compelled to write based on something deep within me.

3. Writing online creates serendipity 

“Writing online is a guaranteed way to shrink the world. A well-written article can change your life because the internet rewards people who think well,” argues David Parrell. “Everything you write is an advertisement for the kinds of people and opportunities you want to attract, and if you have a voice, you can build a platform.” 

I’ve experienced this – both back when I was 16 and started writing online and it changed my life then, to the reality of the last year or so that I’ve begun writing again – the people, the connections, the choices. It’s all been an incredible experience and amidst my conversation with Rick, it became apparent that although the outcomes aren’t clear at the moment, what I’m doing so far is “working.” 

It’s working because I’ve developed incredible relationships and connections with people I never thought possible, I’ve attended events and have been on calls I never dreamed could happen, and have opportunities and options in front of me that didn’t exist six months ago.

Most of all – I’ve had fun. 

Be Good Repeatedly or Write Great Essays?

As I’ve begun this journey to accomplish these desired outcomes: the published magazine articles, the potential book (or books), and the speaking opportunities — I’ve wrestled with how I proceed.

Initially it’s been all about the repetitions and consistency. But I’ve struggled with the desire to focus solely on quality over quantity.

What should I do to accomplish my dreams?

It turns out there are a lot of viewpoints on navigating this journey.

Tim Urban argues that “Doing a pretty good article every week is far less likely to build a big career, than writing a great article sporadically, because the great article will stand out and people will forget [the rest].” 

On the opposing side, Steph Smith has an incredible essay called “How to Be Great? Just Be Good, Repeatedly.” 

So which way, young man?

SWYX has an incredible graphic showing this seemingly impossible tension and options we seem to have as creators: consistent output with inconsistent quality or consistent quality with inconsistent output.

How do we find an innovative way to choose both consistent quality and consistent output? There are two options according to SWYX: cut your scope or default to consistency.

Cutting the Scope

“Maybe you can’t produce a great essay every week. But perhaps you could scale it down and make one great tweet or newsletter,” he says. “Make up for lack of skill by spending disproportionately more hours on a thing than people normally do for that format. Relative effort stands out and the constraint breeds creativity.”

This could mean quality in a 15 minute podcast episode vs. over an hour, or essays that are 500 words or less. Constraints could allow for both consistency and quality, albeit in smaller packages.

Default to Consistency

It seems that every creator you read, from Seth Godin, Ali Abdaal, James Clear, or Tim Urban all believe you should start with consistency. Only after creating 100 things should there be a consideration of shifting somewhat to a focus on quality of the product. Again, there’s a tension that remains no matter how large the audience grows.

Perhaps like an ice skater shifting side-to-side in order to move forward, you have to find the cadence between both quality and consistency to move yourself forward.

My Question

So, I have some major decisions to make as I pursue these goals and these desired outcomes. I’ve admitted my fears, but the fears have not receded in the least — I can feel their shadows leering over me even as I fight to complete this essay.

So, I continue to wrestle and ask questions like:

• Should I try new ways to keep up the consistency (Wednesdays and Fridays), or take more time to craft the work to next level quality even if that means not doing it as often?

• Should I keep doing things the way I am, even if sometimes it's great and sometimes it's…well, not so great?

The journey continues.

Thank you all for reading.

Tim

---

Thank you also to

Mohammad Khan

and

Anthony D'Apolito III

for their feedback, their thoughts, and continued support as I navigate this journey. There are so many more from Write of Passage. Thank you.