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We’ve all heard it: “The grass is greener on the other side.”
Some cynics add that it’s greener because it’s fertilised with bullshit. (some elements of truth)
But after two decades of entrepreneurship, I’ve discovered a deeper truth: the grass is greener where you water it.
When It Rains, It Pours
My mid-twenties weren’t exactly the golden years people dream about.
I’d already weathered two back-to-back layoffs during the dotcom crisis.
Now, as SARS ravaged the global economy (to my Gen Z readers: that was the OG Covid-19 in 2003), I found myself in possibly the worst place to be – selling spare parts to airlines when planes worldwide were grounded.
I can still remember that emergency meeting.
Our Managing Director stood before us, voice steady but eyes betraying concern, attempting to pacify a room full of anxious employees.
His resignation a week later said more than any corporate memo could.
The thought of scoring what I darkly called a “layoff hat-trick” wasn’t just a fear – it felt inevitable.
Seeds of Change
That’s when I spotted an unlikely inspiration – a friend running a networking cabling business from a modest flat, using floors as makeshift tables.
Not exactly the glamorous startup story you read about in TechCrunch.
But I saw something beyond the mess: freedom and flexibility.
More importantly, I saw control over my own destiny.
Without overthinking, I took the leap and started my own staffing company.
The Growing Pains
Reality hit hard.
We were complete novices in the business world, let alone the complex landscape of staffing.
Every day felt like a crash course in “how not to run a company.”
For every three steps forward, we stumbled two steps back.
Early attempts at everything from client acquisition to project management were textbook examples of what not to do.
Cash flow?
That was a luxury we couldn’t afford.
Bootstrapping meant relying on dwindling savings and maxed-out credit cards just to keep the lights on.
Working 996 (9am-9pm, 6 days/week) before it became a buzzword.
My “fine dining” consisted of alternating between nasi lemak and beef fried rice – humble soul food that fuelled me through the endless grind.
First Harvest
But we kept watering.
Day after day. Little by little.
Each mistake taught us something valuable. Each setback made us more resilient.
Each small victory gave us the confidence to push harder.
The lessons compounded like interest – painful at first, but increasingly valuable over time.
That persistence paid off.
We grew to 29 people and hit $5M in annual revenue at our peak.
Not unicorn status, but enough to attract acquisition interest in 2006/2007.
Seasons of Change
The path after that wasn’t the straight line to success you might expect.
I embarked on what I now call my “entrepreneurial wandering years.”
First came solo career coaching – a venture that proved harder to sustain than anticipated.
That business eventually found a home through acquisition by a resume-writing company.
Not one to stay idle, I launched a resume optimisation website, only to face similar sustainability challenges.
That too was eventually sold.
The corporate world pulled me back three times – not out of choice, but necessity.
The reality of putting food on the table sometimes means taking detours on your entrepreneurial journey.
A consulting business showed promise but relied heavily on government grants.
When those dried up, so did our operations.
Going Solo
My last corporate stint lasted just ten months, ending when the CEO started monitoring my LinkedIn activity and asked me to modify one of my posts.
I chose freedom over compliance and walked away.
The final push toward full-time solopreneurship came during a job interview when the interviewer expressed concerns about my “influencer status.”
That was when I embraced my public persona and fully went solo again.
The View From Here
Now here I am, three years into my current chapter as a solopreneur.
Running a one-person show is even more challenging than managing a small business.
There’s nowhere to hide when you’re the only arms and legs.
Yet the journey has been rich enough to fill a book I wrote.
The fascinating thing about entrepreneurship is how it mirrors that grass metaphor.
Whether thrived or withered, each venturetaught me the same lesson: success isn’t about finding the perfect patch of grass.
It’s about committing to nurturing whatever ground you’re standing on.
Those “failed” ventures?
They weren’t failures at all.
They were different patches of grass that needed various kinds of water.
Some thrived briefly before being transplanted through acquisition.
Others needed to be left fallow so something new could grow.
Even the corporate returns served their purpose – providing nutrients for the next growth phase.
Stop second-guessing yourself.
Whatever path you choose is right – IF you commit to nurturing it.
Your grass will green up.
It just needs consistent watering.
Still watering, still growing.
And you know what?
The view from here is pretty damn green.