Boundless #32: Three Questions That Shape My Journey

Dec 18, 2018

#1 Three Questions That Guide My Journey

A little over a year ago I booked a flight to Taipei to visit one of my friends who had quit the corporate world and decided to reinvent himself. Little did I know that on that trip I would begin to imagine a new possibility of living and working nomadically.

There is no way a year ago I would predict that I would be writing this from Thailand in a $15 a night villa overlooking the beautiful mountains in Pai with an incredible partner on a path of her own. Nor is there any way I could have predicted I would have gotten rid of most of my possessions, have earned the lowest income of my "career" and completely re-imagined my relationship with money and work.

As I've written about in the past, I feel incredibly lucky to be on this path, a "pathless" one at that, a phrase I've adopted from David Whyte.

This newsletter has evolved into a place where I can ponder Seth Godin's favorite question "what is it all for?" The long workweeks, the career without any breaks, the idea that one should work even if the work is demeaning, low-wage and without benefits, the idea that a vacation is enough leisure for a person, the hustle, the pursuit of money over generosity, the pursuit of "meaningful work" that only applies to a selected type of worker, the charts, spreadsheets, and endless analysis.

What is it all for indeed?

I don't have the answers, but I'm excited to go deeper. To experiment on my own life, share stories from others carving their own paths and continue to have curiosity conversations with anyone who is curious about these same questions (I'm fully available to chat from December 26th - Jan 12th on US time).

My hypothesis is that there is no e-book, there is no roadmap or plan or strategy to help answer these questions. The answer is likely more questions and commitment to continued reflection and reinvention.

I wrote this piece for Quartz the three questions I keep coming back to:How much money do I really need?What is the work that calls me?How do I want to spend my time?It doesn't offer clear answers, but perhaps it might resonate and show you that there are other people out there that don't know what they are doing but are trying to figure it out anyway.

👉 The three questions that have guided me...

☕ Curiosity Conversation - Let's connect

This newsletter has unexpectedly grown a lot in the past several months. It is now to the point where most of you are strangers. I'd love to change that. Over the holidays I will be on Eastern US time and have set aside a lot of time for "curiosity conversations" - short chats to learn about each other and share stories. No agenda, no sales pitches, just curiosity.

☕ Book a Curiosity Convo (December 26th - Jan 10th)

#2 Four Day Reflections from Basecamp

Boundless reader Kris Niles forwarded me an excellent article he wrote about Basecamp's seasonal 4-day weeks in the summer. Basecamp is a company I've written about many times and think is perhaps one of the best examples of a company that "gets it."

Kris shares his own reflections:

"I was a product designer at Basecamp for a few years, where we worked 4 days a week during the summer months. For us, seasonality was a key to making it a sustainable and enjoyable practice...we enjoyed transitioning into (and out of) them each season, which kept things fresh"

I love this. In the article he shared, he mentions that the key benefit of the summer four day weeks was the hard cap on the number of hours. 32 hours. That's it. As he says. "the key is in the constraint...Removing a day each week forces you to prioritize the work that really matters, and let the rest go"

This is my central argument for trying the four day week. It doesn't have to be year-round, maybe try three months or just the summer. Basecamp is a company already obsessed with maximizing the useful work they do and it is no surprise they have experimented with a shorter workweek as well.

I could see how shifting in an out of a 4-day/5-day cycle could give you even more lasting benefits to drive a continued focus on work that matters than a one time shift.

All I hope is that companies try something. Even my consulting friends who tend to enjoy their work e-mail me telling me how much nonsense they spend their time on, either creating reports to impress their partners or doing endless analyses because they "can't just leave."

Here is my formal endorsement of the summer 4-day workweek. Who's in?

#3 PODCAST! - Bryan Victor didn't go to university, he created his own education instead.

Bryan Victor has never taken a traditional path but he doesn’t know any other way. Perhaps that is why he started his own podcast in Singapore, Misfits, which interviews unconventional Singaporeans. At 20, he saved up $10,000 while he was serving required military time and decided he would travel the world for a year. During the trip, he realized this was all the “schooling” he needed (see 10 things I learned). After learning how he could live simply on very little money, he knew that this opened up many options for him.

He knew that he would always value flexibility over maximizing income, learning this lesson earlier than others.Regardless of any position towards “formal” schooling, his chosen path, wedding planning, wasn’t something you learned at school. He knew he had to create his own internship. So before his trip, he wrote to 50 American wedding planners (the best, he says), to ask if he could work with them. One person gave him a chance and he was able to learn while making enough money to live.

🎧 LISTEN 🎧
Web • Apple Podcasts • Stitcher • Google Podcasts
Overcast • Spotify • PlayerFM

#4 Quotes

Activity vs. Leisure

What is not taken into account is the motivation of activity. Take for instance a man driven to incessant work by a sense of deep insecurity and loneliness; or another one driven by ambition, or greed for money. In all these cases the person is the slave of a passion, and his activity is in reality a “passivity” because he is driven; he is the sufferer, not the “actor.”

Erich Fromm, The Art Of Loving

#5 Reads / Listens

Podcast: Larry Summers spends 20-ish minutes on The Future Of Work and reinforces the technocratic view of the future of work (what I call conversation #1). While he points out that in the 1960's "it used to be that one out of 20 of those people (prime-age men) were not working. And today, even though we have 3.7 percent unemployment, it’s more like one in seven of those people are not working" he seems to miss any identification of the underlying factors and his only policy solution is to increase the importance of work in society.

This long-term decline of work (slightly offset by a temporary increase in women in the workforce) has been happening for over 40 years and we should be asking deeper questions to design a future that is more imaginative than re-creating the 1960s.

Five #goodreads: Weekly Reads #99 (Issue #100 will be out next week with over 175 links)

New Reads: An amazing gift experience while traveling in Thailand

Past Reads: Ten Most Surprising Benefits Of Self-Employment

Time: About Time, Why Western Philosophy Can Only Teach Us So Much:

"Getting to know others requires avoiding the twin dangers of overestimating either how much we have in common or how much divides us. Our shared humanity and the perennial problems of life mean that we can always learn from and identify with the thoughts and practices of others, no matter how alien they might at first appear. At the same time, differences in ways of thinking can be both deep and subtle. If we assume too readily that we can see things from others’ points of view, we end up seeing them from merely a variation of our own.