Adventure Inspiration Travelogues

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.

Me and my first seaplane ride
Me and my first seaplane ride, one of the perks of the job to the envy of all my friends

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.

me and my dirty trekking boots at mount rinjani
Me and my hardy hiking boots

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.

At the top of the mountain captivated by the beauty of the landscape | Mount Pulag in Philippines
At the top of the mountain captivated by the beauty of the landscape | Mount Pulag in Philippines


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.

Constantly working on the go
Constantly working on the go, even on the flight when there is no 3G. There is always a report you can do, a blog post you can write or an album of images you can edit. If you think a full-time traveller’s life is all easy and fun, then you are just finding out the dark truth.
Immersing in the beauty of nature in my journeys whenever I can squeeze time out after the 'office hours' to stroll through the forests and immerse in the beauty | Walking through Slovak Paradise in Kosice Slovakia
Immersing in the beauty of nature in my journeys whenever I can squeeze time out after the ‘office hours’ to stroll through the forests and immerse in the beauty | Walking through Slovak Paradise in Kosice Slovakia

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 work top in our Air BnB when working remotely from Spain
My worktop in our accommodation when working remotely from Spain, with Agness my fellow travel blogger buddy working very hard as well | Life of a Digital Nomad


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).

The storm clouds approach during our hike in Mount Ugo | Hiking the Twin Peaks of Corderilla with Trek for Hope
The storm clouds approach during our hike in Mount Ugo | Hiking the Twin Peaks of Corderilla with Trek for Hope

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.

How I ditched my High Heels for Hiking Boots | The 30 Edition
Life’s a journey we are embarking on, but are you aware and prepared for the path you choose to take


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.

Some days you have the whole room to yourself to work | Working from a sleeper train from Gdansk to Krakow, Poland
Some days you have the whole room to yourself to work | Working from a sleeper train from Gdansk to Krakow, Poland

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.

Some days you are too exhausted that you fall asleep in the most unsightly way, to the sheer amusement of your very gracious travel buddies
Some days you are too exhausted that you fall asleep in the most unsightly way, to the sheer amusement of your very gracious travel buddies

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.

Many unknowns but its part of the journey
Many unknowns but its part of the journey


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.

Enjoy the journey and the lessons learned along the way
Enjoy the journey and the lessons learned along the way

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.

Enjoying the journey

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

But no regrets:)

Always wanted to travel more & change your lifestyle? Sharing with you how I set about changing my life to pursue what I want & how you can do that as well!
How Travelling Changed my Life and Mindset | Travel in your 30s Edition
How I ditched my High Heels for Hiking Boots | The 30 Edition

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  • Reply
    July 5, 2018 at 7:02 am

    A very inspirational story on how you pursued your dream – it is so important that we do what we love and I certainly think that you are doing exactly that!

    Miriam xx

    • Reply
      Lydia Yang
      July 5, 2018 at 12:52 pm

      Thanks, Miriam. That’s probably the most important thing in life!

  • Reply
    July 5, 2018 at 9:29 am

    Love this post. I hate the people promising digital nomads easy life without hard work and preparation which is just BS! You have to work to make your dream come true. I’m glad you were able to trade those high heels for boots :-). I think we took that airline in the Maldives to Vilamendhoo.

    • Reply
      Lydia Yang
      July 5, 2018 at 12:59 pm

      Thanks a bunch, Kemkem. Working hard is essential if you want to succeed in life! 🙂

  • Reply
    July 5, 2018 at 3:27 pm

    This is such an incredible post. You are an absolute INSPIRATION for being so real about your transition from heels to hiking boots. So often people sugarcoat life as a digital nomad. Ummm….nope! It’s a ridiculously hard lifestyle to keep up and I always appreciate it so much when people are honest about that fact. Keep up the hard work!

    • Reply
      Lydia Yang
      July 5, 2018 at 7:09 pm

      Thanks a bunch, Kasie. Every line of your comment means the world to me! 😉

  • Reply
    July 5, 2018 at 3:34 pm

    This was a wonderful post, which I think many of us can relate to. Thanks for the link on best solo trips too. I didn’t see a LIKE button for this post. Oh, and thanks for stopping by my Blog, I am enjoying your Blog too!

    • Reply
      Lydia Yang
      July 5, 2018 at 7:10 pm

      Thank you a lot! Glad you like my blog as much as I like yours. 😉

  • Reply
    Tim UrbanDuniya
    July 6, 2018 at 1:21 am

    Well done! What makes a person happy is different for each person, and can’t be easily defined! It’s very inspirational to read the story of how you came to this point, and you are certainly very good at what you do – so more power to you 🙂

    • Reply
      Lydia Yang
      July 17, 2018 at 5:10 am

      Thank you Tim. You are such an encouragement. Lets power on as well!!:)

  • Reply
    July 10, 2018 at 3:38 pm

    Congrats! Great post, so good to see you pursuing your dreams and leaving the office life behind. See you soon!

    • Reply
      Lydia Yang
      July 17, 2018 at 5:06 am

      Thanks Todd;) Indeed its always a great learning journey. See you soon!

  • Reply
    July 11, 2018 at 5:08 pm

    This is really really good advice!! I still have my 9-5 job, but because of blogging, I’ve opened up so many opportunities for myself to travel. I even got my current job BECAUSE of my blog. It’s a full circle thing haha. This is really inspirational lady. I agree that traveling is a drug that keeps drawing you back in.

    • Reply
      Lydia Yang
      July 17, 2018 at 5:08 am

      Looks like we started on the same track. Glad that you are pursuing your dreams too Emily! Keep striving!

  • Reply
    Gilda Baxter
    July 12, 2018 at 3:30 pm

    Lydia, I think your sturdy hiking boots will carry you to greater heights and a more fulfilling life than those fashionable but flimsy high heels. You are designing the life that you want to live. Not the easiest of paths, but well done for taking the leap. Great blog 🙂

    • Reply
      Lydia Yang
      July 17, 2018 at 5:09 am

      Thanks Glida. Yes, not easy to take the path less trodden, but boy, this was one of the best decisions in my life!

  • Reply
    August 6, 2018 at 9:15 am

    Very inspiring post! Nice to read about this kind of story coming from a Singaporean – lots of nuggets of wisdom about life in and out of Singapore! 🙂

  • Reply
    Grant Baird
    August 18, 2018 at 3:51 pm

    Great post. We too made a similar shift, leaving the corporate world in our 30s in search of real life. We find that the satisfaction coming from living with people from different background, lessers means, and in nature, away from many of the creature comforts of the corporate world, is far more gratifying. True enjoyment does not come from expensive luxury which can be bought by anyone with the money, but from the adventures, misadventures, and inspiration found at odd places throughout the world.

    • Reply
      Lydia Yang
      August 19, 2018 at 8:27 am

      Thanks, Grant! I couldn’t agree more with everything you said. 🙂

  • Reply
    August 19, 2018 at 3:58 pm

    Inspiring! Wish you the best. 🙂

  • Reply
    Randall Collis
    August 21, 2018 at 6:18 pm

    Could not agree with you more. Life goes up another notch or two when stepping out of our comfort zones, especially if it means getting out of the office. The corporate world is such a soul drain, and I still battle with it ~ but it makes getting out to seek adventures and experiences that much more valuable. Wising you many safe and great travels 🙂

    • Reply
      Lydia Yang
      August 24, 2018 at 10:49 am

      Yes it is indeed always a challenge Randall. But there is always a mix of timing, hard work and opportunity. Don’t give up, life is worth fighting for what you want it to be! Keep striving!

  • Reply
    August 28, 2018 at 11:44 pm

    Isn’t it just amazing to be out in nature? It honestly makes me want to just get up and leave my every day life too. So glad you get the opportunity to get out and enjoy it like you do!

    • Reply
      Lydia Yang
      September 26, 2018 at 10:48 am

      It’s always the 1st step that is the hardest. Give it a try and you will not regret it when you look back!

  • Reply
    October 30, 2018 at 7:25 am

    Love your sharing Lydia! Must be real hard work, hope you get your rest and time with family too while traveling! 🙂

    • Reply
      Lydia Yang
      October 31, 2018 at 5:45 am

      Thanks Elizabeth!:D Yes it is super hard work, though few would see all of it – only the ‘glamourous’ and envious side of things;) Yes, back in Singapore now and spending some time with family too!:D
      Hope you have been well??

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