Gen Y Speaks: How I transited from a full-time salaried job to self-employment

I confess: I used to think I was a hotshot. 
In university, I frequently enjoyed fancy meals with senior members of staff in my role as a board director of the student union charity, which had an annual turnover of S$14 million. 
I thought I was smarter, better and more efficient than most of my colleagues. After all, with a first-class honours degree, awards, and glowing recommendations, I seemed fairly competitive. 
Not anymore. Not after the past 29 months, in which 278 job applications and 39 interviews turned up rejection after rejection. 
In October 2021, I decided not to renew my contract in social services. I wasn’t a cultural fit with the organisation. I also hoped to explore a different job, albeit in the same industry. 
At the time, I figured: “How hard can it get? The social service industry always needs people.” 
I had been actively applying for jobs from March 2021, but got no offers. I even chased down the emails of human resources personnel, trying to get them to give me some feedback. 
You would think that after getting rejected so many times, it would get easier. 
It never did. 
But what did get easier was taking control of my own destiny. 
At first, I thought I would get a new job fairly quickly. Sadly, that didn’t materialise. 
But I’d always had side interests. Even during my full-time job, I had been actively nurturing my skills in training, writing, and facilitating. 
I went for SkillsFuture courses like the Advanced Certificate in Learning and Performance, a train-the-trainer qualification. I even paid S$13,000 for a course on becoming a better speaker (though I definitely do not recommend you pay that amount). 
In August 2021, two months before I left my full-time job, one university offered to pay me for some training I would do for them. 
Granted, it may not be a significant amount of money to many — only S$1,000 — but it was money I had earned independently. I hadn’t relied on the reputation of a larger organisation. 
All I had was a tiny Private Limited company that I had incorporated in June 2020, with its grand office address being none other than my home. 
Whilst having my full-time job in 2020, I incorporated the company. I wanted to create an alternative source of financial security that didn’t come from my job.
In November 2021, my first month out of a full-time job, I earned all of S$700. 
It’s not much, but it was enough money not to have to ask my parents for an allowance. And that, to me, was worth celebrating. 
As time passed, I picked up more gigs.
I wrote articles about kindness, which paid S$150 per article. I facilitated focus group discussions about issues such as total defence. I served as tech support for an online training. 
I fumbled around with gigs like this for a year. All the while, I was still applying for jobs, but no one accepted me. I kept going with the gigs, not really knowing where I was going — just that I was still surviving. 
A year later, someone asked if I could help with their websites. At the time, I had only a rudimentary knowledge of making my own websites, but I was willing to try. 
From websites, I moved into digital marketing, running Google AdGrants, search engine optimisation campaigns, and helping businesses to rank higher on Google’s page one results. I had fun, and discovered maxims like “The best place to hide a dead body is on the second page of Google search results”. 
Today, I still do all of these — speaking, training, writing, marketing, web development, facilitating, on different days of the week. 
Some might think this is a “bad” way to lead a life, especially as a university graduate. People have asked: “What’s your long-term plan? How long can you survive like this?” 
What they are really asking is: “Are you being reckless?” 
Having seen my parents retrenched several times, and friends my age falling into despair after losing their “secure” full-time positions, I’ve come to see the precariousness of our jobs today. 
In a rapidly changing world, there are no guarantees that one will be able to keep their “steady” job.
There is also no certainty that our skills will even continue to be relevant to the jobs we are currently in. 
Renowned strategic thinker Charles Handy suggests that in the S-curve of life, the moment we must transit is not at point B, where things have begun to take a downturn. 
This may be where we’re told we will be retrenched. 
Instead, it’s at point A, where things may be steadily getting better in your career. Because life is made up of cycles — what goes up will and must, sooner or later, come down. 
I was fortunate that I built these newfound skills while I still had the safety net of a full-time pay. But it wasn’t because I had more foresight than anyone else. There had never been any grand plan to survive so long without a job.
It was simply because I was getting tired of what I was doing and wanted something new to engage me. 
Preparing ourselves for change by focusing on our strengths, and building or acquiring skills complementary to those strengths, allows us to ride the curve. 
When I first started working independently, the hardest thing was taking bus 51 back home. 
I would sit on the top level of the double-decker as it wound through Bugis Junction, looking at people queueing for restaurants like Hey! Yakiniku. I would feel a deep pang — of hunger, as my stomach growled, but also of uncertainty. 
I wondered: Would I ever feel financially secure enough to buy a meal at a restaurant, without worrying about the cost?
With no income visibility from the stability of a full-time job, I felt it foolish to treat myself. 
I was hungry for that fancy meal. But I was also hungrier to make something work out on my own. 
With no one willing to give me a chance with a full-time job, my back was to the wall, and I had to fight. 
And I think it’s in that fighting that you find life itself, and something worth fighting for. One of my favourite quotes comes from When Breath Becomes Air, a book neurosurgeon Paul Kalanithi wrote when he was diagnosed with terminal cancer.
“Years ago, it had occurred to me that Darwin and Nietzsche agreed on one thing: the defining characteristic of the organism is striving. 
Describing life otherwise was like painting a tiger without stripes. 
After so many years of living with death, I’d come to understand that the easiest death wasn’t necessarily the best. We talked it over. Our families gave their blessing. We decided to have a child. 
We would carry on living, instead of dying.”
Looking for work is a difficult process. Some may never have to fully understand or experience how tough it can be. 
But when no employer will give you a chance, sometimes what helps is to give yourself the first chance. 
To look for the small gigs you’ve always wanted to do, however little they pay. 
To make something that you can sell — cupcakes, or even your yoga teaching services.
To worry less about the future, and to take life one day at a time. 
To move away from thinking in polarities: It’s not really about having a job or being jobless, but learning to manage the tension between planning long-term and surviving for the short term. 
Each day we have a choice between choosing to live, making the most of this fighting chance, or letting ourselves succumb to dark, life-defeating thoughts. 
Reframing “I am jobless”, to “I am fighting for my livelihood” reminded me that there was something worth fighting for. 
Things might not get immediately better, but you will get stronger.
ABOUT THE AUTHOR:
John Lim writes on how young adults can “adult” better at liveyoungandwell.com and runs content marketing agency Media Lede.