The Pros and Cons of Being Your Own Boss

Author: Tim Berry

Tim Berry

Tim Berry

5 min. read

Updated October 25, 2023

One of the more common half-truths of startups and entrepreneurship is the one about being your own boss.

I’ve called it a myth before, but half-truth is better because there are some real positives with being your own boss.

But naturally, there are a number of negatives, too.

I’ve spent a lot of years theoretically “being my own boss,” including more than 10 years as sole proprietor business planning consultant, working on my own with clients; and more than 10 years building a company, as founder and owner, working with employees.

In my case, working to “be my own boss” was never really why I did what I did.

I left a good job to start consulting on my own because I wanted to do the work, not supervise others. And I built a software company because I believed the product was needed.

The “own boss factor” was something that simply came along with it.

Before I get started, a quick note on one of my favorite start-your-business books, Melinda Emerson’s “Become Your Own Boss,” recently updated with a new version.

I’ve known Melinda for years and watched her earn her excellent reputation through hard work, common sense, and telling the truth.

Honestly though, I’ve never been a fan of the title of her book, because of the underlying ambiguity of being one’s own boss (and I’ve told her that).

But, this is one of the top books on going out on your own, and I highly recommend it. Along with Pamela Slim’s “Escape From Cubicle Nation,” it’s one of the two best books on the subject out there.

I also taught a piece of a longer presentation, embedded here, about being your own boss. It’s a theme that’s bugged me for a while. It’s an excerpt from my video Startups and Entrepreneurship: Beyond the Clichés. I’ve left that one at the bottom of this article, in case you’re interested.

Pros of being your own boss

1. You’re at the wheel. You make the decisions yourself.

There’s great satisfaction in being able to act on hunches, make guesses, and just do it. Take the risk, spend the money.

We often talk about owning the job as a key to job satisfaction; and when you’re the boss, you own it. Not having to ask anybody can mean a great deal.

This is a big deal to me. I’m one of those people (are you also?) who feels safer when I’m driving than when I’m a passenger. Especially in business.

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2. You set your own hours.

Maybe you’re an early riser, or you don’t want to work certain afternoon hours to do kids’ activities instead, or your own activities. Maybe you like to work in spurts.

When you are your own boss, you eliminate the old-fashioned need to warm a chair for specific hours.

You become responsible for your output, not your hours (unless, of course, you are a service business with clients—that’s in the cons, below).

3. You set your own work style, workplace environment, and (to the extent that you can afford it) workplace equipment.

Some bosses are better than others at upgrading the technology, choosing the location, arranging for parking, and so on.

How fast is your internet? When you’re the boss, that’s up to you.

Do you like a stand-up desk, or any desk? Up to you. A good view? Good coffee in the kitchen? That’s all up to you.

4. You set your own location.

Don’t stay in Cleveland if you prefer Klamath Falls.

Don’t take that frustrating subway commute to Manhattan, stay in Brooklyn. Meet people in Starbucks, or spend every day in Starbucks—why not? You’re the boss. You decide.

Cons of being your own boss

1. Your customers are your boss. Your clients are your boss.

Over and over, during the decade and a half that I was a sole proprietor consulting on business planning with clients, I ended up late at night, tired, stuck with finishing up a presentation due the next day.

I was never able to go the normal worker’s route, in which you either get it done or have a reason for not having done it. I needed the business, I needed the money, so I wasn’t in charge. My clients were in charge.

Even later in my career, after I’d built a business selling to thousands of customers every month, the customers were in charge.

We need to get the software finished, tested, and published. We needed to keep our website up to date. We needed to meet marketing deadlines, product development, finances, the whole thing.

In a business, the health of the business is your boss.

2. Your commitments—to vendors, to allies, to business activities—are your boss.

You can’t miss commitments very often and still be successful. Your word is your most powerful asset.

Meetings, deadlines, and promises are commitments. You can’t really run a business without them.

3. If you have employees, there are some ways in which your employees are your boss.

You lead, and—whether you like it or not—leadership is as leadership does. Meaning that your employees are watching you.

You can’t do less than you ask of them. You as boss is probably the most important factor in so-called corporate (or company) culture.

If you leave early, everybody leaves early.

4. You spend your own money.

Do you see point three in the pros, about you making decisions on equipment, technology, bandwidth, and so on?

Great—but then you have to pay for everything you decide you need. It comes out of your budget, not your employer’s budget.

When times are tough you may need that upgrade; but can you pay for it?

5. You earn what you earn.

You have no assurance of salary and compensation. It all depends on you, your business, your clients, your market, and your business offering.

The sole proprietor, startup founder, or small business owner doesn’t have an employer setting a stable compensation plan. There is no real assurance of how much you’ll have next month.

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Content Author: Tim Berry

Tim Berry is the founder and chairman of Palo Alto Software , a co-founder of Borland International, and a recognized expert in business planning. He has an MBA from Stanford and degrees with honors from the University of Oregon and the University of Notre Dame. Today, Tim dedicates most of his time to blogging, teaching and evangelizing for business planning.