My Self-Employed Journey – Part 2: Honest Pros and Cons of Self-Employment

Before taking the leap of faith to go into self-employment, I would ferociously google various topics about solopreneurship and running small businesses.

One of the topics I found myself googling over and over again is the pros and cons of self-employment. Because I want to know what it looks like being self-employed.

There is no one in my inner circle of friends who are going through this path, that I could ask for advice. So, I learned it the hard way.

(Looking back, I could’ve joined some co-working places and network with strangers. But I didn’t want to spend extra money on things that don’t immediately generate income.)

Anyway, here is an honest list of pros and cons of self-employment, that I learned from my own experience working on a small online business as a solopreneur. It may be different for other self-employed people in other fields, such as teaching, real estate, financial consultancy or gig economy.


Pro: No income ceiling

No income ceiling is obviously everyone’s dream. What you earn is not limited to your fixed monthly salary. The more you put effort in it, the more you’ll earn. The sky is the limit.

Just because there’s no income ceiling, it doesn’t mean you will be guaranteed to earn more than your previous salary. It takes time to master your craft. It takes time for people to know your name. And it takes longer time for people to feel comfortable paying you what you’re worth.

Con: Irregular income

Your income will be irregular. Sometimes you have a windfall. Other times, you will have mishaps and lost some fortunes. You can’t plan the windfall, and you can’t escape the mishaps. Hence, you need a buffer. A LOT of buffer.

For me, I have a budget that helps me cushion income volatility. I’ll write about this more in a future post.


Con: No CPF contribution

Ever since I started full-timing in my small business, my CPF amount stays pretty flat every month, because I’ve not voluntarily contributed any CPF apart from the compulsory Medisave contribution and housing refund.

Some people may see no CPF contribution as a blessing because cash is king when you’re self-employed. I completely agree, that’s why I haven’t made any voluntary contribution.

It’s just that I miss the employer’s CPF contribution :’)

Pro: Flexible working schedule and location

When working in corporate, I often daydreamed about flexible working schedule and location. You can sleep until however long you want. And you can travel anywhere you want; you don’t need to apply leave and worried about your boss not approving it. I imagined that I’ll have the flexibility to work in chic cafes or in hotels when I travel.

The verdict? Well, I love being able to sleep in everyday, and sip my coffee slowly in the morning, in the comfort of my pajamas. And I love not having to commute to somewhere to work, I just work from home (save time, save money).

But, I do not bring my laptop when I travel now, because laptop is heavy and I want to spend my time traveling, not looking at laptop!


Con: Time management is hard

Especially when no one is watching over you. Sometimes you work 12-14 hours a day, sometimes watch YouTube all day long.

Sometimes, your family members want to keep talking to you or ask you to do chores because they see that you’re at home and available!

Right now, I’m in a DINK family nucleus. I can’t imagine if our family is expanding and I’ll need to spend an exorbitant time caring for the new family member.

Con: You become workaholic

This becomes your mentality: if you work less, you will earn less. Therefore, most of the time, you will push yourself to work as much as possible. You become a workaholic.

And you become overprotective with your time, you spend less time with your family and friends because time spent not working is a loss of income opportunity.


Pro: No bosses to report to, no office politics

I do not have any issues working with all my previous bosses. But I do have issues with office politics, and I’m so glad I don’t have to deal with it anymore.

Con: No corporate benefits

This is absolutely a bummer. No paid sick leave, I now have to pay out of my own pocket to see doctor. When I got covid, I shelled out 90 freaking bucks just to get tested and to get a couple of medicines.

No employer’s CPF contribution as mentioned in one of the sections above.

No free CNY dinner or company D&D.

No BONUS!!! Gone are the days when you get extra money just because the company is doing well. Now, every single dollar you receive is hard-earned.


Con: You need to motivate yourself and be accountable to yourself

Sometimes (well, A LOT of time), you get burned out and you question why you haven’t succeeded yet. Then you get demotivated and spend days watching YouTube. Then you complain that time management is hard.

Then you get a sudden burst of motivation and you work like crazy because you’ve wasted so many days not working. It’s a cycle that repeats itself, and you need to push through this challenge to stay in the business.

You need to find ways to motivate yourself to get up after every burnout. No boss or colleagues will motivate you, you’re on your own.

You have to fulfil your work for your client regardless whether you’re in a motivated state or a burnout state. You must hold yourself accountable. You have to stop being a baby and start taking responsibility.


Pro: You have full control over your business

You are your own boss, you get to make all the calls. You decide which way your business is going towards, you choose your own goals and deadlines.

Con: You need to do 8856247692 things yourself

Being a solopreneur, that means you have to do everything yourself. From admin tasks, finance tasks, marketing tasks, sales tasks, field tasks to CEO tasks.

Website crashed? You need to investigate what’s wrong, and decide whether you can fix it or you need to contact the relevant person to fix it. Need field data/information? You need to get down to the field to collect it.

Got a new client? You need to negotiate the contract and deliverables. Client not paying? You need to send multiple follow-up emails. Client sent you money? You need to check whether the amount is correct.

Website traffic down? You need to find out whether it’s due to seasonality, google algo update, growing competition, seo attack, technical issues, or global issues. Website traffic up? You need to investigate whether it’s bot or real traffic, whether your article meet the audience’s intent or not, whether you can expand/replicate it, and so on.

People copying your article and paraphrasing it, or stealing your images? You need to decide whether it’s worth going through the legal route, or let them go.

Income goes down? You need to figure out if it’s something you can fix, or it’s something out of your control; fix it if you can, let it go if you can’t. Need more income? You need to learn new strategies, implement then and monitor them. And so on…


Con: You’re consistently thinking about business, it’s hard to switch off

No single day passes without you thinking about your business. You’re constantly thinking about how to optimize & improve your income.

Con: May be difficult to get credit cards

Since being a full-time self-employed person, I’ve only applied for 3 credit cards, two of them got approved and one got rejected. I guess I have to embrace the new normal where I can’t get credit cards as easily as in the past when I was still an employed person.

Con: It is a lonely journey

I don’t have close friends who are also entrepreneur/creator. I don’t have anyone else to talk face-to-face about business strategies except my spouse. So, I turned to Facebook groups. I joined various groups and exchange ideas with strangers who I’ve never met and will probably never meet.

Loneliness is a price to pay for taking the off-the-beaten path.


Pro: It’s a rewarding journey

Despite the occasional loneliness, the frequent burnout, the black swan events (like covid) and the many challenges along the way, entrepreneurship is a truly rewarding journey for me.

I learned to push through unimaginable roadblocks. I learned to persevere for 7 years until my business makes enough money for me to work on it full time. I learned to pivot and diversify when Covid decimated my income (thanks Covid).

I learned to value my work and refused to work for free or for a low fee. I learned to talk on the camera even though I was scared shitless and my spoken English could barely make it. I braved myself to pitch potential partners even though I didn’t have any prior pitching experience.

Final words

If you’re at the crossroad in life where you’re contemplating whether to take the leap of faith into self-employment, and you need motivating words, here are some that I believe in.

Life happens outside your comfort zone. Entrepreneurship is a great way to get yourself out of the comfort zone and to discover your true potential.

Don’t be afraid of challenges. You can’t escape it; the only way is through.


If you find this post helpful, feel free to buy me a coffee :)

This Post Has 2 Comments

  1. KC

    You determine the corporate benefits yourself. For example, I opened a pte limited and charge health screening, secret lab purchase, laptop purchase, whatever purchase to my company account to save tax

    1. prudentdreamer

      Hi KC, currently I’m still on sole-prop. Sole-prop can’t deduct owner’s medical cost, so Pte Ltd is definitely a great way to deduct certain expenses which are not allowed in sole-prop. Thanks for your advice, I’ll definitely upgrade to Pte Ltd in a couple of years!

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