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The Pros and Cons of Being Your Own Boss

November 8, 2021
By James Gussie

With the advancements of technology, people have become increasingly more eager to start their own business and be their own boss. However, this trend comes with a host of risks that may or not be worth it for individuals who are willing to take the plunge.

The “what are the advantages of being your own boss” is a question that many people ask themselves. The answer to this question can vary, as there are pros and cons to being your own boss.

The half-truth about becoming your own boss is one of the most frequent half-truths in the startup and entrepreneurial world.

I’ve called it a fiction before, but half-truth is preferable since being your own boss has some genuine benefits.

However, there are a number of drawbacks as well.

I’ve spent a lot of time “being my own boss,” including more than ten years as a single proprietor business planning consultant, working with clients on my own; and more than ten years as the founder and owner of a firm, working with staff.

Working to “be my own boss” was never truly why I did what I did in my situation.

Because I wanted to perform the work rather than manage people, I quit a solid position to start consulting on my own. I also started a software business because I thought the product was necessary.

The ability to be your own boss was something that just came with it.

On the fourteenth edition of The Bcast, Bplan’s official podcast, Peter and Jonathan discuss being your own boss: Subscribe to The Bcast on iTunes by clicking here »

Before I begin, a word on one of my favorite start-up books, Melinda Emerson’s “Become Your Own Boss,” which was just updated with a new edition.

I’ve known Melinda for years and have seen her work hard, use common sense, and speak the truth to achieve her great reputation.

However, due of the underlying ambiguity of being one’s own boss (as I’ve informed her), I’ve never been a fan of her book’s title.

However, this is one of the best books about venturing out on your own, and I strongly suggest it. It’s one of the two finest books on the topic, along with Pamela Slim’s “Escape From Cubicle Nation.”

I also presented a segment of a larger lecture on becoming your own employer, which is embedded below. It’s a topic that’s been bothering me for a long time. It’s from my video Startups and Entrepreneurship: Beyond the Cliches. If you’re interested, I’ve included it at the bottom of this post.

Table of Contents

The Benefits of Being Your Own Boss

1. You’re in the driver’s seat. You are the one who makes the choices.

It’s a wonderful feeling to be able to act on hunches, make educated predictions, and simply do it. Take a chance and spend the money.

When it comes to work happiness, we frequently speak about owning the job, and when you’re the boss, you own it. It may be very beneficial to not have to ask anybody.

To me, this is a huge issue. I’m one of those individuals (are you?) who feels safer behind the wheel than in the passenger seat. Especially in the business world.

2. You are in charge of your own schedule.

Perhaps you’re an early riser, or you prefer not to work specific afternoon hours in order to devote yourself to your children’s activities or your own. Perhaps you like to work in bursts.

When you work for yourself, you don’t have to worry about warming a chair for certain hours.

You are now accountable for your production rather than your hours (unless you are a service company with customers, which is covered in the cons section below).

3. You choose your own work style, work atmosphere, and workplace equipment (to the degree that you can afford it).

Some employers are better than others when it comes to technological upgrades, site selection, parking arrangements, and so on.

What is the speed of your internet connection? It’s up to you when you’re the boss.

Do you prefer a standing desk or a regular desk? It is all up to you. Is there a nice vantage point? Is there any good coffee in the kitchen? It’s all up to you.

4. You decide where you want to go.

If you like Klamath Falls, don’t stay in Cleveland.

Stay in Brooklyn instead of taking the inconvenient train ride to Manhattan. Why not meet folks at Starbucks or spend every day there? You’re the one in charge. It’s all up to you.

The disadvantages of becoming your own boss

1. Your consumers are in charge of you. Your employer is your customers.

Throughout my decade and a half as a single entrepreneur advising on business planning with customers, I often found myself up late at night, exhausted, and tasked with completing a presentation due the following day.

I was never able to take the traditional worker’s path, where you either get things done or make an excuse for not doing it. I needed the money and the business, so I wasn’t in control. My customers were the ones in control.

Consumers were in control even later in my career, when I’d established a company selling to thousands of customers every month.

We need to complete the program, test it, and publish it. Our website needs to be kept up to date. We had to fulfill marketing deadlines, product development deadlines, financial deadlines, and everything else.

In a firm, your boss is the company’s health.

2. You are the ruler of your commitments—to suppliers, allies, and business activities.

You can’t keep missing obligations and yet be successful. Your most valuable asset is your word.

Commitments include meetings, deadlines, and pledges. Without them, you can’t truly operate a company.

3. If you have workers, they may act as your boss in certain situations.

You are the leader, and whether you like it or not, leadership is what it is. That is to say, your coworkers are keeping an eye on you.

You can’t expect them to accomplish less than you ask. In so-called corporate (or business) culture, you, as the manager, are arguably the most significant element.

When you leave early, everyone else does as well.

4. You are the one who spends your own money.

Do you notice point three in the pros, where you make equipment, technology, bandwidth, and other decisions?

That’s great, but you’ll have to pay for anything you feel you need. It’s paid for out of your own pocket, not your employer’s.

When circumstances are difficult, you may need an update; but, are you able to afford it?

5. You get what you deserve.

You don’t know what your pay and benefits will be. It all relies on you, your company, your customers, your market, and your product or service.

There is no employer establishing a permanent pay plan for the single entrepreneur, startup founder, or small company owner. There’s no way of knowing how much money you’ll have next month.

Tim Berry’s “Be Your Own Boss” vs. Reality from Tim Berry on Vimeo.

Being your own boss is a big decision, but it can also be an advantage. The “advantage of being an employer” is that you are in control of your work life and the hours you put into it. You decide how much time to spend with family or friends, and when to take vacations.

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Frequently Asked Questions

What are the cons of being your own boss?

A: Its hard to balance the pros and cons of being your own boss, as each one is different for every person.

What is the advantage of being your own boss?

A: The advantage of being your own boss is that when you become independent, then you are able to control your life and dictate how much work or time it takes for yourself. Youre in charge of the amount of hours you put into what matters most to yourself, which often leads to greater success than working an unappealing job.

What are 5 advantages of being your own boss?

A: Being your own boss means you make all of the decisions and take complete control of everything that comes with it. There are many advantages, but some include being able to set your work schedule according to whats best for yourself and enjoying a greater sense of freedom than working for someone else.