On Becoming A Writer

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When Jeff Nobbs (my partner) and I returned to San Francisco last September after several months on the road, I fell into a deep panic because I didn’t know what the heck I was going to do next with my life. Naturally, the most frequently asked question of us at that time was: “So, what’s next for you guys?”

This anxiety was further magnified because Jeff always had a good answer to the question — he had many options awaiting him, and by October, he’d picked one and pursued it. Yes, yes, I know comparison is the thief of joy, but I felt like I’d regressed to my post-college years, totally clueless as to what my life calling was, what I was good at, what I enjoyed and where I might add value. I was simultaneously paralyzed by the infinite optionality put forth by modern society. At one point, I’d listed out 30+ career paths I would be interested in exploring further, one of which was a “Wholeness Mentor” — like wtf is that? I don’t even know.

For the next couple of months, I worked on a project here, a project there, and explored, however briefly, what it would be like to start a business with my best friend. It was fun while it lasted, but I came to realize while I liked the idea of being an entrepreneur, I didn’t actually like being one. The zealous city of San Francisco and its people had primed me into thinking everyone and anyone could be an entrepreneur, including myself, but when it came down to it, I, quite simply, didn’t enjoy the day-to-day of being one, of always having to be “on” and having to answer to everyone and their mothers. I’d deluded myself into believing I wanted to be an entrepreneur, but I quickly realized: 1) I’m not that motivated by problem-solving, and 2) I’m not that ambitious.

These are lamentable things to admit to yourself, especially living in a city that often feels like it’s populated by the world’s valedictorians, over-achievers and people who won “Best All-Around” in their high school yearbook, where every single person wants to change the world for the better. To admit that I didn’t care much about making the world a better place without eroding my sense of self-worth was tough, really tough.


I didn’t want to go back to a typical 9-to-5, or even to a more flexible, remote arrangement. Because I lack a technical, hard skill, most jobs I had in the past emphasized soft skills — communication, management, organization — and while I realize these skills are, to some extent, valuable in organizations and teams, to me, it felt like a lot of paper-pushing, “lobbying,” playing games of telephone, sitting in unproductive meetings and appearing busy rather than truly producing anything of value. I felt deeply unsatisfied and unfulfilled.

At every company I’d ever worked at, I realized, I had been dispensable, replaceable. Sure, I was missed by colleagues and it took a few weeks, maybe months, to find and train someone new, but I didn’t have the kind of impact I’d hoped to have, nor did I create or produce anything tangible or lasting to show for it.

Around this time, I read Deep Work by Cal Newport, and I saw how most of my days had been spent performing shallow work. I grew desperate, hungry even, for the ability to sink into extended periods of deep, profound, uninterrupted thinking and work that would challenge and fulfill me.

I wanted to create something I could stand behind and call my own. But what was that something? What could I do that didn’t involve going back to school, starting a business, teaching myself to code and ideally, didn’t require starting from ground zero?


Writing had always been my most loyal secret lover, though I didn’t dare associate myself with it or consider myself a writer publicly. At best, I was a diarist, maybe. But a writer? Most definitely not.

I started my first blog in 1999, first on Blogger and then on LiveJournal, where I unabashedly and quite explicitly wrote about my exploits as a teenager. (It’s horrifying to read those entries now — do not ask me for them.) Since then, I’ve flitted around with writing, treating her like a small-town first love who was always readily available for me to dump all my shit on when life got hairy in the big city.

Throughout my teens and 20s, writing was the lover who was always reliably there, even though I was disloyal, non-committal and unappreciative. Sometimes, I’d go away for months or a year, but eventually, I’d crawl back to her and dump my burdensome, black ink onto her pure, white pages.

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I had always loved the idea of being a writer, just as I had with being an entrepreneur, but perhaps even more so. To me, writers have a golden glow about them. A writer is the most honorable and privileged thing one can aspire to be. To be a writer is to join a highly exclusive, elite club. To write is an act of the highest order, an act reserved only for the worthy. And so, with all that in mind, the idea of becoming a writer was impossible, forever unattainable. I am not a writer, I thought, and will never be a good writer. I will never be worthy of such a club, so why try?

I don’t have any of the qualities often associated with writers: I wasn’t (and am still not) a voracious or fast reader (I didn’t read much at all until my late 20s), I didn’t major in English, literature or journalism, I neglect grammar, I’m not particularly observant and hence am not great with descriptions — metaphors do not come easily or naturally to me, and the saying “show, don’t tell” always sends me into a frenzy, my vocabulary is far from extensive (I blame this on English being my second language, but the truth is, I’m just lazy).

Yet, I continued to write, secretly, of course, not for anybody else, but for myself. Because the singular act of writing was the one thing I enjoyed, the one thing that energized me, the one thing I lost track of time doing. It still is.


Last November, in a state of total boredom and dismal idling, I decided to fuck all and explore what “being a writer” might mean and look like, just for a couple of months. I wanted to see if I was just in love with the idea of being a writer, or if I would actually like the day-to-day of what being a writer entails. If I hated it, I figured, nobody would ever need to know.

So I challenged myself to write every single day for the next however many months, without worrying about what I wrote — short stories, poems, blogs, journal entries, vignettes, whatever came to mind, whatever piqued my interest, whatever poured out of my heart or mind, would be acceptable. This wouldn’t be for anybody but myself. And in the beginning, I wrote strictly for myself, but after a few weeks, some of my writing started to evolve organically towards an imaginary audience, an imaginary friend. There were many days when I’d spend 8, 9, up to 10 hours a day writing, brainstorming, editing, researching, reading, re-writing, and the weeks began to flutter away like autumn leaves.

Fast forward to today, I still find myself waking up every morning excited and energized by the prospect of writing. On days when I have errands to run and a limited amount of uninterrupted hours to focus on writing, I feel agitated and misaligned. I still don’t feel like a writer — imposter syndrome is a real thing — and on days when I wake up on the right side of the bed and can say to myself those three, simple words: “I’m a writer,” I quickly shoot myself down because I’m not yet a good writer, and if I’m not a good writer, I’m not a writer at all. So I tell myself.

These thoughts continue to permeate my headspace, but what’s empowering is the recognition that I don’t care anymore if I’m a good writer — my love for the act and process of writing far outweighs my self-doubt. And if I persist, I know I’ll get better in time, even if it takes me decades to get from average to good, from good to great.

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In January, I decided to dedicate this year (and hopefully more years to come) to writing, to see where it takes me. It’s taken me a long time to work up the courage to write daily, to call myself a writer, and now, to share this with all of you.

I’ve started so many projects, ideas, Instagram accounts in the past only to leave them all unfinished, I think I may have worked up a reputation as a non-finisher or quitter. I worried the same pattern would repeat itself here with writing, which is why I’d been elusive about what I’ve been up to with friends and family. I wanted to spend at least a few months doing what I say I want to do before talking about it. I didn’t (and don’t) want to abuse their trust, their attention, their support, until I had something concrete to show for it, until I knew this would be something lasting, something I intend to wholeheartedly pursue.

Last month, I started writing more regularly on Medium, and launched this website, which houses a collection of some of the same posts. My intention is to continue to write and publish on both of these platforms, and over the next several months, to narrow my niche, discover and develop my “voice,” grow a loyal readership base (which I hope will include some of you), and to continue to improve my craft.

In some ways, this is one of the scariest things I’ve done in a long time — to open myself and my innards in this way — to surrender myself to encouragement, discouragement, feedback and criticism on something that is so deeply personal and important to me. But I’m finally ready for it.

With that, I thank you for making it all the way through this (unnecessarily?) long post, and invite you to read and follow me on Medium or via this site. Likes, claps, follows, shares, comments, grammatical corrections and feedback of the positive, neutral or negative variety on my work are welcome — I just ask that you make it constructive if it’s negative.

If you’d like to receive my monthly newsletter which spotlights my most recent musings as well as what I’m reading, listening to, thinking about, you can sign up for that HERE.


Special thanks to Jeff Nobbs, my beyond supportive partner, who not only encouraged me to pursue such a path, but has provided me the space and time necessary to truly see something like this through. Also, a shout out to my dear friends Paulina and Sajjad, two incredibly talented writers, who continue to trust and inspire me with their creations.

If you enjoyed this post or if these words resonated with you, I thank you in advance for however many claps your thumb or index finger can manage.