Living Outside the Box~ My favorite unconventional lifestyle Gurus

“You’ll Never Need to Retire?!”

My father told me this when I was 21 and its one of the best quotes to live by, in my world.  Why should we wait until our most capable and youthful years are behind us to retire and enjoy our lives?  Shouldn’t we strive to enjoy everyday, no matter what age we are, as if we were ‘retired?’  Shouldn’t our professions reflect this desire to live a meaningful life- even in work?

I know this goes against the ‘conventional’ perspectives instilled by the previous generations into their children.  Get an education, get a job, get a 401K, get a mortgage and squirrel away all your money for the likely event that you’ll still be working for the same company at age 55, you’re 401K will still be solid by 60 and you’ll be able to spend the remaining years of your life waiting for the weekly bingo game and the early bird special at your favorite buffet.  Really?  As young 20/30/40 somethings, should we not strive to make everyday as fabulous as it can be and exactly what we want it to be?  And hasn’t the ‘Great Recession’ shown us that none of those conventions of previous generations are a certainty in a world of globalization and corporate capitalism?

Yes, I know, there is a valid place for savings accounts, stability, home ownership, and making a living.  I’m not arguing against this, I’m just making a point that we should strive to merge our likes and our interests with our trades and professions, so that we aren’t spending everyday in a meaningless vortex anxiously awaiting our weekends and longing for the gold watch in 30 years and a some free time.



Below are a few of my favorite unconventional gurus and a few books and blogs that reflect the movement towards a life well lived.

1. Thoreau-  No need to point out the obvious here, but devoting some time to Thoreau’s readings make the case for escaping the rat race and entering a symbiotic existence with nature and things as they are.   Grab a coffee, a copy of Walden  and pontificate the merits of a simple life.

2. Kerouac
-  Again, not to be dwelling on the obvious, but really, who writes it better than Jack .  Venture past on the road and into Dharma Bums and Big Sur.  Its worth it.  And if you haven’t read On the Road yet, seriously, get the coffeepot out again and get to work.

3.  Steinbeck
- Um, hi, Travels with Charlie  Who can resist a travel camper, a man and his best four-legged friend on the wide open road?

4.  Huckleberry Finn and Tom Sawyer- These characters may explain, in part, my case of  adult-onset wanderlust.  By far my favorite book as a child and I recall wanting to be Huck Finn each year at Halloween as a child.  Go figure.

The Motto at the One Cup coffeeshop in Eugene, OR.

The Motto at the One Cup coffeeshop in Eugene, OR.

A little modern unconventionalism on the web.

There is a growing movement for ‘lifestyle design’ or location independent living on the internet.  The evolution of the Web, coupled with the realization that life is fleeting and to spend a majority of it in a cubicle is a sin, has given a breeding ground for this movement.  A few of my favorites include:

Tim Ferris and the 4 Hour Work Week .  Seriously.  Just read it.  Bypass the cheesy title and don’t expect to work only 4 hours a week- you’ll drive yourself and everyone around you absolutely insane.  Read it and embrace the concept of ‘mini-retirement.’  Implement the automation aspects to your daily life and embrace the ‘Muses’ section.  The blog and book may spawn ideas you never knew you possessed, you may wake up one morning with more free time to spend with your family and loved ones, you may find that you have totally automated your income and can be the philanthropist you’ve always dreamed of or you may just chuck everything in storage and find yourself executing a life on the road- free from the normal constraints of rent, paychecks and staff meetings.  Again, Seriously.  Read it.  Enough said.

The Art of Non-Conformity This blog takes the lifestyle design concepts and puts them into action.  The author, Chris Guillebeau shows that not everyone leads a conventional life and you aren’t the only black-sheep wanderer in the world.  The Manifesto is free and interesting and may spawn your creativity in ways you hadn’t anticipated.  I’ve purchased one of his E-Books, about art and commerce, and its been a good resource as well.

Eat. Pray. Love. I avoided reading this for some time because it seemed rather cliche, but once I started reading, I couldn’t stop.  Loved it, loved the concept and props to the author for putting herself out there and just doing it.  Again, seriously.  Read it.

Zen Habits , Vagabonding, Matador and the Frugal Traveler .  Excellent blogs and each one has a different theme revolving around travel.  Each one has threads and links that will lead you to people living an unconventional life.  I enjoy reading each of these blogs and try to scan them weekly for some relevant content or to find a new person living a different life.


A few musicians in Seattle working a different way.

There are so many more, I realize I’m doing a massive injustice to the remaining unconventional life-stylers out there.  Please feel free to post your favorites in the comments section below. I’d love to hear of more fabulous living and expand my horizons.


  1. Thomas says

    As always, love your writing and experiences. I think you are true to yourself, I have always tried to live my own life by that motto. There are 5 rings of life and each year I make goals for each of them to balance myself out. Balancing adventures, work, family, etc is a hard thing to do but not enough people “get it” until they are too old to “enjoy it”. Remember our RURec shirt:
    “You can learn more about a person in an hour of play than you can from a lifetime of conversation.” -Plato
    You are a true adventure guru. Keep it going!

    • says

      @Thomas~ Thanks! I love your comment and yes, I think this adventurous mentality was instilled in us during our formative college days- maybe the best thing we got from that program- besides friendships! Keep blazing your path as well- we’ll meet in the middle one day! Keep your balance and show others that it can be done! Take care!