Mike and I saddled into our seats on the idling Icelandair 612 at New York’s JFK and marinated on the moment for a bit. Eventually we turned toward each other, cracked the identical smiles we’d been fighting back, and started giggling like giddy school girls.

Then the fresh-faced, tanned, and breathtakingly storybook Swedish girl sat in the remaining seat beside us. Being fans of cute Scandinavian girls (we were headed to Iceland after all), we took this as an obvious sign from the universe: each of us had made the right choice to be here. The aura of possibility swirling around us was electric. We snapped a picture to eternalize the moment.

For me, it was the beginning of an unstructured and unplanned seven month European wandering (save the oneway flight to Iceland), enabled by the sabbatical I had negotiated with my employer of over four years. I needed a break from working in my life, and thought a long-term foreign adventure would give me proper space to begin working deliberately on my life.

For Mike, it was the start of a playful six-week purgatory between leaving his job at an uninspiring Chicago industrial parts manufacturer and kicking off an MBA program at Carnegie Mellon’s Tepper School of Business in Pittsburgh. He too sought to recalibrate his career and life, and had decided a short adventure coupled with a two-year masters education would do the trick.

Getting here was no easy task; it took a while to find our seats on Icelandair 612. But now, side-by-side and stabilized at ground control, we had finally set out upon our own individual roads to truth. And while they would take different trajectories eventually, both roads began in Iceland.

Yet the fact that the launch of our individual transitory periods were occurring at the same time was less of a rare coincidence than it was the result of two years of positive peer pressure we had applied on each other as roommates in Chicago.

Also, it was because of a book club.


It started as a normal Sunday dinner in Chicago’s Old Town. We were bantering back and forth in typical weekend-ending lament — recalling the girls we met at the bar the night before; the depressing realization of our early commute the next morning; admitting our guilty pleasure of dancing to Party in the USA. You know, typical guy stuff.

The conversation made its way to a book we each had read: The 4-Hour Workweek by Tim Ferriss. I can’t remember the specific points that were discussed and which ones we agreed or disagreed on, but I remember how the conversation felt. In talking about the book, and sharing how it inspired and challenged us, we began to view our preconceived notions of work and life with fresh and glistening eyes. The philosophical debate was a welcomed detour from typical pub chatter. An Alan Keightly quote seems to best describe what occurred over the course of dinner:

“Once in a while it really hits people that they don’t have to experience the world in the way they have been told to.”

Encouraged, we committed to read and discuss other books together. We began to invite more of our twenty-something friends to join us. We called ourselves the Chicago Business Book Club, and each month we discussed a new book: Start Something That MattersDelivering HappinessSwitch, the Steve Jobs biography, among others.

The monthly discussions filled an apparent void between water cooler talk with colleagues and bullshit banter with friends. It was refreshing. But Mike and I noticed something curious happening at each meeting — the conversation seemed to inch closer and closer to an odd but retrospectively inevitable place: what the hell did we want to get out of life?

Like Fight Club. But with Books.

Each member of the club was on a slightly different path — a consultant, an engineer, an accountant, a corporate sales guy, an insurance broker, an investment banker, and an MBA student on a private equity track. But there was no mistaking we were all on career paths — sensible, credible career paths we had been primed and prepared to traverse since the day we entered high school.

Yet inside “Book Club,” the undercurrent of the conversations was laced with questions like:

Is this really the beginning of the rest of our lives?

Isn’t there more to life than this?

Am I living the life I’m best fit to live?

And if not this, then what?

And the mother of all questions: what gives us the balls to ask such questions?

We were where we expected ourselves (and where others expected us) to be. Yet these questions found the cracks between our well-laid plans and nestled themselves cozily inside. Perhaps we were realizing how little we actually had figured out.

On the surface we were talking about things like building businesses and making money, while drinking beers and eating pub food. Yet when the lights dimmed lower, we realized what was really happening: we had created group therapy for quarter-life guys — a slightly masculine-ified group therapy session for guys who gawk at silly things like group therapy.

The book club gave us a place to admit that we felt something lacking in our day-to-day lives. It created the time and space to discuss what we wanted out of life. For perhaps the first time for each of us, here we were, a bunch of guys sitting around talking about our life aspirations, our hopes and dreams, and the emptiness we found inside the things that were meant to fill us up.

Mike and I quickly realized the Chicago Business Book Club was becoming a front for something potentially lethal to life as we knew it — something that could alter our mindsets forever and challenge us to think about our livelihood and careers in crazy and unconventional ways. It felt like we were operating a cute pizzeria in the front during the day, and hosting Fight Club in the basement at night — albeit a much nerdier one, trading fists for books and violence for discussion and mutual improvement.

Benjamin Franklin and the Leather Apron Club

On a crisp autumn day in 1727, Benjamin Franklin rallied together a group of twelve friends into a Philadelphia tavern — a printer, a surveyor, a cabinetmaker, a mathematician, a clerk, a shoemaker, and a bartender, among several others. He called the meeting the Junto (or originally, Leather Apron Club, because most tradesmen like Franklin wore leather aprons to work). Franklin brought them together to discuss intellectual, personal, business, and community matters of the day.

In his own words, Franklin wanted to facilitate a structured form of “mutual improvement,” something that would be “conducted in the sincere spirit of inquiry after truth.” The Junto met every Friday and this discourse continued for 30 years.

Franklin devised a list of questions to be discussed at each gathering, most notably:

“Have you met with any thing in the author you last read, remarkable, or suitable to be communicated to the Junto? particularly in history, morality, poetry, physics, travels, mechanic arts, or other parts of knowledge?” 

For the sake of this essay, I’m going to say that Benjamin Franklin started a book club. Maybe they didn’t have access to an Amazon.com-sized catalog or the information explosion of the internet. And maybe Mike and I aren’t exactly your modern-day, kite and key wielding Ben Franklins. But I like to imagine that the Leather Apron Club was just a much cleverly named Chicago Business Book Club.

What Franklin understood (and what Mike and I stumbled upon) is that there’s great power in positive peer pressure. There’s a sort of magic in group sessions like a Junto or a Book Club (or a Fight Club, I suppose). When the time and space is created to air out the ideas, problems, and dreams that are suffocating inside our heads, they begin to take on another form. When a safe space is created in the spirit of mutual improvement, we can push one another to get over ourselves, and to do the big, weird, or unconventional things we sometimes struggle to find the courage to do.

Which brings us back to Icelandair 612.

How a Book Club Can Change Your Life

When I expressed my dreams of long-term travel, of creating a location-independent life and existence, Mike encouraged me. We went on mini adventures and travel meet-ups together; we brainstormed business ideas that could be operated from anywhere; he introduced me to organizations like Escape the City; he listened as I crafted up my idea for GiveLiveExplore.com. And in my moment of desperation, when I decided I had had enough postponing the things I really wanted to do in my life and booked that oneway ticket to Iceland — Mike booked a ticket too.

Likewise, when Mike expressed his interest in moving from technical engineering work to physical product design, I supported him. I passed along opportunities at top design organizations like IDEO; I’d make suggestions of people he could connect with; I’d toss product design ideas at him to challenge him to become who he wanted to become. And when he decided to pursue an MBA to propel himself down that road, I wished him well.

And what about the other cast of characters we drew into the book club?

The accountant left his job to hike the Appalachian Trail for 6 months.

The sales guy decided to pursue his passion in hospitality, left his job to learn how to run a bar, and is now opening his own bar in Cleveland, Ohio.

The investment banker, insurance broker, and private equity guy all stayed on their track, and are doing extremely well in their careers.

While some of us made drastic leaps and others stayed on their straight and narrow, all of us came to our own individual conclusions on what we wanted to get out of work and life. And we did so deliberately. Fueled by the space created inside the Book Club, we gave each other the time and support to explore the big questions lingering in our own heads.

Had the Chicago Business Book Club never formed, I doubt Mike and I would have ever found our seats on Icelandair 612.

The Power of Positive Peer Pressure

“If you want to lift yourself up, lift up someone else.” –Booker T. Washington

If you’re struggling to make a big career change, to go on a big adventure, or pursue a more purposeful life, maybe something like a Book Club could do wonders for you. Whether it’s a book club, a Junto, a Friday night drinking club — I don’t think the name or subject matters. So long as you’re surrounding yourself with like-minded peers (and like-minded ideas), the power of positive peer pressure can make its mark.

Luckily, I’m not alone in my belief in this power. Some of my heroes-turned-friends are doing some incredible things in this space. Amber Rae just launched “The Alive Tribe,” a 6-month creative collective + mastermind experience. Victor Saad of The Leapyear Project kicked off The Experience Institute, an alternative school based on real world experiences. Carla created Tea+Purpose, a way for twenty-something women to gather and have authentic, action-oriented conversations over tea.

So if you’re having a hard time forming your own, join something like these. Or if you’re in London, go to our weekly Escape Evening events. Peruse Meetups in your area. Attend Creative Mornings. At the very least, watch some TED talks.

It’s commonly said that you’re the average of the people you hang around most. It makes sense. If you’re constantly surrounded by people who have no ambitions to  or go on big adventures, or worse, who want to do these things, but have given up, then you’ll forever feel crazy in your ambitions. You’ll never have the support network needed to make a big move.

But if you’re surrounded by people who inspire you, who encourage you, who ask tough questions and who challenge you to ask the same, you have a shot. You can get through the toughest of journeys. You can make big, scary moves.

The fact is that we’re all on tough journeys. They may look and sound different, but that doesn’t mean they feel any different, or that they’re any less challenging. So maybe the best thing we can do is acknowledge this, and gather together. Grab a book, a beer, a cup of tea, or get into fisticuffs and exchange a few playful punches.

And when you’ve accomplished the thing that you thought you couldn’t, when you’re about to embark on a new trajectory, when you’re about to lift upward and onward to Iceland, cherish the moment.

It’s okay to be giddy. It’s acceptable to giggle like a school girl. Maybe it’s even acceptable to have a “boy dance party”.

Especially when Party in the USA starts playing.

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