The Online Writing Guide

How I Overcame Writer’s Block

After I shut down my corporate laptop around 5 PM, I began to think about the most exciting part of the day:

What I’m going to share with my daily readers tonight?

Before I started writing, I would go on a walk, get some fresh air, and play an episode of Friends. Then, I would ask Chris our dinner plans and unwind for a few hours.

After dinner, I would have 1:1s with my team to talk about key projects and milestones. In today’s 1:1, Elaine shared a challenge, “I couldn’t write a compelling story because I didn’t have relevant personal experience…”

“Bad excuse.”

Here is what I told Elaine, “Look at the news written by journalists. Are they a domain expert on every topic they reported?” Then I went on to address the underlying challenge she faced — writer’s block.

Most authors face writer’s block. Writer’s block could be a lack of motivation, energy, or resources to write up a story. While helping Elaine unblock her writer’s block, I quickly realized that I was the one who needed help.

After writing for 100+ days, I productized the process of turning my inspirations into articles every day. As I wrote this story, I realized a recurring pattern in my life — I was easily bored. I needed new challenges to get ready for the work.

But why the heck do I want to make my life harder? Why don’t I just comfortably sit down, write a short piece, and call it a day?

Maybe I was born this way.

Growing up, I would get myself to do the hardest things. When I started school, I quickly noticed a general curriculum would not work for me. I was terribly bored with what was taught in class. I kept asking myself: “Why can’t the teacher go faster? Why can’t I just read the textbook and skip the rest? Why do I have to sit in for stuff I can easily learn on my own?”

Luckily, my mother recognized my wanting for new challenges, so she borrowed stacks of library books to let me read in the class. She also found tutors and after-school classes to help me learn at my own pace. As a result, I was studying high school math and sciences when I was in junior high school. When I got to high school, I passed the tests and opted out of English and Math classes. I have bought myself so much time. After a decade of learning and growing at my own pace, I knew that I could create and play my own game in life.

In college, I first declared a major in computer science. Algorithms and data structures were different enough to keep me hooked. However, after a year or two, I began to find the patterns and got bored as I finished the concentration requirements. To re-engage my intellectual curiosity, I sought out applied mathematics to up-level my thinking in a new way. After I found the patterns in applied math, I took on Economics too. If time permitted, I would have added a fourth major in political science. By studying each topic, I was able to push my knowledge boundary forward to become the very best version of myself.

I found the same pattern in my career.

I was fortunate to start my career with running my own startups. As my own boss, I could challenge myself to my very limits (which require deep self-awareness). Most importantly, it taught me what dream jobs feel like.

For each of my career steps, I would pick the jobs that could help me learn most. I went on to learn about building products at scale at Google. I then applied my math and CS skills to heading the TA program for Brown’s Data Science Master’s Program. Then I applied my technical and business knowledge to startups and product management. Before I began my full-time job, I started LivingOS, knowing that there was nothing more fulfilling than working on a mission that strongly reflects who I am.

If you take another look at my path, you will see that it’s a path of pursuing self-actualization. By optimizing for the path of higher growth, I was able to get on a trajectory fully aligned with who I am.

My happiness came from my pursuit of personal growth.

If you are interested in adding this high-growth metric to your career, here are a few skills that you might want to build:

If you find yourself losing motivation, try to make the tasks at hand more challenging.

Here’s how I helped Elaine unblock her writer’s block.

First, I asked her to tell me about the content she was working with. Then, I deconstructed the story and picked a few elements that stood out to me. We then brainstormed ideas around the interesting elements. After we gathered together the raw materials, I shared the Nugget Story Writing Framework to help her expand the core idea with concrete examples. This technique is pretty similar to what you learn in an academic writing class in college.

After helping her overcome the challenge, I realized that I was also suffering from writer’s block. Therefore, I decided to apply the Nugget Framework to my writing today. To honor my challenge-seeking nature, I recorded my writing LIVE. I ended up writing two stories in 74min. Check out the live recording here!

The Emotional Journey of Creating Anything Great

After studying the creator industry for a few months, I found that most challenges fall into one of the following three categories:

  1. Fail to prioritize creating over their busy life
  2. Feel obligated to create lots of content and burnout
  3. Succumb to hurtful comments (e.g. Michelle Phan’s Why I Left)
  4. Give up when there is not enough momentum in the first few months

To overcome these challenges, creators need to work on something they are truly passionate about. More importantly, they need to enjoy the process, rather than the vanity metrics. This mindset is universal to anyone who wants to create anything great.

When you take on something challenging, you will go through frustrations. While you may not be able to immediately escape the swamp, you may find it helpful to keep the full picture in mind. The key to keep moving forward is to find something bigger than your biggest excuse.

Take online writing for example. It is very challenging to create interesting and valuable content every day. However, once you can get over the fear of being judged or the worry of producing below your taste, you begin to grow. Then, if you can find an audience that loves your stuff, you start building the feedback loop. Through producing a volume of work, you can close the gap between your work and your ambitions. Keep in mind that people only remember your best work.

  • Can you schedule the time and commit to the task each week?
  • Can you bear with setbacks and push forward regardless?
  • Can you learn from experts and iterate on what you are doing?

If you can commit to all of the traits above, you are on your way to achieve what you want.

Why I Write with Substack

I started my first newsletter in 2017 as I wrapped up Perfect College App.

Life gets in the way, so I didn’t manage to send a consistent letter until earlier this year. Inspired by my friend Valentin, I brought my subscribers from Mailchimp to Revue. I love Revue’s modular design, engagement analysis, and auto-posting features.

However, Substack branding was strong. I took a look at their pricing plan: a 10% fee on all paid subscriptions; free for the rest. I am intrigued by this simple business model, so I moved my subscribers to Substack.

User Interface

The minimalist design stood out. Unlike other newsletter clients, Substack is surprisingly simple to navigate. This interface also reminded of Medium.

New Post on Substack

Though I know my obsession with pretty interface, I totally underestimated the huge influence it has on my creativity.

When I write on Revue, my brain was stuck in the editing mode to keep each section short. I would spend more than four hours writing a letter and still couldn’t finish the piece. On the other hand, when I write on Substack, everything just flows. It took me about an hour to write today’s newsletter, and it has easily become my favorite one.

H️ere’s a comment I received today ❤️

That’s 4x productivity and 10x satisfaction right here.

Value Prop

Substack is built on the opposite value prop of Medium.

Homepage of Substack (up) vs Medium (down)

If you look at Medium’s homepage, you will find that the best post will surface, regardless of the writers. On the other hand, Substack is built around writers — it is built on the thesis that people would subscribe to voices they trust.

Creator Community

I am super impressed by the newsletter quality on Substack.

Here are just a few of my favorites to start:

Free Newsletter For You