I’ve used the following technique to write 1,000 blog posts.
You ready?
Write letters to your younger self.
Let me give you an example..
Last year I wrote an article titled “I Invested $10K Into A Failing Crypto Market — Here’s 5 Lessons Learned.”
It doesn’t look like it, but this article was really just a letter to a former, crypto-skeptical version of myself.
I was basically saying “Hey Tom, don’t worry if your crypto portfolio tanks — it’s part of the game.”
Back in January of 2021 I thought crypto was some scam.
This article was a letter sent back in time to my former self, but that’s not all.
It was also a letter to current crypto skeptics.
And that’s where the magic happens.
Many writing experts say that you shouldn’t write for yourself — you should write for an audience.
But that’s some of the biggest bullshit I’ve ever heard (with all due respect).
With my method you’re killing two birds with one stone.
You’re writing for yourself, and you’re also writing for an audience.
Look, chances are if you had a particular thought in your life, someone else probably had the same thought, too.
Maybe a lot of people did.
Choosing the “letter to former self” path to idea generation is brilliant because you probably know your topic better than anyone.
You have direct experience with the problem, after all!
I could write letters to young Tom about my Crohn’s Disease ALL DAY LONG.
I created one of the most popular Medium publications, The Post-Grad Survival Guide, because I wanted to write letters to a younger Tom who just graduated college.
Turns out a lot of people wanted to do the same thing.
We got half a million page views one month.
I live by one writing mantra:
If it’s helpful for me, it’s probably helpful for somebody else.
That’s all you need. Let’s get into how to actually generate writing ideas using this strategy.
How To Write Letters To Your Younger Self
What were the five most difficult moments of your life?
Write them down.
For me they were:
My first few years out of college.
My 4-year battle with Crohn’s Disease
Rebuilding my whole life in Mexico last year
Getting bullied for 7 years in elementary school
Paying off my student loan debt
Why do we start from pain?
Because what are the best parts from our favorite movies?
When there’s conflict!
When do the main characters grow and learn new things?
With conflict!
The same thing happens to us when we go through conflict in our lives — we learn things worth telling other people.
Now that we have our five hardest moments, all we need to think about are what we wish we knew back then in those tough moments.
If you could hand-deliver a letter to a younger version of you going through hell, what would it say?
Now go write it. Please, go write it.
Some of your hard moments will be a gold mine of content. I created a publication that published thousands of stories about my toughest moment — the years directly after college.
We probably published more than 10,000 stories.
That’s all you need to do.
Welcome to my newsletter, 150 days to blogging mastery. This is the second of 150 lessons, which we’ll publish every Monday, Wednesday, and Friday until the end of the year. Please subscribe here on Substack.
For the next month, we’ll be talking about how to generate great writing ideas.
Hope to see you on Friday!
Love this one man! Definitely stealing this. I've already written about a bunch of my failures/biggest struggles but think it's time to revisit and expand into some more lessons. Plus, reminders are always good.
What to write about is such a problem for me, so I'm looking forward to you "talking about how to generate great writing ideas." I've been in such a writing slump since even before the pandemic, so I'm hoping this course will kickstart me. Like you, Jason, I've written about my struggles but I really have a hard time writing personal stories.