How to Quit Your Job & Travel the World in 2020 – Part 2

By: Naomi Matlow

So, you know what you don’t want your life to look like (See: “How to Quit Your Job & Travel the World in 2020 – Part 1”). Now, you’re beginning to establish what it is you really want out of this next chapter. One of the best reminders the universe can give you? You’re not alone. We’ve all been there, or in similar situations, at some point in our lives. 

What have some of Unsettled’s past participants, who have collecively walked many, many miles in those shoes, wished they’d known before embarking on their adventures?

We asked 5 Unsettled alumni what they wished they knew before quitting their jobs and traveling the world. 

Here’s what they said:

“I wish I knew that I would meet other people like me. People who found the courage to take the leap, aren’t exactly sure what’s next, and are open to exploring possibilities. I found so much comfort knowing that I wasn’t the only one navigating this scary yet exciting journey.”

– Alice Livermore, Unsettled Bali


“Quitting your job to travel is a virtuous endeavor – it gives you the opportunity to really take the time to evaluate yourself, your values, your path in life, and to get more in tune with what brings you joy. And, of course, to connect with people from all walks of life with their own stories to share. Although I don’t regret quitting my job and my busy life in New York City – it is one of the hardest things I’ve ever done…yet the most rewarding. You’re going against the grain of social mores, so it entails being ready to emotionally detach yourself from your old identity, and be strong in your convictions. You will have naysayers that will want to, sometimes inadvertently, make you doubt your decision. But one of the many things I’ve learned in my journey so far, is that investing in yourself and following those almighty visceral feelings in your gut and in your heart…that is one of the best ways to honor yourself in life…” 

– Tahlia McLeod, Unsettled Buenos Aires


“Know that your path won’t be linear. Leaving a job or a position of stability exposes you to the randomness and uncertainty of the world. If you head into that uncertainty thinking you can forge a clear path or design an outcome you’ll stress yourself out. Follow your curiosity and embrace the tangents, backroads, and detours that ultimately converge on a clearer path (rarely perfectly clear).”

Max Joles, Unsettled Cape Town


“I wish I knew how fast this season of travel would come & go! There were definitely moments where I felt pressure societally to come back home and find a traditional job, but I wish I would have worried less about the future. You really do have your whole life to work and try on new jobs for size and while there is admittedly a lot of privilege baked into the opportunity to quit and travel, it is important not to take it for granted! Sure, at times it can be daunting to check on the status of a dwindling savings account, but the time and space to explore new ideas, challenge your convictions, make connections with people that are different than you, appreciate the beauty & nuances of new cultures and get fully acquainted with yourself is truly priceless. Travel should be viewed as an investment in your future self, because these experiences on the road, whether seemingly significant in the moment or not, will serve you for years to come in surprising and serendipitous ways. When you commit to soaking up each sensory experience and being present, it feels like opportunities come knocking and you are in tune enough with yourself to hear them….and answer!” 

Renee Standage, Unsettled Cape Town & Community Team 


“For the second time, I have quit my job without a plan in place other than to travel. I have since started making Mala necklaces, and hope to have it take off as an income source, but in the meantime I am just enjoying the wild ride and the ability to be creative. I started in New York and then spent five weeks travelling Europe (2 weeks of which were with Unsettled in Tuscany), and am now travelling across Canada, from west coast to east coast and back again. There are very few things I wish I knew before I decided to quit my job and begin to travel endlessly (as I am always one to embrace the unknown and just go with the flow!), however, here are a few. 1. It would have been nice to know that suddenly, everyone plus their aunt thinks that your personal finances are their business. If I am not ‘working’, I am obviously capable of doing so, and it is such a strange thing to be repeatedly asked how much money I have and how I can be doing this. 2. It can get really expensive, if you get too excited and don’t look at your options. I personally wing it, but I do recommend planning ahead if you are on a strict budget, there are plenty of ways to travel very cheaply. 3. It is going to be SO much freaking fun! You are going to have the time of your life, see the most unbelievable places, and meet the most interesting people – every day. You only get one life, enjoy the heck out of it while you can.”

– Ashley Wilson, Unsettled Bali & Tuscany

Ready to join the fold? Here’s where we are heading for the rest of 2019 and through 2020.

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