Do something 100 times

Last week, I wrote about inertia. Specifically, the type of inertia where an object at rest stays at rest. 

This week, I’m writing the 100th issue of Wishful Working. You’re reading it right now!

So while I do often struggle to maintain momentum, I am still writing Wishful Working more than two years and 100 issues in. 

How?

Honestly, I’m not sure 😂

I don’t have any life hacks for consistency or for newsletters. I don’t block a certain time to write it. I don’t batch write issues ahead of time. I wrote this at 10am on Thursday, February 26, sitting at my parents’ dining table in Iowa. I’m finishing and sending it after 8pm. I could have skipped this week because I’m traveling, but I really wanted to send something for #100!

Here are my tips for sending a newsletter consistently. These tips may or may not apply to other habits. Take ‘em or leave ‘em:

Early on, I was very committed to sending this newsletter every Thursday at 9am Central Time. I soon found myself struggling to meet that self-imposed deadline. Then, I realized: No one cares when I send this. 

I stick to Thursdays, mostly, but I don’t pay much attention to the send time. It’s afternoon, mostly. Sometimes evening. I trust that no one is refreshing their inbox, wondering why they haven’t received Wishful Working yet.

This tip applies to many things in work and life: Posting on LinkedIn/social media, exercising, working on creative projects. It feels cringe. We fear scrutiny from our peers. But mostly, people are too caught up in their own stuff to notice what you’re doing. Embrace the cringe.

I got this tip from author Phoebe Thompson on TikTok. She said it in the context of writing a novel, but I think it applies to anything. Essentially, you’re more likely to make steady, sustainable progress on something if you are somewhat rigorous (i.e. strict, rigid) but not serious (i.e. playful, light). 

I am rigorous about Wishful Working. I send it basically every Thursday, with some exceptions for travel and breaks. I spend several hours per week writing drafts, posting, formatting, and designing.

But I am playful about Wishful Working because I treat it as a fun, creative outlet, and I allow my whims to influence the design and content. I know that the stakes are incredibly low and that my main goals are self-expression, connection, and enjoying something that’s entirely my own.

The concept of “dailyish” comes from one of my favorite writers, Oliver Burkeman. He encourages his readers to hold themselves to a flexible standard that allows for occasional mistakes and misses. 

If you’re trying to do something every single day and you miss a day, you might lose motivation to continue. If you’re doing something “dailyish,” you’re allowed to miss a day while still maintaining momentum.

I’m now realizing that this tip sort of contradicts the previous tip about rigor and strictness. But the point is to find the level of strictness that actually works for you: Rigid enough to make steady progress, flexible enough to allow for the unexpected.

There’s a lot to be said for repetition and stubborn perseverance. The more you do something, the easier it is to keep doing it. 

One of the big reasons Wishful Working #100 exists because I just keep writing, week after week. It’s a habit — not completely automatic, but definitely part of my routine. There’s muscle memory here, and it’s a muscle I’m going to keep building.

Thanks for joining me, week after week.

Or weeklyish. 😉

See you next week,

Kara

Kara Detwiller is a writer and creative based in small-town Saskatchewan. She specializes in long-form content writing for enterprise SaaS, cybersecurity, and manufacturing clients. She is also working on her first novel, among other creative pursuits. To connect, reply to this email or find Kara on LinkedIn.

Why Wishful Working? I want to help people thrive in a world obsessed with work and productivity. Together, we’re expanding the definition of productivity, rediscovering life balance, and exploring the many kinds of work that make life possible.