In the past few weeks, I was juggling quite a few things and although I look busy and productive on the outside, I was reminded recently that a busy life doesn’t automatically translate into a fulfilled life. Meeting with people from different backgrounds has been an eye-opener, even as I challenge myself to ask better questions with each encounter. Sometimes, I find myself rushing the process and feel a tinge of disappointment after that for not being thorough enough. Thankfully, there were people around me who grounded me in the realities of doing a mid-career switch, and especially from an employee to a self-employed. Perhaps patience is something I need to revisit again in this new season.

At the end of the day, I know I have to take a step back and focus on this: purpose and meaning. No matter what happens, if I am clear on my why, I believe I will be able to move forward. This trip will be an open one and I did not plan out anything besides asking a few friends for cafe recommendations. Now it seems like it can also double up as a timely avenue to sit with myself, reflect on how I have been doing things, and decide if I want to make any changes moving forward. Though uncomfortable, it is important to sit with our emotions and feelings once in awhile so that we get a chance to recalibrate our life’s direction. This time round, I also brought Nir Eyal’s latest book with me and hope to gain more insight into how our beliefs shape our thoughts and actions!

Cheers,
Sam :)

Over the weekend, I had the chance to attend a sharing by Shao Chun, who made headlines last year when he shared his story and it was picked up by a few news outlets. As someone who also took a non-conventional pathway, I was intrigued by his journey and curious to hear about what he had to share. Thankfully, I also managed to jio @budgetbyyerim and we attended the session together.

I will not go into too much detail as I already shared about the points that resonated with me here, but I was greatly encouraged and reminded once again that good things take time. After he got laid off and decided to start his Youtube channel, it took him 18 months before he got his first collaboration deal. I recently got licensed earlier this year and have spent most of my time learning as much as I can, preparing myself mentally that the first 3 - 6 months would either be low or zero income. Thankfully, the tuition side of things firmed up in March so I can sustain my basic expenses while waiting to see how things play out for my business. If you are keen to sort out your finances, you can fill up this form and I will get in touch.

As we approach the end of Q1 2026, I continue to be grateful that I get to live this life and retain control over how and when I work. I also learnt that saying no and guarding what matters to me might not always close all doors. Recently, one of my ex-bosses reached out to see if I could do a relief teaching stint from mid April to end May, but since I have already decided to move on from classroom teaching I just told her that I have stepped into a new career and will be focusing on that. To my surprise, she mentioned that she had a group of students who formed a Financial Literacy Interest Group and asked if I was open to collaborate! At that moment, the saying “when one door closes, another door opens” became so real to me even though nothing was confirmed yet. It just reminded me that saying no doesn’t necessarily end the previous opportunity or relationship, and when we are truly committed to what we do, there will always be new opportunities coming our way.

April will also be an exciting month, with a short weekend getaway to KL coming up, a coding workshop that I have been looking forward to attend, as well as catching Checkpoint Theatre’s Secondary: The Musical. In between all that, I’ll also be doing 2 sessions of sharing on my dividend investing journey and hopefully launch my first passive income tracker on Mythos! Exciting times ahead indeed!!

Cheers to a great Q2,
Sam :)

It also dawned on me that today was a special Friday, one that I used to countdown to years ago when I was still teaching. What’s so special about today? It is the last day of the school term. The day when my adrenaline would be at the peak as I rushed to complete the never-ending tasks, hoping to find some closure for as many of them as possible before the school holidays started. If there is a parent-teacher meeting scheduled for today then it would be even crazier, as we will be at the epitome of multi-tasking, but that’s a story for another day.

I still keep track of term schedules because that is the only time when I have the highest odds of catching up with my ex-colleagues turned friends, assuming that they are in Singapore. This time round, I know of quite a number who will be away for the whole week, so the meetups will have to wait. Pro-tip if you want to meet your teacher friends: ask them for their overseas trip schedules and work around that. You will have a higher chance of success if you book them at least 1 - 2 months beforehand.

15 months after leaving the service, this adrenaline rush is something I don’t miss. Compared to years ago, I am thankful for how I spent today. Woke up at around 9am and had a leisurely breakfast, then did a quick check on the markets before going for my fitness class. After lunch, I have some downtime which I am using to write this post as I did not manage to write anything the past 2 weeks. Thankfully I am still able to keep to my fortnightly writing routine so far. Later in the afternoon I’m going for a coaching session where I’ll be guiding my first student on how to build a dividend portfolio from scratch. Really looking forward to that! If you want a quick guide on dividend investing you can get it from my blog. Thereafter it will be dinner before heading to church for the young adults service. A full but fulfilled day :)

In any case, that’s enough of my ramblings. If you are a school teacher, congratulations on making it to the end of Term 1! Otherwise, enjoy your weekend and be prepared for higher public transport traffic next week :D Oh yes, one final shoutout for our event tomorrow morning. If you are keen on business and entrepreneurship, you have to drop by to hear Boss Ming share his candid journey on how to fail forward and move one step closer to the life you want. Brought to you by the amazing peeps at The Saturday Book Club!

Happy School Holidays,
Sam :)

“One of the most difficult but important realisations I had in adulthood is that there are rarely ‘right’ or ‘wrong’ choices in life, just different paths to take. With every choice you make, you have to grieve the loss of all you didn’t get or choose. In this way, growth and grief are inextricably intertwined.”
Emily Anhalt, author of Flex Your Feelings

Earlier this month when I was in Taiwan, this quote jumped out at me while I was reading in a cafe. I read it again, and then once more. With every rereading, I found myself in awe at both the simplicity and complexity of these few sentences.

It is simple because I realise that most of the so-called '“wrong” paths we took also contain valuable lessons and help us make better choices the next round. If not for those “mistakes”, we would not be who we are today - wiser, more grounded, having a deeper sense of what we truly prioritise. They help us to pause, reflect, and become better versions of ourselves. If we view it this way, are there really “wrong” choices if they eventually make us a better person?

Yet this statement is also complex because I resonate with how it mentions that growth and grief are inextricably intertwined. In the last few years, I have chosen to take the path less traveled, and although there is growth, the grief I feel can be equally real. Walking away from a stable job means grieving the loss of income certainty and wondering if I made the right choice. I still think about what I gave up as I continue to walk in the consequences of my decision. Taking this route also means coming to terms that there will be friends and loved ones who will never truly understand why I did what I did. This path can get lonely at times because there are not many in my circle of friends who have stayed on it for sustained periods of time.

Maybe it’s just me, but I read that we are more likely to pause and reflect on our lives as we approach the tail end of a decade. So those who are 29, 39, 49, 59 etc. tend to be more reflective. Perhaps that is why this post will turn out to be more lengthy than usual.

I turned 39 earlier this month, and the one thing that I have come to terms with is this: we will always be figuring life out. Whether it is our career, health, finances or relationships. Rather than having it all figured out, I suspect that we are supposed to normalise not having all the answers. There is no textbook answer in life, and the path ahead is hardly linear. The crucial thing is to keep trying to pick the right people to take this journey with us. That last point can’t be emphasized enough.

It is cliche but you truly are the average of the 5 people that you spend the most time with. If they are constantly complaining and whiny, you eventually become like them whether you like it or not. If they are adaptable and love to embrace uncertainty, some of that will also rub off on you. So choose who you hangout with wisely, and ask yourself along the way whether you like who you are becoming.

Before I end off, I just want to do a shoutout to the 50 of you who are subscribed to this Substack. Some of you are reading this in your inbox as you count down to the weekend, while some of you may have totally forgotten about it. Nevertheless, thank you for indulging me the past few months by having my article sit in one of your email slots :)

As usual, if there are any articles or stories you would like to like to see more of in future, feel free to hit “reply” and drop me an email.

Have a great weekend!
Sam

It was not easy to learn everything from scratch, but the foundation that I subsequently built gave me the confidence to walk away from my next job and take a sabbatical. For the first time, I had the time and space to reflect on what truly mattered. It was a precious season of exploring whether it was possible to earn enough while designing a life I genuinely enjoyed. Throughout this journey, I was very blessed to have different opportunities open up to me. From teaching financial literacy at schools, sharing about my investing journey online, and being part of a panel discussion on REITs, I realised that sharing financial knowledge is something I enjoy.

Along the way, it dawned on me that when money is managed well, it becomes a powerful tool in our lives. Not to buy us more stuff, but to buy us more time. Knowing my numbers allowed me to be intentional during my break and explore different interests without being constantly anxious. The financial structures and buffers that I had built granted me the freedom to lean in to my sabbatical fully.

Having walked this journey myself, I hope to help others gain clarity in their finances too. If money feels overwhelming or confusing, you don’t have to figure it out alone. And if you have always wanted to do something about it but are not sure where to start, I would be happy to explore that with you. My goal is simple: provide clarity over complexity, guidance over pressure, and help you make decisions that you can sleep well with. If you are curious about how this might look for you, feel free to drop me a DM at @financialpilgrim or fill in this form and I will get in touch with you!

Cheers,
Sam

Believe it or not, the extended break was not something I intentionally planned for but rather it was the outcome of intentional thinking and reflection of how I can design the life that I want bit by bit. You may be wondering now: how is it possible to take a career break for more than a year? While I don’t have a model answer for you, I can share how I prepared, what I discovered, as well as the journey that transpired.

For most people, the main constraint of how long a break can last is money. I may be enjoying myself and doing many things that I like, but if I can’t put food on the table I’ll eventually have to go back to work at some point in time. To mitigate this and stretch my dollar more, I first saved up 6 months of basic expenses. Then I saved up for a separate travel fund which really helped as I was away for more than 2 months last year (spread over 8 trips), so essentially I just added 2 more months to my local runway.

The next layer of buffer I had was an 8-month part-time teaching stint which required about 3 hours of teaching and another 3 hours of prep time weekly. That helped to fund almost 50% of my basic expenses and I used part of my savings to cover the shortfall. Having this as a base anchor allowed me to be more at ease during the initial months of my break.

Interestingly, because I had more head space to think and plan once I exited my full time job, other opportunities also started to stream in and I could capitalise on them because I had the time and space to do so. This wasn’t something I planned to depend on, but the few additional side gigs added another few more months to my runway. Many of these opportunities only materialised after the 6 month point, so before that I was also constantly weighing how long I can actually stretch my break for. It was a humbling lesson on embracing uncertainty, and I got a small taste of success and freedom each time I managed to extend my break for yet another month.

The final layer of buffer I had was my dividend portfolio which I started building up 2 years before I took the leap of faith. I did not intend to utilise the dividends but knew that I had an additional $350 per month to fall back on in the worst case scenario. Thankfully it was all untouched and that amount has now gone up to $550 monthly. I view this last layer as more psychological, as I did not plan to use it as income during my break but knowing that I can consume the dividends if I really needed to added another layer of assurance for me.

So when will my money run out? Looking at how much savings I have now, most likely in 2-3 months’ time. Thankfully, I have also started transitioning into a new area of self-employed work and started laying some foundations. If things work out, I might have just enough to tide me through the next few months while I work on slowly growing my active income again. In time to come, I will also be sharing more about my next season, so stay tuned to find out!

Before I end, just wanted to share my nice B&B space from where I am finishing this post up from. I Was having a casual chat with the owner and he recommended a day tour along the coast so I’ll be going for that tomorrow. Totally unplanned, but yet another opportunity to explore what nature has in store for me :) I guess not living life all planned out has its perks too :D

Cheers,
Sam :)

As for me, however, I am still figuring my way around. Even for this post, I was unsure of what to write about, but then I remembered the promise I made to myself: just keep writing. So here is a quick update about what I’ve been up in the first 2 weeks of the year so far.

Recently I met up with @vansncents, a lovely friend I met on IG, and it was interesting to hear her perspective on how she manages money. It was also a reminder for me to pursue personal growth and not stay stagnant at where I’m at. When I get too comfortable, it’s probably time to do things that will make me feel uncomfortable.

During the 2nd weekend of the year, I attended a volunteer training conducted by @thesaturdaybookclub and got to know their vision and mission better. Founded in July 2022, they aim to be a third place for readers, dreamers and thinkers. This year they have bold plans to expand to a second location in Punggol in addition to their usual venue at Bugis, and there are a few exciting author events coming up as well! If you are looking for a community of readers and primarily enjoy non-fiction books, you are most welcome to join us every 3rd Saturday of the month :)

After the training, I went for an event organised by Happiness Initiative, in collaboration with The Woke Salaryman, titled “Can Money Buy Happiness?”
As usual, it was great to hear from Rui Ming and Wei Choon, and also from Sherman, co-founder of Happiness Initiative. One of the ice-breaker activities was a simple poll on what we would give up for 1 Billion dollars. The options ranged from simpler stuff like “not being able to buy clothes ever again”, “losing the ability to travel”, to more thought-provoking options such as “giving up all your close friendships” and “losing your physical and mental health”, prompting all of us to weigh the truly important things in life. It was a good reminder as we embark on a new year to invest and sow into what truly matters to us.

There are quite a few things that I will be working for this year which I will share in due time, but for now I’m just looking forward to my first trip of 2026! It will be a 2 week solo trip to Taiwan, and this time I will be exploring the East Coast (Tai Tung —> Hualien —> Yilan —> Taipei). If you have great food / scenery recommendations, feel free to reply to this email or drop a comment below and share them with me!

Cheers,
Sam

In the first week of 2025, I figured I was going to take it slow. I was leaving for Hong Kong in a few days, and my 3 week solo trip to Taiwan in February was confirmed. On the income side of things, I was still awaiting confirmation to start a part-time teaching stint after I got back from Taiwan. Everything else was a blank canvas. A clean slate. Fresh for me to paint the next chapter of my life. The taste of freedom was alluring, but it was mixed with a slight tinge of apprehension.

Fast forward one year later. It is the first week of 2026. I realise that I am in transition once again. Remember that blank canvas one year ago? I managed to paint in some colours and it eventually became a tapestry of beauty. It now feels like I am confronted with a fresh white sheet once again. I have a slightly better grasp of the transition this time round. There is a more intentional pivot and a few concrete things I can start working on in the first quarter of the year.

Unsurprisingly, Taiwan is popping up again, but a shorter trip of 2 weeks would have to suffice this time round. It will be a slow exploration along the Eastern Coast, starting with Tai Tung, one of the few major cities that I have yet to visit in Taiwan. I held back from visiting because I wasn’t sure whether it would be worth staying a few nights there. But I also realised that the way I measure worth has slowly evolved over the years. If my intention is to just immerse in the local culture and not tick off a checklist of places to visit, surely exploring a new area would be of value. At the very least, I will learn something unique to that region from speaking to the locals there.

Before you get sucked into the busyness of life, I invite you to ponder on what is of worth to you. Who are the people that you want to spend more time with this year? How do you want to allocate your energy on activities that bring you life? What boundaries will you fiercely guard to stay in peace? I hope you give it some thought.

Here’s wishing you a most blessed new year! May 2026 bring you more clarity, purpose and a sense of fulfilment as you continue on this journey of life :)

Rooting for you always,
Sam

Personally, I take some time out (usually a whole afternoon) to scroll through my photo album down through the year - this helps to jot my memory on events that I might have missed out or forgotten about. I recall the events I went to, trips that I took, as well as the people that I met. This year was especially eventful because it was the first time in my life that I was intentional with the time I regained while stepping away from full-time work to take a career break.

As we stand on the cusp of a new year, the mixed feelings tend to reveal themselves. On the one hand, we are hopeful and excited about stepping into a new year with new adventures and possibilities, but on the other hand there is always a measure of apprehension in not knowing how the future will turn out. This mixture of hope and uncertainty that we feel is actually more common than we think.

It may make us uncomfortable, but I have come to realise that this is a very normal process. Instead of letting the thoughts swirl around in your head, why not write them down somewhere? I have found that writing helps us to gain clarity on our thoughts, and it allows us to mentally offload things that are bothering us. This is why I am challenging myself to write more in 2026. Not to produce perfect posts, but to cultivate a habit that can bring calm and clarity into my life.

As we make the transition into a new year, know that you are not alone. We are all bringing our collective hopes and dreams into 2026, and as we strive to be better versions of ourselves, they will eventually materialise. I truly believe so. Enjoy the final days of 2025 and I’ll see you in 2026!

At the beginning of this year when I took my career break, one of the things I wanted to do more of was writing. I even took up a writing course to learn how to write better stories and had every intention to put the skills learnt to good use. Eventually, I wrote a grand total of 2 posts as part of the course assignment, and published 1 other post on my blog. Suffice to say I did not really write as much as I wanted this year, and before I know it we are going to turn the page soon and reach the 2026 chapter.

After discovering how easy it is to set up a Substack publication, I set a personal challenge for myself: to write and publish consistently once every 2 weeks in 2026. Personal finance has always been a natural interest, and recently I have also been exploring how to slow down in life, be more present, and cherish the friendships around me. So this is probably what you can expect me to write more about, at least in the beginning.

Will I succeed in this endeavour or will my efforts taper off by February or March? Honestly I don’t know. So thank you once again for your faith and trust in me. I cannot guarantee consistency, but I will strive to write each post sincerely. In the meantime, have a most blessed Christmas and Happy New Year!