Working for Yourself: What Being Your Own Boss Is Really Like

When I first started my self-employed journey, people around me had a lot of assumptions about what being your own boss looked like.

“Wah, you must be very free hor.”

“You must be earning a lot now.”

“You can work anytime, anywhere. So shiok sia.”

To be honest, before I started working for myself, I used to think the same thing about other business owners too.

I imagined freedom, flexibility and having complete control over my time and income. I thought being your own boss meant waking up whenever you wanted, choosing your own working hours and enjoying life on your own terms.

And while some of that is true, there is another side to self-employment that people don't always see. Being your own boss gives you freedom, but it also means carrying a lot more responsibility on your own shoulders.

After going through it myself, I've realized that working for yourself requires a completely different level of discipline, commitment and self-management than I expected.

What Does Being Your Own Boss Actually Mean?

Being your own boss means you have more control over how, when and where you work. You decide what projects to take on, who you want to work with, what direction you want your business to go in and how you structure your day.

That flexibility is one of the biggest benefits of being self-employed.

But having no boss doesn't mean having no one to answer to. You still have clients waiting for you to deliver what you promised. You still have deadlines to meet. You still have bills to pay. And when something goes wrong, you're usually the one who has to sort it out.

When you're employed, a lot of the structure and SOPs are already there. You have working hours, responsibilities, deadlines, processes, colleagues and someone to report to.

When you're self-employed, you have to create that structure yourself. Nobody is going to remind you to follow up with a potential client. Nobody is going to ask why you haven't worked on your own marketing. Nobody is going to check whether you're actually getting anything done.

You're the person doing the work, and you're also the person responsible for making sure the work gets done.

The Freedom of Being Your Own Boss

One of the biggest reasons people want to work for themselves is freedom.

And they're not wrong.

Being self-employed can give you much more flexibility over your schedule. You can choose when and where to work, whether that's from home, from a café or somewhere else entirely. If you need to rearrange your day, you usually have the flexibility to do that.

Yes, you can work anytime, anywhere. But sometimes that turns into working all the time, everywhere. Without clear working hours, it can be surprisingly difficult to know when the workday actually ends.

I've had days where I've closed my laptop but still couldn't stop thinking about work. I would suddenly remember a client I needed to reply to, something I needed to finish or a problem I hadn't solved.

Then there are other things on your mind too.

Where is my next project coming from? What should I be working on next? Am I doing enough?

Sometimes the laptop is closed, but your mind is still at work.

This is especially hard when you work from home because there isn't always a clear separation between work and everything else.

I've had to learn when to stop working too, and I'm still working on that.

What People Don't See About Being Your Own Boss

When people look at a business, they usually see the finished result.

They see the website you launched, the project you completed, the social media post you published or the business slowly growing.

What they don't always see is everything happening behind the scenes. There are nights spent planning, client messages at odd hours and projects that don't go according to plan. Sometimes you also have to learn something new simply because you realize you need to know how to do it.

Then there are the quiet periods when you're wondering where your next client or project will come from. And even when you have plenty of client work, there's always something else to do.

There's marketing, admin, following up with potential clients, updating your website and planning what to work on next.

The work doesn't really run out. You just have to decide what needs to be done now and what can wait.

Being Your Own Boss Requires Self-Discipline

When you work for yourself, no one is there to make sure you stay on track.

You have to manage your own time, decide what needs to be done and actually follow through, even on days when you don't feel like it.

There will also be days when you're tired, distracted or simply don't feel like working. But clients still need replies, deadlines still need to be met and there are things you can't keep putting off.

If you don't do the work, the work doesn't get done.

Having control over your time is great, but you also have to be responsible for how you use it.

You Will Probably Question Yourself Sometimes

There have been times when I've wondered whether I was making the right decision, whether my work was good enough or whether I actually knew what I was doing.

When you work for yourself, you have to make a lot of decisions on your own, and you won't always know if you're heading in the right direction. This can be especially difficult when things don't go according to plan. A potential client says no, a project doesn't turn out the way you expected or work gets quiet for a while. It's easy for one small thing to make you start questioning everything else.

This is also why I think having a right mentor can be helpful, especially when you're starting out. Having someone with more experience to turn to can guide you when you're stuck, keep you accountable and help you see things from a different point of view. You still have to make your own decisions, but you don't have to figure everything out on your own.

I've had moments where I wasn't sure what to do, and I'm sure I'll continue to have them. I've learnt that not having all the answers doesn't mean you're doing something wrong. Sometimes you're dealing with something for the first time, and having the right person to ask can make it much easier to work through.

What Are the Benefits of Being Your Own Boss?

Despite the challenges, there are still plenty of things I enjoy about being my own boss.

I like being able to choose the kind of work I want to take on and the people I want to work with. I also get to decide how I want to run my business instead of having those decisions made for me.

Another thing I appreciate is being able to see what I've built over time. From getting my first client to taking on bigger projects and becoming more confident in the work I do, there are small milestones that remind me how far I've come.

I think that's one of the most rewarding parts of working for myself. There's a different sense of satisfaction when you know that what you have today came from something you started yourself.

What Are the Downsides of Being Your Own Boss?

Of course, there are downsides too.

Your income isn't always predictable. Some months can be busy, while others are much quieter, and there's no guaranteed paycheck waiting for you at the end of the month.

You also don't have some of the benefits that usually come with being employed, such as paid leave. Taking time off can mean not earning during that period, and it can sometimes be difficult to completely switch off when you know there is work waiting for you.

There is also less certainty. A client can decide not to continue, a project can fall through or you might go through a period where new work isn't coming in as quickly as you'd like.

There's no such thing as a perfect working life. Even if you're employed, you'll have your own set of challenges too.

There will always be ups and downs. Like the Chinese saying: "先苦后甜", sometimes you have to go through the hard parts before you get to enjoy the good ones.

Is Being Your Own Boss Worth It?

For me, yes.

There are definitely days when I wonder why I chose this for myself 😂, but there are also many days that remind me why I did.

I enjoy the work that I do and having something that I can call my own. When I look back at where I started and where I am today, I'm glad I gave myself the chance to try.

But whether being your own boss is worth it really depends on the person.

There are challenges whether you choose to work for someone else or work for yourself. When you're employed, you may have more stability, but you also have less control over certain things. When you're self-employed, you may have more flexibility, but you also take on more responsibility.

Neither option is perfect. Both come with things you'll enjoy and things you'll find difficult. What works for one person may not work for another, so it really comes down to what matters more to you and what you're willing to deal with.

At the end of the day, every path comes with its own version of hard. You just have to decide which one you're willing to choose.

Choose your hard.