Pros and Cons of Being a Boss, Employee, and Freelancer

In the world of work and employment, I think there are three main types of people one can be: an employer, an employee, or a freelancer. As a co-owner of a small business, a freelancer whose work you are now reading, and someone who just got his first full-time job as an employee, I’m writing this to share my experiences and thoughts on these three distinct career paths.


As the co-owner of a small tuition business, I’ve learned a thing or two about the challenges and triumphs of being a boss.

One of the cons is cost, and boy this is a big one. Staff pay and bonuses, rental costs, insurance premiums, advertising budgets… the list goes on and on. Just when you think you have your expenses under control, another creeps up on you like a pesky insurance agent at an MRT station.

Even doing something simple like adding a partition to split a room into two requires all kinds of certification and approvals, with every step of the way needing some form of fee or professional service to be paid. Something like fire safety certification also costs a few thousand dollars just for someone to come in and poke around to ensure that there are places for people to run out to in the event of a fire.


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There are also endless things to worry about – the economy, staff morale, lease renewals among other things. A business owner can spend time and money doing up the place, only for the lease not to be renewed, or more likely a doubling of the rent. Or the mall could unceremoniously close down, never mind the fact that fancy renovation fitting of the mall’s requirements was done only a few years ago. Fun fact: we were approached by JCube a couple of years back to take a unit there and thank goodness we didn’t.

It can be overwhelming, but that’s part of the risks and return of running your own business. If you’re successful, the potential returns are huge. Not only do you get to earn a good chunk of money from your business, but you also have the potential to make it a passive source of income.

As the boss, you also have the authority to set rules and impose your own standards on the company. One of the more enjoyable things we did as a business was allow for a more casual environment. We designed our own uniform, and most days you’ll find us strolling into the office in slippers and comfortable shorts. It’s a far cry from the suits and ties of a traditional workplace.

But perhaps the greatest joy of starting your own business is the sense of ownership and satisfaction that comes with it. There’s something special about walking into a place that you’ve created from scratch, knowing that it’s yours and that you’re in charge. Seeing your business have an impact on people, providing employment, and delivering value to customers is truly a unique experience.


On the other side of things, being an employee, as with most things, comes with its own set of pros and cons. In the middle of 2022, I took up my first full-time job with the blessings of my business partners so that I can experience the life of an employee with a 9 to 6 grind.

As an employee, I finally have a taste of having a regular pay cheque each month which can be a big plus for personal financial planning. As someone who has been receiving irregular income for more than a decade now, the fact that I know exactly how much and when I would get my salary is still amazing to me even more than half a year since I’ve started my job.


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Being an employee also frees up a lot of mental stresses that business owners and freelancers tend to contend with. Steady income aside, employees are generally free of the burdens of entrepreneurship. There are no cost pressures nor business considerations to worry about, and you generally just busy yourself with your own job function.

You even get government mandated sick leave and annual leave on top of CPF contributions, and most employers also offer a host of perks and benefits. My company even gives us a budget to travel with each year, pay for insurance premiums, or learn just about anything we want.

One of the biggest cons of being an employee is that your day job, well, takes up your days. A 9 to 6 commitment on weekdays is some 45 hours a week without factoring travel time and the occasional overtime hours, and that’s a lot of time that can be used towards other pursuits.

Thankfully, I find my time mostly meaningfully spent during office hours, and my employer is fairly progressive in balancing the need for face time at the workplace and still offering the flexibility of remote working.

Ultimately, a business hires someone usually because they can derive revenues a few multiples of what they are paying the person. As someone who does not assume the risk like the business does, you’d never get the lion’s share of the profits, and you need to be okay with that as an employee.


Finally, we have the life of a freelancer. Freelancing is like a wild west of careers and you can do anything you want, even if it’s something as laughable as starting a YouTube channel. You also have to do everything yourself. From the strategy to marketing, to even being the cleaning crew and everything in between, you are the Chief Everything Officer of your trade.

But, with great power comes… great freedom. You can work from anywhere you want, whether that’s a coffee shop, a beach, or your own couch. And you get to choose the projects you work on, so you can pick and choose what you’re passionate about. There’s no leave to be applied and no supervisor to report to, and you can do things at your own pace and comfort level.

The freedom is a double-edged sword too, and for the ill-disciplined, the flexibility to do anything you want might just lead to that – you would just do things that you want to do and overlook uninteresting but important work. Creating and sending invoices, for some reason, is the bane of my freelancing life, and I can’t be the other one who always procrastinates on sending invoices and chasing for payment.

It’s made worse considering how the biggest downside of freelancing is the unpredictability of income. You never know when you’re going to get your next paycheck, which can be a real stressor. Clients could take forever to pay you, or your business may just not be great despite your efforts. I’ve had a great January to start 2023 with, but February is suddenly dead in the water. I’m mostly used to such income irregularity, and it helps to have to make sure there’s enough savings to tide through the lean times.

Let’s not forget about the lack of benefits – you don’t have to apply for leave because you basically don’t have leave. Sick days? Lost income. Holiday? Go for as long as you want since you’re not being paid when you’re not working.

One major downside that isn’t as obvious is that freelancing can get lonely after a while. It turns out that not having colleagues can be a rather demoralising thing because few people can really quite get what you are going through depending on how niche your freelance job is. Who am I to discuss about a credit card referral link not working, or YouTube being finicky with its view counts? Having people to commiserate over shared issues is something I find sorely lacking as a freelancer, and sometimes just having someone who gets what you’re going through to rant to makes all the difference.

Jack of all trades

2023 is an exciting year for me as my first full year of juggling all three things. I’ve streamlined my tuition responsibilities to one weekend each week, my site and YouTube channel are growing well, and my full-time job responsibilities are picking up. Each career path has its own unique ups and downs, and I am enjoying the ride so far. Of course, it also helps that each adds to my list of income streams, and I couldn’t be happier making my keep while being productive.

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