Nassim Nicholas Taleb infamously said, "The three most harmful addictions are heroin, carbohydrates, and a monthly salary.”

I think that a lot of my hesitation to take a paycheck job has been driven by a fear that I won’t be able to continue the creative, “weird” endeavors I’m passionate about. I remember fantasizing in a previous job, “man if I just didn’t have to do these brainless meetings I would have so much more time to tinker and write and create!” I was still thinking that my “creative” work needed to be Forty Hours of Full Time Work in order to Qualify as Nourishing to My Soul.

Here I am a few years later, with almost complete ownership of my time. The reality is that I spend about 30 hours a week stressing about not having a job, 10 hours a week working on hunting for a new one, and maybe 5-8 hours actually working on the projects I want to work on.

As I’ve wandered through communities of folks imagining new conceptions of work and meaning, like the Yak Collective and the Pathless Path, the vibe has been to rebel against traditional “paycheck” jobs. Much of the sentiment is around escaping them, either by taking a sabbatical or making the leap to become an independent consultant. I think this is valid, especially in the process of challenging our assumptions around what’s possible from work. My own sabbatical that started in November has been incredibly generative - a break after founding FindOurView helped me realize that perhaps there were other futures available to me beyond only entrepreneurship and product work.

In the study group I help facilitate at the Yak Collective, several indies felt caught in a dilemma after leaping out of a paycheck job, or preparing for such a leap - prioritize financially lucrative work, or the weird work that we want to actually do?

I think the reality is that financial insecurity is toxic to the experimentation that lays the foundation for discovering aligned work.

If I’m demoralized, I can’t experiment, and I can’t create. I’ve resisted taking a paycheck job because I anticipate it will demoralize me. But it’s not the paycheck that’ll demoralize me - it’s my expectations.

If I expect the paycheck job to be filled with fulfilling work 100% of the time, I am going to be disappointed and this will demoralize me and I’ll struggle to create.

If I expect to do 40 hours of paycheck work and then another 20 hours of creative work outside of work, I am going to be disappointed and this will demoralize me and I’ll struggle to create.

If I expect that I’ll build up a body of work in 3 months and jump ship to a Fulfilling Job then I’ll be disappointed and this will demoralize me and I’ll struggle to create.

Instead, if I set my short-term expectations lower I have a much better shot at building the body of work that Venkatesh Rao describes as crucial to getting paid for interesting work:

I think you just have to do whatever most energizes you and produces a lot of output, and let the work/opportunities find you. I have never gotten an enjoyable weird gig out of going fishing myself. You choose boring, normal work, but interesting, weird work chooses you.

Quantity has a quality all its own as Lenin said. The sheer volume of your work is what works as a signal of weirdness, because anyone can be do a one-off weird thing, but only volume can signal a consistently weird production sensibility that will inspire people betting on you. The energy evident in a body of work is the most honest signal about it that makes people trust you to do things for them.

“Parth, I have a question. Why should I set my expectations LOWER? How can you say that? That’s a recipe for an unfulfilled life. Shouldn’t I set high expectations for my life, reach higher and wider and imagine even more wildly?”

Aha Parth, thank you for the question - you should! But here’s the key - set big long-term expectations, and small short-term expectations. Build vast megaforests by planting small seeds. Small bets, every day. These will compound.

Seth Godin talks a lot about playing Infinite Games. Connect with that inner sense of the life you want to live - perhaps it is a life of creation. (This is where sabbaticals are really powerful, if you feel the momentum of your work has prevented you from seeing what possibilities are out there). If it is, then you have your entire life to live it. You are playing an infinite game. Do what you need to, to stay in that game.

Lawrence Yeo highlights this in his Arc of the Practical Creator. Great read. Spend time every day growing your creative work.

And Visakan Veerasamy double highlights the path to getting paid for interesting work:

Stage 1: Do unpaid work for yourself

Stage 2: Use that as leverage to negotiate a position where you get paid to do work for others

Stage 3: Save up enough so you can be free to do more, higher-quality unpaid work for yourself <--- I am currently here

Stage 4: We’ll see

— Visakan Veerasamy (@visakanv) July 7, 2018

It’s possible to do Stage 1, in small bits every day or every week, at a paycheck job.

For me, my big expectations and dreams for my life include:

• deep, intense exploration of the questions that animate me
• exploring how technology can bring us closer in harmony with each other and the more-than-human world
• running an interactive media studio making strange, surreal, sometimes terrifying experiences that capture what it is like to be inside a dream
• creating an ai research/cybernetics/naturalist laboratory inventing nature-inspired AI models like sakana.ai
• getting paid for all of this work, supporting myself completely independently, creating my own “tenure”
• channeling the completely embodied, mad scientist-inventor energy of Cliff Stoll
• founding startups, maybe founding a startup all the way of my own, if I find a project compelling enough
• helping people see what startups are and what they aren’t, and helping them make bigger and bolder and more correct bets that are better aligned with passion and potential.
• creating a documentary and storytelling projects as unafraid to grapple with human complexity, as HUMAN and StoryCorps

Small expectations, small compounding ways I can work towards these today:

• creating a workbench page to build publicly, where I can host my projects and bench notes (update: it's up! /workbench)
• writing my letter every week to explore intimacy, physicality, and connection
• blogging frequently, posting updates to my workbench
• tweeting updates to my projects when they feel tweetable (shipped something small, reached an MVP)
• continuing to participate in and facilitate the Yak Collective reading group on jump-starting an indie lifestyle
• creating a reading group at Fractal Library for collective intelligence, cybernetics, AI, dynamic systems
• doing a talk → hosting a meetup → running a startup accelerator at Fractal University
• preparing for and completing my full-stack lite bootcamp at Fractal so that I can get better at shipping things
• hosting a Ship Night at Fractal to get people together and drive some activation energy to “ship” something they’ve been putting off (a poem, a piece of code, a tweet thread)
• and more….