Jess Stanton: A Journey to Happiness

Emily Milsom
The Travelling Womxn
5 min readSep 11, 2020

Jess Stanton, 26, Canada, is a freelancer who is learning to live in the moment. Travelling to the US, Europe and South East Asia, Jess had gone further than ever, before returning home and surprisingly, finding herself.

Western Canada

From running her own business to building eCommerce websites, Jess has already achieved a lot in her working career, she should be proud but deep down it feels like there’s always been something more she’s wanted, something only travelling might teach her.

When she was young, the words ‘family’ and ‘travel’ meant the same thing, happiness. The trips they took as a whole family were one of the only times they were all together, and that feeling of happiness whilst travelling never left. As Jess grew up and began travelling on her own, she still craved that sense of freedom but in a new way.

Trips to Find Freedom

Born in Ontario, Jess’s initial travels at 18 were to New York City, somewhere Jess could reach on a $40 roundtrip ticket. Time and time again, she would visit the big city, fascinated by the sheer energy of the place and its people. Various trips followed with friends and family, and then trips going beyond, and further afield into the US. The one thing they all had in common was they enabled Jess to feel something more in her everyday life.

The trips became a lifeline for young Jess. Any time her world became hard to face or she was feeling incredibly low, she would focus on an upcoming trip and keep going till she reached that point. In a way, it became like a drug for Jess, one she didn’t want to live without.

A summer working for Disney World, trips to NYC to see theatre shows and pilgrimages to Israel during University holidays, kept the travel dream alive but they were all temporary and the happiness effect wore off eventually. In fact, life after University was much more stationary for Jess.

Left feeling stuck in a life she wasn’t sure she wanted. Especially being subconsciously influenced by the people around her, who were content in their lives and the places they grew up, Jess kept dreaming of being on the road, but money was an issue. It wasn’t necessarily just a lack of it but she also harboured a fear of spending it, even on the little things. It kept her small and unable to move.

A Chance on Herself

What really changed Jess’s trajectory was a simple chance she took. She booked a trip to Bali on her credit card and put her faith in that things would work out. There wasn’t a plan, nor was there any vast pile of savings behind her. All Jess had was a bunch of debt and the absolute certainty that there could be more to her life than she was currently experiencing.

Bali was chosen because Jess wanted to be around people who lived differently. The ones who had figured out the remote work life already, and were, what she presumed, happy. But it was slow going. Jess had no income when she left Canada and the money she did have flowed away a little more each day, even on the tightest of budgets.

Things changed after a chance encounter with a new friend. One who was willing to swap skills and help Jess bid for work on the site ‘Upwork’. A new profile and a few jobs later, Jess began taking on small website building projects. She’d always been savvy at tech and no stranger to hard work, so she got her head down, working unsocial hours if she had to.

However, it was all piecemeal and couldn’t support her in the long run. The moment of true change in her life was when she began a job working for a company back in Canada that struck a chord with her. The work was okay, but the part that made her think there could be more to it was working with the project manager, Lindsay. Jess knew it was a job she would be willing to go above and beyond for, and without knowing how it would turn out, took to giving her all.

Jess having fun at Universal Singapore.

Live as you Live

It paid off. A partnership was born. Jess took on more and more work, becoming a vital member of the team (in spirit, as she was still freelance). The steady flow of work empowered her to start travelling more and even, to her shock, spending more. Having learnt from travel friends that spending a little extra here and there was okay. That life was meant to be lived as you lived it.

Soon her average income became a steady enough to thrive, she ventured onto Singapore, Malaysia and Thailand, and it was more than enough to return and live on in Canada when the COVID pandemic hit. Though she wasn’t returning home to the person she was, or the place she had come from.

Instead, she arrived in Canada a new person, who was more confident in who she was and her abilities. Jess wasn’t held back by the fears of her past anymore. She was a person with a renewed interest in exploring her country and to continue learning more about who she wanted to be.

Jess had learnt that working with a team was essential to her mental health and working life success. She also discovered that if you don’t try something different, you will never get new results.

As she moves forward into the unknown times of COVID-19, Jess wants to both avoid making plans and at the same time, dream of all the places she will travel one day. Reminding her always that there is always hope, and to be happy where you’re at because this is all part of the journey too.

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Emily Milsom
The Travelling Womxn

Live each day with Joy. Coach & Writer, telling stories to inspire change. Lover of #Tea 🍵 Talking 😄 & #Travel 🌏.