In 2022, I felt the calling to take a step back from work and re-evaluate the things most important to me.

I explained my decision in the previous article, “How I knew it was time to quit my job for a career break (and how it is going one year in)”. The TL;DR is that it has been an incredibly rewarding journey, though not without its fair share of challenges. I’ve learned a tremendous amount about my unhealthy relationship with productivity and my fears of uncertainty. By allowing myself time to travel, visit family, and learn new skills, I rediscovered the inspiration that had been buried over time.

The following is part 2 of my Career Break series where I share the honest realizations from the struggles I faced and how I navigated it. If you are at a similar crossroads in life, I hope that my experience can help provide a more realistic picture of the less romanticized parts of this endeavor — and why I still believe it’s one of the best investments I’ve ever made.

Takeaway 1: Define your personal definition of enough, or the hamster wheel will follow you

Detaching from the overachievement mentality was way harder than I anticipated.

After the first couple of fulfilling months of traveling and doing volunteering projects, I had a period of down time where I was between destinations. This was when the comparison trap started getting a hold of me.

Aimlessly scrolling the LinkedIn updates, a little voice started creeping up inside reminding me of the uncertainties ahead:

“What am I doing?”

“Look at everyone else getting promotions…am I wasting my time out here?”

“What do I have to show for my year off?”

And I knew exactly where that familiar little voice came from.

Growing up in a turbulent family dynamic, I was driven by anxiety to keep the peace. It was painful for me to constantly see my loved ones in pain, so I tried everything I could to not mess anything up. During those early years, I developed a habit of over-optimizing for everything and started linking my self-worth to accomplishments. I needed an illusion of control.

The result of that was becoming a Grade A people pleaser.

The crazier thing is that society heavily rewards some of these personality traits that are actually symptoms of trauma in disguise. We live in a world that rewards us for swallowing our feelings and just be in the constant pursuit of more — more success, more money, more prestige, more material upgrades. More of everything. More always seems better, safer, and more respectable.

While I’m thankful for where this hustle had taken me so far in life, I eventually started feeling stuck in it. I realized what drove me to prioritize others’ approval over the work-life balance I thought I wanted was a mindset of scarcity and insecurity. No matter what I did, I never felt like I was enough.

This was exactly what I was looking to heal by stepping away from my work, although I didn’t realize exactly how much work I needed to do on my inner self.

When I went on the career break, the first thing I wanted to do was set concrete goals for myself to accomplish with the free time. While it was good to have things to strive toward, the problem was the perfectionism with which I set those goals. I wanted to have something impressive to show for my time “off”.

Over-fixated on a picture perfect career break story, I was impatient with myself in the moments of non-doing. Without that external validation, I felt lost.

But the truth is, external validation doesn’t lead us to contentment and fulfillment. It only keeps us chasing more.

I finally recognized that if my goal is to heal a toxic relationship with productivity, I can’t simply replace an endless pursuit of work achievements with an endless pursuit of bucket list items. Otherwise, I’ll still be chained to expectations and forever hustling toward more superficial embellishments to enhance my “life resume.”

I want to live a good life, not just appear to be living one.

This is completely an internal shift. To reach this point, I first need to have a clear enough picture of what kind of life I actually want to live. We will perpetually chase after some arbitrary metric and feel behind unless we can answer for ourselves this age-old question: “Do I want what I want because I truly want it, or because society said I want it?”

When we aren’t clear on our version of success, we end up measuring our lives against someone else’s definition of success. That’s why we feel behind in life.

True freedom requires patience and understanding of where we are and where we are trying to go. Finding our own freedom is the real work of our lives.

Realizing that I have the power to define ‘enough’ for myself was the turning point. It took many deep reflections on what gives me joy, what my personal values are, and what I truly consider as success in life, but I gradually arrived at peace.

The secret? I started practicing measuring life by fulfillment instead of achievements.

Realizing that I am motivated by deep connection, learning, and creativity, I now reflect on my weeks based on how much I invest into the relationships in my life, how much space I have for learning and creating, how content I feel each day, and how aware I am of my own needs.

I started embracing the idea that as long as I do something every day to get close to living out these values of mine, I’m in a good place. I no longer berate myself trying to make up for lost time because I’m running my own race. By measuring backwards rather than forward, I can make incremental gains while appreciating that I’m much further along than I think I am.

Instead of fretting over the unfinished tasks on my to-do list, I practice getting into flow state. I actively seek out experiences that bring joy, excitement, and contentment. These days, I wake up with abundant energy, excited to take on what the day has to offer.

Things might not always unfold as I wish, and some of my goals may take longer than I intended. However, I no longer operate from a place of fear, constantly striving to prove my worth. Knowing that I have the power to be the protagonist of my own story, I now try my best to stay present and care for my holistic health — physical, mental, emotional, spiritual, and intellectual. If that means taking a slower day from time to time to ensure alignment, so be it.

A life well-lived doesn’t necessarily align with society’s predetermined milestones.

Some days, the progress I’m making might not look like much from the outside. Nevertheless, I am fulfilled.

Takeaway 2: Walking your own path is a lonely journey. Fostering a sense of belonging for others can help you feel it yourself.

About 6 months into my career break, I started feeling a sense of loneliness.

The surprising thing was this loneliness actually did not come from traveling solo.

I had chosen a slower travel style which worked wonderfully well for me from the start. Instead of bouncing from destination to destination on a weekly basis, I spent more time in each location to establish a routine of regular exercise, cooking, reading and engaging in other hobbies. This approach allowed me to take sightseeing at my own pace so as to not feel exhausted by a packed agenda. I had also weaved in volunteer or work projects in certain places, which provided built-in structure and social environments.

I was in no shortage of good company. So what was the problem?

The disconnect stemmed from something deeper within me — something that wasn’t related to traveling itself, but had to do with being in a different stage of life as my friends.

You see, when you take an unconventional path such as taking a career break for soul-searching, you expose yourself to endless possibilities as well as the byproduct — the uncertainties.

Not everyone will understand what you are doing or how you are doing it. Not everyone will understand new values you adopt along the way. Not everyone will understand the internal battle.

Perhaps you gain a new outlook on how to pivot your career. Perhaps you conceive new ideas about where in the world you’d like to live or with whom. Perhaps you embark on a new business venture that requires considerable risk. Perhaps you realize your desire to continue leading an unconventional life. Your community might expect you to resume your previous life after the break, but you know internally that you’ve evolved to want something different.

For me, it was a few of those realizations combined. I gained much more clarity on the type of life I want, or more importantly, don’t want. And at least from what I perceived at the time, this path would look a lot different from the path most of my friends walk or one that my parents expected of me.

That’s a scary realization because we all inherently crave being seen and understood for who we are.

Any step outside of the traditional path can be met with a spectrum of reactions from your circle. The internal landscape becomes chaotic. You might find yourself in a transitional phase of identity exploration, standing in between the old and the new.

You feel the pull of the new adventure, yet fear losing the sense of acceptance and belonging if you opt for the road less taken.

What gradually grounded me was shifting my focus away from myself to others.

At the beginning of this year, I reached out to my friend circles to start a weekly online meditation accountability group for anyone who wanted to practice mindfulness and emotional awareness.

We met week after week to share what life had been teaching us. Old friendships strengthened and new friendships blossomed. This community has since then become such an anchor for everyone involved, providing a safe space to be real about the challenges we are working through.

I remain grateful for this group for teaching me that when you help foster community for others, you will feel at home yourself. Instead of thinking about what others can offer us, the real rewards come when we spend more time thinking about what we can offer to others.

I realize even if people aren’t in the same phase of life that I am in, they are still humans in their own journey of renewal and all experience fears and doubts in similar ways. When you create a space to share your vulnerable side, others open up as well. Common human emotions create connections beyond our differences.

The separateness fades in the presence of empathy.

Knowing the power of empathy, I also approached travel friendships with much more intention. Instead of being merely a visitor of a new place I travel to, I made it a point to get to know the individual stories of the locals and travellers alike.

With little shared context in life and sometimes a thick language barrier, we were still able to learn about each other’s families, loves, dreams, joys and challenges. As it turns out, we all have more in common than we’d think. The lifelong friendships that came out of this year were invaluable.

It’s true that not everyone will comprehend your endeavours and choices, but there will be people who do. When you extend your heart to the world, the world will respond. The love you pour out will return to you — though it might not always be through the avenues you expect.

Recognizing that meaningful connections await wherever I go, I no longer feel lonely.

Takeaway 3: Things rarely go exactly as planned. Let go of attachments to ideals and “should’s”.

Very few things unfold exactly as planned.

Among the joys of this year, I also encountered quite a few adversities including a heartbreak, newly diagnosed family health problems, and shifts in the job market. Throughout this windy journey, I was confronted again and again with my attachment to comfort, certainty, and control.

I initially planned my break with such an idealized view of how a career break should transpire that any changes in the external circumstances triggered anxiety and stress.

Modern conveniences have conditioned us to be less and less patient when things don’t go our way. We leave little room for boredom, annoyance, stress or sadness these days. Instead of facing our own emotions, we can give ourselves the dopamine hit just by scrolling at our phones. Everything has a solution. Everything is optimized — on paper, at least.

Our minds do an excellent job at pumping out thoughts. We go about our days constantly thinking of what needs to be done in order for everything to go seamlessly.

“I should do this.”

“Things should be that way.”

Eventually the “should’s” begin to weigh down on us when reality kicks in. No matter how much we plan — there is so much beyond our control.

Even the idea of “should be happy” can become a trap.

“The worst way to be happy is to try to be happy.” — Jeff Goins

Our memories tend to sort our past into a smooth and linear path, which makes us believe growth follows a gradual upward slope. In reality, we live through extended periods of stagnancy interspersed by sudden, rigorous changes accompanied by great uncertainty.

I’ve learned to let myself feel the rawness of a full range of emotions this year. These were the parts of me that I normally hid away by taking on more work or more entertainment. It was amazingly fulfilling, and it was heart-wrenchingly painful. It was a necessary process to arrive at acceptance.

The value of changing lies in further exploration rather than a certain result.

Everything has its course to run. In face of changing times, we cannot just push with brute force. Sometimes, it requires taking a step back to allow things to flow.

Everything we go through today is not only for ourselves. Life has a way of teaching us lessons and working through us. We can be open to experiencing not just the happiness but also the pain, because here we learn how to navigate it and how to help those who will go through similar trials in the future.

Trusting that these experiences served me rather than happened to me, I started making friends with the unexpected events, approaching them as opportunities for growth. I now practice letting go of the tendency to want to control the uncontrollable, knowing that I can always come home to myself.

It’s like the moment when I jumped out of the plane at 15,000 feet, trying skydiving for the first time in Australia. My heart was beating so fast from anticipation the entire ride up.

To my surprise, a few seconds into the jump, everything looked…not so scary anymore.

In this leap of faith, my brain realized 2 things:

1. how small I and my worries are
2. there’s nothing else to process but to simply let go

The result?

Pure, present, contentment.

NOTE: All this being said, we aren’t jumping out of the plane without a parachute. Practical planning is necessary and comes in incredibly handy to mitigate the impact from unexpected changes. Traveling frugally (mostly through volunteer/work exchanges that cover accommodation and food) and saving up double the amount that I thought I needed had helped tremendously in the times of uncertainty. Stay tuned for part 3 of the Career Break series if you’d like to know how I went about career break budgeting, financial and logistics planning. :)

For a visual representation of our metaphor, here is….

Nervous laughter before the moment of truth✈️ 🪂

Immediately after the leap, having every doubt in the world. Why did I sign up for this again???

Arriving at peace and appreciating the breathtaking view :)

Final thoughts

To be in the position of living on your own terms is absolutely a privilege. As I’ve written in part 1, I acknowledge and am immensely thankful for all the circumstances and conditions that allowed me to save up and take this extended break.

What I will emphasize is, the freedom mindset is an important muscle to build. For as long as we still live under the constraints of our limiting beliefs, everything will seem unattainable. From the moment we gain true internal freedom, we are always living on our own terms.

It was such a blessing to hear from many of you who resonated with my story in part 1 and many others who offered wisdom from personal experience! If you are in a transitional period of life, I hope that your next steps reveal themselves when the time is right. Growth emerges from experimentation, and I’m excited to witness your journey.