Boundless #41: Beyond "work sucks!"

Reinvention, transformation & people who actually carve their own paths

Mar 02, 2019

March 2nd, 2019 - Taipei, Taiwan

The Boundless Newsletter explores the relationship between work & life, unlocking our creative potential and thoughts on the so-called "future of work" Visit Site

In today’s article, based on a record number of people that e-mailed me Derek Thompson’s “Workism” article, I wanted to highlight my reaction to the piece and offer some deeper reflection on what this recent explosion of “work sucks!” articles means

💭📚💡 “Re-imagine Work” Kicking Off March 24th - Join the experiment and be part of co-creating the course. Offering on a gift / pay-what-feels-right basis.

If you want to support this journey, consider becoming a patron on Patreon or becoming a subscriber:

#1 Beyond “Work Sucks” Articles

In “Workism Is Making Americans Miserable,” Derek Thompson has correctly identified some of the fundamental problems and symptoms of the modern state of work in America (and increasingly many global cities). Thompson has been ahead of the curve, spotting these trends in his timeless article “A World Without Work” which in 2015 was a bit more revolutionary for its time.

However, in this article, Thompson still seems stuck in a systemic view of work and the symptoms and fails to address the fundamental question of how to build a life around work. Perhaps his inability to get there comes from his own internal struggle:

“This is the right time for a confession. I am the very thing that I am criticizing.”

As someone who has spent the last two years of my life trying to solve this seemingly impossible puzzle and writing about it through the eyes of others, I know there are many ways to “hack a living” as the practical philosopher Andrew Taggart would put it. Taggart has written one of the most powerful assessments of this crisis in his book “The Good Life and Sustaining Life: An Inquiry Into Our Great Vexation” where I believe he correctly frames the challenge:

“There may be no greater vexation in our time than the question of how to make a living in a manner that accords with leading a good life.”

As he identifies in his inquiry, “One cannot deny that the question of the good life must come before that of sustaining life.” This is Aristotle’s good life, not the Kardashian good life. If we look at Thompson’s essay through this lens we start to see the problem. Many of the workers he details have the Kardashian good life, or at least the modern professional equivalent. They have solved many of the problems of sustaining life and but lack their own deeper definition of the Aristotelian good life. It is choosing pour over coffee and luxurious vacations rather than the ability to do whatever you want on a Tuesday.

Anne Helen Peters actually gets closer to a possible question towards the end of her “Millennial Burnout” essay, which Thompson references, but never takes us any further.

“It’s a way of thinking about life, and what joy and meaning we can derive not just from optimizing it, but living it. Which is another way of saying: It’s life’s actual work.”

Thompson and Petersen’s articles were shared like crazy, but they never offered next steps. Part of me wonders if this is due to the business model of digital content which tends toward writing that people can share saying “this is me, understand me!” or “if only people looked at this issue like me the world would be better!”

If they posted some stories or how-to guides about one might possible do, that wouldn’t be as shareable. One would have to look at the article and instead say “damn you, that’s totally practical advice!”

The New York Times had its own recent “work sucks” piece appropriately titled “America’s Professional Elite: Wealthy, Successful and Miserable” which shares stories of people making gobs of money, but left utterly miserable. Even people who see a potential short-term solution seem utterly unwilling to do anything about it:

“I feel like I’m wasting my life,” he told me. “When I die, is anyone going to care that I earned an extra percentage point of return? My work feels totally meaningless.” He recognized the incredible privilege of his pay and status, but his anguish seemed genuine. “If you spend 12 hours a day doing work you hate, at some point it doesn’t matter what your paycheck says,” he told me. There’s no magic salary at which a bad job becomes good. He had received an offer at a start-up, and he would have loved to take it, but it paid half as much, and he felt locked into a lifestyle that made this pay cut impossible. “My wife laughed when I told her about it,” he said.

Symptoms and stories but no deeper questions.

Based on the number of people that forwarded me these articles, they are still worthwhile. They are hitting a nerve. The pain is real and people are not sure what to do. That’s why I’d love to see more articles exploring and highlighting two things:

Stories of the countless people who are experimenting with new ways of living
What it takes to actually transform and reinvent yourself throughout different life stages

On the first point, I’ve highlighted the stories of many unconventional humans.

Jen Morilla traveled the world until she figured out a new career for herself; Lydia Lee relocating to Bali to live a more balanced life;
Jacqueline Jensen took a sabbatical to figure out if work should, in fact, be the center of her life;
Candace Moore accidentally building a business by generously making yoga YouTube videos to help people across the globe;
Chris Donohoe built his own consulting firm around a 40-hour workweek and bringing his full self to the world every day;
Andrew Taggart helping entrepreneurs with the “good life question” and operating in the gift economy;
Ervin Ling quitting his job at 30 to work 15 hours a week as an English teacher;
Bryan Victor skipped the traditional path of university in Singapore to learn through life experiments. The countless people from nations like Malaysia, Nigeria, Saudi Arabia and Indonesia reinventing themselves as a first option. I could go on.

Experimentation is not limited to personal transformation either. Wade Foster finds that defaulting to a remote team at Zapier has helped his team live better lives. Tash Walker thought “flextime” was BS and implemented a real 4-day workweek for her firm in London without compromising profits.

At the center of these stories is an uncomfortable truth. You often have to leave the traditional full-time paradigm to build a more reasonable life that makes sense for you. It's just hard to dodge the judgement and guilt that comes from “stepping back” in the traditional full-time work context. This is why so many of these people I’ve talked to have left and carved their own paths. If you are going to compromise on traditional metrics of success in the short term, you mine as well do it on your own terms.

The second point worth more attention is the answers to the question of “how do I actually reinvent myself?” This is a hard question but one I think very much worth pondering.

First, for many people, there is some sort of crisis or life event. This can be a health issue, a loss of a loved one, a job loss or even a positive event like getting married, having a baby or moving to a new city. For others there is a profound moment of possibility that emerges through a conversation, book or life event that lingers in the brain until the person builds the courage to listen and say “it's time to get going.”

The next thing that seems to matter in my experience is that they need one or two friends that will support the new way of being. These are typically friends or family that have lived life in an “unusual” way and see some value in experimenting or compromising on short term success. I have found in my coaching work that people are often seeking me out as that friend rather than looking for the “how-tos.”

Finally, the person needs to have a long-term vision or redefinition of success that they are committed to. The people that lack this element seem to be more susceptible to the criticism that comes from daring to live in a new way.

This is not a criticism of Thompson’s article. He has been ahead of the curve in questioning why we are working so much despite becoming so much more productive in his amazing essay A World Without Work. Similarly, Thompson’s article is a positive addition to the modern conversation on work. However, I’d love to see the Atlantic, Buzzfeed, New York Times and others do a better job of highlighting the stories of amazing people globally already starting the hard work of reinventing themselves and looking beyond the traditional path that works remarkable well for some, but leaves many hoping for a deeper connection to live.

#2 Four Lessons Launching An Online Brand For “Actually Slim Dress Shirts” For Asian-Americans

Wesley Kang and his partner Tanya Zhang will be doing a series of guest posts on their journey starting Nimble Made, a company that offers “actually slim” dress shirts for Asian Americans

Wesley offers his reflections on feeling like three years in finance was more than enough for him

I came to NY in the summer of 2015 for my first real job, working at a big bank. After 3 years of working there, I realized there wasn’t much more I could learn and I grew tired of the put-your-ass-in-a-chair-and-get-promoted-every-2-or-3-years environment. It felt like a constant race to see who could sit the longest.

He eventually joined a startup where he was exposed to the e-commerce world, but spent his time thinking about “how I could use the newly gained data skills, marketing knowledge, and financial reporting skills to create my own thing that I could be proud of.” Eventually his dreams demanded to be answered.

I could no longer go to work for 8-12 hours a day while my mind was elsewhere, dreaming. I realized I could never be truly good or passionate about working for someone else and I craved the control and creative freedom entrepreneurship would offer.

and putting it all in perspective throughout the journey:

At worst. I re-enter the job market with a much more well-rounded skillset that not many others will have.

Do read the full post here or buy a shirt if you are a skinny Asian-American (or just a skinny dude who can’t find clothes that fit like me)

Note: not a sponsored post, if you’d like to guest blog about carving your own path e-mail me.

#3 Reflections For Our Grandchildren

I posted an extended reflection on John Maynard Keynes famous essay from 1930 on my website.

In the essay, he predicts that “the standard of life in progressive countries one hundred years hence will be between four and eight times as high as it is to-day” which has mostly been realized (about six in the US). His point is that this standard of living might open up new possibilities or what he states, “greater progress still.”

What he is getting to is that at some point in the future (for him, 2030), we may have moved beyond our “traditional purpose” or “the struggle for subsistence” towards a world where we may have to contemplate other ways of being.

He goes on,

Thus for the first time since his creation man will be faced with his real, his permanent problem – how to use his freedom from pressing economic cares, how to occupy the leisure, which science and compound interest will have won for him, to live wisely and agreeably and well.

Read my full reflection on Boundless

#4Reads, Listens & Quotes

👉 Boundless Reads #107 - Five Good Reads Each Week (yes, please)

🎧 Patty McCord & Michel Falcon - What actually works at work? (Where Others Won’t Podcast with Cody Royle)

📚 If you’ve ever want to learn more about Taiwan, Green Island is an amazing English Novel about the modern history of the island (affiliate)

💬 Adam Smith in the Wealth of Nations:

The demand for those who live by wages, therefore, necessarily increases with the increase of the revenue and stock of every country, and cannot possibly increase without it. The increase of revenue and stock is the increase of national wealth. The demand for those who live by wages, therefore, naturally increases with the increase of national wealth, and cannot possibly increase without it.

#5 Questions I’m Pondering

What if phones and the worlds we inhabit within them become more enjoyable and fulfilling than the real world? Are our obsessions with the “real world” just a form of keeping us tied to relationships which area painful and frustrating?
What is community? For me, I find that if I have at least one long lunch conversation with a friend or two talking about the deep questions of life that makes me feel part of something.
Why do so many “educated” people claim to love learning, but rarely spend time learning and why do so many people from non-Western countries e-mail me with relentless motivation to learn and absorb knowledge?

What questions are on your mind? Send me an e-mail or share in the slack group here.

🔥 Take The Three-Week Self-Employment Challenge over at BoundlessU

💬 Join the conversation in the Boundless slack community

☕ Interested in Working with Paul?

🔨 Download the fear setting exercise, freelance target income calculator or career transition playbook for free or a gift

🏫 Want to learn the secrets of strategy consultants? Take my Think Like A Strategy Consultant Course. Enroll now for $199.

🎁 Want to become a supporter of this humble newsletter? Support on Patreon or click below.