I listed out everything I'm working on for the first time in 75 months | #237
August 28th, 2023: Greetings from Taipei. A couple of of days “late” with the newsletter because I did a phone and computer-less weekend and read Pachinko (which was excellent) most of the weekend while hanging out with family.
Want To Write Online? I watched Angie take Write of Passage in 2022 and I was blown away by her own transformation (she’s now writing all the time and might be writing a book) and also by the quality of the experience. It convinced me to radically upgrade everything I was doing with my virtual experiences at StrategyU and generally just made me more bullish on the future of the internet and online courses.
They’re hosting a number of free events before their next cohort including a How to Write Online session and a free test drive of the course. I’m a big fan of what David and his team are doing not only because of the impact I saw it have on Angie but because it’s also probably helped unleash more people onto pathless paths (and helped create readers for me🤣) than any other universe on the internet. (Affiliate links)
#1 I did a “PARA” Audit
This past week I was feeling a bit overwhelmed. I had been in constant motion over the previous two months, never spending more than 14 days in one location. When I am in motion, my deep work and thinking time get deprioritized and since there’s now a cute baby in the mix, a lot of other work got deprioritized too.
The problem with this on a path like mine is that I’m fully responsible for almost everything. This is also the main feature of a path like mine. I can decide to deprioritize work for months at a time.
The last couple of months have been really fun and I’ve been able to be fully present in my life. Vacationing with my cousin and her kids in Maine. Spending time with my parents and family in Connecticut. Visiting my single cousin who keeps a crib in his apartment in New York. And then introducing Michelle to the extended family in Taiwan.
But given that I do enjoy some of my work, want to publish more books, and have more time for creative experiments, I realized that I need a new approach. Six-plus years of working on a wide range of projects means I’ve had a decent amount of maintenance creep. If I don’t actively spend time taking care of a bunch of small tasks, they can add up. And when I take a few months to lean away from work (and in this case, most of the past six months), it can make me feel stuck.
So I sat down last week and decided to list out everything I’m working on. I decided that I should take a look at what Tiago Forte had to say about this since he’s someone who’s excellent at creating systems. I dug into his PARA system, which stands for projects, areas, resources, and archives. The most helpful thing I found was his video where he showed his own project structure.
I then started writing out all the “areas” of things I am working on. I was surprised at how many things I had going on:
I realized that I was basically managing the tradeoffs between all of these in my head. What I worked on for most days was really just a product of what felt most alive and/or urgent. This has been a useful heuristic for figuring out what to work on, especially when I had more time than interesting things to work on but I think given less time to work (I don’t plan on building a life around a traditional 40-hour workweek) it can be a blocker to working on the longer-term more meaningful projects like a book or something else I can’t imagine yet.
I now realize why I wasn’t getting more writing done. Sixty minutes of admin on eight different things can really eat up a week.
Here’s a listing of the “live” projects I’m either thinking about or taking action on:
The obvious conclusion from this is that I was trying to do too much in too little time. Add to that the reality that my observed preference when I’m around my daughter is to spend time with her. Work is cool but have you tried trying to make a baby laugh for two hours?!
My strategy to deal with my lack of willpower to avoid playing with my daughter is to leave the house for three four-hour blocks per week for the next couple of months. In that time, I’m hoping to either take action on projects, hire people to help me with specific things, or decide NOT to do them at all.
By writing down what I am working on or thinking about, I have a clearer map of what I’m trying to do. It’s helping me say no to anything else and start executing on some of these things I’ve either been thinking about for far too long or am only muddling through.
I commented to a friend recently, “These paths never stop being weird, huh?!” Every month is new territory and the approach that got me here might not help me in the months and years ahead.
This, of course, is the wonderful thing about this path. I love the puzzle of trying to orient my life in interesting ways to do work I care about and spend time in ways that give me satisfaction.
#2 What Do You Want?!
Fellow David Whyte admirer and friend Calvin Rosser recently shared an essay about a challenge he was having with a friend. The friend was thinking about quitting their job and wanted advice.
Except they didn’t have an answer to a simple question, “What do you want?”
His friend’s response:
“Hmm, I don’t know. I haven’t really thought about that.”
Before we get to Calvin’s advice (which is great), I liked how he framed the choice of life paths:
Taking the default path is not safe. It’s more like opting into a game of Russian roulette, where the cost of losing is wasting your one chance to enjoy your life.
Despite the many faults of the default path, the lesson is not that you should avoid it. It may work for you; it may not. The lesson is that there are no paths that can guarantee that you will move through life without any risk of messing it up. Creating a life worth living is like embarking on an ocean crossing. There is no route or amount of preparation that can ensure you won’t get caught in a violent storm.
I like this a lot. It seems that the allure of the default path for many is that people see it as safe and because others agree with this assessment, people will not ask you questions about your worries and insecurities (which will happen all the time if you take a pathless path).
Calvin’s first counsel to his friend is to TRY STUFF. This sounds simple and obvious but I don’t think it is. Instead of taking action to figure out what you want, it seems that people think they should just be able to conjure a clear answer in their head. This is probably one of the biggest errors people make in the modern world: thinking that too many things are thinking problems when they are actually action problems:
As soon as you can, expose yourself to as many new things as possible. Travel. Change jobs. Date around. Read voraciously. Interview old people. Try new hobbies. Follow the whims of your heart.
But this can be hard because of how people see you:
People may call you non-commital and directionless during your exploratory period. Ignore them. What they don’t understand and what you won’t understand until later is that meandering for enough time is the only reliable way to create a higher-resolution map of your desires.
When you explore in an unfettered way, a beautiful order begins to arise from the chaos. Little by little, as you expose yourself to the many paths the world has to offer, you begin to understand the nuances of what you want and don’t want.
The second piece of counsel which I think is great is that you should learn to think in trade-offs. On the default path, a lot of trade-offs are “priced in” and are made for you. For example, the hours you work and where you have to do that work are out of your control and pretty similar to everyone else on the same path. This can be great for “fitting in” but can also be a trap because you aren’t consciously making these trades.
On your own path, you start to see the “price” of trade-offs more clearly. Calvin, who is a lot braver than me, left the default path after only one year. As he said:
I understood the trade. I knew that I would gain freedom and lose security, money, and prestige.
I think one advantage of being on your own path, especially early in life, is that you learn to assess trade-offs
The whole essay is worth reading and his newsletter is worth subscribing to as well.
#3 Fear Of Shipping A Book…What Comes Next?
🎙️Link to full podcast episode with Tom Critchlow
Long-time co-conspirator and friend Tom Critchlow asked to record a conversation with me last month. He was one of the first episodes on my podcast back in 2018 (episode 7 I think!), so it was a delight to catch up with him again.
He was feeling stuck. He had been working on a book for a few years and knew he might be getting to the finish line. He had a lot of questions:
When he published it, would he lose interest in consulting?
He has a course that people love - is that his thing now?
Who is he if he isn’t working on a book?
Battling identity on the pathless path is a challenge and this conversation was very good if I do say so myself.
Key Themes from the Video:
Self-Reflection on Writing Journey: Tom talks about how much he likes writing and how he feels about the book
Consulting Through the Lens of Writing: Every consulting client Tom engages with becomes a learning opportunity for his book.
Fear of Post-Completion: There's an underlying apprehension about what life and work will look like after the book is finished.
Challenges of Writing Without a Blueprint: Writing a book, especially the final 10%, is more challenging than he expected.
Quotes from Tom:
On Wandering and Non-Doing (10:15): "I haven't given myself an admission and time to do nothing... I'll go work out or take time to myself, but that's slightly different than doing nothing."
Writing's Impact on Life (26:00): "Writing this book has been the happiest period of my life like in New York I can't attribute all of that to writing in the book but like the last five or six years of my life have been incredibly generative."
Consulting and Writing (26:51): "Writing the book has been a way for me to really enjoy doing consulting like the every Consulting client I have I'm putting through the lens of you know what am I going to learn about the practice of Consulting that I can then distill into my book."
Fear of Finishing the Book (27:21): "I've enjoyed the process of writing the book so much that the act of finishing the book is closing that chapter…I don't think I'm gonna stop writing but I think that there is uh there is a little bit of uh just like on fear of the unknown I guess right of like you know well what should I write about afterward."
Thanks For Reading!
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This is such a good idea. I'm going to attempt this.
LOVED Pachinko. Enjoy the ride, Paul!