How I decided to Take a Backpacking Trip

Like dieting, there’s no magic pill to finding your best life.

I didn’t wake up and book a ticket to Thailand. For months I was considering the possibility of taking a little “meternity leave” (omg, hello controversy!). At the end of the day, what made the dream become reality was preparation and timing.

I started thinking about and researching this journey well before certain things happened. I knew 2 things: Southeast Asia is a well documented and safer destination for budget travelers and I am a budget traveler looking for a safe destination. Unhappy in my job, I started planning to resign my current role as a contract copywriter at the end of summer. That would give me plenty of time to save and prep. But then two of my best friends announced their wedding reception would be held in mid-September [Congrats, Maq and Atara!]. I obviously can’t miss that. Time to look for a new plan.

This was just dumb luck, but the plan found me. I was given a 30-day notice that I would be out of a job April 22. The stars were starting to align. I hadn’t really started saving for this specific reason, however I had started putting money away for a downpayment on a house. I also have consistent freelance work and a great network of people to reach out to for side gigs.

At first it all seemed like a bad idea. I applied to jobs, went to networking events and submitted the appropriate paperwork to collect unemployment. I half-heartedly interviewed and sent the most basic cover letters known to man. It was embarrassing. Then I made the best decision I’ve made in a long time.

I hired a Life Coach, appropriately named Hope. It’s a bit hard to admit, it almost feels like something that shouldn’t be talked about, like mental health, but she helped clarify so many things in my life. I was feeling so lost. I woke up feeling defeated every day. It showed in my relationships, work and daily interactions. I stopped doing things I loved and didn’t feel like myself. I was on autopilot and hated it.

Hope asked me hard questions, ones I’ve avoided answering or even considering. She gave me homework that consisted of a lot of self-reflection and writing for clarification. She gave me good advice about toxic behaviors. She wasn’t judgmental or quick to tell me what’s right or wrong. She just acted as a guide, a coach. I realized I beat myself up for a lot of things that are completely out of my control.

Ever get depressed looking at Facebook? Yup, so does everyone else. it’s a part of our lives now and it has meaningful aspects. I like Facebook. But I couldn’t help seeing engagements, marriages, babies, new homes, promotions, etc, and thinking what am I doing wrong, why am I failing? These negative, comparative, counter-productive thoughts are so useless. I don’t even want a baby. I think they resemble anchors. And I haven’t seriously wanted to marry any man I’ve been with. And when it came down to it, why the hell would I buy a house? For my shoes? Hope gave me the courage that allowed me to be ok with not wanting those things right now. Accepting that it’s not right for my life… yet.

Finding my best life was going to have to start by admitting that I’ve been on a mechanical trajectory. What do I want? Who should go along for the ride? I started expelling toxic people that made me sad or didn’t lift me up. I considered alternative employment opportunities. I forgave people that hurt me but wanted to make it right again. I started feeling free and undocked myself from the thoughts that I had to settle down and climb a ladder to “fit in” or be happy.

OK, The Good Stuff.

I collected one unemployment check and then decided the trip was the best thing for me, not job hunting. I wanted to take advantage of this amazing opportunity and then look for a new job, probably in a new field, with fresh eyes and a revitalized outlook on life. I found a sublet for my apartment (saving thousands of dollars over 3 months). I paid off bills or auto paid anything that needed to be set before I left. I used my Delta Skymiles American Express miles (40,000 miles + $129 in taxes and fees) for my ticket to Chiang Mai. My miles will also cover my return ticket, but it is yet to be booked. I researched costs and asked those with more experience (Jordan Trigilio) to give me a basic rundown.

Based on an estimated $100 per week budget, things were looking good. I had enough cash to last me 12-budgeted weeks traveling, comfortably. (As an example, I’m staying at Mercy Hostel in Chiang Rai for $6/night) Next, I approached my freelance bosses and asked if they’d be cool with me taking my work on the road. They supported it and we changed our payments from physical checks to Paypal. Even more comfort!

Things were taking shape. I’ll admit getting to Thailand has been more expensive than I imagined. Buying travel goods for this type of trip, vaccines, extended Visa…upfront costs have been rough. [I’ll provide that info in a video to come this weekend once I can lay out an expense list.] But it’s all worth it.

So now you know WHY and HOW I’m taking this trip. Next step is actually packing and leaving. I can’t wait to experience all the world has to offer. Yes, I’m nervous and anxious and scared. But I’m starting to understand that’s actually my happy place. Taking on adventure and risk is my comfort zone. The unknown is my version of settling down. One day I’ll buy a house and throw a few people I love in it. But I’m ok being on my own right now and taking this journey solo.

Follow along with me as I make my way from Norther Thailand to Bali, Indonesia. I leave May 24! (Instgram: jennyfitz21 Twitter: JennyFitzCopy)

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