My Thoughts on Turning 50

August 24, 2020 Personal Branding 2 comments

It is my 50th birthday today. Five decades have passed from the time of my birth to the present.

While many consider 50 as a golden jubilee, spending it amidst the global coronavirus pandemic made it more poignant than jubilant.

What does it mean to be 50? How does it differ from all my other years on the planet?

In this birthday essay, I’ll mimic the narrative arc used by Charles Dickens in The Christmas Carol to reflect on my past, present, and future.

My Past Life in Five Minutes (or Less)

I do not have a dramatic rags-to-riches story. I didn’t fail majorly in life or have a sensational turnaround tale.

However, my life wasn’t all sugar, spice and everything nice too.

Childhood, NS and School

Born into a middle-class family, I am privileged to have financially prudent and hardworking parents. They provided my brother and I with most of our material needs—we were never in want.

My infant and toddler years were spent in the Moulmein Rise area. I can’t recall how those years were like as I was too little. Back then, my dad helmed a nursery as an orchid farmer. He took over from my grand dad who passed on in his middle-aged years.

My childhood and early teens were spent in Serangoon Gardens—a neighbourhood which my family adored. As both my parents worked (we had a succession of domestic helpers), my brother and I spent much of our free time together.

We roamed far and wide around the estate; catching fishes and fighting spiders in school; cycling to the different parks in the estate; drinking canned coffee and tea; saving up coins to play Space Invaders, Pac Man and Galaxian at the arcade; and watching movies at the old Paramount cinema (E.T. was my favourite).

School was both terrific and terrifying. As I had Irritable Bowel Syndrome (IBS), I literally sh*t in my pants during primary school and had to be “rescued” by my helper. Secondary school was better, although I encountered bullies who called me names. (A reason why I’m dead against any form of bullying—cyber or physical—and found meaning in my work as an advocate for the Media Literacy Council.)

Junior College (JC) life was a blur of late-teen angst, feeling unmotivated during certain classes (especially physics!) and failing in my Chinese.

It was the 70s and 80s then. Our music tastes swung from Abba and the Bee Gees to the Bangles, Debbie Gibson, Tiffany, Rick Astley (way before rick-rolled became a thing), Man At Work, Culture Club, Duran Duran, Bananarama, and all those other brit-pop groups. There was also a time when J-Pop became popular—Seiko Matsuda and Anzen Chitai anyone?

When National Service (NS) arrived in 1989, my life changed quite significantly. I was whipped into ship-shape—from a flabby and idle teen to a trim and fit adult.

NS was also the time when I gained a love for running. I haven’t stopped exercising regularly ever since (with occasional breaks of a month or two in between, but never longer).

After I ORD-ed in 1991, I continued my education at the National University of Singapore (NUS). Due to my less-than-stellar academic results, I could only get into the Science faculty (it was a dumping ground then) and majored in Botany.

University life was pretty interesting—certainly a major improvement over army life—and I enjoyed the many facets of living in a hostel. Somehow or other (without me understanding why), I did well academically and obtained several academic awards and prizes.

Entering the Working World, Marriage and Parenthood

I got my first job in August 1995. This technically meant that at 50, I’ve spent half my life working (or running my business), and the other half learning and studying.

I began my career in the Ministry of Home Affairs (MHA), handling planning and development work. Life as a young executive was quite different from being an undergraduate, but I’m blessed to have great leaders and mentors in my early working years, who taught and showed me the ropes.

As the years passed, I hopped on to different government, private sector, and people sector organisations.

At the Productivity and Standards Board (PSB)—now Enterprise Singapore (ESG)—I honed my skills in analysing the business performance of companies. I learned how to read and analyse financial statements, calculate the value-added per worker, and assess the business viability of Small and Medium Enterprises (SMEs).

The best thing that happened to me at PSB was meeting my dear wife Tina. Our first date was together with mutual friends at Kenny Rogers at Great World City. The year was 1999, and we crossed the millennium together. We also got married in 2002.

At Singapore Press Holdings (SPH), I learned to multi-task like crazy and organise events from scratch. These skills were further honed during my years at NTUC Club, where I discovered my gift of writing, speaking and pitching stories to the media. I also uncovered my ability to pivot—in this case, from industry development to marketing and corporate communications.

My longest working stint was at the National Heritage Board (NHB). That decade was filled with many memories—some delightful, others less so—but I was glad to work with many amazing colleagues.

The best thing that happened to me during this period? The birth of my son Ethan in 2003. He is now 17 in Year 5 of an IB/IP programme and pretty independent where it comes to his school career.

(The worst thing was that I was hospitalised twice—thankfully those were short stints and not serious ailments!)

Perhaps my greatest career achievement there was to bring the organisation to the social age as a pioneer of social media. The year was 2006 when we launched our agency’s first blog This was followed by rolling out Facebook pages, Twitter accounts, Instagram accounts, and YouTube channels.

I also spent a short stint at the Inland Revenue Authority of Singapore (IRAS). I loved its close and collegial environment there, but the constraints of a tax agency meant that I couldn’t experiment as much as I’d like to.

Even though I had a comfortable career in senior management then, I somehow felt that retiring as a public officer wasn’t the thing for me. I quitted without a job on May 2014, and thought I could take a sabbatical year before I looked for my next job.

But things didn’t quite turn out that way…

My Present Life as a Digital Entrepreneur

This brings us to the next chapter of my story—becoming an entrepreneur at the ripe-old age of 44. How did I stumble into what I’m currently doing?

From Blogs to Social Networks and More…

Remember when I launched a blog for NHB in 2006? Well, prior to that in 2005, I started my own blog called Cooler Insights.

It was a free Blogger blog ( I wrote anything I fancied—family outings, vacations, events, thoughts on the news.

At one time, I even blogged daily! (Now my frequency is a more manageable weekly).

As new social networks popped up—Twitter, Facebook, LinkedIn, Instagram, YouTube, Google Plus (which have since disappeared) and Pinterest—I created social media accounts on each of these and grew my following organically.

While my peers watched television at night, I blogged.

While they played games on their smartphones, I posted on Facebook and LinkedIn.

While they watched concerts and plays during weekends, I read marketing books and listened to social media marketing podcasts.

It became something of an obsession. (Still does, although I do try to diversify my content consumption these days.)

Each time I completed a book, I would write about its key lessons. Ditto for podcasts I listen to, or occasional YouTube videos I watched.

I’ll then share it on my social networks—usually as a link posts, but occasionally as a video or infographic.

I didn’t really care about becoming an influencer. I never felt comfortable with my identity as a blogger. I enjoyed attending events, taking photographs and sharing them with captions—but I was more interested in the business aspect of social media.

What I really enjoyed doing was to learn, apply and teach others about the new wave of marketing—focusing on social media marketing, content marketing, storytelling, behavioural economics, and Search Engine Optimization (SEO).

I only left full-time work on 14 May 2014. That’s nine long years AFTER my first foray into social media.

Starting an Agency, becoming a Trainer and Adjunct Teaching

In 2014, I registered a business called “Cooler Insights” as a sole proprietorship, which my wife and I incorporated in 2017 as a Pte Ltd. The name came from my blog which we later turned into a WordPress website (the one that you’re reading now).

Thanks to my regular content sharing on social media—blog articles, LinkedIn, Facebook, Twitter, Instagram and others—we attracted inbound leads and partnership opportunities.

(We now get a couple of leads every week—and they’re mostly organic.)

This led to mutually beneficial partnerships with agencies and training providers. Some of these “bros” and “pals” are close buddies whom I wouldn’t trade for anything.

I also did some adjunct teaching at a polytechnic. My interactions with the youths were particularly enjoyable—teaching brought a fresh dimension to my life, and helped me to understand how teens and young adults function.

I love what I’m currently doing, but it isn’t easy. Digital marketing is a highly competitive arena. Algorithms keep changing. Consumer tastes keep switching. Interfaces keep updating. Hence, you need to be always on your toes.

Moreover, as partners in life and at work, my wife and I have to balance many balls in the air. We do get into minor conflicts every now and then. We also made our fair share of disappointments and mistakes.

However, the pros far outweigh the cons. Nothing gives us more satisfaction than seeing our clients and trainees achieving significant online success.

Like getting on SERP zero on Google. Or doubling of organic traffic through SEO-friendly content. Or breaking records in lead generation. Or securing a 5-figure income through Facebook advertising. Or reducing their cost-per-results by 10-fold.

My Plans for the Future?

This is quite difficult to answer, considering that my life thus far was more serendipity than strategy.

Right now, I’ve launched new courses in marketing psychology and brand storytelling. I’m exploring training in online copywriting—I’ve amassed a tonne of written material, but lack the time to package them into a workshop.

There are a few areas that I’m keen to further deepen our expertise in too. They include setting up sales and marketing funnels, Conversion Rate Optimization (CRO), and video marketing. My goal is to package them into value-added services for clients.

I’m also hoping to pivot to a less hectic role in another 5 to 10 years or so. (Right now, I wouldn’t dream of changing what I do for anything else.)

As I approach my mid-50s, and as our son goes to NS, university and the working world thereafter, I wish to build (or co-own) an eCommerce or purely online business. I’ll then apply everything I know to grow it sustainably.

Beyond the business and career front, I’ll want to spend more time helping others. I’ll guide them on the best path forward and help them avoid mistakes which I myself have made.

Spiritually, I intend to do a lot more for God. I’m seeking His guidance and direction on where I can invest my time and talents in the best way possible.

(I’m careful about committing to charities or non-profits at this point as my time is stretched. Hopefully things will change down the road as we grow our team and I’m able to delegate more of my responsibilities.)

Whatever little successes I have achieved thus far has been largely due to the support, friendship and help I’ve received from many 恩人 (benefactors) throughout my life. My ex-colleagues and ex-bosses. My friends from both the real and online world. My business partners and associates. And most definitely, my family members and loved ones.

Thank you for joining me in this meandering discourse of my life!

For those of you celebrating a milestone year, what reflections and desires do you have for your life?

By Walter
Founder of Cooler Insights, I am a geek marketer with almost 24 years of senior management experience in marketing, public relations and strategic planning. Since becoming an entrepreneur 5 years ago, my team and I have helped 58 companies and over 2,200 trainees in digital marketing, focusing on content, social media and brand storytelling.


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