5 Lessons from My First Year as a Writer

I started writing to help people.

At the ripe age of 24, I had graduated from an Ivy League university, elevated myself out of poverty, and procured a fulfilling job that allowed me to work from anywhere in the world.

For the first time in my life, I felt a deep and enduring sense of calm, gratitude, and joy. I wanted to help other people reach this state of fulfillment, and I felt that what most of us learn from society, friends and family, and formal schooling does not help us get to this enjoyable place.

And while I still had a lot of things to figure out, I felt that I had uncovered at least a few of the universal ingredients to the secret sauce for creating a meaningful and fulfilling life. I chose writing as the medium to start clarifying and sharing those ingredients with others. Writing became my path to paying it forward.

It’s been a year since I started my journey as a writer, and I wanted to share a few of the unexpected lessons that I’ve uncovered along the way.

1. Learn to conquer self-doubt, or you will not write.

“If you hear a voice within you say ‘you cannot paint,’ then by all means paint, and that voice will be silenced.” – Van Gogh

Writing is a journey riddled with self-doubt. As you embark on this journey to find the words that accurately express your thoughts and ideas, you grapple with a scary little voice:

“What makes me qualified to talk about this topic? Is what I’m saying worth talking about? I have no talent. Should I just stop trying?”

If you want to be a writer, you must learn to accept, understand, and live with this self-doubt. No matter how much you write or how good your writing is, it doesn’t go away. Steinbeck captured this self-doubt beautifully in a diary he kept while writing The Grapes of Wrath, a book that earned him the Pulitzer Prize:

“My many weaknesses are beginning to show their heads. I simply must get this thing out of my system. I’m not a writer. I’ve been fooling myself and other people. I wish I were.”

“If only I could do this book properly it would be one of the really fine books and a truly American book. But I am assailed with my own ignorance and inability.”

“This book has become a misery to me because of my inadequacy.”

Self-doubt is an inherent part of the writer’s journey. I certainly have not been immune from this scary facet of attempting to produce work worth reading. While I sit at my computer on a sleepless night, I wonder whether what I’m saying is worth talking about. I wonder if I’m wasting my effort during my brief time on this earth. I wonder if the self-doubt will eventually defeat me.

My approach to this self-doubt is to accept and embrace it as a part of my work. And with this genuine acceptance, I’ve found the courage to keep going. I’ve been able to survive the times when the voice gets louder. And every time I make it through and finish a piece, I’m glad that I did.

Learn to conquer self-doubt, or you will not write.

2. If you want to be a writer, start writing.

People assume that I’ve been a writer for years. When I tell them that I’ve only been writing for a few months and that they can write as well, they believe that I have formal training or a natural talent that they don’t. As much as I’d like to have these things, it’s not the case. I learned English growing up and wrote papers in college, but that’s it.

To be a writer, you just need to write. You don’t need formal training, a robust lexicon, or natural talent. Becoming a writer starts with opening a blank page and attempting to express your thoughts. This process is incredibly challenging. More often than not, I spend countless hours staring at a screen and failing to write anything worth reading.

But if you just start and keep going, a beautiful journey unfolds. As you think deeply about the topic at hand, your muddy thoughts turn into a few clear sentences. You continue writing, and you start to see a path through the fog. You keep chopping down the limbs hanging in your way and trust that you’ll eventually find the sunlight.

After many more hours of work, you see a small beam of light that lets you know that you are close to distilling the mess into something that another person can understand. After a few more rewrites, you accept the imperfect nature of your work, and you hit publish.

Sometimes this process leads to a great article. Most times, it doesn’t. Every time, it makes you at least one percent clearer on your thoughts about the topic at hand.

Over time, writing gets a little easier, but not much. You experiment with new techniques. You start to find your voice. You settle into the imperfection. Along the way, you learn to live with the self-doubt and rest easy knowing that you’re doing your best. You accept that good enough is indeed good enough.

To become a writer, you need to brace yourself for this challenging journey and start writing. Stop waiting. Stop analyzing other writers. Stop looking for courses to take.

If you want to be a writer, start writing.

3. To teach and inspire, tell a story.

I write articles to communicate ideas, values, and principles that have empowered me to find a fulfilling path. I hope that readers of my work walk away with practical thoughts and ideas that they can use to improve their life.

To be effective in this pursuit, I must master the art of teaching and inspiring with words. This is not an easy task. People are very different. We all have unique contexts, motivations, and ways of understanding information.

My experience as a writer has shown me that good storytelling can help solve these challenges created by our individual differences. For example, imagine that I want to teach you that paying it forward is an important value that you should start practicing. Here’s one approach:

“If you learn to pay it forward, your life will improve. Harvard studies show that people who spend time helping others are 45 percent happier than those who don’t. In addition to increasing your personal happiness, paying it forward makes you more likable, and being perceived as more likable increases the number of job opportunities and life partners available to you. You should consider paying it forward if you want to live a good life.”

This prescriptive, data-driven approach is the norm in our science-obsessed world. But let me introduce a different approach. Let me tell you a story:

“As a teenager growing up in poverty, I believed that getting into an Ivy League school would help improve my circumstances. When I was 16 years old, a complete stranger, Howard Sherman, took me under his wing to help me in my pursuit. He taught me about the Ivy League admissions process, helped me craft a compelling personal narrative, and funded my first trip overseas. With his help, I was accepted to Princeton University, and my life has been on an upward trajectory since then. For all of his help, all Howard asked of me was that I pay it forward. To Howard, paying it forward was at the center of living a meaningful life. Sadly, Howard passed away of cardiac arrest a few years ago. I continue his legacy by finding small ways to pay it forward every day. Without him, I might still be a poor kid in Orlando.”

Which approach would inspire you to think more deeply about spending more time paying it forward? As long as you’re not an API, the story wins every time.

Stories are an ancient art form that have helped us survive and bond for thousands of years. They communicate our values, experiences, and understanding of the world in a way that the prescriptive, data-driven approach cannot. And in doing so, they have the power to increase empathy, shift our attitudes and beliefs, and inspire us to take action.

To teach and inspire, tell a story.

4. Vulnerability builds deep, genuine connections.

A week after I started writing and began my mission to empower 10 million people to live a more conscious and fulfilling life, my mom committed suicide. This was a soul-penetrating blow.

But instead of separating my writing and mission from my personal story and pain, I shared my experience knowing that I was not the only one suffering. I wrote about the lessons my mom taught me, my attempt to find meaning in my suffering, and my mom’s path to suicide.

In candidly expressing my most vulnerable thoughts and experiences, I received hundreds of messages from people across the globe. I spoke with people who decided not to commit suicide because of what I said. I heard from individuals who were suffering deeply and who revealed that suffering to me, a random stranger, for the first time.

Not only did these conversations allow me to connect with others and help them confront their pain, but they also helped me understand and process my struggles. This was a powerful co-created experience.

Vulnerability takes courage, but it’s worth it. It requires us to get comfortable with expressing our authentic selves, regardless of what others might think. Learning to embrace and share my vulnerability has been immensely valuable. It’s allowed me to connect with complete strangers, deepen my relationships with people I know, and better understand how pain and suffering are indispensable parts of the human experience.

Vulnerability builds deep, genuine connections.

5. Writing is a messy, weird process.

Earlier this year, a piercing thought overtook me while I was swimming laps on a hot afternoon in Nicaragua. The thought instructed me to write about practices that have improved the quality of my life. I stopped swimming immediately, grabbed my laptop before drying off, and sat on a beanbag for 4 hours frantically writing what later became 12 Practices That Have Improved My Life, an article that has received significant attention and praise from readers.

What’s bizarre is that I had no intention of writing that piece. The idea consumed my being without notice and at an inconvenient time, and for some reason, I couldn’t shake the thought. And while my first draft required weeks of editing and refining, it eventually became a list of practices that have inspired and helped many people on their journey.

The more I write, the more I’ve learned to embrace these unexplainable moments where an external force exerts its influence and yanks me in an unexpected direction. Instead of resisting or trying to understand this force, I accept the calling, stop what I’m doing, and start writing. At the end of this process, which sometimes occurs in the middle of the night when I’d rather be sleeping, I trust that something important or meaningful will result.

Sometimes, I wish I could have a more regular writing process where I develop and prioritize a pipeline of articles, do the research, write the piece, edit, and hit publish. But that’s not how my writing process looks. More often than not, I wake up at 3am with a surge of anxiety and an idea that imprisons my mind until I open up my computer and discover what my muse wants to say.

Writing is a messy, weird process.

If you decide to become a writer, brace yourself for a wild ride. It’s a uniquely fun, frightening, and rewarding journey. I wish you luck.