3 Lessons Learned As I Reflect Back on 30 Days of Digital Writing with Ship30for30 (and what’s next)

Robert Gillespie
2 min readMay 22, 2022

I was on the fence about joining Ship30for30.

Being a marketer of 17+ years, I’ve written a ton of ads, emails, and sales copy. I’ve launched multiple podcasts and sold numerous digital courses. But deep down I hated the thought of writing something…ANYTHING in fact!

And it was all down to perfectionism. I wanted my writing to be perfect. But that curse meant I very rarely wrote anything or published anything.

Something had to change. So I took a leap of faith and joined. And it’s one of the best decisions I have ever made.

So what the heck have I learned over the last 30 days?

Here’s the 3 key lessons I learned over the last 30 days:

#1 — Writing and publishing is a habit I actually enjoy…

Having a clear goal to write 250 words for 30 days straight gave me the focus I needed to get out of my own way. Add in some planning around the topics I wanted to write about and thankfully I achieved my goal.

I’ve enjoyed testing new topics for different audiences. It’s much easier to write when you have a passion for something and a clear audience in mind. I enjoy placing small writing bets now and seeing what the data tells me. Oh, and my fear of publishing has gone.

#2 — I enjoyed the community for once…

I definitely didn’t join Ship30for30 for the community. As someone who slants towards being an introvert, I hate in-person events and having to make small talk. I like to do my own thing.

Very quickly, however, I realised the power of this community. From the first minute essays were published you could see the rallying support from everyone. People who didn’t know each other were leaving comments and giving valuable advice.

#3 — I still have so much more to learn…

On the first live call, there was talk of something called ‘The Captain’s Table’ — the level after Ship30for30 for those who wanted to go deeper with digital writing. I had no intention of joining it. Yet here I am as a member and super excited to continue my learning.

I’m excited to explore new styles of writing. Try twitter threads. Build more digital products. Dig deeper into my own category. And transfer my writing over to LinkedIn.

So as the ship docks…

I wanted to thank the Ship30for30 community for making this journey a valuable and memorable experience.

Read this post and more on my Typeshare Social Blog



Robert Gillespie

I write about Digital Entrepreneurship, Marketing and @Notionhq | Currently Vice President of Marketing @JPMorgan Chase | UK Entrepreneur of The Year final