The Multi-Job Hustle: How a Singaporean Navigates Overemployment in Singapore

In the past 12 months, the labour market has been shrouded with news around retrenchments and in recent weeks, the government has moved to increase the retirement age and re-employment age to give a longer statutory protection to senior workers who want to work longer. Essentially, most of my peers are trying to stay employed.

In a recent Seedly event, I bumped into my friend, Stanley who I got to know through an ex-colleague more than a year ago. Contrary to most Singaporeans who typically hold a full-time job, he is overemployed, holding 4 fractional full-time jobs in 4 different companies. On top of it all, all his bosses are aware of his situation and approve of this.

I could smell an interesting story from this so I arranged to have a 1-hour interview with him to learn more about his overemployment situation.

So what does overemployed mean?

For those new to the term, overemployed refers to the condition of working more than one job, where individuals, typically in the context of remote or gig work, take on multiple employment roles simultaneously. This often involves juggling several full-time positions or a combination of full-time and part-time jobs, leveraging the flexibility of remote work arrangements to maximise income and career opportunities.

In the United States, overemployment in the form of holding multiple remote jobs, is more common and culturally accepted due to the gig economy and at-will employment laws. Americans often leverage the flexibility offered by remote work to work for multiple employers, a trend that has grown with the increase in remote working arrangements. This situation is facilitated by a more flexible legal and employment environment compared to Singapore, where contractual and statutory obligations, such as CPF contributions, can make juggling multiple full-time jobs more challenging and less common.

Zooming back to Stanley, he is currently holding senior-level roles in 4 media/creative agencies where his role requires him to pitch and close client opportunities, oversee production shoots and provide advisory services to internal stakeholders.

Let’s start with Stanley’s Origin Story

During my conversation, I learnt that Stanley started working part-time in his teenage years and was even taking part-time jobs during his studies. After finishing his national service, he chose to enter the workforce instead of getting a university degree.

Working his way up his career along with a few job switches, Stanley eventually hit a glass ceiling where there are limited number of roles he could progress upward for a higher salary. This is a common scene for many Singaporeans who are a good number of years into their career.

How did Stanley get his first overemployment opportunity?

As the media industry is very small and that Stanley’s work focuses on both business development and creative production, he has built a good network of connections in the media industry.

In a casual catch up with a work acquaintance who runs a media agency, Stanley was asked if he would be interested to take on a fractional advisory role to help the agency grow its business and scale. This fractional advisory role would only require Stanley to be spend 1-2 days each week with the agency, hence the term, fractional. At that time, Stanley’s motivation in taking up the advisory role was not about money, but the possibility of being exposed to working with a wider variety of clients and an expansion of the scope of work he would be doing.

Unlike the common overemployment trend in United States where employees would moonlight several jobs without telling their employers, this wouldn’t be possible in Singapore where everyone knows everyone in each industry.

At the same time, Stanley wanted to be open and transparent about the offer that he has just received. So he had a conversation with his current employer to convince him that he would be able to juggle the work on both roles and that he can be trusted to manage potential conflicts of interests. If his current employer wasn’t okay with the arrangement, he wouldn’t proceed with it. As we already know (otherwise there wouldn’t be this article), he was able to convince his current employer and took up the offer with the second media agency.

Stanley’s third overemployed opportunity came in the same way as well, while the fourth opportunity came as a request from the sister agency of his first employer. The takeaway here is that overemployment opportunities definitely would not come from LinkedIn Jobs. That’s for sure.

How do you juggle between 4 jobs?

Being overemployed with 4 jobs requires a lot of focus and being a whizz at time management. I was interested to find out how Stanley is able to pull this off.

As we can imagine, it isn’t easy to juggle tasks accumulated from 4 jobs. Stanley would have to manage his calendar well, ensuring that there aren’t overlapping meetings with his stakeholders in the various jobs. It helps that he has already built rapport and SOPs with his team so that they would contact him to confirm his time before blocking his calendar. But Stanley admits that he hasn’t always been up to speed with his administrative tasks and he often spends time working on them during spare time between meetings or during commutes.

One of the way Stanley uses to manage his time is to plan his day ahead of time. He would create a WhatsApp chat group with himself and use it to create a list of tasks he needs to work on for the day. The list of tasks typically amount to around 10-15 tasks.

During pre-Covid times, it was more challenging for Stanley to manage multiple jobs as it was still a norm to work onsite in offices. He had to spend 3 days in the office of his first employer and 2 days in the office of his second employer.

After remote working became a norm during Covid, Stanley was able to transition to a full remote work arrangement, even until today. Working remotely allowed Stanley to better mange the different tasks from each job and be physically present when there is a real need for it.

What does it take for a good overemployed worker?

While Stanley believes that anyone can be overemployed without any issues, he admits that it is important to have four traits–ethics, discipline, motivation and commitment. In his own words, “your word is your bond.”

In terms of skills, Stanley highlighted that it is important for overemployed workers to have good communication skills, emotional intelligence and negotiation skills. These skills are essential for managing stakeholders, be it upwards, downwards or lateral.

Stanley also shared that while we are able to negotiate the days and hours spent for each fractional role, we need to be cognizant that in most cases, it is very common that we may have to spend more time than negotiated to be able to do the job well.

Another point that Stanley talked about, is navigating conflict of interests. While he is working in multiple media agencies, he first ensures that his scope of work in each agency does not overlap one another. For tasks that one of the agency is not able to do, he would refer one of the other three agencies that he works in, that would be a great fit for the tasks.

If you think about it, this is a win-win for both agencies because they both get to profit from the work and at the same time, with Stanley as the bridge, he can ensure that the work done by the contracted agency will be up to the client’s expectations.

What is your advice for Aspiring Overemployed Professionals?

For working professionals who aspire to be overemployed, Stanley believes that being overemployed is a happy middle between being an employee and starting out on your own (whether as a freelance professional or running a business).

That’s because an overemployed professional is rewarded a lot more financially as compared to peers who are working in the same role, but holding just one full-time employment. At the same time, an overemployed professional does not bear the risks of a freelance professional or business owner, where there can be significant business overheads, and profitability is solely dependent on one’s business development skills.

Here are three pieces of advice from Stanley for aspiring overemployed professionals.

Be damn good at your current job

To be a good overemployed professional, Stanley believes that a fundamental pre-requisite is to be “damn good at your job” that your bosses will be unwilling to let you go. This also means building the trust and credibility with your stakeholders so that they do not equate your physical presence in the office with productivity. Your stakeholders need to believe that you are getting things done and can be trusted to deliver your assigned tasks within the committed deadlines.

Ensure that everything is above board

Never commit to an overemployed opportunity without informing your current employer first. The industry that you are in, is likely very small and concentrated where everybody knows everybody. There’s no way you can hide your overemployed status from your employer and it is simply a matter of time before the secret gets out. Stanley would ensure that new overemployment opportunities are always discussed with his current employers first and get the nod before he would proceed with them.

Start as an advisor first

Before diving head-first into the first overemployed opportunity, Stanley advises to start as an advisor to the business first. It’s gets you access into the new employer’s business which in turn, allows you to immerse yourself in the working culture and the people whom you would be working with. If you like what you are seeing, then deliver the value you have promised and negotiate a factional full-time role.

What is your financial approach with the excess income from overemployment?

As this blog has a strong focus on about personal finance, I am naturally curious about how Stanley manages the excess income from his overemployment.

I learnt that Stanley believes that saving is important and both he and his wife have a joint savings account where they would save a fixed amount of money every month. From this joint savings account, the couple would discuss and agree on investments decisions.

While his wife is savvy and makes most of the equity investments, Stanley chooses to invests in business ventures with his friends where he receives a small percentage of the equity and is a sleeping partner to the business. His aim is to build up a nest egg of passive income from the profit-sharing if these business ventures are successful.

Stanley also believes in building a financial safety net with his CPF and he aspires to meet the Full Retirement Sum by the age of 45. Due to his overemployment status, the contribution to his CPF account is 50% more than a Singaporean holding a full-time employment. I believe that he would be able to hit the Full Retirement Sum way ahead of his target.

The Future of Overemployment

After concluding the interview, I took some time to reflect back on our conversations and my own experiences. If we think back to the balls of life story that former Coca-Cola CEO Bryan Dyson, spoke about in a 1991 Georgia Tech commencement speech, we can imagine life as a game in which you are juggling 5 balls: work, family, health, friends, and spirit. While work is a rubber ball that bounces back, overemployment requires us to juggle multiple rubber balls together with the remaining 4 balls of life.

The reality is that most people are not equipped with the skills to be great jugglers. But for those who are, can reap great financial rewards.

But I am very much for a future of overemployment.

From the employer’s perspective, they get the benefits of an experienced professional without having to pay for a full 5-day work week if the role doesn’t require it. But if an employer wants to have a dedicated service of an employee, overemployment also forces them to pay market price for continued employment instead of exploiting employee loyalty discounts with below-market increments.

For employees, we are in a very uncertain labour market where there is very little employment protection for working professionals by non-existent labour unions, my opinion is that those who can, should strive to be overemployed so that our financial security is not at the mercy of just one employer who could choose layoffs when there is a need to beautify financial reports.

There is also no need for working professionals who are not interested in fighting for the top 1% for c-suite positions to worry about wage ceilings because they can be financially rewarded by providing their experience and expertise to more than one employer.

Are you for or against overemployment? I would love to hear your thoughts on this topic in the comments section below.