Plan Your Next
Plan Your Next
Here's your bravery test

Here's your bravery test

Plan Your Next #77

👋 Good morning from Santa Barbara! I'm Nate Kadlac, and this is #77 of Plan Your Next. A Sunday newsletter that connects design, creativity, and how you prepare for your next thing.

Bob Ross
“And here’s your bravery test.”—Bob Ross

In the last two minutes of each episode during the 11 year run of, “The Joy of Painting,” Bob Ross would routinely look into the camera and say, “And here’s your bravery test.”

Immediately after the proclamation, Bob took a large 2-inch flat paintbrush and dipped it in a pool of paint. Almost recklessly, in one sweeping motion, he brushed across a 1/3 of the seemingly finished landscape.

At first, it looked like he ruined the painting. Over the next two minutes, he would quickly fill in the details of a tree in the foreground, adding a layer of depth to the consistently rendered landscape.

The producer of the show mentioned that every time he did this, it caused her anxiety that he wouldn't finish on time. But every time, he did.

While the depth of the foreground element nudged the quality of the painting forward, Bob was risking failure with such little time left in the show. The confidence he had in his own skills came from his ability to trust the process and be open to failure.

Since hearing this story, I think about this line a lot when I design, write, or when I made the decision to quit my job.

As they say, God is in the details. But the details mean little without conviction in yourself.

Just earlier today I had a conversation with a friend where I expressed the perception I have of myself prevented me from contributing in larger group settings.

In his own way, he urged me to take a brush and paint a line through my own perception, filling it in with a new identity in those situations. The bravery test is a way to throw caution to the wind and to trust in the process, even if you don’t have full trust in yourself.

Applying this idea to my design work, it could be as simple as flipping some colors around at the last minute to create a different visual hierarchy. When I worked with Charlie Bleecker on her own design kit, we scrapped her entire palette and tried something new. Then we landed here.

In writing, it might mean cutting out your best line and pasting it as the hook. Or during the editing process, taking a machete and hacking off sentences or words that aren’t necessary. “Kill your darlings,” as they say.

To me, the bravery test is about shocking your creative process with a defibrillator, sometimes at the last minute to try something new or courageous.

If you’re stuck this week, think of Bob Ross and find a way to test your creative bravery.

⚡️ Tidbits for next week

💎 Can the value of a physical diamond be transferred digitally into an NFT if it’s physically destroyed? This experiment by Tascha started as a tweet, then was minted on OpenSea to test the hypothesis. The following question I have now is how the status of bidding on this item compares to the status of owning a physical diamond. I’d argue it’s a convincingly stronger status signal because you can showcase it as an NFT to the world vs the people physically around you.

Read Taschen’s hilarious conversation with her mom trying to explain this to her.

💼 If you consider yourself a generalist, writer, and YouTuber Michael Ashcroft points out in his latest newsletter that seeking answers is important to your survival. I never really thought about it this way, but if I’m having a conversation with someone whose intellectual reach doesn’t cross domains, it might be a subtle flag for how feral your opportunity radar is.

Add to this the fact that many of these people are, increasingly, feral free agents, as @visakanv puts it. They operate and navigate in the world without jobs or strong affiliations, which means their need to understand how things work is important for their survival.

Put another way, if you have a secure job then your ability to make sense of things outside the domain of your job doesn't really affect your security, unless you miss macro trends that cause your job to go away or change dramatically. This is not the case if you're a feral free agent where, in my opinion and limited experience at least, you need to be able to hold a much more flexible and broader perspective to be able to navigate and identify opportunities you could pursue.

👶 It’s becoming increasingly more difficult writing newsletters with this cute ding-dong staring at me all day. We’ll prevail, hopefully.

Baby Rowan
Baby Rowan!

👋 See you next Sunday

If you’ve forgotten who I am, here’s a little bit about me. As always, my calendar is open to chat about your next adventure, crazy idea, or if you’re feeling creatively stuck.

Have a great week,


p.s. If you enjoyed this letter, would you please let me know by tapping on the heart below?

Plan Your Next
Plan Your Next
I'm Nate Kadlac, designer of Plan Your Next. A weekly newsletter that connects design, creativity, and how you prepare for your next thing.