Peggy Bree was once a regular, Toronto university student. She went to school at OCAD for graphic design & advertising, with hopes of making a name for herself in creative content like copy writing, social media managing, photography and web design. Soon after graduation, she got bit by the travel bug, and hoped she could start her career around the world.

Peggy successfully transited from a student to an entrepreneur, creating her own business and brand creating content for companies like The Truth Beauty Co to Crofter's Organic! We got to sit down with Peggy and discuss what it takes to be your own boss and travel the globe! 

via @peggybree

What inspired you to get up and leave Toronto? 

Peggy: "When my boyfriend of 5 years passed away during my last year of school, my heart broke. All the memories and photographs are no longer shared, they’re just mine now. I reflected and thought to myself after graduation, that the time is now.

I had no kids or boys in my life - nothing to tie me down. I decided right there that I needed to take advantage of the now. I also wanted to make purpose of his death, and not have him just be a passing fleet of thought to other people. I wanted to see the world for him too, but thought to myself, how? Through research, I fell in love with this digital nomad lifestyle. I wanted to travel and work and build what I already had. I had a few clients while in school already, and decided to dive right in, research, build and learn.


What did you go to school for?

P: I went to OCAD University for Graphic Design / Advertising. In this creative field, there is so much room for growth. Creative direction has no limits and I stretched so far into content creating. I specialize in creating brand identities by helping clients establish their visual direction and vision!  


When did you decide to leave and where did you go?

P: I decided after graduation that my moving date would be November, and to Playa del Carmen, Mexico. This gave me lots of time to plan my life direction and to research into this lifestyle during summer. I joined many Digital Nomad facebook community groups, read blogs on the best budget friendly places to live, and gathered inspiration on how others make money.

I decided to solo it out and bought a one way ticket to Mexico, relying on the advices from other digital nomads. When I got there, I met so many people who have been doing this for many years, (and even met a best friend!). The beauty in this is that we all inspire each other to do more. I don’t see anyone as competition, I want everyone to do well. I want to collaborate and help each other grow and build! 


What are the biggest challenges of working remotely in foreign places?

P: The biggest challenge of working remotely in a foreign place would be overcoming fear.  This comes in many forms, ranging from the fear to jump right into the local digital community to socialize, and the fear of failure in a foreign country far from home. However, the support I found online though Instagram and Facebook, has made me overcome these fears and remind me that I am not alone. I’ve met many friends that are on the same journey so it never really feels so foreign. 


via @peggybree

Alternatively, what makes you happiest/is most exciting about what you do?

P: What makes me the happiest, is the freedom to explore and see the world, while meeting people with the same wanderlust and hustling mentality. I love learning from and contributing to start-ups and being a part of a community of growth. As a fresh graduate, being on the beach and working away on my laptop has been my fuel to do more and I’m constantly excited for projects and what’s to come. 


via @peggybree

What advice would you give someone who wants to work remotely and travel like you? 

P:Building and crafting this lifestyle takes time, it isn’t something that is overnight. If you are a millennial and you want to do this too, you need to build and start now. Make sure you’re mentally ready for this life change. The digital nomad life is different from backpacking. It is finding a home in different locations and working hard to hustle your way online.

In Mexico, I was still working from Mondays to Fridays in café’s and coffee shops and saved my weekends for exploration and activities. You need to have self-motivation and a drive to keep building and networking. Reach out to the vast resource that is the digital world. I met so many freelance writers, marketers, business owners and bloggers/vloggers that helped me along the way!


How do you budget your lifestyle - especially while travelling? And how do you make contacts/find work in different countries? 

P: I knew I wouldn't be living a lavish and glamourous lifestyle as a new travelling nomad. While in Mexico, I budgeted my lifestyle by limiting and being as minimal as possible. I realized that I didn’t need that much stuff and didn’t need to buy much, like I did in Toronto. 

Building your personal brand and your online presence is very important in finding work. I found lots of work through client referrals and outreaching to different agencies and opening remote jobs!  I ended up finding an agency that was remote based and allowed me to work full time. In the future, I hope to have a well established personal brand and my own agency. 


via @peggybree

What are your biggest/best travel tips?

My best travel tip would be to embrace the uncontrollable chaos that comes with traveling, and to learn to flow with it when it happens. In December, the high season, one of my Airbnb listings cancelled on me last minute and I was supposed to stay there for 5+ months. I remember crying on the streets of Mexico at night by myself, but decided that I came too far to be so hopeless.

I ended up staying at a hostel for a bit to figure out my new rental plan. There are always setbacks and uncontrollable events that aren’t according to plan when travelling, but learn to laugh at it. Find positivity in a chaotic environment and create an adventure out of it. That would be one of my best travel tips. Oh and of course, always scope out the area before deciding to officially base yourself there. 


Lastly, where are you off to next?! 

P: My upcoming move is in November (again) and I will be in Chiang Mai, Thailand! I would love to collaborate and meet more digital nomads!  

To check out Peggy's Instagram click here

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