š Welcome! I'm Mike, and this newsletter is for people building creative projects alongside or instead of the 9-5. Each week I share honest insights about the messy reality of pursuing meaningful work while paying the bills. I spend my days as a tech lead and my early mornings/weekends building a podcast and this newsletter about that very thing.
I also offer a limited number of coaching slots for people at creative crossroads, whether thatās a job change, moving into leadership, or figuring out what meaningful work looks like for you.
To my surprise, I've been writing a lot of fiction lately. Don't worry, I won't share it. It's awful! But it's been a lot of fun.
This would have surprised me two years ago. How could you have fun being terrible at something? Iāve always been haunted by what Ira Glass calls The Gap. You get into doing creative work because you have good taste, then you do the work, and itās awful. Your taste is killer, your skill is trash.
Most people quit before they can get over this hurdle.
But recently I've found a way to bridge that gap that actually makes the process enjoyable.
Iām re-reading Tiny Experiments right now, which reframed this struggle for me in a really helpful way. The book suggests running small personal experiments with set durations: "I will write fiction every day for 30 days" rather than open-ended commitments to "become a successful writer."
From Prove Mode to Play Mode
This approach shifts you from prove mode to play mode.
In prove mode, every piece of work carries the weight of validation. Will this make me look smart? Will people think I'm talented? Will this get my attention, subscribers, more money? The stakes feel enormous because you've made the work about you.
In play mode, the work is about the work. You're exploring, experimenting, discovering. You might āfailā, but failure is just another data point, not a judgment on your worth.
My terrible fiction writing lives in play mode. I'm not trying to prove I'm the next great novelist. I'm just fascinated by storytelling, how it works, and if I want to keep doing it.
Embracing your suckiness
The people who create consistently aren't necessarily more talented, they just donāt worry about looking stupid temporarily if it means getting smart permanently.
After returning from Korea and deciding to pursue writing, author Brandon Sanderson had heard the advice that "your first five books are generally terrible". Instead of being discouraged, he describes it as freeing, "I said well that's good, I don't have to be good yet." His sixth book, Elantris, was published.
I recently had a chat with a podcaster I admire whoās been in the game for years. He told me the same: "I knew the first 50 episodes Iād put out were going to be crappy, so I said great, they donāt need to be good. Iāll put out 50 crappy episodes, but make each one slightly better than the last." This wasn't defeat, it was strategy. By accepting the learning curve upfront, he removed the pressure that kills most creative projects before they start.
The Long Game
The beautiful thing is that this mindset makes creating and trying new things sustainable. You're not grinding toward some distant goal, you're following your genuine interest right now. You're not trying to force outcomes, you're creating conditions for discovery.
My fiction writing might never become good. But it's already successful by the only metric that matters to me right now: it's keeping me curious, keeping me playing, keeping me writing.
And who knows? Maybe by story number 50, something interesting will emerge.
On the Pod
Be it working in tech, building up this newsletter, or working on my podcast, I feel like communication is a huge part of everything. Thatās why I was excited to chat with Dr. Michael Gerharz, a communication expert, about this very topic. We dig into why curiosity beats being right every time, plus his PATH framework for strategic communication and how Southwest Airlines revolutionised an industry with just two words.
You can check it out on Spotify, Apple, or wherever you get your podcasts.
Worth Your Time
āØ Flounder mode - Very related to todays article, Kevin Kellyās career shows that you can make a meaningful impact by joyfully following your interests and working on diverse projects, rather than chasing traditional definitions of greatness or success.
š¤ A useful guide on using AI right now from the newsletter One Useful Thing
Speaking of AI, š§ Brainfork, built by previous podcast guest Phil Bennett, lets you setup your own MCP server and actually own your own AI knowledge-base, rather than handing it off to a third party (or your boss). Iām remaining hopeful that weāll see more ethical AI tooling like this in the near future!
š Build a business, not an audience - Jakob Greenfield argues for focusing on doing meaningful work and sharing real experiences, not just creating content for contentās sake. I absolutely love the phrase āThe Creative Worldās Bullshit Industrial Complexā.
šÆ I found the above link through
ās great article Ryan Reynolds as a Maker Creator which is fully worth a read as well.šµ And lastly, chill out with this wonderful electro-jazz-pop from Amelie Holt Kleive. Think Norwegian-Bjork-Thom-Yorke. By far my favourite musical find as of late!
Thanks for the Brainfork shoutout, looking forward to catch up on the new episode!
Thank you for the mention, Mike! There are so many good links in this- going to take me a moment to get through them :)