If you feel like you never have anything interesting to say, e.g. you:

  • struggle with small talk,
  • can’t hold a conversation with someone,
  • shy away from connecting with people,
  • suffer from “writer’s block”,

then this bite-sized essay is for you.

There are a few bad habits that cause you to hesitate expressing yourself. Here they are in brief:

  • Self-censoring: You might believe that whatever you want to say isn’t good enough. You might think it’s not worth saying. This is not true. Not every story needs to be about wild adventures or rare occurrences. People have mundane conversations all the time and find them fun. Anything you have to say can be made interesting if you present it as a story.
  • Bailing: You start telling a story but you justify and explain yourself. “So yeah umm, that’s it”“I thought it was interesting”“I certainly think so. You might not. It’s my opinion.” This is a bit of a chicken and egg situation. People will enjoy your stories if you think they are enjoyable and structure them well. But to structure your stories well, you need to learn what people enjoy. If you’re an absolute beginner, start by auditing your stories to find the point in them. What are you leading up to? Then when you tell that story, make that point at the end. From there, pay attention to what people enjoy and don’t enjoy. You’ll pick up habits to stop you from bailing.
  • Transacting: You experience your life as a series of events one after another. Storytelling involves feelings. Get into the habit of checking in with yourself – how do you feel about something that just happened? That’ll give your stories an external dimension (what happened) and an internal dimension (how you felt about it). That makes your stories richer and more interesting.
  • Monologuing: You share your stories and opinions outside of context. If I’m talking to someone about coffee shops, I’m not going to tell them a story about the time I deadlifted 110kg. It’s not relevant. In a conversation, ask yourself “what does this remind me of?” You’ll find a relevant story to share. A conversation is a game you’re playing with someone. Have fun and go back and forth. Don’t be anxious to share your one cool story. Find a relevant continuation of the conversation you’re having.

All these pitfalls apply to conversations with people in real life, as well as writing online.

To be an interesting writer online:

  • Choose anything that interests you. That’s good enough to be written about (no self-censoring).
  • Put together a story that leads up to a point and make it with strength and style (no bailing).
  • Give that story multiple dimensions by explaining why the event mattered and how you felt (no transactioning).
  • Write again, based on what your readers (or singular reader) find interesting (no monologuing).

For example, here’s an offhand story. See if you can identify how I tackle the four barriers.

I’ve never been a fan of travel. When I was a child, my father would take the family on vacations every 3 years to different parts of India. It was my privilege to see so many places – Jammu, Goa, Kodaikanal, Ooty, and more.

But I never enjoyed these vacations because our family is middle-class, which means that we focused on maximizing value, not enjoying ourselves. My memories of vacationing are me being dragged to 8 places a day. We had to “see everything” so that we got the most value out of the trip.

As a result, I didn’t look forward to vacations even as I grew older. As an adult, I’ve worked myself into burnout because vacations are just as hectic but less productive. I hated travel, even intracity, and became a homebody. I worked from home for 5 years before it became the norm. For years, I stopped going out altogether, and needed a task or a job to justify stepping out.

However, earlier this year, I changed jobs and took a short break in between. I didn’t really have the patience to travel out of town, so I tried to travel intracity as much as possible. To make the effort frictionless, I invited several friends to coffee dates. I went out 8 times in 2 weeks.

It did feel hectic, to travel all over the city meeting people day after day, but it felt good. It was the good kind of exhausting. One-on-one conversations are my favorite kind, and spending a couple of hours talking to people made the travel worth it.

Since then, I’ve started working at my new job, but I’m making time to go out once every couple of weeks and meet someone.

In fact, I’m trying to get to my favorite coffee shops across town every Friday. I sit alone and write for a few hours, and I invite friends in the area to meet. If they come, great. If they don’t, I’m at least getting some writing done.

I’m excited to see if this intracity travel project evolves into a desire to travel to other places. By going out whether I’m meeting someone or not, I’m building the patience and stamina to travel alone without agenda.

These are my baby steps to redefine my relationship with the outside world.

Don’t be afraid to tell stories.

Find a narrative and make it interesting. You’re a human being, which means you have unlimited stories to tell.


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