Fresh Start Monday #053: Three lessons from writing a weekly newsletter for one year

Last week was issue #52 of Fresh Start Monday, which means I've been writing a weekly newsletter for one year!

That was my original goal, and I'm proud I saw it through! I'll continue writing them for now, but we'll see how they evolve. Thanks for reading!

Here are three lessons I've learned since starting:

Life is like a video game

I was a gamer in high school. I remember coming home from school and playing for hours and hours until either someone yelled at me to stop or dinner time, or sometimes it was time for bed.

Back then, I thought my obsession was with video games. In retrospect, it was not the video games themselves but the instant feedback and improvement at something.

With video games, you start at the first level. As you build your skills and unlock new powers, the gameplay becomes increasingly more difficult until you reach the final boss. Or you reach the next level of play or improve your rating.

While writing this weekly newsletter, I realized that sometimes we skip levels, and that's why we get stuck.

I've wanted to write and share my thoughts online for a while now, but when you read advice online, it usually says you must post daily and across multiple platforms.

That's like reading the manual of a videogame to learn the controls and then facing the final boss next. It's setting yourself up for failure.

Starting a weekly newsletter was the right level for me. My writing felt fragile and in its infancy. I only shared the newsletter a few times when I started. It became a safe space to share my thoughts, learn how to generate ideas, and improve my writing.

Unlike a video game, not everyone starts at the same level when you start a business or go after something you want. With everything being online nowadays, it's easy to get caught up with what level everyone else is at.

But you may need to build the skills and confidence before reaching that level.

Unlike a video game, it's hard to know which level you're at. You don't receive a rating or a score.

You might be skipping levels if you keep stopping and starting, procrastinating, or feeling stuck. There's always an easier level to build some momentum. Or it might help to map out ten levels and see where you fall.

A year later, I feel done with this level. It's gotten easy and no longer challenging. And nobody keeps playing a game they're bored with. It's why I've started sharing more recently on social media, now trying to add subscribers, and maybe that comes with a larger volume of writing.

The beginning is always the hardest

When I started writing this weekly newsletter last September, I remember thinking how unsustainable it was. It took writing and editing every day of the week to feel ready to publish.

Thoughts about stopping the newsletter became a daily newsletter delivered right when I opened my laptop every morning. I never missed an edition.

There's incredible power to setting a big goal and deciding not to quit. You have to trust that your body and brain will figure out a way once you start.

The resistance you feel before you start is enormous, and the early going will be hard, but it won't feel like that forever.

This is true not only for the "doing" but also mentally. Sending the newsletter may have been the most challenging part. It felt and continues to feel vulnerable, but that's become easier, too.

Set a deadline

Perfectionism is one thing that's always stopped me from creating something. Having a weekly deadline is a forcing mechanism. If I said I wanted to write more this year, that may have been 20 posts? 10? 0?

Would I have liked to flesh out some of the ideas more? Spent more time researching on busier weeks? Written longer posts? Yes, yes, and yes, but consistency and volume of work are two antidotes to perfectionism.

Another aspect of setting deadlines is removing any excuses I could come up with. If I was going away for a whole weekend and couldn't write, I still knew on Wednesday that I had a deadline to hit. Otherwise, our minds are incredibly creative in coming up with all sorts of excuses.

It created an accountability system.