How To Overcome The Fear of Writing
3 Years and 3,000,000 Words Later
You’re not a writer—Stephen King is a writer.
You can’t write anything about marketing—Seth Godin has written it all.
No one wants to read your opinions—everyone has their own opinions to sort through.
You have no writing credentials. You didn’t go to school for writing. You’re terrible at grammar, punctuation, and using parentheses. (I still don’t think I do this “correctly.”) People don’t need yet another thing to read.
Three years ago, those were the thoughts that filled my mind as I decided to commit to becoming a full-time writer. Now, granted, I didn’t actually realize I was committing to becoming a full-time writer. I had merely decided to step away from a business and the audience of 25,000+ people that came with it. I had decided I would instead share my experiences as an entrepreneur—the real experiences, not the hacks/tips/secrets/3 easy steps that pepper the headlines of prominent media outlets.
But when you have zero experience writing, except for 140-character messages to random strangers on Twitter, where do you start?
From everything I read, I had to build a writing practice. And from the experience I had filming daily YouTube videos, this made perfect sense. When I started filming daily videos for my previous IWearYourShirt business, I had absolutely zero experience (the same experience I had as a writer). But I went from nearly soul-crushing thoughts of self-doubt and overwhelm to creating over 2,000 videos with millions of views. The first videos I created were cringeworthy; in fact, I still can’t watch them. My writing would probably follow suit, and that needed to be okay. Just as I forced myself to film a video every day, no matter what, I would sit down and write, no matter what.
Starting with a daily writing practice
Based on my research, I committed to four things when I made the decision to stick to a daily writing practice:
Write 500 words at the same time every morning (and block off the time on my calendar).
Write without judgment or concern for the writing being “good” (or even coherent).
Be completely okay with the fact that all 500 words might be 100% worthless.
Stick to a daily writing practice for two months.
And so I committed, starting on June 1, 2013. I didn’t have a repository of writing topics. I didn’t know exactly what I wanted to be writing about. I just knew I wanted to try out this writing thing.
The first few days? Not fun. As soon as my butt hit my blue yoga ball (what I sat on at the time), the doubts I wrote at the beginning of this article ran rampant through my mind. But instead of letting those thoughts control me, I fought them by hitting the keys on my keyboard. Without a succinct topic to write about, I’d just write my exact feelings or stream of thoughts.
Related article: 800,000 words
Day after day, the writing practice got easier. The pressure I put on myself to write something worthwhile started to lessen. Once every couple of days, I’d have an idea for an article that seemed interesting or that I thought may be valuable for other people. There was no Action Army back then. There were no Road Runner Rules. I had no idea who I was writing for or why I thought they would even want to read my writing. I just wanted to share my thoughts.
In the beginning, I did what came easily: I shared my life
Coming off a business where I hosted a daily live video show that shared 90% of my life, I knew I could make an easy transition into writing something similar. Instead of trying to create some fancy way of writing or spending arduous hours trying to figure out interesting topics, I’d just leverage something I had at my disposal: my life.
“Sharing my life” was familiar to me, but it also looked a certain way. During my days of hosting a live video show and representing a different company on my t-shirt every day, I couldn’t have bad days. I couldn’t complain, be upset, or be honest if I was feeling pressure and stress. That would reflect negatively on the brand that was paying me, and I knew that wasn’t fair to them. Sure, I probably should have seen the writing on the wall that it wasn’t a healthy way to operate my life/business, but we all make mistakes.
My writing efforts veered onto a new path when I started getting vulnerable.
Once I removed the shackles of worrying about representing a company, I felt the freedom to share what was actually going on. I felt a burning desire to let the world know that everything wasn’t okay, because I knew everything wasn’t okay for other people as well (or at least I hoped I wasn’t alone in thinking that).
That shackle-removal was the best thing I did for my journey into writing. Being more vulnerable and honest about my life and business pushed away people who only wanted to see a perfect life and pulled in people who could relate and who shared my thoughts and feelings. Writing about Feeling Lost, Letting Go, Friendships, and various other topics attracted the types of people who were going through (or had gone through) similar things. And when they commented or emailed to thank me for my words, it was a life-changing revelation to me:
I could be real about things not going perfectly, and people wouldn’t scatter away like cockroaches when you flick on a light in a dark dingy motel room.
Defining who you are writing for is helpful, even if that definition changes over time
Defining the audience I was writing for was extremely painful for me, but I knew it was necessary. I had seen with my previous business that having a very broad audience led to a lot of surface-level connections. Without a deep-rooted (and defined) connection, those audience members would leave at the drop of a hat to find the next shiny object. Luckily, my life partner eats bowls of soul-searching-deep-rooted connections for breakfast.
I had countless conversations with my girlfriend, Caroline, about “who I wanted to be writing to” and “why I wanted to be writing to them.” Just typing those words makes my stomach do a slight turn. Not because it’s cliche or extremely commonplace to think about those things, but because it felt so limiting and constrictive to me.
How I thought about defining my audience: This will limit the amount of people I can attract, which will limit the amount of money I can make, which will make me feel unimportant and not unique.
How defining my audience actually makes me feel: I have attracted a specific group of people who can benefit from my writing. I’m empowered to know I’m making an impact on people’s lives (impact > number of eyeballs).
Bonus resource: I sweet-talked Caroline into letting me share the Ideal Audience Profile PDF that we used to help me define my audience. This PDF is actually only available in her Better Branding Course, but you’re getting it for free because I’m a master negotiator (and because I agreed to do the dishes a few extra nights).
As I’ve written this article, it’s for the Action Army, a group of people who want to take control of their businesses and do things in ways that align with who they are (not who society says they should be). But the Action Army could transition into something completely different in six months or two years. I’m 100% okay with and open to that change, because I know I’ll continue to evolve the definition of who my writing is for.
Writing is always evolving, but should also always be useful
I didn’t have the Road Runner Rules exercise when I first started writing. Instead, I had one guiding principle: I wanted my writing to be useful to other people.
Actually, I think I had two guiding principles: My writing would be helpful, and I would avoid the awful trend of articles that start with “27 tips to…” and “6 important hacks for…”. Sure, every now and again, I’ll write an article that has a number in the title, but out of my past 100 articles, only 8 of them have had numbers in the title. I’d say that’s sticking to my second writing principle.
Whenever I sat down to write or finish an article, I would ask myself, “Is this useful?” The answer means 90% of my writing never sees the light of day. It’s not useful. It’s just words, jumbled together, often without a cohesive thread. I keep doing it because I like the writing process, but I’m being 100% serious when I say I have 24 articles in drafts right now, most of which are between ½ and ¾ complete because they’re not really useful. Yesterday, I wrote an entire article about what I learned from taking out my smelly trash. That was fun, but I think I’ll trash it. 
