Tips for writing every day

It's been a few weeks since we issued our #100Days challenge, where writers of any level challenge themselves to write every single day for 100 days. Why? To explore. To discover a deeper well from where our thoughts come. At some point, you'll run out of things to say—so what will you write about then? That's the challenge. And make no mistake about it—it's not easy. But you come out the other side stronger. Keener. Sharper. Writing becomes a natural instinct. You never stare at a blank document and think to yourself—there's no way I can fill this with words. You don't think that, because you've done this a hundred times. You've filled a blank space with words over and over again, and now, any self-doubt is annihilated.

What's hard about writing every day is not the writing. It's the doing. It's the discipline of doing something every day. You'll likely encounter the same breed of resistance you encounter when the thought of going to the gym, or cleaning your kitchen, comes to mind: Na, I don't feel like it. That's about it. It's a really shallow affair. You don't want to do something good for you, simply because you don't feel like it. But that, quite honestly, is not good enough. Who's really in control anyway? This simple, pre-historical mind that wants to rest and save energy after every meal? Or the modern being within you wanting to explode with creativity and expression—if only you would let it?

Creativity awaits

If the old Disney-fairytale mentality was, find yourself—it's somewhere within you, and the new modern tale is that you must invent yourself, then writing every day is a play on both. Writing is the act of authorship. It's the act of inventing. It's codifying words into stories and thoughts into expressions. When you write, you build worlds. You see reflections of yourself that are not seeable through any other surface. Writing every day for 100 days is in some ways a bootcamp for your writer mind. If you do make it out alive, you come out hardened. You come out proud. And it's a skill that never ever degrades in value.

When you're confident in writing, you become confident in your communication. You convey yourself better. You're less misunderstood. You make better transactions. If you're entrepreneurially minded, you connect with your customer more. You become a better seller. You build a better company. The skill of writing confidently is the same skill as communicating confidently. It's charisma. And it will be one of your most valuable assets.

I say all this because I've been through this bootcamp, of challenging myself to write every single day, if for no reason other than to prove to myself I could. And the experience has been one of the most valuable in my lifetime.

But, it wasn't easy. There were times when words just emptied onto paper with little friction, and other times when my hands felt like dumbbells and could not be lifted. It was all mental of course, and it's why this exercise is so important. You're letting out that energetic part of you that wants to work, and be creative, and explore, and suppressing that pre-historic part of you that always wants to rest.

There's absolutely no wrong way to go about this challenge, but if you do find yourself flirting with resistance, I can share a few tips that helped me.

A few tips

One is, I always wrote first thing in the morning, immediately after waking up. Your mind is most clear at this point, and I find morning routines to be the stickiest. That is, you can almost sleepwalk your morning routine. Your body tends to internalize it really well. So if writing is the first thing you do upon waking, your body will just let you. It won't try to bother you and tell you to rest, or do other things. It's ready to take on the day. It's why it's common productivity wisdom to do your most important work in the morning. You just grow more tired from there.

You can write with keyboard or on paper. Personally, I did paper for the first half of the challenge. Why paper? One is, it's kind of quaint. It's a lost art. There's something warm about writing with pen and paper. And it's neat when these papers pile up over the course of a few weeks. You feel really accomplished. And it feels real. You can touch your words. I also find that on paper, I'm less likely to edit myself, which is very important for the 100 day challenge. Your goal is to write freely, and without worry. When I write for myself and know that my words will never be seen, I make ridiculous typos and grammatical errors, and don't really care. It's for me. I'll understand it. You want the same mindset here. There are no rules. No one's grading your writing.

Writing on paper also allowed me to feel more spontaneous. I could instruct my hand to just "begin writing" and it would. With keyboard, you kind of have to know what you want to write.

Early in your challenge, the hardest part will be, what will I possibly write about today? But that's not necessarily the right outlook. Your writing does not need to have a topic. You'll find, anyhow, that as you begin to fill your pages with more words, a topic will pop out naturally, without any doing from you.

So, how should you start every day's writing?

Here's the trick: you wake up, prepare your cup of coffee, and come to your desk, where you have before you a stack of 3 white printer paper and a pen. You lift the pen. What's the first thing you write? Literally: the first thing that comes to your mind. DO NOT DISCRIMINATE. I repeat, do not discriminate against this initial strain of thought. It will be your most important. When I say "first thing," I mean it. If your first thought is about your growling stomach, then begin writing "My stomach is growling. I must be hungry." Then, you follow that thought. It will take you to wonderful places. "It must be because I didn't have a good dinner yesterday. You see, usually on Sunday nights I like to cook, but there was this documentary on." And you just keep writing spontaneously like that, until you fill out about 2-3 physical papers. Then type it up. The hardest part is just starting. The rest is easy.

If you simply transcribe what your mind is thinking, then there's no way you fail this challenge. Have you ever observed your mind not chatting incessantly? It's impossible. It just goes on and on, for better or worse. Your job is to simply sample a small timeline of those thoughts onto paper. You're not doing any work here other than transcribing the thoughts that naturally flow through your mind onto paper.

And, if you do run into a point where you think, I simply have nothing to write about today: write about that.

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