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A Year of Creative Experiments - 2022 ✅

Charlotte Grysolle
Charlotte Grysolle
8 min read

At the start of 2022, I made myself 1 promise:

Every month, I will complete a creative experiment related to writing online.

No guidelines, no expectations.

As long as I'm trying new stuff, sharing online, and most importantly, feeling shy about it.

(I got the idea after Scott Adam's tough-love-approach in the book How To Fail at Almost Everything and Still Win Big.)

Fast forward 12 months, and this year-long experimental approach has been transformational.

There are the tangible benefits - like earning my first dollars through digital products, growing an audience and making a huge career switch.

This is great, of course.

But than anything, I've gone through a complete mindset and identity shift:

"I'm not creative, disciplined or interesting enough to share online."


"I see a way forward to build a sustainable creative, online business for myself."

That's pretty remarkable and will have spill-over effects in every other area of my life, for years to come.

My December experiment was a live workshop around how to start (and stick with!) your own Year of Creative Experiments. I'll be running more workshops so if you're interested to stay posted, send me a DM on Twitter or email me at

Here's a full rundown of the experiments:

January ✅

Start a bi-weekly newsletter

I had been 'planning' to start a newsletter for a while, but I kept putting it off. "I need a great name", "I need a niche", "I need to get better at writing first",…

My first experiment was obvious: just start the damn thing. Pick any name, and figure out the format and structure as you go. No one cares if you change the name in the future.

'Stretch' was born.

I ended the year with 24 editions and 1,422 subscribers. Check out all editions here.

30,000 words. Countless hours. So proud to see this overview!

February ✅

Launch of my first Gumroad digital product: a Writing Guide

When I started writing online, I saw so many people creating all kinds of 'digital products', and publicly sharing what they know. I was puzzled about how they do that. Who gave them permission? Where do they get the confidence?

It slowly started to sink in.

You don't need anyone's permission!

We live in an age where anyone with an internet connection can reach millions of people with one click.

And I don't need to be an 'expert' to share what I know. There are people just a couple of steps behind me on their writing journey who will benefit from what I have learned.

Huge mindset shift.

So, I created a Notion guide on my Consistent Writing Habit.

I put it on Gumroad for free. Gumroad is an e-commerce platform where people sell digital products (ebooks, templates, tutorials, apps, etc.), making it very easy to earn your first dollar online.

Even though it was free, a few people paid for it, which was great. My first $$ earned online through a product.

March ✅

5-week writing course Write of Passage

I signed up for an intense 5-week writing course and decided to challenge myself to engage 100% with the course and the community.

This meant:

  • Joining all the mentor sessions in my time zone
  • Actively engaging in the breakout rooms, sharing what I'm thinking
  • Giving detailed feedback & following up with other students
  • Hopping on 1–1 calls
  • Being active in the online forum

To some people, this might sound easy and obvious.

Not to me. I had done too many courses by then where I dutifully joined the sessions and delivered the assignments but did not make 1 single connection that lasted until after the course — or didn't even finish the entire course because I lost interest.

Write of Passage was transformative.

Becoming part of a thriving, online community of people with such diverse backgrounds and lifestyles opened my eyes, and gave me the final push I needed to walk away from my 10-year advertising career.

And here's the best part:

I announced my 'pivot' in one of my newsletters, which led to an interview at Write of Passage.

3 months later, I joined the Write of Passage team full-time as Student Success Lead.

April ✅

Daily Tweet + CopyThat Challenge

I want to become much, much better at online writing. Copywriting is an important part of that. Compelling, punchy, concise copy.

It's a skill you can learn, and one of the old-school ways to do it is through Copywork.

Copywork is an old practice where you copy other people's writing by hand to improve your own writing.

Word for word. Commas and periods included.

By hand.

I was skeptical at first, but I have to admit I started looking at words differently. There's something about taking the time to closely read every word and how the sentences are structured. It's painstakingly boring, but that's probably why it works.

I did that every day for 30 minutes for 2 weeks, based on Sam Parr's challenge.

This month's experiment was also about being more consistent on Twitter - tweeting and engaging daily. That was tough. I wasn't able to do it every day and I saw little progress, but I reminded myself: there are no goals to hit.

May ✅

Notion Minimalist Task Manager + a Loom tutorial

The May Experiment was again about creating a Notion template and sharing it on Gumroad. This time, I would also record a Loom tutorial.

The intention was to systemize a solution I created for a problem I was experiencing: how to stay on top of endless to-dos and admin tasks.

For the past 2 years, my system has been a simple Notion database based on the Getting Things Done productivity system. You can read all the details on the Gumroad page and check out the template if interested.

The Loom tutorial was about recording myself on camera while talking through the tutorial and posting that online. I had never done that before, and the feelings of cringe were intense. But I'm glad I did it.

Self-desensitization to embarrassment one Loom tutorial at a time!

June ✅

Better Ideas Challenge by Jakob Greenfeld

Jakob Greenfeld is one of my favorite people to follow on Twitter. He's prolific in building & writing online, so there's much to learn from him when it comes to creativity & ideation.

He distilled everything he's learned in 15 ultra-actionable lessons — sharing resources, frameworks, prompts & existing biz ideas to research.

So, for 15 days in a row, every morning for 20 minutes, I wrote a bunch of random ideas down — shushing the ever-present inner critic.

I can’t say I’ve found the next billion $$$ ideas, but this exercise showed me once again how coming up with good ideas is not just for 'creative' people. More than anything, you need to trust your brain and let it do its thing. It's also a skill you can learn; with frameworks & mental models, you can study & practice.

July ✅

Power Writing course

A copywriting course by entrepreneur Shaan Puri.

It was good. We learned about writing cold emails, internal memos, landing pages, etc. I learned some good tricks and frameworks to make my copy stronger and punchier.

Funnily enough, the best part about the course had nothing to do with writing.

I learned just as much (maybe more) about the importance of having infectious energy and a positive mindset. About taking yourself less seriously and dropping the formality — not just in writing but in life in general.

I write here about the 5 philosophies and frameworks I learned from Shaan to do just that.

August ❌

I tried to experiment with getting an experiment done while travelling around for the summer, and it failed.

September ✅

My first podcast interview

I didn't feel too bad about August because I feel like I made up for it with the September experiment:

My very first podcast interview. Me - talking on a podcast! About creativity, writing and neuroplasticity.

Crazy. Never in a million years did I think I would be doing that.

And it was surprisingly fun to do. That's mostly because Sam is just such a nice, casual, easy-to-talk-to guy.

In any case, this experience has inspired me to focus more on public speaking, maybe get a coach, and look

You can check out the episode here (and just follow Sam - he's great.)

October ✅

A series of TikTok videos

The video experiment had been on my mind since the very start of the year, but I kept talking myself out of it.

Perhaps emboldened by my podcast interview, I pushed myself to go through with it. There were a few barriers I wanted to break:

  • Fear of embarrassment. I'd imagine friends watching these videos and thinking it’s absolutely ridiculous, and who do I think I am?!
  • Need for perfection: I’m trying to imagine the perfect topic and the perfect video. It feels cringe to put something completely random out there, like me just talking to the camera. Huh?
  • Resisting new technologies and platforms. I noticed thoughts like "I'm too old for TikTok" and "it's too late anyway". Exactly the kinds of thoughts I want to challenge with my experiments.

It was surprisingly fun to do but I didn't manage to do 1 every day as I had initially set out to do. I ended up doing 1 per day during the last week of the month.

November ✅

Daily Twitter thread

Josh Cadorette, a Write of Passage student, started a daily Twitter thread challenge so I jumped in.

A Twitter thread is a series of connected Tweets. I struggled with writing a daily Tweet earlier in the year, so I wasn't sure how writing a daily thread would go for me.

This was a great exercise in ‘non-judgment’.

The moment I pick a topic and I start writing; I start doubting. Is the topic good? Is the thread too long? Is it too boring? Is it interesting? Should I change topics? No, I should just keep writing and finish it. I have 30 of these to do. I can’t go through those kinds of questions every single time.

I hit jackpot with thread #10. Went viral. It's also the one that took me the least time to write.

Posting every day was difficult, and since it's an experiment, I allowed myself to skip a couple of days.

End of the month, I managed to post a thread for 26/30 days.

I gained 2,052 followers and almost doubled my newsletter subscribers.

December ✅

Live workshop on 'A Year of Creative Experiments'

To end the year with a bang, my final experiment was to run an a live 1-hour workshop talking about my experiences and how to start your own Year of Creative Experiments.

I mentioned the idea of a workshop on Twitter, and 1 person responded.

I mentioned it in a newsletter, and no one responded!

Pre-Experiment Charlotte would've taken that as a clear sign not to go ahead with it. There's no interest.

However since this was just another Experiment, it didn't matter. I had to do it - even if no one showed up.

Ultimately, I had 96 signups and 37 people joining. I got some great feedback afterwards and have lots of ideas on how to improve the workshop and create more materials around this concept.  

If you'd like to stay updated, send me a DM on Twitter or email me at


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