Ship, Quit & Learn | #172
March 5th, 2022: Greetings from Austin. I started taking DJ classes last week and loved it. It’s something I’ve thought about doing for years and am glad I finally ended up somewhere living right next door to my apartment. More to come!
The last few months have been pretty jam-packed with all sorts of different projects, book conversations, and client work. I am excited for a lighter month in March. I’ve blocked most of my schedule off from the 10th-20th as well for SXSW. Let me know if you plan to be in town - I plan to be in full wander & serendipity mode.
👉 My friend Alex wrote a vulnerable and well-written account of what it’s like being from Ukraine. I think he’s a great writer and worth following. Check it out here.
Today’s newsletter is sponsored by CrowdHealth. When I was shopping for healthcare I stumbled upon health sharing plans. If I was more certain about staying in one place for a long time I think this is the option I’d be taking. It’s a really interesting option - one of many that seem to be popping up to deal with the disappointing state of US healthcare options.
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#1 Ship, Quit & Learn
How do you figure out what to work on?
This is a question I get a lot. Since even before quitting my job, I had the hunch that aiming at big goals in the early stages of a project was not something that was going to work for me. Instead of maximizing for success, I’ve had better luck embracing what I’m now calling “ship, quit, and learn.”
Part of this is because I’m scared. Scared of commitment, scared of being stuck pushing towards goals that aren’t mine, and of course, scared of simply creating another job for myself.
My approach is probably a bit too risk-averse for some but can be powerful, especially if you are able to implement it often. It resonates with people who have done very little creative exploration or public sharing of their work. Designing for action and leaning is something anyone can do - designing for outcomes or success is typically out of your control and harder to do.
Let’s break down the three parts:
Ship: You have something you want to do but have been scared. What’s the minimum action you can take that would still feel like you are pushing yourself out of your comfort zone? Do that. For example, if you want to launch a podcast, open up your recording app, and record a monologue of why you are launching a podcast. My friend Lucy Liang just did this and discovered she likes podcasting a lot!
Quit: Design your experiment for quitting. When I started my podcast, I decided that if I didn’t like it hat much. Many of us were raised with the idea that you should never quit anything. This is useful for some things but absolutely terrible advice for creative pursuits. Quitting lots of things is probably the best way to find the things you want to commit to. When you design for quitting, you also put less pressure on yourself because it doesn’t make sense to overinvest in time or money. When I launched my podcast, I had a crappy cover I threw together in PowerPoint in 5 minutes and didn’t spend any money on anything else.
I was terrified when I launched my podcast but by lowering the stakes I was able to power through that first phase of discomfort and discover the magic of hosting a podcast and having deep conversations with people I admired.
Learn: This may sound too obvious or too simple, but the goal of any experiment should really be to figure out what to do next. If this sounds like some sort of infinite game, you’d be right. Almost everything I do is oriented towards finding things worth doing, indefinitely. The spirit of “ship, quit & learn” is openness to experience and being willing to see what emerges when we lean into creativity and spontaneity. Often there are three routes people take: scale-up, continue going, or quit. After I launched my podcast, I decided that “keep going” was what I wanted to do. I liked being able to keep the show small and not having the pressure to grow or use it to make money. Over time I’ve made incremental improvements and have gotten better at interviewing but the spirit of the podcast is still the same.
Testing Out Hosting Meetups
I took this approach to test out hosting a small gathering in Austin. I recently read a preview of Nick Gray’s amazing book which outlines an approach for hosting “two-hour cocktail parties.”
His tagline is “don't attend bad events, host great parties.”
His take is that people either put too much pressure on themselves when hosting events or don’t put enough thought into creating structure for attendees who get stressed about attending!
I had been talking with Dickie Bush online about meeting up while he was in Austin and he suggested hosting a small meetup. I knew this was a chance to test out Nick’s approach.
So I decided to ship - I posted a tweet announcing a meetup on Twitter with a link to a simple signup page on Mixily and I knew that as soon as one person RSVP’d I would have to follow through.
It was also naturally designed for quitting - it was only one event.
So what did I learn?
People appreciated me hosting an event much more than I expected. Multiple people came up and thanked me. Some people had not been out of the house in a while and were grateful for the chance to connect with new people.
People appreciated the structured icebreakers much more than I expected (Nick always suggests doing structured activities, it gives a chance for people to find out about a lot of people at once and not get stuck in conversations).
Even during the event, hosting an event still felt scary. The moment before I asked everyone to get together for an ice breaker, I felt tremendous pressure to skip it. I’m glad I didn’t.
It was a lot easier than I expected and I definitely want to host more meetups and get-togethers this year. Nick’s framework is an easy way to avoid overthinking.
I highly recommend checking out this post on his party planning approach (and recommend signing up for his mailing list, which comes once a month or so and is always good!). I’ll definitely share a link to his book when it drops.
Forcing Function with Chris Sparks
My favorite thing about this podcast was that immediately after recording we decided to spontaneously go on a bike ride around the river (Chris lives in Austin too).
Chris is a former poker player (and corporate world escapee) and our conversation goes into the nuances of goals, intentions, and doing work that matters.
“Conversations” With Nick McCray
I talked with Nicholas McCray who is a former journalist and studying in Germany right now on his own pathless path. I love how much care and thoughtfulness he puts into everything he creates. Here is a link to our conversation
Check out this cool cover image!
Jason Levin wrote an essay about “decentralized friendships” which is more or less about making friends online. I liked it!
I like Sam Smith’s essay on not knowing what he is doing. If you’ve read my book, you’ll see that he’s likely unlocked the power of wonder.
I love the fact that I don’t know what I am capable of or what will happen if I turn left instead of right. And that is what excites me. Saying yes to things I normally wouldn’t and saying big, fat no’s to the people and things I was on auto-pilot with is totally liberating. What happens next is always better than anything I could’ve dreamt up whilst sat at my desk drawing up the pros and cons in my journal.
Thomas J. Bevan has a thoughtful essay on the attention traps of the internet and creating our own virtuous cycles despite the traps of spending a lot of time online.
Having been reacquainted with flow we realise that creation and mastery is an end in itself rather than a mere means to make metrics move. And as we act in this manner we attract others who feel the same way, who are also acting the same way. We regain our focus more and more. We do our little bit, in our own little corner to reverse the attention span downward spiral and instead create a virtuous circle.
Chris Williamson’s podcast episode with Ana Codrea-Rado on the modern state of work is fantastic. Ana is one of the deepest thinkers about our relationship to work. Why is she so good? For one she’s a trained writer. However, what makes her perspective so interesting is that she’s experimenting in her own life. She’s moved out of a city and doing a lot of experiments of working on her own. Highly recommend!
My friend sent me this comic on Instagram. It fits well with my take on the ten “hustle traps” for self-employed creators.
#4 Book Stats
Latest book update: broke 1,200 books sold. Should pass 1k sales on Amazon in the next week or so.
From Amazon - a trend of the sales:
Also uploaded the book to Google Books and working on a local Indian distributor in the next month so that books will be a little cheaper for that market (target 500 rupees!) - stay tuned!
I’m also starting recording the audiobook version of the book at the same studio I’m currently taking DJ lessons. Might add a mix to my book!
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