Beyond Work Sucks: What To Actually Do If You Are Miserable

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).

However, in this article, Thompson still seems stuck in a systemic view of work and the symptoms of that system. By doing this, he 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 any ideas about what to do next.  

Our social media environment incentivizes this. It’s much safer to share something that shows vulnerability and gets a “me too!” reaction than something that might challenge the status quo.

I’ve read articles slamming co-living communities for being utopian, privileged, escapist and out of touch paradises. So last year when I went to visit one of these communities, I was shocked to find people from all over the world who were craving (and achieving) a deeper connection to others and aspiring to build a life-less centered around work.

This attitude of “well what the hell can we do?” most powerfully came through in a recent New York Times “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.

However, they are missing the countless people across the world (and from all countries) who are reinventing their lives and living in new ways. I’d love to see more articles exploring and highlighting two things:

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

What can we learn from people that have carved their own paths?

Over the past two years, 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-day 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;
  • Laura Gallaher joining Remote Year with her co-worker and employee to shift her business from an in-person one to a digital one
  • Ervin Ling quitting his job at 30 to work 15 hours a week as an English teacher;
  • Bryan Victor skipped the traditional path of the university in Singapore to learn through life experiments.
  • Khe Hy leaving Wall Street to be a sensemaker for the miserable elite
  • Christine Bader “learning to quit” rather than missing out on seeing her children grow up because of work

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. Tyler Tringas investing in founders who want to build “calm companies.”

At the center of these stories is an uncomfortable truth.  One has to leave the traditional full-time paradigm to build a more reasonable life that makes sense.  

It’s just hard to dodge the judgment 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’re willing to compromise on traditional metrics of success in the short term, you mine as well do it on your own terms.

How Does Change Actually Happen?

Stories of reinvention are great, but they are not sufficient. Most people can find enough difference with another person to explain away that person’s success. “Oh they could do that because they worked at X” or “sure they probably had a ton of savings.” The reason people do this is not because they don’t think they are capable, but because change is not fun and its quite hard. I think this is why it is important to demystify the process a bit. Here are three “steps” I have seen in many people’s journeys:

STEP 1 – A Crisis?: For many, there is a crisis or major 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 me, dealing with a health crisis in my late twenties and taking several months leave from work forced me to come face to face the fact that I was too deeply tied to my identity as a “successful” worker.

Yet these crises rarely lead directly to a dramatic leap despite our belief in that narrative. A crisis often shatters our beliefs and then gradually as we start to pick up the pieces, the possibility of change appears as a result of profound conversations, books or other life events that linger in the brain until the person is ready to start taking action.

For Lydia Lee, she found herself literally and figuratively burned out in a Russian hotel room, but did not start to imagine a different way of life until she had a profound conversation on a boat visiting her home country of Malaysia with a German who was running a business remotely.  This piqued her interest and planted the seeds for her to start to think about her work and life in a new way.  When she returned to Canada, she re-visited Tim Ferriss’ 4-Hour Work Week with new eyes and started to apply some of the lessons to how she might work with more freedom.

STEP 2 – Friends: The next thing that seems to matter is that you need at least one or two friends that will support the new way of being.  This appears to help people get “permission” to move forward and have someone to confide in when they are uncomfortable or find themselves a bit lost. These people 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.

Candace Moore, who now is an author and yoga entrepreneur, she has support and inspiration from her mother, who was always a natural entrepreneur starting businesses in her home and adapting to her circumstances. Tony Triumph didn’t realize his family was any different until later in life, but reflected that he grew up around people that were always working in different ways to make a living.

One thing I have my coaching clients do is find someone online they can have a “path perspective” conversation with. Whatever you feel pulled towards, there is probably doing something like that already. I have them send a short note asking for advice and see if they’d be willing to offer 15-30 minutes of their time to share insights on what to avoid, what to think about and how to be prepared. People are often surprised at how willing people are to help others that want to follow in their footsteps.

STEP 3 – ASPIRE: Finally, the person needs to have a long-term vision of who they want to become.

People often arrive at this point after first questioning something they have taken for granted, like how they think about “success” and have it be a gateway to a deeper contemplation of who they really might want to be.

Then it comes down to actually shifting energy towards those new possibilities. As much as life hacks and “how-to” guides would want us to believe that change is a straight line and can be planned, the philosopher Agnes Callard gives us a different model. She believes that when we aspire to be a different person, we often have a hard time explaining our motives.

This is often the case in people I talk to. They may not have a clear vision of a future self, but they are open to experimenting in new ways. Callard might say that these people have a vague sense of “something better” in the future but have trouble articulating it. Instead, transformation is a process of “trying on values”

we “aspire” to self-transformation by trying on the values that we hope one day to possess

This is also why from the outside it is so hard to differentiate the money-driven entrepreneur from the self-employed person trying to hack a life. The people I know who are most fulfilled carving a different path are also the ones that have no idea how to explain what they are doing to anyone.

But deep down, they have a pull towards a journey or a life that tells they, “yes this is the right way.”

The “Work Sucks” Perspective Is Still Valuable

A close friend e-mailed me Thompson’s article and said “this is me.” He probably sent it to me because we’ve talked countless times over the past few years about this persons predicament. We walso talked about his unwillingness to do anything about it.

Thompson has added tremendous depth to the discussion around work. 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

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 remarkably well for some, but leaves many hoping for a deeper connection to life.

Want to take action? Paul is launching Reimagine Work a digital online learning x coaching x experiment that will deliver activities, community and connection to people that want to carve a new path. Explore now.

About Paul Millerd

Paul is a writer, creator, and curious human that is passionate about how people can reimagine their relationship with work to do things that matter. He published The Pathless Path in 2022.

Leave a Comment