being your own boss

Hard Truths About Being Your Own Boss

Social media has finally convinced you to ditch the 9-5 life, chase your dreams, and strike out on your own. You want to launch that product you’ve always been passionate about, open a food business, or become a full-time Youtuber. 

But before you fall for the glamorized promise of entrepreneurship, know that the media is only showing you the tip of the iceberg. Want to be your own boss? Make sure you can come to terms with these hard truths. 

Freedom isn’t guaranteed

Our media today is infiltrated with messages that venerate business tycoons and make them the ultimate standard definition for success. In return, everyone feels pressured to quit their day job, become their own boss, and follow the footsteps of Elon Musk and Jeff Bezos.

While there’s no intention of ruining the entrepreneurial spirit here, there is however a necessity to reveal the truth of the matter: Being an entrepreneur does not guarantee absolute freedom, autonomy, and independence. In fact, it might just be the opposite. You might be surprised to find out that becoming an entrepreneur means wearing different hats, working longer hours, getting less sleep, and taking in a lot more pressure. 

The reality is that entrepreneurship is not for everyone. Having the drive to success and visionary artistic talent is just one element in being a successful business owner. While the media today only shows the end product of becoming your own boss, you’ll have to be more interested in the process which is key to becoming a successful entrepreneur. 

Some of the different hats you have to wear

So, before quitting your day job, get to know these few things that you’ll need to do on a daily basis if you become an entrepreneur. If you’re starting out as a solo entrepreneur, which will likely be the case, be ready to take on these roles yourself. 


Say you finally want to bring that amazing recipe that’s been passed from different generations into life. You want to start your own restaurant. Once you start moving forward, you’ll realize that now, you’re not just the cook- you’re also your own accountant. 

As your own accountant, you will have to be hands-on with your own business’ financial records. You might find yourself having to learn a few accounting tools to track your income, costs, quarterly taxes, and payroll. And, you may hire an external accountant once a year to audit your work.

No matter what kind of business you may have, cash is the lifeblood that will keep it alive. No matter how good your product is, or how much it appeals to your target market, mismanaged revenue and expenses will be the bane of your business’s existence.

Human resources

You will also have to be your own company’s head of human resources. This means that you first and foremost be in charge of hiring people into your team, spending months training them, figuring out their payroll, and securing benefits.

Even if you don’t have a staff, guess what? You have yourself. Yes, that’s right. That means securing your own health insurance, figuring out a retirement plan, and making your own individual tax return that you used to split with your employer. As your own head of HR, you’re responsible for keeping yourself motivated while having an irregular income.

Eventually, as your business grows, you’ll have to find the right employees. Many successful entrepreneurs credit their success to having the most intelligent and talented people in their team. But these aren’t usually enough. You will have to constantly keep your team happy and motivated to retain them. 


The next role that you will have to take is an enormous one – being your own marketing department. Marketing is a complicated and multi-layered subject that involves various activities relating to customer psychology, audience statistics, and art. Attracting your potential customers is an extensive duty.

You will have to constantly conduct marketing research, manage a website and social media, design and test advertising campaigns, and curate promotional materials.

If you have the resources to hire a marketing specialist, you can do so. However, many startup businesses may find it strategic to figure it out themselves first before allowing other people to decide on marketing strategies.

One important thing about marketing is that it is a constant job. No matter how big a hit your products or services are, you will always have to keep reminding people about it. You will always have to stay relevant among your target audience so they will always choose you among a very saturated market. You will always need to find the right marketing strategies to gain a competitive advantage.


So your marketing efforts have worked and you’ve attracted plenty of customers. Now what? It’s time for your head of sales to work it out with your customers, communicate with them, and seal the deal. News flash: that’s still you. 

All of the previous efforts you’ve made are to get yourself into the end of closing a sale. However, marketing and sales go hand in hand. If marketing serves as your public image, sales are the personal relationship you make with your customers. 

And no, being a salesperson isn’t an inborn talent. It comes by having the right experience of honing and practicing the right skills to sell your product. This means having good active listening and communicating skills so you can network effectively with a bunch of strangers who can be potential partners or customers. 

You will also have to create strategic steps to gain initial interest from customers and nurture that interest all the way to the sale and beyond. As your own salesperson, you will also have to develop the skill of knowing how to successfully move forward after rejection without taking it personally. 

Don’t forget customer service, logistics or legal compliance …

We hate to break it to you but this isn’t where it all ends. Numerous other hats await that deal with other areas of your business such as customer service, logistics, and legal matters- to name a few.

In reality, being your own boss doesn’t guarantee absolute freedom, long hours of free time, and independence from arduous tasks that you used to do at work.

Social media can be filled with messages that only show the final output, but don’t show the many years of hard work, failures, and sleepless nights.

It’s not for everybody and that’s okay

If these roles don’t seem like something you want to do- that’s totally okay. Being your own boss isn’t the only indicator of success. Having a fulfilling regular job doesn’t make you any less than others who do it differently. 

With all that said, while being your boss isn’t for everyone, it can definitely be for you too. All these hats will eventually make sense together given enough time, experience, fortitude, and patience. If you think being an entrepreneur is the right track for you, all these roles shouldn’t stop you from doing so. The right entrepreneurs will always be ready to face whatever adversities that come their way – no matter how big or scary they seem to be. 

If you choose to go down this path – good luck and may the universe bless you with the determination to conquer the hurdles that come with it! If you’re settling with a 9-5, as long as you’re fulfilled and happy, you should be just fine!

Read More: How To Start An Online Freelancing Business

This article was first published in August 2021 and has been updated for freshness, accuracy and comprehensiveness.

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