How I ditched my High Heels for Hiking Boots | The 30 Edition

I have always loved the power of heels.

And no, I am not a fan of walking in them beyond 20 minutes, but I do agree the superpower eludes out when you stand there in your power suit on those ridiculous torture devices, that transforms you to look 2 times better, feel 5 times more confident and more often than not – ace that work presentation.

And that was me then – a late 20s Singaporean lady working in one of the most successful cities in the world, dressing up every day with my makeup on, meeting plenty of people and having a career marketing high-end luxury dream resorts.

eHowever, when I do get that little bit of leave to whisk away from the concrete paths of Singapore and desktop life – and escape into the nature trails in the destinations I visit, I’ve always found great pleasure wandering through the forest in my good old 4-5 year old purplish grey waterproof hiking boots ( one boot oddly half a size bigger than the other), hearing the muffled crunch of the dirt underneath, the sturdy grip around my ankles when I bound from rock to rock and inch closer and closer to the mountaintop.

When I eventually reached the top, stand up straight perched on a little rock while trying to keep your balance, I look up at all that splendour, and that’s when..I feel at home.

One with nature, and one with myself.

But how long can one stay at the mountaintop before coming back down to ‘reality valley’?

It wasn’t easy. Every return trip will fill you with great longing and itch for the new adventure. But there will always be limitations.

It can be lack of leave, lack of resources, lack of time, lack of travel companions facing the exact same reasons. It took me a while before I managed to inch by inch build my capacity/ skill set to work remotely on all my projects and assignments and eventually converted into a digital nomad. I got to escape the city life more often and immerse in the environment I love best. With my hardy laptop by my side + 3G signal, I hunt for places where I can work hard, yet surrounded by a natural environment and the scent of new adventures/ cities.

It was only 2018, the year of my big 30, I managed to officially throw off my high heels, leave them in the cupboards of my Singapore home, and trot forward in my hiking boots into the great unknown out there – to pursue the location-free working remote lifestyle I always dreamed off.

How I stepped out of my world of skyscrapers & elevators to a world of AirBnBs & Google Maps.

It started off small initially, with just little doses of the love to go on a vacation. Then the interest grew and become addictive, like a drug that draws you back to it every time the mundane of the corporate working world/ drudgery kicks in.

Nothing comes easy, you need to work hard for it as people will not throw opportunities into your lap. So if you want a certain lifestyle that is good and sustainable, you fight for it.

And that’s what I did. Work very hard at my work, learn to work smart and pick a good work environment to foster that. Grow in a niche/ specialized set of skills that are useful, relevant, transferable and helps you grow as an individual to pursue your passion or the lifestyle you desire. In my case, it is digital marketing consultancy work.

It can be anything, from being able to work remotely more efficiently than in an office, working a more mobile job and interact with people, working in another country and yet build your savings. And the list goes on.

Whatever matters to you, there are ways to find out how to get it.

My top travel quotes that inspires me to be who I am today

Learn to be nimble and adaptable to your situations

Like all who get ready to climb a mountain or do a long hike, we need to be sufficiently prepared for the elements that come along. I have done enough hikes to know the various but similar type of outcomes when people do not come prepared.

No doubt, you cannot transform yourself into Superman and escape disaster in seconds, but you can be prepared to learn how to minimise it, be prepared to come up with ideas and find solutions. So in the context of a mountain hike, things like wearing the right gear, bringing the right set of additional clothing ( waterproof/ windproof/ chill proof jacket and pants). Others include learning to be resourceful when weather conditions change or problems arise ( getting lost/ injured/ getting into arguments/ face with thirst).

List of best solo travel destinations to take this year, have you checked them out yet?

And if I link this back to our daily lives, there is much we can learn…

When we step out of our comfort zones/ office and salaried jobs to pursue something we want, it is not about dropping everything and just fearlessly dashing out and fight, not knowing what to expect but just be brave and bold.

But when we do decide to move – plan properly in advance before the move, sharpen our skills, build your resources/ savings and go out with a mindset that – though I do not know whether I am prepared for everything that comes my way, I will have sufficient means and the right mindset/ skillset to face it, fester over it and eventually overcome it.

The travelling gets rough and tiring

And once you are on the road (literally and figuratively), it is just the beginning. It is unlike a nice train ride where you just tag along. There will be stops and detours and breakdowns. And that’s when the real test of endurance starts.

Just like every mountain hike.

Many who are based in a location permanently would see travelling as a holiday or vacation, but when they start to understand what it means to be a full-time traveller and yet work on the go, the glamorous side of it slowly seeps away.

Travelling constantly on the road gets exhausting when you need to adjust to time zones , figure things out every day, resolve hiccups and unforeseen problems on the way, using a good mix of physical, mental and emotional willpower.

Jack be nimble, Jack be quick…

There are elements that are uncontrollable but you learn to accept it, change it or thrive in it. It trains your reflexes, ability to respond to situation change, control your emotions/ temper/ fears, coz you do not have time to crawl home and hide in bed to cry. You are at that moment, where you need to react fast and seek the best way to overcome the obstacle/ problem.

And when you do resolve it, it is an immense relief and satisfaction. Bask in it for a while before the adrenaline dies off and gets replaced with fatigue. Where you have to say – enough drama for a while, that’s when you need to sleep and be still for a while.

However, it’s when you keep moving you keep growing

Travelling and being constantly faced with new situations and circumstance sharpens your skillset, your adaptability. You learn to be more open-minded, to learn to accept help or look for help, to be independent and not just curdle up and complain. Instead, you learn to be good at interacting with people, and when I say people, it’s not just your travel partners or your fellow countryman, its any stranger that comes your way.

Coz that’s survival.

When you are faced with trouble, your best way to overcome it is sometimes, just learning to find the right people to help you out of it.

Sometimes, you will get into stages where you will have the capacity to look beyond yourself and even help those around in the community you live in, whether it is the poor, the hungry living in slums or the ones who need a listening ear.

So ending this little post as part of the Thirties 30s Edition, penning some thoughts about why I jump out of the corporate train, put on my hiking boots and choose a different path.

And at the end of the day, there is a lot of climbing, a lot of sweating.

But no regrets:)