How To Make Progress Without Goals | #145

June 19th, 2021: Greetings from Hualien. We finally discovered an outdoor beach to wander around that wasn’t shut down due to covid. Here’s a view from the beach and also one of our first nights with a clear view of the mountains

If you’re stumbling on this from the web feel free to join this infinite game.


#1 Progress Without Goals?

Today’s post is the simplest model of how I think about finding work I want to do. It covers two phases one hard to design and the second easy. The first phases is one in which you lose faith in your default scripts and a second in which you shift away from “getting ahead” towards future goals and simply towards “coming alive.”

As I wrote in issue #100 I think the secret of work is simply about finding the work you want to keep doing. I’ve written this a few times but don’t think I realized I was saying it in contrast to escaping work until it was pointed out in one of Venktesh Rao’s newsletters. There are many recipes to figure out how to find work you like but the best involve tinkering and iteration. This is also easier being self-employed than employed because you can change what you do every day if you desire.

Phase 1: Emergent Energy

In 2014 after I started to recover from Lyme disease, I had a hunger for life. Some Academics have called this “post-traumatic growth” which describes a state of renewed energy for life on the other side of a life challenge.

I’m not sure how to replicate this without going through a crisis but I’ve seen this kind of spirit emerge from breakups, health crises, losing a job, or sabbaticals (which we covered last week). Some people have also had similar kinds of shifts after experiences with psychedelics but I don’t have much wisdom to offer there. In 2020 it seems many of you went through some sort of crisis moment even if you were afraid to fully admit that.

In 2018 I was having a conversation with Tiago Forte about course creation when we both realized that our journeys started with a health crisis. He has a great post about how this influenced his journey:

Speaking with people about my experience over the years, I’ve been surprised to find that many of them have some sort of chronic condition. A bad knee, a mysterious allergy, a recurring infection, or an addiction that they can’t kick no matter how hard they try. The medical system isn’t designed to treat us holistically. If it can’t be fixed with a pill or a surgery, it falls on you to organize your records and change things up when they’re not working. It was around this time that I began to seriously think about the potential of digital notes to improve people’s health, whether they are sick or just need better self-care. What if instead of a patient chart with indecipherable scribbles only available to doctors, we had an organized and accessible database of our entire health history across every doctor?

From 2014-2017 I remained employed which kept me a bit blind from the energy that was emerging but when I look back and put the pieces together all I see are experiment after experiment leading me towards leaving my job.

I didn’t have a good understanding of what I was doing at the time but it’s clear that I have a very simple approach that has helped me win the slow, dumb & long game.

Phase 2: Try Stuff Without Goals

The second part is the easier part and I’m confident that almost anyone could attempt something with my trusty action challenge framework:

The whole point? Do something that pushes you slightly beyond your comfort zone in an area you’re interested in. Don’t focus on any metrics of success. Merely notice if you like doing the thing. In my reinvent course, which I ran in 2019, the third week is devoted to an “action challenge”. In one week you have to do something like:

  • Hosting a cooking class

  • Publishing one podcast episode or youtube episode

  • Writing one newsletter issue

  • Host a dinner

  • Go on a microadventure

  • Announce an event

  • Create a landing page

I’ve compiled a bunch of examples you can browse here.

The intention is to short circuit some of the ways we typically think about new projects or activities in our life: as things that need to succeed, all-or-nothing leaps, or things we might suck at.

The only goal here is simply to try something, laugh about it and see if you still have any interest in carrying on. Some people love big goals but this is the strategy that works best for me. It’s the one I took over the last five years in my course creator journey.

Why? Invert, Always Invert

I have a fear of designing a life and/or work I don’t actually want. This strategy gives me many decision points in which I can notice if my gut is telling me “I hate this!”

I have made the error of convincing myself that the voice is not telling the truth many times but since I usually follow it up with another small experiment, I can usually pull off the exit ramp before I make it too far.

Will this work for you? Perhaps. But at least try something. You know you want to.


#2 Sabbaticals With Sean McCabe

I had a conversation with Sean McCabe who I quoted in my sabbatical essay from last week. He runs a company where he gives all his employees every 7th week off and he’s making it his mission to spread this model to the entire world by 2047. Crazy enough to get the Boundless endorsement.

🎧Check out our conversation: Podcast


#3 Four Interesting Tweets

Interesting theory about how our work beliefs got “stuck” in 2018

Did a short thread about all the interesting reactions you get when you write about work and how hard it is to talk about:

Holy demographics

Work hard, or else:


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