18 Lessons I Learned from Failing to Write Every Day

Notes from the October Daily Writing Challenge

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October was a pretty big month for me.

I made a commitment to myself to publish on Medium every single day. In my head, I was gearing up for writing an entire novel in November for National Novel Writing Month (NaNoWriMo) — so much so that I’ve even booked myself a week in Copenhagen to see out the month and to finish it up.

I was feeling fancy.

27,706 words & 18 Published Blog Posts Later

Well, I kind of failed in my target. I also have 13 unpublished posts sitting across my Medium drafts and my Macbook. That’s 4,615 words in draft.

That means that in October, I wrote 32, 321 words.

That’s a great deal more than I’ve written the entire rest of the year combined. In fact, up until October, I’d just about managed to publish 16 posts, which come in at 20,898 words.

So it does seem I’ve upped my writing game — and I guess that was the point.

And, yes, I failed my daily writing challenge. But here’s what I learned in the process.

1. The world didn’t end just because I didn’t make my goal.

In fact. Nothing happened. Nobody even noticed, probably. Except me. And it certainly doesn’t matter. I’m still here: breathing, thinking, writing, working – and it’s just possible I’m doing all those things better precisely because I did not make my goal.

2. That was just the beginning.

At the outset I thought I’d give it a bash. See what was possible. And I genuinely thought once I got to 30 days that would be it — experiment over. But as it turns out, that was just the beginning.

3. I improved.

My writing style got better. I wrote faster, clearer and more succinctly. My thought process straightened out a bit. I got better at headlines, subheadings and SEO. I got better at editing — I’m more ruthless, more constructive, and, compared to a month ago, I think my knack for writing is just better.

4. I Let Go of Perfectionism.

One of the things that held me back from blogging, writing and publishing previously was this debilitating, paralysing perfectionism. I had a huge attachment to the outcome.

Forcing yourself to write whole essays and then often publishing them the same day meant I couldn’t afford to worry about it being perfect, or even good enough.

“Done is better than perfect,” is my coach’s motto.

I’m inclined to agree. No one is reading, engaging with, commenting on or following me because of my unpublished work. Nobody.

I surrendered to practice and I let go of perfectionism.

5. It is actually WORKING

Or to put it another way — I realised my previous idea of what success is was pretty detrimental to my mental health, and I hadn’t actually considered the in-between bit — when things are just working, and what that might look like.

All throughout this entrepreneurial journey, I’ve been so focused on the results — on this idea of ‘success’. It kept me going, but it was a giant figure plucked from thin air. I had never actually given any credence to alternatives — and to what ‘working’ actually meant. Like, rather than think of success, think of what would it mean for it all to just work, and for me to be happy.

This idea of success had put me under a shit tonne of pressure and I was drowning chasing it.

But when I look at it from a perspective of what would it look like for it to be working? — as in I am getting what I need from it? — that means writing daily.

If that happens, then it’s working.

This month’s daily writing challenge got me out of that exhausting ‘(chasing) success mindset’ and into a more practical ‘working mindset’ — and I feel a lot healthier for it. I am more productive, more positive, and funnily enough, I feel successful…


6. Gratitude

I actually write for myself. It’s cathartic, it’s therapeutic, and it’s also a snapshot in time of where I’ve been, what I’ve been thinking about or what I’ve been working on.

I haven’t really yet mastered the whole write-to-help-other-people thing. I’m still processing a bunch of shit and trying to make sense of life. But when people take the time to read my work, or they share it or comment on it — it blows my mind. I’m beyond grateful. I’m humbled. And it pushes me to be better — for myself, and for the people who take the time to stick around and read it.

7. I’m Growing Faster

Any kind of daily practice is a pretty good stomping ground for personal development.
I always said to my yoga students that if you practice once a week you’ll get some benefits. But if you practice every day, your progress will be exponential.

That’s how this month has felt in terms of my own writing practice. I’ve covered more ground, got more done, and Jesus, I’ve learned all these lessons — just from one experiment that technically failed.

That’s growth.

8. I Got Closure.

Sure, I could just leave it for my journal to let me process and heal. But when I take those ideas and work them through, develop them (and maybe even close some of them out!!)… and then…. I freaking publish them? Ha!

It has put an end to my Pure OCD, kind of. It put a stop to the endless and dementing cycle of going round and round and round and round the same old problems.

I got closure, and I moved on. Now I feel like I’m in some kind of new part of the universe, or my mind, which I’ve never even got close to before. It’s spacious.

9. Freed up Mental Space & Completely Reframed my Productivity

In Getting Things Done, David Allen talks about the alleged advantage of to-do lists. They’re meant to be a place to dump our tasks and obligations so that we don’t have to carry them around and have them take up headspace all day — that’s the idea anyway… In practice, to-do lists are notorious for that not being the case.

Anyways. Once I started taking ideas and developing them, running them into full-blown blog posts, and publishing them — all of a sudden they were out of my mind, off my plate, and released into the world. I was free of them. Free to move on to something else, with a hell of a lot more headspace and capacity for more… stuff.

More writing. More fun. More life. I seemed to have escaped the trap of overthinking.

10. I did not run out of ideas

I was highly concerned (and 99% sure) that I would not be able to find something to write about for 30 days — that was my excuse and I held on to it for grim life.

Until last month. Obviously, I didn’t publish 31 posts, but I embraced my fear, tackled it head-on, and sure enough, I didn’t actually ever run out of ideas in that time.

In fact, the opposite happened. I have too many ideas. They keep coming. It’s kind of overwhelming.

I went from being tight and fairly blocked to ideas, to being an idea machine. I’m definitely not promising they’re all good — they don’t have to be. But a daily practice of writing or creating basically taps you into the ideas vein, and I’m pretty confident that — contrary to my fear — it’s an infinite resource.

11. I Get Resistance like a MoFo.

Oh dear. I admitted it. Resistance comes to me every day.

That’s the reason I don’t have 31 blog posts published. The resistance was huge. But I did publish 18, so that’s a massive up-yours to resistance.

I hope I gave him a run for his money. I hope he realises I’m serious. I hope he realises I’m not afraid of him. And I hope — I’m not holding my breath or anything — but I hope that he stops visiting me on a daily basis. He’s a pretty shitty guest to have around, he’s not welcome and I don’t like him. So I’ll just get back to my writing thank you very much. Resistance, you can F-off.

12. Doing Pretty Much Anything Daily is A Valuable Asset.

I’m all about self-discipline — I think it’s the most valuable asset you can have. (Attempting to) write daily really honed my self-discipline — it certainly wasn’t perfect, but it’s the strongest its been all year.

It got to the point that when I didn’t write it felt super weird, like if you forget to clean your teeth. Awkward TMI. But writing became a habit — and the benefit of that is that you can stack habits.

So I stacked writing on top of my other daily practices as best I could, and slowly but surely, over the course of the month, my self-discipline got stronger.

I can’t stress this enough. Self-discipline is the gateway to freedom — it’s at least the framework for it.
So I might as well just come out and say it — writing every day set me free.

Okay. Yuk. That’s a bit strong, and I jest. But I faced a lot of demons this month, and it was tough. I fell off the wagon on many an occasion. But having a degree of self-discipline helped me get back on. It helped me feel stronger, it helped me move through hard times faster, and it really helped me stay the course. Self discipline truly is a superpower.

13. I Burst The Romantic Bubble of “Being a Writer”

Look. I wanted to write a novel this month coming. I was totally in love with this gorgeous, romantic idea of being a writer. An artist. A struggling writer.

I was one of those writers that just wrote when the inspiration struck.

That does not work. That’s not what being a writer is all about. It’s mostly hard work, grunt and grit. It’s about writing when you don’t want to, writing crap a lot of the time, and having things work out differently than you expected to.

I wanted to write this book. I wanted it to be big and important. That’s why I’m quite focused on the word count, you’ll notice. But then an idea for a children’s book came to me and I haven’t been able to shake it off. It doesn’t fit with my vision of being a writer (and I mean absolutely no offence for writers of children’s books. That shiz is a real challenge.)

But whatever I think being a writer is changed when I started to write every damn day. I went from dabbling in it to actually feeling like a writer.

14. I Found My Writing Voice.

Or at least I thought I did — that children’s book idea has slightly thrown me off somewhat. But I write the way that I write — and that’s fine. This itself is a practice of self-acceptance — and a much-needed one.

15. Writing Takes Less Time Than I Think It Does

I write pretty quickly, I admit. That comes with its own set of pros and cons (see point 16 below), but according to my time tracker on my laptop, I’ve spent 21 hours on Medium, and 12 hours in Pages over the course of October. That’s maximum 33 hours of writing in one month, across 18 published (and 13 draft) pieces. That’s less than 10 hours a week.

I just keep thinking… what if I put a bit more effort in? More time in?

Because I think by objective standards, I have room for that.

And just like that, another one of my excuses disappears off the face of the planet.

16. My Writing Still Frustrates Me

I know I said earlier that my writing has improved — personal opinion btw — but there is a critical element that still frustrates me.

It’s superficial.

I think, referencing the above point, I write quickly. Way too quickly. I want to go deeper, but I feel like I’m scratching around in the surface dirt.

My writing style is quick and dirty, but I fantasize that if I actually spent more time on it, I’d get to the depths that I desire.

Maybe a daily writing challenge is not the right medium for that kind of writing — for me.

Or maybe I need to keep exploring and challenge that belief too. To be continued…

17. I have Zero Writing Strategy (Unless, Maybe I Do?)

This one might as well be called, No Strategy, No Personal Brand, No Confidence.

For the first time, today I wrote down the titles of all my published posts in a list in my bullet journal — so that I could get the word count, obv. Apparently, this is the kind of thing that Trello would be good for, but I’m sticking to my analog system thanks very much. It’s a beaut.

Apart from, ouch — that is some in-your-face accountability — with this list of published posts against the dates, I could see a pattern not just in my publishing frequency, but also in my content.

I could see the vague outline of a strategy, even though when I sit down to write, it’s anybody’s bet what is going to come out… Even if I have a post title in mind, there’s every chance it will just take its own direction and I just have to go with it. That’s how I roll. Zero strategy, friends.

But the pattern is always clearer in hindsight. Whatever pattern this is is a pattern of nature — I don’t have control over it, it just exists, and I’m just the vehicle, or the Medium. (Omg, see what I did there.)

Maybe what I’ve learned isn’t so much that I don’t have a strategy, but that I am just not that confident of a writer (yet.)

So please, bear with me. This one is also To Be Continued…

18. I am Creative (& sidenote: We All Are)

I used to confuse being creative with being an artist — and I’m talking specifically about drawing. I can’t draw for shit.
For Shit.

I can’t stress that enough.

I can’t draw for shit.

There we go. But I can create. And I did. Not as much as I wanted — but still. I did actually surprise myself. Over the course of the month, I also switched away from consuming content about business, and success and entrepreneurship and all those things, and I started to soak up all things creative.

I’m halfway through Chase Jarvis’s new book, Creative Calling, and I l-o-v-e it.

I’m learning that creativity is not about the output, but the process. It’s about the practice.

And I intend to keep it up.

This daily writing challenge has actually changed my life — I think it has legitimately rewired my brain, and oh my gosh, I needed something like that to boost me out of the writing rut I was in.

If you are a writer, and you haven’t tried a daily writing practice — or a daily publishing challenge — do it.

Do. It.

I urge you.

That is all.

What you’ll learn about yourself in the process, irrespective of whether you nail it or not, is simply a goldmine.

Founder, feminist, entrepreneur, coffee + self care

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