Boundless #40: Reinvention & Dreaming Bigger
Why is it so hard to imagine different possibilities? My future of work panel reflections
February 23rd, 2019 - Bail, Indonesia 🌴
The Boundless Newsletter explores the relationship between work & life, unlocking our creative potential and thoughts on the so-called "future of work" Visit Site
💭📚💡 “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 On Dreaming Bigger
About a year ago, I had booked a trip to Asia for a month. I did this five months ahead of time not knowing what I’d be doing in terms of work or life, but had wanted to visit a friend living in Taipei and attend a friend’s wedding in Malaysia. I also realized that the only way to ever plan a “vacation” in my solopreneur life was to just book it and try to plan work around it.
In the months before the trip, I lost several projects and then lost a great project because they weren’t comfortable with me working remotely while I was in Asia.
I was feeling pretty crappy. I had turned down projects for a couple of months prior to focus on some creative projects, but was feeling pretty desperate to land some work so I didn’t feel so worthless in a busy American city.
A couple weeks before my trip, I had a client reach out about a potential project which was right in my wheelhouse. Towards the end of my pitch, I said “sooooo I have this trip planned to Asia. Would you be open to me proposing how I could still do this work remotely?”
They said sure. I was shocked.
The next day I sent them a proposal to spend 25% of my time working on this project from Asia for an hourly rate that would easily support my life over the next couple of months. They accepted it immediately.
A few weeks later in a surf-side cliff town in Uluwatu on the island of Bali, I spent about 5 hour working on the project for the first time from the location pictured below. Just out of sight is the $20 a night room I was sharing with a friend.
As I worked that day, it was one of the first times I was working and didn’t really have any resentment towards that work. How could I with such a view?
It was also the first time where I felt a little silly that I had spent almost a year freelancing and didn’t think about leaving Boston or New York to explore more of the world or visit friends.
This past week, I visited this same place traveling with my partner and realized that this moment, this day of working remotely and abroad at the same time, was a moment that forced me to dream a little bigger and question my own limitations I was putting on my life.
So here I am a year later wondering what I’m not dreaming big enough about now.
#2 Future Of Work = Reinvention
This past week, I sat on a panel at a co-working space in Bali with the topic of “Future of Work: Reinvention.” It was a fascinating panel and I thought I would share some more detailed answers for the questions asked:
1. As you look into your crystal ball and see the future of work, what is one thing you see that you don't see many people talking about?
I talk about this in my article that details the five different conversations that people are having. I think people get a bit confused when talking about work. If you were trying to make sense of what is happening based on the news you would be convinced that the robot apocalypse is upon us. The mass media / public conversation is mostly focused on systemic trends like AI, jobs gains and losses, and technology. These trends are real and are important, but this conversation tends to assume:
People will and should continue working in the same ways
Jobs are the fundamental metric of importance we should pay attention to
Skills and learning are the answer to help people shift from dying or low-wage jobs to good jobs
On the first two points, we tend to assume that work happens within the framework of a 40 hour week, which when we look at the data, we realize that most people (as shown in the US below) do not actually work in that way:
On the last point, Andrew Yang who is running for president on a Universal Basic Income platform points out the painful truth about our hopes to retrain and “re-skill” workers:
The single biggest change has been the elimination of five million manufacturing jobs over the last 15 years, 4 million of which were due to automation and new technologies. When I studied economics at Brown University, my economics textbook said that if you were to get rid of a large number of manufacturing workers they would be retrained, reskilled, they move for new opportunities, the economy would grow, and we would adapt. So, when I was researching my book, I looked into what actually happened to the manufacturing workers in Michigan, Indiana and in the South.
When workers lost their jobs, they did not behave like the textbooks said that they would. Almost half of them left the workforce and never worked again.
I think the blind spot in this conversation is that we miss the opportunity to ask deeper questions:
What is it all for?
What are we trying to achieve via work?
What might be a better way to assess the health of a nation or economy beyond “jobs”?
How are people working in new ways already and how can we learn from them?
In 2009, when President Obama was trying to pass his health care plan, he caved to demands (especially from Joe Lieberman, who represented a state with many insurance companies) to avoid including a public option, which many people felt (and still feel) would have helped eliminate some of the inefficiency of the healthcare system and lower costs. Obama explicitly acknowledges this:
“Everybody who supports single-payer health care says, ‘Look at all this money we would be saving from insurance and paperwork.’ That represents one million, two million, three million jobs [filled by] people who are working at Blue Cross Blue Shield or Kaiser or other places. What are we doing with them? Where are we employing them?”
Goldman Sachs estimate that his plan has since helped create 500,000 new jobs.
This is all to say that I think the thing the future of work conversation misses is that we create blind spots by assuming that our future solutions will be built on the backs of full-time jobs. This assumption is both disconnected from the current reality and not practical for addressing the continued shift of people away from meaningful work and towards either low-wage low-stability jobs or towards no job at all.
2. What was the moment you started looking at the “future of work” through a new lens?
This biggest shift was reading Andrew Taggart’s essay “If work dominated your every moment, would life be worth living?” and his introduction to Josef Pieper’s original work Leisure: The Basis Of Culture written in the late 1940s in Germany.
Pieper and Taggart both highlight how work has creeped into life as the fundamental operating model of life. Pieper here:
The simple ”break” from work - the kind that lasts an hour, or the kind that lasts a week or longer - is part and parcel of daily working life. It is something that has been built into the whole working process, a part of the schedule.
This was written by Pieper the 1940’s and 70 years later, as I shared last week, HBR is writing how-to guides about how to play the banjo at your desk so you can get back to the hustle.
The second shift for me was discovering the beautiful language of David Whyte, who seems to be able to frame the pain of modern work and the constant need to reinvent through poetry in a way that no business book or business “thought leader” has really ever been able to. Sure Simon Sinek has his “why?” but it is still fundamentally based on a model of work as the center of your life.
Here is Whyte:
The core of difficulty at the heart of modern work life is its abstraction from many of the ancient cycles of life that allow the silence and time in which true appreciation and experience can take place. The hurried child becomes the pressured student, and finally the harassed manager. The process is begun very young, and can be so in our bones, depending on the pressure of our upbringing, that the inability to pay real attention to our world may be difficult to recognize.
When I share Whyte’s writing with conversation partners or adopt some of the language (my favorite being the “pathless path”) it seems to hit a nerve at a deeper level than “I need to find a new job.”
3. Paul, you’ve talked to hundreds of people about their careers and paths over the past few years, what are some of the lessons you’ve learned about the people that are “successful” carving a new path?
I’ve learned a few things.
First, the person has to be completely willing to give up their current state. Most of us have a deep attachment to our current identity - whether it be a full-time worker, freelancer who does X or entrepreneur who is building Y. Part of this is because these roles help us to be self-sufficient and not have to rely on others. Being willing to let that go and step into an unknown future is scary. The only antidote I have seen to this unknown is to accept that the world is more generous than we thin. Rebecca Solnit puts this best:
it’s okay to sometimes experience not knowing what to do next, to run into a barrier. It’s okay to realize that life has a mysterious quality to it, it has an element of uncertainty, it’s okay to realize that we do need help, that calling out for help is a very generous act because it allows others to help us and it allows us to be helped… It’s not so necessary in a generous world, in a world where help is available, to be so adamant about the world according to me.”
Second, there needs to be some deeper reflection of your own definition of success. This is incredibly hard for people because if you define success different than most people, you are going to likely be in subtle rebellion against your culture, your family or even your partner. This means you have to spend more time constantly reflecting and refining this definition of success, telling people what matters to you and continuously shifting your life to better align with your states definition. Oh and taking shit from people who either disagree with your choices or are a bit upset that you are making them think about theirs.
Third, and this is the hard part, there needs to be a “fuck it, its time” moment or a crisis that shifts you into action or behaving in new ways. You can’t think in a new way, you can only act your way towards new ways of thinking. This is the thing that eludes me the most. I’m not sure you can get to this moment without going through a fundamental crisis. Most of the time these come in the suffering form - depression, health crisis, getting fired from a job. Many people that go through these types of crisis experience post-traumatic growth that can ignite a new appreciation of life, new possibilities in life and spiritual change.
I am fascinated about ways it might be possible to make a shift in a positive way, without the crisis. I’ve started to see a few examples. One is in new relationships where one partner is able to make a bold shift with the support of the other partner who has already made some sort of shift in their life. Another is when people shift their full-time office jobs to remote jobs or go full-nomad through things like Remote Year. And even some people just boldly have with support of online communities like FIRE.
🔥 Take The Three-Week Self-Employment Challenge over at BoundlessU
☕ 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.