10 Things You Might Hate About Working for Yourself

10 Things You Might Hate About Working for Yourself

You have it all figured out. You will submit your resignation letter tomorrow and serve the three-month notice as per your contract. Once you’re free, you will take a month off to rejuvenate your mind, body and soul before throwing yourself head on into your business plan.

You know it’s going to be difficult, but you’ve scrimped and saved a year’s worth of financial reserve and you’re sure that your passion will pull you through the hard times. Working for yourself can’t be much worse than what you’re currently doing…

Can it?


Everyone knows what they hate about their current job. But very few people stop to consider what they might hate about being their own boss. Even if they want to, it’s not an insight that presents itself easily. As a person who has personally experienced this for close to two years, I hope this article will help you make a more informed decision, be it to stay or to leave.


1. You might learn to resent the very thing you’re passionate about


I’ve always loved to draw and I think I’m quite decent at it. When I was still a part of the corporate world, my colleagues would say, “Why are you working in a bank again? You should be an artist!”

After quitting my job, I had what I thought was a pretty logical and solid plan of action which fell to pieces within a mere two months. As I retreated to patch up my wounded self-esteem, I decided to take on some commission work. The money, I reasoned, would make me feel a bit better about myself.

The essence of ‘work’ basically is to trade a product or expertise in exchange for income. In a trade, you must have what your customers want. Since you need to produce results based on their specifications, you might not always like what they ask for and they are most certainly not obliged to like what you do just because you’ve put a lot of hard work into it.

I resented the requests made by my clients to draw a variety of things that I couldn’t care less about. Not only did the money not make me feel better, it killed me a little inside when I had to deliver something not befitting my style. I was also inexperienced and didn’t know where to draw the line and when to actually say no to a customer.

Throughout that painful period, I could feel the resentment bubbling up every time I had to pick up my drawing tools. Like a relationship, a passion is something that needs to be protected. After that ordeal, I vowed to never draw in exchange for money ever again in an effort to preserve my love and passion for drawing.

From this experience, I discovered that there is a difference between ‘passion’ and ‘strength’.

Passion denotes powerful emotional investment. You love doing something so much because it gives you a lot of pleasure, regardless of whether you’re good at it or not.

Strength on the other hand is something that you are good at doing, regardless of whether you like it or not. Unlike passion, your strength is an objective fact.

If you think starting a business based on your passion is a good idea, you need to really sit down and think about whether this passion of yours has ever been subjected to the pressures of differing expectations. Doing something when you feel like it is very different from doing something because someone is paying you money for it. If you expect to earn money with your passion, you must be prepared to bring many strangers into your personal space and opening yourself up to criticism. For me, drawing is an act of refuge, a deeply private space. It explains why I got so emotional when people started asking me to change this or that about my art.

While your strength and passion can be the same thing, the more emotionally invested you are in your work, the less suitable it is for trade, especially if money is your main concern. I say this because love cannot be measured by money. When someone wants to buy something you love, how can you put a price tag to it?

Luckily, I found out that my interest in writing is not charged with the same emotional investment I have for drawing. For this reason, I can safely say that writing is the right way to go for me.


2. You need to chart your own path


The fantastic appeal of corporate life is that your potential paths into the future are well-trodden. If you’re not sure where to go, there are plenty of people you can seek advice from.

When you leave the system and try to make it on your own, the trail is covered in absolute darkness. You have to clear your own path based solely on what you think you can offer the world. Mentors and friends in uncharted waters are hard-earned. Even in the age of internet, being inundated with an excess of information is not much better than knowing nothing at all.

For example, I now know that writing, not drawing, is the way to go professionally.

But what kind of writer should I be? I could be a reporter working for the newspaper, a columnist for a magazine, a freelancing travel writer, technical writer, analyst, novelist, ghost writer, blogger. The list is endless. Each of them requires different working styles and offers different working conditions. And then there’s the matter of topic. Should I write about travel? Or food? Photography? Art? Real estate? Finance? Even within finance, there is personal finance and business finance. You can break it down into so many small parts that it can be hard to decide what to focus on.

If you have not yet put in the work to really know yourself as a person and to discover what your preferences and motivations are, it might take some time to determine this.

Whatever your dreams may be, the best thing you can do for yourself is to really dissect every detail of that image you have in your mind and always connect it to reality. If you want to open a restaurant in the posh part of town, can you afford the rent and for how long? What kind of food will you be serving and what is your competitive advantage over your competitors? How will you train your workers and what are the health regulations you have to adhere to? And above all, whatever you have to sell, who will buy them? Can their demand help you break even, at least? Is one year of financial reserve really enough time to get your restaurant to be a profit-making venture?

You have to be willing to put in the work to know yourself better than anyone else. It seems an easy task, but we are often an enigma to ourselves. Only when you understand your deepest motivations and preferences can you make tough calls on where you life should be headed.


3. You have to downgrade your lifestyle if you want more time to make it work


Unless you’re a Zen Master, you would probably have fallen into the trap of upgrading your lifestyle every time you get a pay raise. Following this logic, when you quit your job, you no longer have any income. Therefore your lifestyle should reflect this. This way, whatever money you have stowed away to support your previously expensive habits can be used to sustain the income-less you longer.

What kind of downgrade am I talking about?

I’m talking selling your expensive car and buying a cheap, working second hand one you can pay for cash. I’m talking selling your nice house or renting it out (whichever more profitable) while you move out to a cheaper accommodation. There will be no more eating out in air-conditioned restaurants in favour of cooking. No more phone upgrades and expensive plans, no more gym membership and no more jet-setting to exotic locations. Holidaying is expensive business.

My magic mantra is to keep cost low. While the future of my self-chosen career might be shrouded in thick, grey fog, my penniless future is quite clear. It means I have to go back to the corporate world and beg for a job after being away for much longer than they are willing to accept. And if I do get that job, I’d probably be working for people ten years younger than me.

If there’s one thing you have to constantly do, it is sacrificing whims and fancy and every instant gratification you encounter in the now in order to give your self-chosen future a fighting chance.


4. You have to motivate yourself


This sounds easy in theory. But the reason companies have bosses is not to make your life miserable. A boss serves as a tool to keep pushing you to deliver results even on days when you’re feeling like crap. A boss is not there to be your friend. They are there to make sure you are at least as productive as how much they are paying you.

When you work for yourself (flexible work time whoooo), it might seem like a good idea to wake up at 11am, ease yourself into the day and slowly get into the groove after having brunch and reading up nonsense articles on Facebook.

But let me tell you this: If you let yourself slip on days you feel lazy, you will feel like the most useless human being in the world. You will hate yourself and there’s a very real spiral of self-loathing that you might not be able to come out of.

I found myself in this position several times over the past two years. At one point, it was so bad that I pushed my family and friends away and kept myself isolated. But I am also lucky to have a very good friend who kept poking her nose into my affairs (even after pushing her away) and trying to include me in a lot of activities. If not because of her, who knows?

The hardest thing about self-motivation, especially if you do not have a detailed plan on how your day, week and month should go is to convince yourself that this deadline needs to be adhered to. When you set a goal, you need to take yourself seriously enough to meet it.

Sometimes it feels stupid to say no to tempting invitations from family and friends in order to meet a self-imposed deadline. You start thinking, “I am the one who set this deadline, surely I can give myself permission to push it forward a bit?”

You do it at a cost to yourself. If you let yourself go, the loser will always be you. Being your own boss doesn’t only mean calling the shots. It means being stern to yourself and making tough choices like saying no to having lunch with your favourite ex-colleagues. If you’ve ever wondered why your boss seemed like he wanted to strangle you, you will get a taste of your own medicine when you work for yourself. At times, I do feel like strangling myself.


5. You will be cut off from your social network


Until you quit your job, you will have absolutely no idea how much you take your social circles for granted. They are small things like walking through the door and saying ‘Good Morning’ to your colleagues, the smiles and polite nods you exchange with the tea lady and everyone you pass along the corridor and the quick remark you share with your cubicle mates when you see something funny happening.

These will be one of the many vacuums you will experience once you start working for yourself. Unless your job requires you to assemble a team and working with them closely (and even then, being a boss is still a very lonely job because you cannot get too familiar with your workers lest they don’t take you seriously), loneliness will be your new friend. When in the past you’ve always had several people to go on a quick lunch with, now you have to make the effort to call or message them and ask if you could still join them for lunch.

As for me, I grew up accustomed to loneliness. It just means that what would usually take a person one week to start feeling lonely, it would take me roughly three months before I would look up from my work and say, “Hey, it’s kind of quiet here, isn’t it?” to no one in particular.

By that time, perhaps some relationships are not so close anymore. And when you do meet up with your ex-colleagues, they will be very interested in what you’ve been up to. If you’re still struggling to find your north star, it’s not a pleasant conversation to have.

Another aspect of loneliness I would like to bring up is the fact that a majority of people you know will not be able to understand what you’re doing. If you meet up with enough people, you will start feeling very tired as they ask multiple questions to try to understand why you would leave a comfortable job to pursue what seems like nothing. They try to determine if you’re either crazy or just another typical Gen Y pursuing a silly dream.

This also goes the other way round. If you go out with a group, they might start talking about work and you realise that while you used to care about these things, now it just sounds like meaningless chatter. Budget time is crazy? Yeah… New regulation on reporting? Meh… New person employed to replace you did something funny? Mkay…

If you are sure you want to work for yourself, I suggest finding your own crowd before you leave. Join Facebook groups of self-employed people. Join clubs or social gatherings for fellow artists. Get to know them and find your new co-worker friends.

Never underestimate the damage loneliness can do to you. Humans are highly social creatures and as such will thrive in a community and wilt without.


6. You have to find your own work space that doesn’t burn a hole in your pocket


Another huge thing about the corporate world that we fail to appreciate until it’s gone is working space. I define a working space as a place where you have the basic amenities to set up your laptop, books and stationeries and can work without interruption. It also has to be a place where you feel safe leaving your laptop for five minutes as you quickly relieve yourself of your morning coffee in the toilet.

One option is to redesign one of the rooms in your house to be an office.

The problem with my home office is that my bed is only a few feet away in a different room. On days that I give in to sleepiness and fatigue, hours of my work day can disappear into thin air just like that.

My house is also designed in such a way that when I walk into the living room (on the way to the kitchen to get more coffee), I will immediately feel like settling into the soft cushy sofa and fall asleep under the rhythmic creaks of the ceiling fan while the soft yellow lamp by the table will permeate my dreams like warm honey.

Another problem with working from home that I gathered from fellow self-employed friends is your family members might think that since you’re ‘at home doing nothing’, you might as well help out with house chores more often like mowing the lawn, getting the groceries, cooking, minding the children, doing laundry and washing the dishes. Before you know it, the house chores will occupy your time and mind so much that you cannot focus on work.

Unless you can set really strict rules for yourself and your family members and actually adhere to them, you can’t get anything done at home. Home is where the mind unravels itself into a useless lump of an organ.

The only other solution to this is to obviously work outside. But where?

You either have to rent an office which is pricey or if your work involves just a laptop and your brains, a nice café would suffice. But sitting in a café means paying for expensive drinks in exchange for a comfortable working space. RM15 every day (if you can hold back from buying their food) for 22 days translates to RM330 a month. This does not include parking for your car, or the LRT fare to get there.

And during lunchtime, will you spend money buying expensive lunch from the café or will you prepare your own food? If you have to leave to eat your food, you might have to pay for another drink when you come back.

I have been known to starve myself for 10 hours straight to make my RM15 drink worth my money.

Under normal circumstances, I would never spend RM15 on a drink for the sake of the drink. But in this case, I consider it as the price I pay for parking my butt there from morning till evening and finishing my work in peace.

This is the kind of cost you have to take into account when you no longer work in a corporate setting. The fuel money you saved from not being in peak hour traffic will now go to buying all the things that your old company used to buy for you.


7. Any attempt at self-improvement will be at your own personal cost


As you try to juggle the different tasks of marketing yourself, producing results, following up on a potential client, doing research and filing for taxes, you thought, “Perhaps what I need is a course on effective time management.” Guess who has to pay for that? You.

Or if you’re a photographer and you realise that you need a RM10,000 lense to minimise the problem of lense distortion in your pictures. Or if you’re a travel writer and you need to pay for your own flight tickets and hotels so you would have some extra material to talk about.

A sugar daddy would sound pretty attractive at this point. You seriously start questioning the merits of a pretty face and six packs. Who needs a good looking man when this fat, bald, old man has money to pay for a new laptop because your old one just broke down?

In all seriousness though, self-improvement is the key to moving forward. No matter what, you cannot afford to stop investing in yourself. If you can find a way to improve your knowledge and conduct for free, I congratulate you. If not, do not be afraid to spend money for knowledge. I can be a complete miser in a lot of things, but I never scrimp on books. It is how I enrich myself in order to keep coming up with posts to write about. When all things are said and done, your only true asset is yourself. Not your car, not your nice clothes and definitely not your cats, no matter how adorable they are (unless your cat is Maru. Maru is definitely an asset).


8. The people who love you the most will be very, very angry with you


The more someone loves you, the more invested they are in your future security. When they see you taking a step in an unconventional direction for reasons as vague as ‘pursuit of meaning and happiness’, they instinctively respond with a subtle ‘ARE YOU STUPID OR ARE YOU CRAZY’?

I had a huge fight with my dad. My brother went silent on me for months. My friends told me what I’m doing isn’t really working.

They are greatly disheartening and emotionally powerful enough to knock the wind out of you. Who else has the power to reduce you to tears if not your closest relatives and friends? One well-placed word can stay on your mind for months. And they could be right. Maybe you could be crazy and stupid at the same time.

But once you are resolved to do something, you must not let self-doubt get in the way. I know this is easier said than done, but in the end, you will be the one living your own life, not them. Do it on your terms. Hug your loved ones and tell them, “I love you, but for the love of God please back off. See you this weekend for the potluck. I’ll bring KFC because I can’t be arsed to cook.”


9. You will be plagued with severe bouts of self-doubt


Who the hell do I think I am? What can someone like me possibly offer to someone else that they would pay for it? What if I never get paid? They will laugh at me. They will think I’m stupid. They will think I’m a silly person with a head full of dreams and fluff and when I come crashing down, they will say ‘I told you so’. I’m just a stupid, stupid person who didn’t know what I got myself into. How can I be so stupid?

Some days you wake up confident and energetic and ready to take on the world.

Some days you will doubt yourself so much that you’re convinced you’ve made the wrongest life decision ever (but not wrong enough to go back to corporate world).

On a day like this, I suggest doing something kind for someone. It sounds clichéd but nothing lifts your spirits up as much as feeling needed and appreciated. Go pick up some rubbish along the road. Water the plants and pull out some weed. Kill that little voice talking down to you by doing mundane manual labour. When a stranger looks at you with appreciation, you can assure yourself that at least for today, you made someone’s day a little better.


10. You will not have a stable income, if not at all


Sometimes, this fact does not really sink in until the very end of the first month of your unemployment.

This is a short point because I want you to stare at this sentence until you can feel the oppressive weight of the reality:

There will be no money in your account at the end of the month.

For some people, the very mention of ‘no stable income’ sends a shiver up and down their spine. If the thought scares you so much until you cannot sleep, then you shouldn’t quit your job. Keep working, keep saving and keep investing. When you retire, don’t give your money to your kids and enjoy the fruits of your labour. The brats can work for it themselves.



Having seen both sides of the coin, I want people to understand that one is not better than the other. They are simply different. If you feel comfortable working for a company, do not feel pressured to leave and ‘pursue meaning’ just because so many people call themselves startup founders nowadays. You are not unimaginative or uncourageous or unpassionate just because you choose to stay in a 9-5 job.

The corporate world is a popular choice because it does have plenty of merits. The company provides everything for you – a motivating force (the boss), constant pay, opportunity for growth, mission and value statement, a conducive place to work, insurance, health benefits, a well-trodden path into the future, intelligent, like-minded colleagues, education, mentors. All you have to do is bring yourself and your willingness to take everything the company has to offer in exchange for your time and efforts. While you work, you get better every day.


If after reading all the above, you still want to work for yourself, there is still much work to be done on the introspection side. Next Wednesday, I will talk about the practical steps I used to figure out what I really want to do in life.


Leave a Reply

Your email address will not be published. Required fields are marked *