Boundless #35 - Relationships over paid work brought me to Bali

Jan 19, 2019

#1 Greetings From Bali (How I got here...)

Greetings from Canggu (pronounced chan-goo) Bali!

I touched down a few days ago after spending an amazing break with my family in the US. As I recovered from 30 straight hours of travel over the previous two days, I was hit with the inevitable uncertainty and doubt that comes with following a path that doesn't make sense.

A few years ago I created a calendar alert in my phone that pops up every morning with the list of priorities. This is something I mentally committed to after recovering from a battle with chronic illness:HealthRelationshipsFun & creativity Paid workThe first thing that likely jumps out for you is that I've put "paid work" last on the list. At first glance, this doesn't make sense and you might be thinking "well how do you afford to live?"

When I first took the leap to self-employment, I didn't stay true to this prioritization. I focused solely on money - both lowering my cost of living and trying to obtain paid work. In reflection, this is probably a necessary thing for anyone leaving full-time employment. Proving that you can, in fact, land paid work seems to be an essential hurdle to move past.

When I realized that this journey was an infinite game that I wanted to keep playing, however, I knew I would need to find work I was drawn to rather than just trying to get paid. About a year ago, I actively rejected all paid work and created space for experiments - that led to the launch of my podcast, a shift to the "Boundless" name and a deeper commitment to writing.

What I found was a type of work, the "fun & creativity" I name above, that felt sustainable at a fundamental level (while perhaps a little more frightening from an income predictability standpoint). Over time, this work has led to more discussions and helped me continually move towards the types of paid work that I'd want to be doing anyway. About a year later I am starting to see more signs that this bet has paid off and can be a sensible long-term strategy. At the core, however, it is still a daily leap of faith.

So how did I end up in Bali? It's really a story of how I make decisions along these priorities. In July, I met a Brit at the World Domination Summit (hey Jonny 👋) who seemed to be on a similar journey and was even braver than me in sharing his vulnerability around that fact.

I found that we were both working on a number of similar things and that he was prioritizing relationships and creative work in a similar way. When he mentioned he was thinking of trying to get some people together in Bali six months later, I almost immediately said: "I'm in."

I am constantly thinking about trying to get myself in these types of situations. Ones where I'm excited about the work or the people I'm around - a 10 out of 10 instead of a 7 out of 10 level of excitement - and then committing and moving forward.

I'm excited to see what I learn and where this journey takes me next...

#2 Podcast: Mike Tannenbaum on his leap to self-employment, learning, making business more human & his

Mike was always a self-driven creator, developing TI-83 apps for his classmates to keep track of their grades from an early age. He spent a lot of time “head in in the clouds, making things.” It is no surprise then, that he eventually found that self-employment was the right fit after several years of trying to make it work in the corporate world.

Mike and I dive into his path in which he slowly made sense of the fact that it was time to take the leap to self-employment. As he was about to take the leap, his company ended up laying him off anyway. Reflecting back, he has found many valuable lessons in his journey and has brought these together in a self-published a workbook called Clear Path Forward. The workbook helps people re-assess their relationship with work. We talk about the process he took to publish the book and where he sees his work taking him over the next couple of years

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#3 Quotes

I just finished Cubed, which was a compelling history of the modern workplace told through the lens of our work environment, from small two-man (literally, men) to cubicles and open offices. I'll be sharing quotes from the book over the next few weeks.

On how psychological testing got started
"Though they had originally been designed to measure abnormality, it was of course only possible to figure out what was abnormal by having first determined what was normal. Soon these tests became widespread measures for corporations to figure out whether their prospect would be a willing organization man: Was he radical or conservative? Did he havegood practical and social judgment? Would he persevere or fold under pressure? Was he stable or unstable? Was he happy or unhappy? Was he a reforming type or a status quo man? Did he have a sense of humor or not? Refusing to answer the questions was itself revealing, for the tests made provisions for understanding what the answers, or lack of them, had suppressed."

Educational inflation drives complexity?

"Drucker’s explanation for the rise of the knowledge worker in the 1950s and 1960s remains striking. Rather than work itself changing, he believed the increasing life span of workers was changing the labor supply, and therefore changing the kinds of jobs available. An individual could imagine him- or herself working longer—in which case, it no longer made sense to drop out of high school, or avoid college, in order to enter the labor force. One didn’t need a high school education to land a desk in the steno pool; neither precalculus nor the history of the War of 1812 would serve you in your work. A kind of educational inflation, however, soon made a high school degree a requirement, as, in our time, a college degree has become, for working virtually any kind of office job. The jobs had not gotten more complex; the individuals working in them had. In other words, “knowledge worker” was the name for an overeducated office worker—someone whose capabilities far exceeded his or her position. “They expect to be ‘intellectuals,’ ” Drucker writes. “And they find that they are just ‘staff.’"

#4 Reads / Listens

1. Forgiveness: This hour-long mashup of TED talks on forgiveness was emotional and very much worth listening to. The story of the mother of the Columbine shooter and her journey of forgiveness as well as other powerful examples: Link

2. The Career Ladder: Thoughts on stepping down the ladder instead of "up"
"All three jobs—at a firm, in a corporate law department, in a newsroom—were good jobs. But each one made me happier than the last. Each one was more satisfying than the last. Each one was I think more valuable than the last."

3. #goodreads: Weekly Reads #101 and 175+ Links From 2018

4. Last week's essay - 10 biggest career myths

#5 Question Of The Week

What is your ideal office or working environment?

Join the conversation here (link for current members)