A Perspective from the Road Less Traveled


I have always tried to live my life by one mantra: make life choices that I won’t regret in my final days.  It sounds simple enough, but has led me down some interesting paths, for better or worse.  I lived in Japan for several years (great choice), married my first boyfriend (bad choice), and have done a bunch of seemingly non-related jobs: IT technician, university professor, stay-at-home mom and game producer.

With few exceptions, I’m happy with how my life has turned out so far.  My experiences have filled me with joy and humility.  It has taught me to appreciate life beyond money or status.   On the flip side, leading a less structured life can wreak havoc on your professional career.  Those non-related jobs I referenced look like lack of focus on a resume.  When you live life on the road less traveled, you’re making it hard to compare your experience to others who are following a more traditional path.

But take heart.  For those of you either on the road less traveled with me or thinking about taking your first steps, there’s a few things I’ve learned:

There will always be opportunities for you.

Every time I’ve taken the plunge to do something different, it has terrified me.  When I had my first child, I quit a lucrative video game producing job that had a lot of career potential.  I knew that I wanted to spend more time with my children, but I had no idea how that would translate when I wanted to return to the workforce.  Yet, I’ve been able to find relevant part-time work as a “stay-at-home mom.”   I’ve taught at a local university.  I’ve consulted for small businesses.  I will soon commit several hours to a start-up company that has an upside for equity in the far distant future.  Just because I ended one career didn’t mean my professional life ended.  It meant many other doors opened for me that I never thought possible.

You increase your odds of being satisfied with your life. 

While there is no guarantee that you will be satisfied with your life, if you’re living it on your terms, you’re more likely to be happy.  While living in Japan, I met so many people who felt stuck with their lot in life that I never wanted to be in that position.  Working a job just for the money or out of obligation never seems to bear out for anyone.  I’ve learned instead to live on less and take jobs that give me more personal life satisfaction.  I’ve rarely regretted decisions that I’ve made, and when I do, I try my best to find new solutions to get out of that rut as quickly as possible.

You aren’t as unique as you think you are. 

You might think that forging your own path makes you unique, but the longer you’re on this road, the more people you meet taking it.  This can make you feel insignificant, especially if you compare yourselves to people who have achieved far greater success than you in the same amount of time.  I’ve been bitten by the jealousy bug more than a few times when I meet wildly successful people.  If you can push past that feeling, though, you can network with many like-minded individuals who can further living your own life.  They will give advice and support you.  And, almost without exception, the other individuals off the beaten path have reminded me just why I try to live life by my own terms (rather than just “get a job” and be done with it).

You will wish that you’d taken the more common road, now and again. 

It’s okay and even advisable to yearn for a more predictable life.  I’ve worked several government jobs in my career that I would consider more along “the beaten path.”  I’ve met many wonderful people and learned lots of things there.  I could have continued on with a full-time career in these jobs.  But staying in one job, or even just in one set of circumstances, just isn’t for me.  Whenever I get too settled in somewhere, I get the urge to be challenged and try something new.  So off I go.

And that’s really what being on the road less traveled is all about.  Moving on.  Growing and changing.  Never stop learning.  If you’re here with me on the road less traveled, I hope you feel as happy as I do.  The future may never turn out as you expected it would, but that’s half of the fun.  And so far, even with a few pitfalls and sorrow in my life, I can honestly say I have very few regrets.

Photo by San Sharma

32 thoughts on “A Perspective from the Road Less Traveled”

  1. Thank you for this! I am living my jubilee year traveling and being totally free. God is guiding me to amazing places and people.

  2. This post hits home for me as I’ve been working towards pursuing a life down the road less traveled this year. Like your experience in Japan, I felt that I just had to settle for where I was in life and go to a job that paid the bills. Now I’m finally starting to see that there is way more to life than just accepting where I am. I think a lot of people just take their life at face value and don’t think to challenge their thinking that it could be better. I covered that mindset in a recent post at http://upgradeinprogress.com/2014/06/25/being-honest-about-the-the-life-you-want/ and found I wasn’t being honest even with myself about where I wanted to direct my life.
    Thanks for sharing your journey so far!

    1. Thanks for sharing your perspective, Carissa. I think part of the journey is discovering who we are too, and the answers aren’t always straight forward. They also change, so if you find yourself wanting something else down the line, that’s normal. Best of luck to you!

  3. Thanks for the reminder Deborah! I’m definitely on the road less traveled myself.
    And yes, I am very happy :).
    I wish you all the best in whatever you do.
    Keep shining!

  4. I am a poster child for the road less traveled. Thank you for this post! And as I get older and more into my career, I find that when you travel the road ON PURPOSE and do things less because that’s what someone said you should do, the more fun you have. Well, the more fun I have, anyway.

    Thanks for the article!

    1. Makes sense to me. If you choose to be ” on the road” for any given reason, you’re happy to be there, rather than just there because you don’t know where you want to be.

  5. I’m not sure sure about the traditional path – I think there’s a lot of propaganda about careers and working hard for the company that’s not in our best interest. The more people who cut their own paths – and there’s a long tradition of that – then the better. Straying off the beaten track means a bit of risk but the gainis in a having life that was worth living. The truth is that most of us will mix the two.

    1. Thanks for your insight, Peter. I agree that many people will do a mix of the more traditional and more stable, and I think that’s great. Everyone’s goal should be to finding that “life worth living,” whatever that means to them. I suspect for many that it changes as they grow.

  6. Hi Deborah,
    I’m in that area of Corporate America where I can use a change. Many years in IT, have realized much success and traveled the world. But now I find myself unfulfilled, like there’s something missing. Your blog provides hope that at the end of the day happiness should be at the forefront and not income level.

    Thank you.

    1. With your experience, you have a lot of opportunities to try something new. Maybe a startup or consulting. Or maybe you can try something completely new. Wherever life leads you, I wish you the best.

  7. Thank you for your perspective and for the motivation. “If you would attain to what you are not yet, you must always be displeased by what you are. For where you are pleased with yourself there you have remained. Keep adding, keep walking, keep advancing. “~Saint Augustine

  8. Thank you so much for this post Deborah! I couldn’t agree with it more! Despite a bunch of fear and many worries, I’m currently trying to forge my own path and live my dreams after quitting a steady (but hideous) job in the hopes that I can travel my own road in my own time and remember that, as you said, there will always be opportunities coming my way and lessons to learn from :)


    1. Good luck on your journey, Toni. You will be amazed at what opportunities will come your way once you decide to try something new. They may not be exactly what you planned, but they can lead you down some exciting new roads.

  9. Hi Deborah,

    I can totally relate to how you feel. When I decided to quit my university education a few years back to go into business for myself, many of my friends and relatives actually dissuade me from doing that. However, inside my heart, I somehow know that this is right path to go. Now, I am so thankful that I made that decision. Living my life on my own terms is much better than living to other people’s expectations.

    The book titled: The Five Secrets You Must Discover Before You Die by John Izzo also inspired me to risk more and live my life with no regrets.


    1. I taught Entrepreneurship at a university, and I met several students who choose the same route as you, Edmund. Quitting school to pursue a business is not for everyone, but many students that I taught were happier plunging straight into their ideas. I’m happy to hear it’s working for you too.

  10. It is far more beneficial and satisifying to live life on your own terms. I spent years purusing a career in law that I didn’t want yet was to frightened to follow my heart. I’m glad I have changed my way of thinking and I am so much happier for it! Life is too short to feel miserable and unfulfilled. Don’t ignore that burning desire from your soul – it yearns to be heard and is communicating to you your true path. ARE YOU GOING TO WALK IT?

  11. Hi Deborah

    Really liked your article. Clear and straight forward and sensible, particularly in recognizing that we are not unique. Unhappiness and general life problems can, I think, make us rather inward looking and self indulgent. A positive and refreshing stance. I’m going to read it again!
    Thank you.

    1. I think a lot of people feel belittled by not being as “unique” as they think they are. It’s actually empowering to be part of a movement like this. Much better than simply doing it on your own.

  12. I love this article. I’ve been doing the road less traveled all my life but recently have been worrying more about my CV and company so reading this and remembering that there are always opportunities is fantastic.

    1. It helps to have an entrepreneurial spirit (which I think many on the road less traveled have). I don’t get the same opportunities as someone climbing the corporate ladder, but I still get a lot of interesting opportunities thrown my way. Networking with others on the path helps too. Good luck with your journey.

  13. Great article! I love the point about increasing your odds of being happy with your life! I’ve also found that as I move through life, the more decisions I make that are based not on other people’s expectations, but my own values, the happier I am.

    I’m living in Japan at the moment, and I have absolutely met no end of people who are frustrated and fed up with their the path they have chosen! I wish all of them would read what you’ve written!

    Thanks for taking the time to write and share this.

  14. I have always been a yes person, whether its a job or a course or even befriending people very unlike me because of which I have made pretty unconventional choices. And even now I think it is better to explore and experiment than wonder ‘what if…’. Thank you, Deborah for the wonderful article.

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