Mondays. You know, the day  we all dread.

You get up at the crack of dawn to get into the office, and join the hoards of drivers taking the same route. Traffic is bumper-to-bumper and moving at a snails pace.

You look at your life and wonder what you’re doing, where you’re going, if you are taking the right path.

A few light changes later, your mind starts to wander… what it would be like to live in some exotic location where the locals don’t speak English, or get in their cars everyday for the hour-long commute across town for work.

Light goes green, and you snap back to reality.

You get to the office at 8.30, get yourself comfortable in your cubicle. Get the upcoming schedule and resource allocation from management… the months go by, you meet your deadlines, over deliver, under budget. You get comfortable. You get good at what you do.

Ask for that raise, maybe you get it, maybe you don’t (I didn’t); and you start to think about your own 5 year plan.

If you’ve ever had itchy feet, a deep desire to get out of town and explore, just see what the world has to offer, how other people live: how they celebrate, how they communicate, how they deal with what life throws at them. But you question yourself. You’re scared.

If you leave your great job, will you be able to get back into something better when you get back?

Will you have enough money?

Will you have fun?

Will you be brave, conquer your fears and put yourself out there?

To help make the decision easier, here is some great advice offered up by Lily from Explore for a Year in her recent post Yup, I quit my 9-5 Job Today!

I’ve daydreamed about leaving my day jobs before, but a few realizations made me follow-through this time:

1. Time will pass no matter what I do. If I don’t leave my job now, I’ll still want to leave 6 months from now, and I would have let 6 months go by without making any progress in myself.
2. If I pursue what I enjoy, I should attain at least the same level of success and income as I have doing what I don’t fully enjoy. By doing what I’m interested in, I will find ways to create and spot opportunities for myself.
3. There will never be a good time to quit. The economy will always be uncertain, my workplace will always be short-staffed, I’ll always have expenses to fund, and I’ll always feel nervous about leaving behind a stable income. If there is never going to be a good time to quit, then the best time is now.

I couldn’t agree more. I felt bad because I was leaving work short-staffed, and felt nervous about leaving a stable income. But, time has gone by (at least 10 years in the making), and the itch is still there.

So, I walked into the bosses office, sat down with him, and gave 4 weeks notice.

I didn’t quit. I actually had approval to get 12-24 months unpaid leave. Which is awesome, and something I’ve seen done before. It means I get to come back to a great job, and it gives me that little bit of security knowing that I wont be completely unemployed and broke when I get back.

If you have similar fears to what I’ve had, it’s worth looking into. See if your job will give you unpaid leave. Of course, its better to have an open-ended ticket, not having to be back by a certain date… but you cant win ‘em all.

Work was great about it, they just said keep in touch via email, and let them know of my plans. They agreed that I was leaving on a positive note, and taking a break to travel would be a great move going forward.

Still, I couldn’t sleep at all the night before.

I tried to sell the whole digital lifestyle thing, work remotely from overseas, but the boss didn’t buy it. They said we needed a man on the ground (at the customer site) for perception. Its easier to have face-to-face time.

At least now I am free to travel, and pursue other freelance options if necessary.

I don’t want to look back on my life and regret not taking the opportunity to travel when i was single, had the money, and the time.

So, I got a friend to rent out my house while I’m gone (still working on the lease, etc.), and look after my Husky x Blue Heeler for me. Gave notice at the job, and I’m starting to set things in motion.

Quitting a job without knowing what tomorrow will bring was not as hard as I thought it would be.

I’ve quit jobs before, but its always been to move onto another job, or start university, or something.

For more reasons towards quitting your job and travel, have a read of the post Why You Should Quit Your Job and Travel Around the World on The Art of Non-Conformity by Chris Guillebeau.

* image credits (cc) laverrue, A|S|W

Ian Cartwright

is a guy who gave up his career and mortgage for solo long-term travel. He travelled extensively across Europe for a year before heading onward to North Africa. He is now planning a trip to Latin America. As always there’s sure to be plenty of laughs, tears, and misadventures along the way.