Five Lessons from the Ship30for30 Writing Challenge
Is it worth $200 to write 30 essays?
What is Ship30?
The goal of Ship30 is to publish a screen-shot-sized (~200 word) essay daily for 30 days. I completed the challenge in February.
Here’s a sample essay I wrote during the challenge.
Below are my five biggest takeaways from completing the challenge.
1. Respect the Writing Process and Chunk Your Work
Every essay involved a few distinct steps: have an idea, brainstorm the main arguments and examples, turn the brainstorm into a draft, edit the draft, title appropriately, format, come up with creative social media captions, and publish.
Doing ALL of that in ONE work session was exhausting.
Instead, my best essays came from following a process. Roughly once a week, I made long lists of essay ideas. At night, I spent 10–20 minutes writing thorough outlines.
This way, in the morning, all I had to do was turn mostly expressed ideas into cleanly formatted essays, add a title, and post.
The key lesson? Find ways to break what you are doing into chunks. This makes both starting and finishing a work session easier and leads to higher quality work.
2. Community & Financial Accountability
You do not need to pay $100 to do this challenge. What’s stopping you from copying the format and committing to writing 30 mini-essays? Not really anything.
So why did I pay for it?
A commitment device. Without clear consequences for failure, I likely wouldn’t have finished Ship30. Ten days into the challenge when a new semester of college started, it would have been extremely easy to quit because I got too busy.
By paying for the challenge, quitting would represent wasting money and looking stupid. That was a strong enough motivator to keep going.
In addition to the financial accountability, Ship30 also had built-in community accountability. Every week, I was paired with another “shipper” in the community Slack channel where we’d introduce ourselves and share our essays daily. If I didn’t ship or was late to post, a real person would harass me for falling short and nudge me to get the work done.
Last, accessing the community gave me access to the group Office Hours which lead to an awesome podcast with Nicolas Cole and potentially a future interview with Khe Hy.
3. Unpredictability & Iteration
Publishing 30 essays taught me the importance of being prolific.
Essays I confidently expected to break the internet because they were so good hardly got noticed. Essays I published for the sake of not skipping a day ended up being some of my most popular.
More or less, I have no idea what content will resonate. Because of this, the most important thing is to continue to take shots-on-goal and to publish often.
David Perell calls this B+ content with A+ consistency.
4. Positive Constraints
I’ve written about this before here, but it is an idea I continue to find useful. The world is chaotic, and positive constraints are a powerful way to impose arbitrary rules to maintain a sense of order.
The point of positive constraints is to make a few decisions upfront that simplify thousands of tiny future decisions that could otherwise be debilitating.
By imposing constraints on
- Essay length and format: 1 screenshot, ~200 words
- Writing time: Mornings within the first 2 hours of waking
- Writing topics: Mine were self-improvement, technology, productivity happiness, and business
- Writing effort: Each essay should be less than 50 mins of work
- Publishing medium: Reddit, Twitter, this Newsletter
the success rate for Ship30 participants has been very high. No time is wasted arguing with yourself asking what to write about, how long to write, whether you can fit writing in your schedule, and what to do with your essays.
If I was going to repeat the challenge, I would make even clearer constraints to remove more decisions, prevent trivial internal battles, and reduce procrastination by analysis paralysis.
5. Invest in Yourself
This is my biggest personal lesson from the challenge.
Because the returns are less quantifiable, we are hesitant to view spending a few hundred dollars on ourselves the same way as buying a few hundred dollars worth of stocks or other traditional investments. This is a tragedy and hilariously irrational.
College is the best/ worst example of this.
We don’t question spending $5,000 to take college courses that reteach high school history. We don’t question spending $2,500 to learn math that has free (superior) alternatives online. We don’t question spending thousands on business degrees to learn (mostly outdated) skills from people who’ve never worked in business.
Yet when someone whose actually been successful at a very specific thing offers to share their playbook for a few hundred dollars, we run and panic?
This makes no sense to me.
The litmus test here is sad and humorous.
When our expensive college courses are canceled (say because of a snow day), we celebrate, but if I lost access to the Ship30 resources or my online gymnastics courses went offline for a few days, I’d be broken up about it.
These uncredentialed alternatives often are more rewarding than traditional “education” for fractions of the cost.
I’ve never regretted an investment in myself.
I’ve never been denied a refund the few times I’ve purchased a course/ program and realized early on that the timing wasn’t right.
It is almost always worth the money to buy winning formulas!
Would I Do It Again?
Absolutely. Ship30 was a great experience and forced me to clarify my thinking on a number of topics. I’d highly recommend it to anyone interested in growing as a writer!
If you are interested in completing the Ship30 challenge, I have my own custom referral link to save $20. (Disclaimer, I do receive a kickback if you buy using this link!)
Last, if you haven’t listened to my interview with Dickie Bush, creator of the challenge, you can check it out here.
