For years I would be the person falling into the category of the first quote above. I started telling people my unrealistic dream job would be to "be paid to travel the world, learn and live other cultures and their language, and then move on." It was just a dream though, and I constantly wondered if trying to pursue such a dream would be immature and irresponsible to my future. What I SHOULD be doing is getting my degree in business or computer science, not Asian Studies. What I SHOULD be doing is ensuring I have a retirement plan and a steady job with high income.
But that isn't me. And it isn't what I WANT to do.
Is that being immature?
Since stumbling across this site, I discovered that maybe my "unrealistic dream job" isn't as unrealistic as I thought. I have felt an almost dangerously strong pull of the road within me and am now struggling with what I SHOULD do as a responsible adult versus what will make me happy. One of my fears, as I'm sure I share with others, is waking up one day behind a desk realizing I've been sitting there for years and have stopped hearing the call of the road. I want to truly LIVE my life to the brim until what I did upon waking feels like last week by the time the sun sets and beyond.
Thanks, Hal. And thank you to Matador and everyone within it. Every blog and post I read gives me hope that maybe I can break away, leave the questions behind, and just dive into life.

Wow. These are the most thought-out and involved comments I've received. Thanks guys, I really appreciate it!

I know my last couple entries veer towards the negative, but in reality I'm quite happy with the life I lead. These are just some things my wife and I have been discussing lately as we acknowledge that it'll be nice to settle down...at some point.

In three hours, I get on a plane to embark on all manner of firsts--first time below the equator, first time living long-term in the Spanish-speaking world, first time volunteering. No, the traveler's life can't be beat. :)

Hal-

I've just gotten home from a meeting with one of my freelance clients. She's 31--like me. She's a psychotherapist (like I was). She has four advanced degrees, working on her 5th. She owns her own business.

Ten years ago--hell, 5 years ago--I thought that I'd be living exactly the life that she's living now. And at one point in the meeting I felt a pang of something. Not regret, exactly, but the flickering thought of, "By the age of 30, I was supposed to have been/done/achieved ______." I felt a little embarrassed-like I wasn't accomplished in my own right or something--and I made some excuses about why I haven't finished my PhD. I looked at the frayed ends of a pair of jeans I've owned for five years and noticed a stain on my sweatshirt.

Then I thought a bit harder. This woman has hired my services because she's totally overextended. She has no romantic partner (not for lack of want, but for lack of time, she says). She hasn't taken a vacation in two years (same reason). She was happy that we met at a restaurant and ate and she marveled at the fact that my husband cooks every night... she normally eats take out while reading e-mails.

It's true: I haven't done any of the things that anyone expected of me, least of all myself. But the fact of the matter is that I don't regret ditching my 9 to 5 job, giving up a 401k plan, or even (most days) having exchanged health insurance for freedom.

And at the end of the day, nothing's really wasted. Every experience promotes our growth, our awareness, and our ability to help others. If I'd stayed in my office, I wouldn't have learned half the things I've learned in the past six months alone. But what I learned in that office has prepared me to be who I am and who I am becoming.

Hey Hal...have you got your hands on that book I recommended before? A few of your recent posts seem to have the common theme of fear of regret. Not that I'm even close to being there, but I think the only way to be truly happy is by living in the moment. It's easy to say, and very catchy. But if one were to really live up to that, anxieties and fears can't exist. These require thought to the future, and usually for things out of our control. Fear of regret isn't regret. It's the thought that in the future you might regret a choice.

I try not to regret anything. It's very difficult. At some level, of course, I wish I could go back and change something that didn't have the outcome that I desired (even if, at the time of the choice, I didn't even realize what my desired outcome was...it's quite silly really). Instead I just try to learn from it and see how I can apply that to something I am doing now.

"There must exist societies whose citizens adhere to a different outlook, who value the comfort and convenience of a sure thing. A world where no one worries about regret because they're perfectly content with what they have in each moment. No seizing of the day required. Do such people lead lives any less fulfilling than our own?"

It's definitely our culture that is doing this to us. Ambition is a noble trait, we're supposed to want more, all the time, to strive. If you're not advancing in your career there must be something wrong with you! Don't you want to be manager?? There have been studies that show happiness levels are virtually the same for anyone who lives above the median income of any given country (I read this in "Enough" by John Naish, another recommendation). Think about that...someone making $25,000 in Canada (or whatever the average is) is just as happy as the millionaire. Winning the lottery or other such instantaneous good thing will spike the happiness a bit, but only for a short time. It will drop back to normal levels. We have a limit to our happiness. So why all the chasing???

I've been thinking similar thoughts myself. And of course, I have heard those comments from people who admire my lifestyle but would never adopt it themselves.

Lately I've been looking around me at coworkers and my friends, and they all seem settled into their routines, not likely to stray from them even though they'd like to take long vacations of their own. And I wonder whether I should be joining them. But they say that we should live for what we're passionate about, and all I can think about right now is where I'm going to travel next. Everything else, like having a career and owning a house, takes a backseat.

I guess what it comes down to is whether you prefer the ordinary or the extraordinary. And who knows, I might look back at this differently in 10-20 years, but I think at this point in my life it's often what I didn't do that I regret more than what I did do.