How To Unlock Your Creativity | #138

April 24th, 2021: Greetings from Taipei. Went to a baseball game with my friend Michael this week. I was impressed with the “superfans” who stand, cheer and perform different choreographed dances during the entire inning when the home team is at bat. Quite fun.

Shoutout to Alex, Nolan and Jamie for becoming paid supporters of the newsletter. If you’d like to join them or simply join the ride for the weekly free Saturday newsletter with 3,886 other subscribers you know what to do:

#1 How I Think About Creating & Writing

Someone asked how to write a “successful” newsletter this week and I thought that was the wrong question. I’m not sure whether mine is successful but I’ve done a lot of issues and a few thousand people are reading it so I thought I’d offer an answer to a different question which is more about how I think about my creative “process.”

Talking of a “creative process” sounds a bit snobby so instead I’m channeling my inner engineer and offering my perspective on my “creative engine.”

Let’s dive in.

The “Creative Engine”

How have I created 138 newsletter issues? What seems to work for me is a formula that combines consumption, time & space to create, consistent output, and feedback.

Step 1: Input

I think most people would be better off by actively blocking the news. Not simply “I try to avoid watching too much news” or “I check out Fox News to balance my viewpoint” but a total blockade.

Here are what my Twitter and Facebook feeds look like:

I installed the Facebook newsfeed eradicator several years ago and now barely check facebook. Part of this is because its not all that interesting and I’ve shifted to twitter where I find a lot more people interested in similar things. Nonetheless, I still run a feed blocker on Twitter and also mute words that attract outrage like biden, trump, brexit as well as unfollowing or blocking any new sites like CNN, Fox, MSNBC, and so on. This seems to leave me with a good signal to noise ratio and a steady stream of like-hearted people to connect with.

I still check the news but maybe 5 minutes a week. It’s easier being 12 hours away from the US too where miraculously the news sites stop updating while people are asleep. If I do want to find out more about a story I go to Ground News where I can entertain myself on the dramatically different framings of the same stories.

I don’t buy the argument that to be a good person you need to “stay up to date” with the news. In general I find that if I am spending time doing the things I like doing, I seem to be a nicer and more helpful person to others around me.

One cool thing about writing online is that every week people send me things I want to read. I get 3-4 “have you seen this?” e-mails, DMs or messages every week and I appreciate every single one of them. This is one of the best reasons to write about things you like.

One advantage I had in terms of “input” is that I’ve always been a voracious reader. I like what Tyler Cowen says about how he reads so much:

The best way to read quickly is to read lots.  And lots.  And to have started a long time ago.  Then maybe you know what is coming in the current book.  Reading quickly is often, in a margin-relevant way, close to not reading much at all. 

I got a late start but at age of 21 I followed a steady stream of curiosity to the current day. I got distracted with 30-50 of the business / pop psychology books but part of me thinks I had to read those first to realize how shallow they were in order to go a bit deeper.

Information Diet

Overall my information consumption looks something like this:

  • 35% books: I am typically reading a few books at once and read about 3-4 books a month. I’m at a slower pace right now because I’m writing my book but I always have a few books I want to be reading next. If I don’t like the book I stop reading and move on. I don’t care about finishing books.

  • 25% longform: There is a lot of good writing on the internet, you just need to have a good eye for it and know where to look. I generally get great recommendations from newsletters like The Browser, Longform, Sunday Long Reads, Rad Reads, and many others writing great newsletter. Anytime I stumble upon something worth reading, I tag it to instapaper or matter and then end up reading it at some later point. I love reading so there is no planned reading time in my life. It just happens.

  • 20% Zeigeist / Shortform / Twitter: I tend to scan a lot of stuff and try to get a feel for things happening in the digital / creator / internet world. I shifted my life in this direction a few years ago and its been fascinating to see the world shift in my direction. It still seems like the digital worlds are a few years ahead of the rest of the “mainstream” world but I expect that gap to more or less close over the next decade. I’ll keep watching until it stops being interesting.

  • 20% Conversations: This is my personal secret sauce. Not because there is anything special about conversations but because I get so inspired by other people. When I’m sharing ideas, answering questions, engaged in e-mail replies or doing podcasts, I always tend to come up with new ways of thinking about things I write about and come up with new ways of talking about something.

Second Brain

Until 2018, I didn’t take notes or store anything I was thinking about. I had always managed everything in my head and that seemed to work just fine for most of my jobs. However, this changed when my friend Jonny shared Tiago Forte’s initial essays about using a “second brain” approach to take notes in Evernote. I hacked together an 80/20 approach in a couple hours and it seems to be the missing piece to my process. In 2019 I moved to roam and really like that because it fits well with my unstructured way of thinking. Here are some apps I use:

  • I pay for Instapaper premium at about $30 per year which lets me save all my highlights and search all the articles I save.

  • I use Matter, which is an amazing app for finding, sharing, taking notes, and even listening to articles. It also syncs to readwise…

  • I use Readwise which collects notes from kindle, e-books, instapaper, and Matter and then sends them directly to Roam. This app is magic.

I have a weekly cadence around this newsletter when I go review:

  • Articles I read in Matter

  • Articles I put in Instapaper

  • Notes I synced to Roam

  • Bookmarks on Twitter

  • Notes from conversations about topics to write about I keep in Roam

How do I decide what to write about? Read on

Step 2: Create

This is where the magic happens. I think an underappreciated thing about creating in written or visual form is that you need some sort of process for researching combined with a “sensemaking algorithm” for how you combine, remix, and synthesize ideas.

Most knowledge economy jobs will give you this skill but it seems that people from Academia, Banking, Consulting, Advertising or other client service jobs have the best tendencies that set them up for knowing how to dive deep into topics and then create things.

For me, the brute force of 1000s of iterations in consulting gave me a mode I can drop into to dissect, understand and explain most topics. I use a few basic principles and apply them to the medium I use to communicate. Over time I have built up more “moves” in terms of how I sequence my writing and I can get a little more playful but the building blocks remain.

Yet even with this skill, I had to move through an initial phase of learning how to find my voice and communicate publicly.

  • Phase 1: Developing a basic creation muscle

  • Phase 2: Tweaking the conditions for the long-game

This is why advice like “find your niche” doesn’t make sense for newbies. It’s something to pay attention to but you should probably figure out if you like creating and how to do it reliably before focusing on any one topic.

Our schools and workplaces tell us that we need credentials or a level in a company to have permission to speak. Phase 1 is about powering through the insecurity, self-sabotage and impostor syndrome that remain. Dickie Bush’s #ship30for30 seems like a great way to move through phase 1 quickly.

For me, I used Quora, where I answered questions about things I knew about like getting an MBA, breaking into consulting, how consultants think, how to deal with health challenges, UConn basketball and so on. There was no purpose other than I found it fun. I probably answered one question a week for a couple years and also attempted some longer pieces on Medium and LinkedIn

In 2018 I moved on to phase 2 and what this means is that I knew that I wanted to keep going indefinitely. Writing brought something alive in me and while I still don’t think I’m all that great, it is now something worth fighting for in terms of earning money to support the habit and protecting the space in my life needed to make it happen.

My formula for creation seems to be some combination of time & space, steady input of interesting ideas and conversations with actual people, walks, hikes and bike rides to let ideas move around and emerge, and then some sort of external motivation to keep going.

Which brings us to Step 3

Step 3: Output

Step 3 is about shipping and you need to decide where you want to share and how you might find people interested in similar things.

Finding an “audience” for your writing can be a tricky thing, especially at first. I highly recommend starting out in places like Quora, LinkedIn, or Medium where there is a built in distribution.

The biggest mistake people I see people make is they work backwards from what is popular and the decide to write about that. This might get you some followed, but check back in six months and 9 times out of 10, you’ve lost interested. It’s quite hard to remain interested in a topic over a period of years.

One thing that more people should do is attempt to write something long. Take a couple months and go deep. Read several books, talk to people about the idea, share drafts with people and go for it. Doing this a few times per year will be more impactful for your own skills and finding an audience than 50 random smaller pieces.

The second thing to do once you’ve written high quality stuff is to share it with people writing similar things. The easiest way to get my attention is to write something incredibly deep on work that makes me think. I also still reach out to anyone who writes something I like. I recently sent Dror Poleg a few messages and we have had a good back and forth about a few topics we’ve both written about.

You might be surprised but many authors of books are almost always down to talk about their writing. I was a bit blow away when Alex Pang agreed to talk with me but then in our conversation I realized he loves talking about these things too.

Nerdy people who go deep on topic X like other nerdy people going deep on topic X.

I’m a big fan of Oshan Jarow’s writing. He wrote one of the most extensive pieces I’ve ever read on UBI. It’s no surprise that he is able to engage directly with some of the most interesting Academics in this field. They read his essay and they think “hey, this is my people!” He didn’t ask for permission. He just went deep.

(One note: I would suggest reaching out to other “indie” types rather than journalists as most journalists won’t respond to you unless you have some formal credential or mark of approval).

Step 4: Results & Feedback

Once you’ve found a place to distribute your writing you need to pay attention to your motivations and how you respond to positive (and negative) feedback.

Ask yourself, are you motivated by money, praise, likes, connections with potential friends, or getting published in a well-known medium? Likely there are a few of these that drive you and the earlier you are honest about them the more you can lean into them in a healthy way.

One thing I’ve tried to do is commit to a weekly cadence of my newsletter. I try to ship most weeks but I think this can easily spiral into a hustle trap where people create a job for themselves rather than sustain something they actually like doing.

I am writing this newsletter today because I find it fun. Yet I am also motivated by:

  • Friends: I love the people I end up connecting with here and the conversations that emerge from what I put out into the world

  • Money: With subscribers and patrons, I am making about $300-400 per months from small donations and while this isn’t going to change my life, it is a huge boost of confidence that 60 people are like “hell yeah, I’ll support this!”

  • Likes: I do like when people share my stuff and get a kick when something I write gets shared and read by a lot of people.

  • Opportunities: It’s pretty exciting that writing publicly is one of the best paths to career stability. My current path has a very uncertain salary but by writing about topics I care about I have a proof-of-work that gives me access to opportunities in the future if I might want them

The biggest challenge with all of these things is being aware of the gap between your own interests and what others are paying attention to. It’s quite clear that if I wrote about startup investing or the culture war, for example, that I could attract more readers but that will crush my creative energy and undermine my process.

It can be very tempting to write about the most salient issues, but the truth is that a year from now you won’t care about it anymore.

Instead, I pay attention to the things that when I talk to other people about them or write about them, I am still excited about it when I am done. For now these are our relationship with work, creating online and in public, carving a non-default path and life, meaning, travel, and meta-musings on the creator economy and labor economy as a whole. The conversations and e-mail exchanges I have are where I fine tune these ideas and then this feeds how I think about adjusting the content I consumer or don’t consume..

Finally, the hardest thing with creating (especially at first) is to do it with a spirit of non-attachment. Publishing lots of things and enjoying writing seem to have cured me of obsessing over outcomes but I am still a sucker for checking my stats just like anyone else. Its nice to see that people seem

However it is nice to see that people seem to keep subscribing and responding that what I’m writing at slightly higher rates over time. Anyone that says they don’t check their stats is lying.

I haven’t leaned to hard into making this a paid newsletter or making a lot of money from my writing. Part of this is definitely a bit of impostor syndrome (“who the hell am I to say I’m a writer?!”) and part of it is the fact that I think I’ll be doing this for a long time and am in no rush to achieve anything. Writing is a “horizon goal” for me, one that I want to do forever.


I’ll update this post and then publish to my blog and YouTube so if you have questions hit reply and let me know what I left out…

#2 Taiwan Days Off Hacks

This cracked me up

In Taiwan, one of the few places in the world to offer marriage leave to couples heading to the altar, a bank employee wed his partner on April 6, 2020.

They got divorced days later, on April 16.

Then they remarried the following day.

Another divorce and a third marriage followed on April 28 and April 29.

After a third divorce, on May 11, they got married for the fourth time, on May 12.

It was all a plot to take advantage of the self-governing island’s time-off policy for couples who get married — eight days of leave — the man’s employer, a bank in Taipei, said in public records.

The bank refused to approve the man’s application for paid time off beyond the mandated eight days for his first marriage. That prompted him to lodge a complaint with the Labor Department for violations of leave entitlements. The bank was fined $700 last October, but appealed the penalty in February, claiming that the employee had abused his rights.

Taiwan only had 7 mandated vacation days for most jobs per year, a human rights violation in my opinion. Well done. I need to find and befriend these people.

#3 Assorted

🏫 Daniel is selling his Harvard degree

🖼 Creator economy market map

🏃‍♂️ Oshan Jarow explores whether or not the “treadmill effect” of capitalism is real

🤼Craig Mod has a great breakdown on year two of his membership program


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