The Pro’s and Con’s of Being Your Own Boss

Being your own boss is something we have all dreamed about at least once.

This lifestyle is also often advertised as a way to work from a laptop or a smartphone while you are on the beach or traveling around the world.

But if you have ever been your own boss, you would know that this also has a downside which you must be aware of.

And if you cannot dedicate yourself to being your own boss, you will not be able to keep up with it.

You just have to have the right personality and mindset to be your own boss.

If you are wondering if being your own boss is the right thing for you and if you can do it – you are in the right place!

Down below, you will learn both the good and the bad of being your own boss so you can be the judge.

How do You Become Your Own Boss?


First of all, if you are not sure how to become one, you are wondering how does someone become their own boss?

Do you need to open your own business or have a million-dollar business idea? While this can help you eventually, it is not necessarily needed to become your own boss.

Instead, you can start freelancing your skills and work with clients to be your own boss.

You can create your own online business from scratch and be the only person responsible for the success of this start-up.

You can even be your own boss as a part of a company that gives you the freedom to work at your own pace but within the deadline.

There are hundreds of diverse ways to become your own boss and while being self-employed is one of them, as long as you are working on an asset that will provide you an income stream where you are fully responsible for it, you can consider being your own boss.

Benefits of Being Your Own Boss

Now, let us get to the good stuff. What does it feel like being your own boss and what are the benefits? What does it feel like being your own boss and what are the benefits?


Of course, the biggest benefit of being your own boss is being able to focus on the most important business tasks where you get to delegate and even outsource time-consuming tasks to others.

Also, being your own boss can often give you the advantage of setting your own working hours, or even the ability to work from home.

Oftentimes, since you will most likely be in charge of important aspects of work and business, and also have greater control, this can also result in higher motivation and morale.

Since you are the sole responsible for important tasks and business operations, you will have greater satisfaction accomplishing things by yourself.

All of this is something that might work for one person and yet might not for another person. Therefore, while the advantages are often overly advertised, being your own boss might not be a great fit for everyone.

But do not get me wrong. At the highs, being your own boss can feel incredible.

Being able to sleep in, set your own schedule, set your own to-do list that you will work on for the day, take longer breaks, be able to network with like-minded individuals, outsource time-consuming work, and even take a day off when you feel like it – all these are just a few of the best rewards of working for yourself.

However, as many rewards as there are, there are also things to watch out for, things that some people might consider a downside or a risk.

The Downside of Being Your Own Boss


The main downside of being your own boss is the huge responsibility that comes with the role. On top of that, you might have a challenging time separating your business hours from your personal life.

At times, you might not have anyone to guide you or at least tell you when you are making an unwise decision.

Depending on your mindset and your personality, working for yourself can oftentimes give you too much freedom that it can actually make you procrastinate and even do less work than you would actually do in a day.

On top of that, if you are solely responsible for your income, you might not have a steady income at all and that is something you would need to get used to. It is also something that many people cannot get used to.

And if you are collaborating with clients, being accessible at all hours might need to be possible for your clients.

Even though you might be your own boss, at times, you might have to wear many hats and do many tasks, including anything from your own marketing, finances, to the work itself.

The financial risk might be present at all times (even when your business is doing really well), and stress and health issues can only follow.

Time commitment is another downside that might not be a downside for everyone, but as I have mentioned earlier, being your own boss definitely requires a certain personality type.

While some people might deal with all of these “downsides” easily, others might find them terrifying up to the point where they would not even try it.

Just like with everything in life, which is completely normal. Not everyone could be a boss, and not everyone could do a regular 9-5 job.

Depending on the type of work you do and all the other circumstances, these downsides might differ, but these are a few the most common ones you should be aware of.

Finding the Right Balance Between Life and Work

Even though you can set your own hours and work your own shifts, the other end of this advantage is the downside of not being able to “turn off” your work at certain times.


It can happen that after a successful and productive day at work where you feel pleased about the results you have achieved; you might feel like you do not want to stop and yet that there is more work you would like to do in that day.

Of course, not everyone might feel this way, but not being able to find the right balance between life and work can be is often the most common issue you can come across.

Setting work hours is not enough at times and instead, setting offline hours when you are not reachable or where you spend time doing a specific thing such as spending time with family is necessary.

There are several ways to achieve this and while some people might not feel this way.

It all comes down to the time commitment you think is good enough for being your own boss but also the time you would like to have for entertainment, friends, and family.

Tips to Get Better at Being Your Own Boss

There’ll always be work to do and there’ll always be something you can do better.


However, being able to get the work done, have a healthy life-work balance, and not feeling like you want to quit and go back to your old job is a victory in itself.

But you might feel like there’s always room for improvement and in a great deal of situations, improvements can be a good thing.

So, if you are ready to be a better boss, what do you do to improve?

It all starts with your office space. Whether you work from home or in the office, you need to have your own office space you will love heading to.

Before even getting down to the work, you should clearly state your goals and even write them down, so you know what you are working towards.

Committing to a better work-life balance can also be a healthy change.

There’s a difference between spending a lot of time at work versus spending enough time at work – and if you are on the latter end of it, you will feel as productive, and yet you’ll have a lot more free time for yourself.

Listening to others is crucial when you are being your own boss.

Since you might not have anyone to guide you or advise you, listening to feedback even if it is coming from your customers can help your business.

And of course, acting after listening to the feedback and combining it with technology to help you take care of the most important work in an organized manner is super important.

It all comes down to the way you do your work, how you get the work done, and how happy you are with your current work state.


Being your own boss can definitely be impressive. And even though it is oftentimes advertised as an overly positive situation you can be in – there are always two sides to the story.

While being a boss might not be a great suit for everyone, it is definitely something most people feel very natural about.

No one can guess the outcome, so it is best to just dive right into it to experience it. It is also best to figure things as you progress instead of overthinking everything at the beginning.

Did you ever consider being your own boss? What attracts you to it but also, what scares you about it?


I would like to hear your thoughts about being your own boss.  Share them below and I will be happy to respond.

All the best,


Founder/Creator:  Living On Lean Means ?

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