A Working Theory on Working

A Working Theory on Working
Photo by Ronan Furuta / Unsplash

When I was a kid, I'd always ask my dad about his day when he got home from work. In response, I'd get a voice-cracking "Work!" (I think it was from some old TV show).

He was out of the house before 6am every day. He used to drink a pot (yes, a pot) of coffee before 10am and another pot by the end of the day. He was home by 6:00 for family dinner, unless he went straight to coach a Little League game or practice. Other days he came home to mediate the day's battles between me and my four older brothers. He didn't have a college degree but pursued certifications (and worked 11- or 12-hour days) to rise from sweeping the floors in his first job to company president in his last job before retirement.

In short, he exemplified white-collar work since the post-WWII explosion of office jobs. Find a job, any job (especially if you don't have a college degree), work hard, get promoted when your manager thinks you deserve it, and retire somewhere between 65 and 70.

Work while on vacation, work on weekends, and miss your kids' events during the day.

Thanks to factors that people smarter than I have written about, our relationship with work has changed, especially since the pandemic. Younger professionals want to be in the office. Older professionals want to work from home. Many are re-assessing work's place in their life and re-considering how they spend their working hours. Some have turned pandemic side projects into careers. Whether remote work, part-time hours, or quiet quitting, it's rare to meet someone whose view of work hasn't changed in the last few years.

And somehow, Cal Newport talked about these issues in his book So Good They Can't Ignore You, published in... 2012. In this phase of re-examining my career while being on sadadical, I re-read So Good. I read it in the past but always put it aside before finishing. This time, I read it on vacation in the mountains with a cup of coffee before the rest of the house was awake.

It feels like a "right place, right time" situation and this time, I read all the way through.

Pursue a career in what you're good at is the (oversimplified) message of So Good. Cal first debunks the Passion Hypothesis, which says the key to happiness is to match your career to a pre-existing passion. He believes the key to a great career is to earn career capital by developing rare and valuable skills using a craftsman mindset and deliberate practice.

Once you have career capital in the bank, Cal advises spending it on two things: 1) control over what you do and how you do it, and 2) a compelling mission (even though they're a little different, I'll use "passion" and "mission" interchangeably).

Cal believes that trying to exert control without career capital is unsustainable because you offer nothing in exchange for control. Although So Good was written in 2012, this point echoes a lot of issues in the professional world today. Employees who want to work from home full-time or reduce their hours have difficulty convincing employers if they're not exceptional.

Cal also believes that pursuing mission before earning career capital is a mistake because your mission may change over time. You may have passions and interests, but turning them into a fulfilling career requires the expertise to understand the adjacent possible, which is what's just beyond the industry's cutting edge. Instead, once you develop expertise, you place little bets, or small steps with concrete feedback, to figure out what's next and find your true mission.

So Good has gotten a reputation as being anti-passion. Conversely, my friend Justin Castelli founded PRST, which helps individuals connect "spirit, mind, body, and money in the pursuit of authentic living." PRST also helps individuals "lean into their passion and continue to bet on themselves to create the life they were meant to live."

In other words, PRST helps people incorporate passion into their lives and careers. On the surface, Cal and Justin seem like complete opposites -- "follow your passion" versus "don't follow your passion." But Cal and Justin's messages have more in common than it seems.

I think So Good's anti-passion reputation is misleading. Cal says later in the book, after discussing the importance of finding a mission:

Take book writing: If I published a book of solid advice for helping recent graduates transition to the job market, you might find this a useful contribution, but probably wouldn't find yourself whipping out your iPhone and Tweeting its praises. On the other hand, if I publish a book that says "follow your passion" is bad advice, (hopefully) this would compel you to spread the word.

Cal goes hard against the Passion Hypothesis because it helps sell the book. In reality, he values mission. He even says, "To have a mission is to have a unifying focus for your career." And earlier in the book, he mentions three disqualifiers for a career path, one being, "The job focuses on something you think is useless or perhaps even actively bad for the world." That sounds a lot like "don't do it if it's not something you're passionate about."

And I think Justin would be the first to tell you that your passion may not be your career now or ever, but incorporating it as a side hustle or hobby is crucial for a fulfilling life. And using terminology from So Good, I'm guessing Justin would agree that applying the craftsman mindset, performing deliberate practice, and placing little bets to explore your passion all help on your PRST.

Here's how I see it: mission is the final destination you put in your GPS on a road trip. You'll need to take a detour or stop for gas (where, bonus, you may even get to have an unexpected meaningful experience). Getting from your front door to the destination is never a straight line. The fun is in the adventure.

Similarly, in your career, you'll have to take jobs early on that aren't a passion fit, but help you on your way to the destination. You may need to stop mid-career to earn more career capital to fuel you on your way. Maybe you first make your passion is a side hustle to incorporate into your career only when you've built rare and valuable skills.

And if you're lucky, by approaching your career with perspective and patience, while always keeping your final destination in mind, maybe you can avoid having to fuel your days with two pots of coffee.