The Writing Challenge!

“I have always been driven to see what really happens when I throw myself at something. Unless you really do that you will never find out. I think I would be sad if I never found that out — If I don’t I would not know my potential is.” 

Jimmy Chin.

In 2017, over Christmas break my friend Aurora, co-founder of Megacool, and I decided to challenge each other to a writing contest.

The challenge lasted for 7 days, we would each write 1 article per day, send to each other for feedback and published the next day. If either of us failed to complete the challenge we would have to run the San Francisco Half Marathon or donate $250 to a Trump organization. If we succeed we would buy each other new workout gear. (Such a San Francisco style gift!)

The Start

The main intention of the challenge for me was to prove to myself that I could commit to writing something every single day and I needed a bit of a kick in the ass to get this done or started.

I always get asked about my journey building a technology startup and what I do every day. I have been meaning to start a blog to get my story/voice/thoughts into the universe, to inspire others and to connect with like-minded individuals. But each time I started, I basically came up with an excuse that prevented me from starting. I need a plan for the articles and/or a better looking personal site etc. etc.

So, ss Sol Lewitt writes:

“Learn to say “Fuck You” to the world once in a while. You have every right to. Just stop thinking, worrying, looking over your shoulder, wondering, doubting, fearing, hurting, hoping for some easy way out, struggling, grasping, confusing, itching, scratching, mumbling, bumbling, grumbling, humbling, stumbling, numbling, rambling, gambling, tumbling, stumbling, scrambling, hitching, hatching, bitching, moaning, groaning, honing, boning, horse-shitting, hair-splitting, nit-picking, piss-trickling, nose sticking, ass-gouging, eyeball-poking, finger-pointing, alleyway-sneaking, long waiting, small stepping, evil-eyeing, back-scratching, searching, perching, besmirching, grinding, grinding, grinding away at yourself.

Stop it and just

DO”

What I Learned

On day 7, I can successfully say that I have accomplished this goal.

Here are four key insights I learned from this challenge and will apply to my life going forward.

1. Quantity leads to quality.

The average article took around two hours to produce a draft. With one article taking 20 minutes and another taking 6+ hours. Is the article that took 6+ hours that much better than the 20-minute article? The majority of the articles were quite generic — with a few insights here and there but no big picture, connecting the dots, exploring real insight or depth.

I wrote similar to Fred Wilson vs. spending real-time to produce content that will be referenced for years, as Paul Graham.

Looking back on the 6 articles I wrote helped me to find my writing voice and gave me an understanding of what topics I am motivated to write: long thought out Paul Graham style essays.

“Every great composer practiced for at least 10 years before they wrote their master work.”

Malcolm Gladwell

2. Magic can happen when in the zone.

Each day the topic that I wrote about was based on experiences I had that day and I would free flow to write. I do believe that true genius can arise from that which is not planned.

That is the moment of magic.

Jonah Hill for the movie “The Wolf of Wallstreet” improvised his entire performance. He was in the zone and had been rehearsing for this part his whole life.

In addition, Melissa McCarthy for her role in Bridesmaids improvised the majority of her part. It’s that moment when you train your whole life for that overnight success.

3. Do it every day to see if it sticks.

After writing every day for this writing challenge for an entire week I realized how much I enjoyed this process. By doing it every day forced me to turn this into a habit which now I can see the value in making writing a normal behavior.

Marc Zuckerberg coined the term “done is better than perfect.” In startup land, you will hear people say over and over “just ship it.” Getting the product out into the world to get feedback as soon as possible.

4. Your best work cannot be forced.

“I just took a deep breath and it came out. The whole song. Stream of consciousness: words, music, chords. Finished it. I mean, I just played it into a tape recorder and I played the whole song and I never played it again. I actually only spent three and a half minutes on that whole song. So I’d come back for days playing that tape, thinking there must be something wrong here because this just came too easy. And then I realized that there’s probably nothing wrong at all.”

Tom Petty.

By forcing myself to write each day I might not have been always producing the best work. Each day there was pressure, feeling of being rushed and this pressure and time constraints can stifle creativity. In conclusion, similar to the philosophy in which we have built our startup, Roomhints — if you are not shipping anything you are not learning,

From this writing challenge, I learned that I loved to write but cannot write good quality content every day. Therefore, going forward I will strive to write every day and post the essays/articles that I feel are worthwhile for the world to read.

Thank you for joining me on this writing journey and reading what I write.