writing

Leading a Writing Challenge Taught Me About Discipline and Creativity

Practical lessons on showing up, staying disciplined, and creating with joy.

Anangsha Alammyan

25 Aug 2025 • 5 min read

Screenshot by the author from the 100-day challenge homepage (now discontinued)

Practical lessons on showing up, staying disciplined, and creating with joy.

In September last year, I started something I had no idea would change the way I look at writing and community.

I launched a 100-Day Writing Challenge where more than 50 writers from across India pledged to write on Medium for 100 days straight. The rules were simple:

publish consistently,
share progress, and
hold each other accountable.

But of course, writing every day isn’t simple.

By Day 10, excuses creep in.

By Day 30, life gets in the way.

By Day 60, the temptation to quit becomes overwhelming.

I knew this myself, because I’d failed similar challenges in the past.

That’s why I built this challenge not just as a solitary goal but as a shared journey. Every two weeks, we got on calls together and spoke about what was working and what wasn’t.

What I didn’t expect was how much I would learn from them.

The different channels we had on our 100-day writing challenge Discord server (Screenshot by the author).

Lesson 1: Too many ideas can be as paralyzing as none

One writer said something that stuck with me:

“I don’t have writer’s block — I have too many ideas. And it’s making me hopeless.”

That hit home.

Most of us think the enemy of creativity is not having ideas. But often, the real struggle is the opposite: we drown in possibilities and can’t commit to one.

What I told them (and reminded myself) was this: pick one idea, any idea, and finish it. Broad, imperfect, messy — it doesn’t matter.

The act of finishing gives clarity. The act of publishing builds momentum.

Lesson 2: Niche isn’t everything, but platform understanding is

In one of the calls, we debated endlessly about “finding a niche.” Should you write about books? Productivity? Tech? Travel?

Here’s what I realized: niche matters less than understanding the platform you’re writing on.

On Medium, your headline can make or break your story.
On Substack, readers care more about connection than SEO.
On Reddit, the right subreddit is more powerful than the most polished draft.

A niche helps, but understanding where you’re speaking matters more.

Writers who adapted to their platform thrived, even if their topics varied.

Lesson 3: Self-rejection is the real killer

One of the writers confessed:

“I don’t feel like I know enough to publish.”

But here’s the truth I kept repeating: perception is reality.

If you write confidently, people will see you as an expert. We are our harshest critics, but readers don’t dissect us with the same scrutiny.

I’ve seen entire careers built not on brilliance, but on the shameless confidence of saying: If they can do it, why can’t I?

That was another unexpected gift of this challenge: watching shy writers learn to publish boldly, and realize no one was judging them as harshly as they judged themselves.

“I got to explore personal writing at a new level. I have been so focussed on writing for my training business for the last decade, that this challenge was a fresh breathe of air in personal writing. I wrote pieces on my life and experiences — something that I did only on my personal blog so far. Imposter syndrome demolished.” — Suman Kher on LinkedIn

Lesson 4: Love vs Money — the eternal tug-of-war

In almost every call, this came up:

“Should I write for love or money?”

My honest answer: both. But in sequence.

First, write for money. Treat it like a job, monetize, learn to pitch, experiment with affiliates. Because once you know how to sustain yourself with words, you earn the right to fall back in love with writing.

But always keep one hobby you never monetize. Something you’re allowed to fail at. Something you do badly, for the joy of it.

Because once you turn everything into a hustle, you’ll wake up one day realizing you’ve stolen the joy out of the very thing that made you feel alive.

Lesson 5: Community beats willpower

By Day 70, many of us were tired.

By Day 80, some had disappeared.

But those who showed up on the calls, even when they hadn’t written, survived.

Discipline doesn’t come from brute force willpower — it comes from community. From someone saying, “I see you. I know it’s hard. Let’s keep going anyway.”

That’s why 100 days felt possible at all. Not because we were individually strong, but because we carried each other when motivation dipped.

“Each participant in the challenge is at a different stage in their writing journey. Some are just starting out, while others have been writing for a while and are working to improve their craft. Each person is benefiting from the challenge in a way that suits their needs.” — Prahalad Rajkumar, Anangsha Alammyan’s 100 Day Writing Challenge is Helping Me Become a Better Writer

A screenshot from Ana’s newsletter. She’s one of the writers who’s a part of the 100-day challenge community.

Final Reflection

At the end of the 100 days, some of us had written 80 pieces, some 40, and a handful all 100. But the number didn’t matter as much as what we discovered along the way:

Too many ideas isn’t a gift — it’s a trap.
Different platforms reward different kinds of writing. Adapt.
Self-rejection kills more dreams than “lack of talent.”
You can write for money and love, but don’t sacrifice one at the altar of the other.
Most of all: discipline grows when nurtured in community.

The challenge ended, but what stayed with me was this: writing isn’t a solo act. It feels like it, especially when it’s just you, a blank page, and the blinking cursor.

But behind every piece that survives the world, there’s a community that made you believe it was worth hitting publish.

And that might be the most important lesson of all.

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