Writing For 365 Days Straight – The Lessons

365 days writing challenge lessons

Writing for 365 days straight was the craziest thing I’ve ever done. “What if I’d write for a whole year? What if I’d publish an article every day for 365 days straight?” It all started to make sense to me, a year and a few days ago. My blog was going nowhere, my writing career had stopped working for a long time and, if I wasn’t ready to do something about it, I’d most likely be selling fast food at the local shawarma place by now.

The idea of the 365 days writing challenge is nothing new for most writers. Some of them have tried it and failed miserably. Many of them tried it for just a week or a month. And some of them even got through with it and are now 365-day writing challenge achievers. I did it too, and now, after 365 days of continuous writing, I’m ready to share my lessons on it.

Lesson #1: Discipline

Discipline. Why do people fail at anything in life? They lack discipline. I was an undisciplined freelance writer for the entirety of 2017. I simply stopped caring about it. Everything fell apart, the online reputation, the Fiverr profile, the mailing list that I’ve been able to gather for all of those years writing for the local media. They all failed to get me any clients.

Why? Because I was severely lacking discipline. I was never sitting down to write. Never putting enough time and effort into developing my skills as a content creator and mastering my craft. Usually, I was complaining about not having clients. And that was about it. Writing for 365 days straight has taught me why discipline is so important. Why it matters more than anything.

-Discipline is showing up every single day and practising your art form, even if you’re sick, unmotivated or angry. Is the cure for your laziness and complaining. Discipline is the motor you need for your boat with no paddles.-

Lesson #2: Better Writing

You might think I went into this challenge knowing everything about writing. It was just a way of showing off my skills and spending my free time. Wrong. One year ago, I was far less of a writer than I am today. The best example is with Grammarly. This service lets you know how many mistakes you’ve made in a certain text. You just paste the text on there and voila!

One year ago, a normal text I’d write would’ve been filled with red lines. Almost every sentence would need some polishing. I’d even have troubles with choosing the right punctuation marks. Nowadays, Grammarly is just a quick glance at a piece of writing I’m positive about. I am confident about everything I put out there, regardless if it’s for me or my clients.

-Writing for 365 days has made me a much better writer than I was one year ago. It totally changed my relationship with grammar, choosing the correct words or punctuation marks, and constructing a good sentence. I write better, faster and cleaner.-

Lesson #3: Online Presence

One of the reasons why I’ve started the challenge was to get some more followers on my social media and, hopefully, a few new clients. This has been hard to get, mainly because the platform, Medium, has gone all “paid membership” on us writers over the year. I didn’t partake in that, so I was sort of left behind. I only managed to get about 1.100 followers on the blog, but it’s okay.

Besides the followers, I managed to get 10 clients, two of which are now my biggest ones, thanks to the blog alone. Which for me is much more than great, giving the fact that I paid zero dollars for marketing. I just wrote because I had to, and then the people who read my articles hired me to write some of theirs. That’s a form of online presence as well.

-Creating an online presence that turned some of my readers into clients has been a great reward from this challenge. It wasn’t easy, earning people’s trust, but I did it. I’m not famous, but just famous enough to have met new business partners.-

Lesson #4: Motivational Juice

Some people might say writing every day for a year can become a burden, not a motivator. And it does, especially in those longer-than-normal days. But for the most part, writing daily has proven up to be nothing else but a strong motivator. 10 days. 100 days. Halfway there. 2/3rd of the way there. 300 days. Final 3 days. Simply creating content for that long is motivating.

Motivation is hard to get as a writer. You’ll always struggle with it. But if you simply do it, if you simply sit down and write, you’ll never lack motivation. Because motivation is never found outside yourself. You won’t find it in Nature, at the supermarket, or in New York. Motivation awaits inside you and is only accessible through work. Start writing, and motivation will follow.

-The thing that keeps you motivated is the same thing that you find motivation in. You’ll never search for motivation for writing from dance, music or everything else. You will find more motivation to write from writing more and more.-

Lesson #5: No Boundaries

365 days is a long time. A whole year. Try thinking about when was the last time you did something for a year straight. Besides breathing, eating and sleeping. When was the last time you read a book every single day for a month? Or when was the last time you washed the dishes for a week straight? Doing things for longer times shows what you’re made out off.

I found out I can destroy any boundaries I might’ve mentally set up for myself before if I really wanted to do so. During the challenge, I’d always question and second-guess myself. I’d always say “that’s it, I’m quitting this thing” and then be mad for three hours. But then, I’d simply write the day’s article and be able to extend the time with one more day, breaking that barrier.

-Reach and then surpass your boundaries. Regardless if you’re a writer, a filmmaker, a poker player, or a doctor, you need to do it in order to grow. You need to prove it to yourself that boundaries are illusions. Then you can break them with ease.-

Final Thoughts

This was the hardest thing I’ve ever done as a writer. It was both incredibly harsh, as well as extremely rewarding. It was incredible to be able to do it, although it had some though parts I’m not ready to even talk about yet. I’ll surely come back at this challenge again in the future and tell you some more about it. My advice after this challenge? Have a go at whatever challenge lays before you.

Maybe you’re afraid to go on a plane. Buy the ticket for the flight and keep it somewhere you can see it. Start small, just picturing yourself on the plane. “What’s the worst it can happen?” Then slowly get accustomed with the idea. And, on flight day, enjoy the flight like you were born to take it on that very day. Regardless of the challenge ahead, take it. It will make a better person out of you, guaranteed.

1 comment
Gabriel Iosa



I’m happy for you being here! I enjoy blogging as much as I did 10 years ago, at the start of my writing journey. If you want me to write something for you, hit the Services page. You can find some snippets of my previous work on the Portfolio page, as well as what my clients have said about my work on the Testimonials page. Hit the About page for some more info on myself and my passions, and when you’re ready, send me an email at the address you’ll find on the Contact page.

Awesome to have you here!