Overcoming the Fear of Quitting Your Job to Start a Life of Travel

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Quitting your job, and your traditional daily life, is one of the biggest and most frightful steps to take when you want to pursue an unconventional life path or travel long term.

I already shared the why of my round the world trip but I want to share a bit more about my quitting process and how frightful it was to me. Honestly, it wasn’t that smooth.

I had already been working for this architecture firm for a few years, and while it was a good, stable job, I wasn’t happy there. I felt that my career was stagnant and that I had hit a wall there.

One day I came to the realization that I had to make a drastic change, otherwise I know that today I would still be doing the same basic tasks I was doing 3 years ago (and with the same pay).

As I mentioned before, due to the recession, another job was almost out of the question, so traveling long term was more than fitting for me.

Putting Things in Motion

In June 2011, I made the plan to quit by the end of February 2012 to start my trip on March 1^st. I felt that it would be enough time to save enough money to quit and travel for a year (in addition to the money I had saved before).

But, a few months before, in March of 2011, I was offered to do the 3-month MatadorU Road Warrior program in Belize. I turned it down, for fear of not being able to leave my job and because I felt I didn’t have enough money to continue traveling, so I would’ve had to return home, jobless, in a not so pretty economy.

In June, I was offered the opportunity again, and again I declined… regretfully. Same excuses.

By the end of July, a third invitation came. Absolutely nothing had changed between June and the end of July, except for the fact that I had maybe $2,000 more in my savings account.

I thought, opportunities like this don’t really come often, and I’ve had it three times already in my footstep. Am I going to turn it down again? I accepted!

My trip was set to start now in October 2011, instead of March 2012 as I had previously planned. I was both excited and scared since I didn’t know exactly how I would financially manage my trip after those three months, but I still wanted to take that leap of faith. I knew that I was determined enough to make it work in the end.

Quitting My Job

I had no idea how to tell my boss about it, but it had to be done.

As I expected, my (former) boss wasn’t thrilled when he heard the news. Even though I was giving a 1-month notice (instead of the customary 2 weeks in the US), he felt I needed to stay longer in the office –until end of December– to continue some of the projects I was working on.

It is easy for people who don’t know the entire thinking/planning process behind your life decisions to think you’re doing something irrational or irresponsible.

To them, it might look that way (even my mom thought that at one point), but when someone decides to take a major step in their life, it’s probable that action has been considered, thought about, and planned for a good while already. At least I did.

So, respectfully I declined his request to stay longer for two reasons: I had already decided on going to Belize, and I didn’t feel there was any incentive (professionally or economically) for me to stay longer.

I didn’t know if I was making a mistake or not, but I felt like I had to move forward. Why would I throw away this amazing opportunity of three months of travel in Belize to stay in the same working situation?

Again, he wasn’t thrilled about my refusal, but we managed to end our professional relationship in good terms and in the end I was bid farewell by my boss with an “I hope you find everything you’re looking for.”

That day, when I walked out of the office the world looked different to me; more vibrant and colorful. Tons of possibilities ahead!

Quitting Changing My Lifestyle

“Quitting” my life in New York, while not as hard, it wasn’t stress-free either. I sold and gave away everything I had. What I wanted to keep, I shipped to my mom’s house or stored temporarily at a friend’s apartment. (Thank you, Heymi!)

That last week before I left New York, my apartment was reduced to an air mattress and a bag full of clothes. One night, as I packed things, I sat down in my empty room and cried almost inconsolably. I thought, “What the hell did I do? In a few days, I’ll have no job, no home, nothing!!” I was scared.

Everything was ready and planned, yet I was still scared. The unconventional path of life will always be scary, no doubt about that, but the trick is not to overcome fear by not having any; you overcome it by knowing how to manage it.

Do one thing everyday that scares you.

-Eleanor Roosevelt

I didn’t know it back then, but somehow I started working for myself the moment I decided to travel long term and make a living on the road. It was unintentional, but the fear of ending up in a ditch in Thailand with no money to come back home made me work hard to keep this dream alive, and not just a dream, a lifestyle.

Instead of fearing failure, I realized what I had to lose and planned to prevent that from happening, or at least minimize my losses.

Today, over three years after I quit my job, I’m still going strong and working hard to continue this life. Fear of failure always creeps up here and there (even now), but when it does, I try to focus it on working more.

And, don’t think failure hasn’t happened to me on the road; it has, several times. But, I learned from them (whether mistakes or lessons), and moved forward to improve and do better things.

How Can You Overcome Your Fear of the Unconventional Path?

So, I want to leave you with a few tips on overcoming your fear of following your dream, quitting your job, traveling long term,  creating that startup, or whatever you might have in mind:

1. Realize rationally what you have to lose

We all have something to lose if things go south, but understanding the fear of losing that can be good encouragement to work hard and smart into accomplishing your dream.

2. Don’t fear failure

It happens. Learn from it, analyze things, and redo with the necessary improvements.

3. Create a perspective

Make that choice that will define the rest of your life. Are you up to take those bold steps to make those dreams and ambitions a reality?

4. Accept and understand reality

An unconventional travel life, a startup, or whatever new that may be; as glamorous as it may sound, it’s probably not easy.

I can say that while I can enjoy beautiful beaches around the world, at the same time I work more hours in my hostel room than I used to work in my previous job in order to keep me afloat.

5. Write down your goals

Studies show that people who write down their goals are five times more likely to achieve them. When would you like to leave your job? Start a business? How much money would you like to save and when? Set goals, and work towards achieving them.

6. Understand there’s never a perfect time

We always think, now is not the right time. Well, it is in our nature to want things perfect, but guess what, the world does not work that way. Something will always happen to make any given moment not perfect.

But, what if you took the risk, worked over your fear, and made the moment work for you? That moment will become the perfect moment because you made it happen.

7. Create and read affirmations

I thank my mom for this one. She always said that what comes out of your mouth is more likely to become true.

A lot of people believe that if you think positively and focus your energy on something, the universe (or supreme being) will conspire to make it happen. I somehow believe that too.

8. Again, overcome fear

Trust yourself more, gain some confidence, create a plan, and understand your worst-case scenarios. And yes, minimize procrastination. (I’m still working on that)

9. Educate yourself

Never stop learning. Knowledge is power and it will take you much farther than you think. Even for a traveler; never stop learning from and about the world.

10. Take the plunge!!

After you do, you’ll see life in a different way.

We all have dreams, but it is up to us to decide whether they will become a reality or stay as dreams and aspirations.

Enjoy the journey!