Escape Shouldlandia | #255

February 3rd, 2024: Greetings from Austin. I was off last week visiting my friend Jonny and his wife Kelly in Boulder, Colorado . What a beautiful place. Some hikes and views inspired lots of ideas to flow…

+ Speaking of Jonny, his Nervous System Mastery cohort is kicking off soon, if you are interested in joining you can use the code PATHLESS for $250 off

+ The Write Of Passage Team is also doing a “shiny dime” writing challenge and the winner gets $1k and access to their upcoming cohort. You might be interested after reading the below. Also if you are thinking about the next cohort of Write of Passage stay tuned, as I may be doing some fun collaborations with them in April.

“Should is a futile word. It's about what didn't happen. It belongs in a parallel universe. It belongs in another dimension of space.”

- Margaret Atwood

As someone that enjoys writing and does so consistently, a lot of people tell me about their own relationship with writing. Many people wish they wrote more. They tell me some form of, “I should write more,” or “I need to write more.”

They live in a world I call Shouldlandia. Inhabitants of Shouldlandia talk about what they should do and what they claim to want to do. But they don’t do it. Often for long stretches of time.

A friend was telling me this week that he “should do more short form video and writing.” I said, “well clearly you don’t want to do those things because you are not doing them.” I asked him, “why don’t you want to do them?” His response was that he actually just finds himself going deep and exploring things in more nuanced ways. He never feels good when he’s doing short form sharing of information. I said, “well you should do that, instead!”

I’ve talked to hundreds of people about their creation habits. If people were as creative with their excuses as they were with their work there would be so many more interesting creations in the world. Which drives me sort of crazy. This friend I was talking to, I love his writing and it’s really good, and I desperately want to help him get unstuck. But I really don’t know how to help him. This essay is my attempt at understanding what is happening when people say they “should” do something.

I’ve been a seasonal resident of Shouldlandia myself. Every few months, I have a “I should do more YouTube” phase. For a two month stretch in 2022, I took action on this by hiring a coach to help me make some cool videos and it worked! I shipped 10 videos that I liked. But then immediately after, I stopped. I have 22k subscribers on my StrategyU channel and it’s already monetized and driving traffic to my course so it’s hard to avoid the thought that keeps popping up in my head that, “I should do more YouTube.”

Over time I’ve gotten better at intercepting that voice in my head with the following, “Well, Pauly, you’re not doing a damn thing to make that happen, so maybe you should just stop bullshitting.” I then agree with the voice and move on. I commit to not committing to YouTube. I pack up my bags and take the next train out of Shouldlandia. Every minute longer I hang out in Shoudlandia is time I end up disappointed at how much time I could have spent doing more interesting things.

Shouldlandia is a sexy place to hang out at the beginning of a creative journey. Instead of facing the uncertainty and discomfort of creation, you can focus on how cool it would be if you created something. You can find others to hang out with in Shouldlandia, too, who are more than happy to swap stories about why they can’t do the thing too or share notes on how, theoretically, eventually, they will definitely start doing the thing, but only when conditions are right.

This is not to dunk on people in Shouldlandia. I think this is likely a brutal and necessary stage for every creative person to go through. Ali Abdaal said in a recent podcast interview that he wanted to start a YouTube channel for SIX years! But now that you know this place exists, you should do whatever is in your power to try to leave. This is why during the first phase of creative, I often suggest that people look for bold, even self-coercive actions like committing to daily or weekly streaks, accountability groups, courses, and bets.¹

Once you’ve gotten past that you need to start updating your stories. You can shift away from “should” and simply starting to notice what you are capable of over time. But this can be hard and sometimes your behaviors start to surpass your stories. Angie was telling me last week how much she wrote over a week and it was impressive. I told her, “that’s amazing!” But her response was, “I could have done more.” She’s still partially living in Shouldlandia. For years she actually has struggled a ton with writing consistently. But now, over the past two months, it’s as if she’s broken through some invisible barrier and she’s writing more and in a powerfully consistent way than ever before. It’s a beautiful thing to watch. In my eyes, it looks like she’s left Shouldlandia but she still hasn’t realized it yet.

Early on my journey it took me a while to realize that writing was the thing I was doing with ease. I remember immediately after quitting my job, I wrote a big long essay called “Crisis at Work.” I hired a professional editor to help me with my writing and paid someone to create graphics for the piece. I only had like 100 subscribers on my newsletter but it didn’t matter. I was excited to work on it. But I was completely oblivious that this sort of energy was worth paying attention to because I spent most of my time in the headspace of thinking I “should” try to become a kick-ass freelance consultant. Eventually, I did pay attention to my own behavior. It’s hard to ignore the fact that I have not had to struggle very much writing 250+ issues of this newsletter over 6+ years. And then this past year, when my life was disrupted because of our daughter and travel, I still sent out nearly 50 issues of this newsletter, chipped away at a draft of a book, and wrote a couple of longer essays. I didn’t have to schedule time for writing or coerce myself to do it. It just happened.

That’s a good clue that I should probably not waste time going to Shouldlandia and talking about my YouTube dreams. A creative person on a creative path will inevitably always create more “shoulds” and we shouldn’t always ignore them. But its important to test them as quick and possible and try to find the exit ramps out of Shouldlandia. My preferred experimentation approach is something I call “Ship, Quit, & Learn.” I design experiments that I plan to quit within a month or two. I may eventually find a way to do YouTube sustainably, but it will come from experimenting with different ways of making it happen in reality, not in the shoulds in my head.

One “should” I’m grateful that I tested was writing a book. Sitting in Mexico in December 2020, I had a powerful SHOULD dancing in my head after a few people asked me to write a book. To test this, I opened a Word doc and immediately became excited about what started to take shape. Almost instantly, the “should” morphed into a powerful energy that was pulling me forward. A few weeks later when I found myself excitedly writing while quarantining in Taiwan, I knew that writing the book was inevitable, it just took putting in the time.

Pay attention to what you actually do. There is no more valuable source of information on a pathless path. It is easy to forget that you are the actual weird, unique, quirky human that actually has to do the things you claim you should be doing. You get distracted by what other people are doing and think you should do those things. It’s often way easier to double down on the things you notice you are doing, right now, given your current circumstances. As a creator you will always make many stops in Shouldlandia and sometimes they may be useful. But the key is just never signing a long-term lease.

+ This post was also partially inspired by a challenge a few of us made to Kelly Wilde-Miller last weekend. She has had trouble executing on her creative desires and a lively conversation ended with a 5-day mini-book writing challenge. It looks like she’s going to pull it off too. So cool.

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Thanks For Reading

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