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The Top 7 Insights I've Learned Writing 100 Weekly Newsletters In A Row

Mitchell Wilson


Mitchell Wilson


Feb 8, 2023

The Top 7 Insights I've Learned Writing 100 Weekly Newsletters In A Row

In Dec. 2020, with trembling hands, I hit send on my 1st ever newsletter to 17 people.

(You may even be one of them 😘)

This is my 100th weekly newsletter IN A ROW.

Other than sleep & eat, I don't think I've ever done anything for 100 weeks in a row. It's now a part of who I am and keeps me sane.

Here are my top 7 insights on how I have made this a sustainable part of my life (even though I’m a busy dad with a day job):

Lean On Curation 🗃

This is massively important in the beginning.

If you've ever tried writing something you're going to send out to lots of people, you know how daunting the blank page can be. It's harder than it looks, I promise you!!

BUT, now I never start with a blank page (that'll keep you stuck).

Instead, to start, you just need to re-share what you’re already consuming.

Pick the things that you think are cool:

• Quotes

• Videos

• Music

• Articles

Throw it in a neat format, add a bit of commentary, & publish.

Make It Sustainable ♻️

Sustainability is the key to consistency.

Plug into your renewable resources.

How can you reliably generate content every single week?

In the beginning of this journey, I would spend so many hours seeking out information, studying, reading, & gathering interesting things to write on.

But eventually I ran out of gas. I couldn't maintain that level of time investment.

Several weeks in, I chose to switch it up to something way more reliable & base it on my:

• Realizations

• Dreams

• Conversations

• Consumption

By making it revolve around my lived experience, I'm never out of material to write about.

The real turning point for me was becoming a more keen observer of life rather than thinking I had to create from scratch every week.

If my heart still beats, I’m good.

Lower Your Bar For Good Enough ✅

Perfectionism hasn't ever been apart of my nature.

But you can bet your ass that as soon as it creeps in, you'll be delaying what you deliver. Of course I want to send out writings that I'm proud of, but I also know that there isn't a concrete limit to what's possible with quality.

Technically, I could spend the rest of my life perfecting every little thing, but that wouldn't do anyone any good.

As long as it gets the point across and you're getting slightly better each and every time, you're set.

You won’t be world-class for a while so forget about it in the beginning.

Even if you only write a couple of sentences, that’s all it takes.

You’ll find your groove.

Be Intrinsically Motivated 🕯

Doing anything over the long-term requires an inner source of motivation.

Metrics shouldn’t be your primary motivation.

Base the value in the act of expressing itself. Leading up to starting this newsletter, I was in desperate need of a way to creatively express myself. I needed an outlet. Somewhere to be more vulnerable than is possible with social media, but also something to be held accountable to. For me, writing a newsletter made the most sense.

Writing helps you think better & pay more attention in life.

Everything else that beneficially arises is all upside.

Use Metrics As A Compass

I try not to care too much as it can be distracting after a certain point, but the numbers tell a story.

So I try to pay enough attention to them that it helps, but doesn't hurt my writing.

Subscribers - was it worth sharing?

Open rates - was the subject line intriguing?

Click rates - was the link wrapped in curiosity?

I let them guide me into a better writer. I don't want to ever bend purely into doing only what other people want me to do. I'd lose my authenticity quick that way and I wouldn't be able to keep up the habit without my heart in it.

Gotta just let the feedback feed it back, nothing more.

Make The Habit Flexible 🤸‍♂️

Force the habit, but flex with life.

I spent most of these 100 weeks trying to always send out this newsletter at 7am on Fridays. And it worked for the most part.

You don’t have to publish it on the same day at the same time every week.

(A schedule makes it way easier though)

Stick to it as best you can.

Things come up occasionally. Kids get sick, travel throws it off, or your sleep gets out of whack.

All good, still do what you gotta do.

This is supposed to go out Sunday morning, but if it goes out a few hours later than that - no biggie.

Bend the habit, but don’t break your streak.

Ship It To Win It 🚢

As soon as you schedule it to be shipped, you've already won the inner game.

You've already beaten:

• Resistance

• Procrastination

• Fear of judgment

The win happens before it's even read by anyone.

The days where I hit publish are my favorite days of the week. I know that if I get this out there, the rest of the day feels downhill. I've achieved my personal goal for the week and no one can take that from me.

This will have you feeling lighter the rest of the day - an incredible feeling.


Applying This Elsewhere 🗺

So much of what I've learned through this process, I've been able to translate to other parts of my life & other projects.

For example:

With Psychedelic Grad, I instilled in the team early on a sense of the sustainability principle - if you can't keep it up forever, then change what you're doing so that you're optimized for the long-term.

With fatherhood, anything I'm teaching my children, I let them know that of course it's going to be bad in the beginning - you've never done it before! But with time, with practice, and with the bar lowered, you'll get there if you stick with it.

Now that I've extracted the insights from the last 2 years of writing, I hope that you too can apply them to whatever it is your heart yearns to do.

Shoot me a reply with your creative outlet, I'd love to support you however I can.

Build top-tier mental wealth

Let's keep your soul off airplane mode.

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