9 Must-Know Pros and Cons of Being an Entrepreneur

Entrepreneurship & Making Money . 9 Min. Read . By: Devon Brown

Being an entrepreneur is sexy as hell. You get to be your own boss, have huge financial potential, have a flexible schedule, and much more. But, let's be real, there are some downsides, too.   

I've been an entrepreneur for over twenty years and I absolutely love it! But honestly, I’d be lying if I told you that the way I feel about it now, is the same way I’ve felt about it for all 20+ years. That’s because I have to consider all the pros and cons of being an entrepreneur when telling you about my experience.

There were some hard times along the way, and I considered throwing in the towel more than a few times. Sometimes, things got so hard that I genuinely contemplated whether or not I’d be better off going back to a regular job where the big decisions (and mounds of stress), could be handled by someone else.

But, like most people who are just born to be entrepreneurs, I just couldn't give up. So I kept pushing forward and learning from my mistakes, and guess what?! I still am! Because successful entrepreneurs never stop progressing.

However, over the years, I have reached success in multiple areas. I am the World's #1 Event MC, I created my own personal development brand, and I've generated a million dollars in sales in my online business. 

So, I know from experience what the pros and cons of entrepreneurship are, which I am going to share with you after my first lesson as an entrepreneur.

My First Lesson as an Entrepreneur

My entrepreneurial dream started when I was about 14 years old. My friend and I thought we found the perfect side hustle to make some extra cash over the summer. We just knew we'd be raking in the dough with this new product... called Fluffy Bunnies.

And no, that's not a euphemism for some street drug. They were literally fluffy bunnies that came disassembled in a kit. It was our job to sew them together, and then sell them back to the company or directly to the customer. Pretty clever for two teenage boys to think outside of the box, right?!


My business partner and I didn't even know how to sew! We opened up the first kit, realized we had no idea what we were doing, and scrapped the whole idea. Everything about the venture looked great at first but once we were in the midst of it, we realized being entrepreneurs wasn't going to be as easy as we'd thought.

The Pros and Cons of Being an Entrepreneur

I’ve learned a lot since those Fluffy Bunny days. I’ve experienced plenty of ups and downs, and am very familiar with the pros and cons of entrepreneurship.

That's why I want to share the pros and cons of being an entrepreneur with you. I want you to understand the obstacles you'll face and the risks you must be willing to take.

 By understanding what lies ahead, you can minimize your risk and mentally prepare for what's to come. And as we go over the pros, you will understand why it's all worth it in the end.

4 Cons of Being an Entrepreneur

Let's start this list of pros and cons of being an entrepreneur with what isn't easy about being an entrepreneur. Then we'll end on a high note with the pros.

1. Long Hours

People often mistakenly think that entrepreneurship is about throwing out the 40-hour workweek in exchange for a freer lifestyle. They think the life of an entrepreneur is less about work and more about life. While that is the goal for the long run, the opposite is true for the short run.

Whenever you start a new business venture, you must be prepared for long hours. Expect to work much harder than if you were an employee. The 40 hours a week you wish to escape from can easily be replaced with a 60-, 70-, or 80-hour week (especially in the early days of starting your own business or as you start to grow & expand).

The extra hours of hard work will certainly interfere with your personal life. It might likely be a struggle to achieve work-life balance, because unlike and employee, you can't leave your work at the office. You are your work! You'll always have a nagging feeling that there's something you should be doing.

So along with the long hours, you have to figure out a balance that you (and your family/significant other/friends) can live with (happily!).

2. Higher Stress Levels

Owning your own company comes with a lot of responsibility. And with more responsibility comes more stress.

This is especially true if you have employees or if you're supporting a family. It's up to you to have a successful business not only for yourself but those who depend on you. That means every decision (and mistake) you make has greater consequences that can greatly weigh on you over time.

My definition of stress was redefined when my business went from making $100,000 a month to struggling to pay payroll. I don’t know that I’ve ever been in a more stressful position in my life than when I had to have a conversation with my team about the fact that they may not get their paychecks.

Luckily I made it through this rough patch and came out on the other side with a completely different respect for entrepreneurship and the stress levels that come with it.

Businesswoman meditating while businessmen bombard her

Learning to manage stress is a big part of becoming an entrepreneur, but at the same time, one of the biggest benefits of becoming an entrepreneur. The best entrepreneurs learn to accept that they are only human and will make mistakes along the way. They learn to convert stress into productivity. They learn from mistakes instead of dwell on them.

If you wish to become an entrepreneur, you should study and develop stress management as one of your key business skills. In fact, it's probably as important as leadership skills.

3. No Guaranteed Income

Financial instability is one of the main reasons many people don't dive head first into entrepreneurship in the first place. Not knowing what your next paycheck is going to be (or even if it’s coming at all) plays heavily into the high-stress levels we just discussed. And many people aren't capable or willing to give up a regular income for the great unknown.

On top of that, you won't have holiday pay, maternity leave, paternity leave, sick days, health benefits, and other benefits from working as an employee in the business sector. Those are all good reasons to stay with a traditional job, and at the end of the day, you have to decide if their value outweighs the risk of pursuing a dream job as an entrepreneur.

The truth of the matter is that as a business owner, you just have to be prepared for highs and lows and more financial risks than if you were an employee.

Entrepreneurs must be willing to take 

more financial risks than employees.

As I mentioned previously, there were times when money was flowing like a river, and other times when it was as dry as a desert. There were times customers bought what I was selling with little to no effort, and also plenty of times I busted my ass all week and made a whopping $0. That’s just the reality of this game (especially when you’re first starting out).

But you don't have to start off completely without a safety net. If you want to make a career shift to becoming an entrepreneur, I suggest you prepare before quitting your day job. First, if you can get started in your new entrepreneurial endeavor on a part-time basis (while you still have your job), do that! A good general rule of thumb is to do this until the income from your new venture matches the income from your job for at least three to six months CONSECUTIVELY.

If you can’t start your new business on a part time basis, then save up a bare minimum of 3 months' worth of living expenses. Reassess your lifestyle and see if there are areas you can cut back and save money. Create a budget and follow it to a tee so you can survive on a limited income.

Understand that cash flow may be fickle, and be real about the fact that a stable monthly income may not be a reality right away.

4. It's Likely Going to Take Longer Than You Think

One of the most frustrating parts of being an entrepreneur is everything taking longer than you expect. Don’t get me wrong, this is true for many things in life, but I’ve found it to be ESPECIALLY true in virtually all aspects of my business.

I remember when I was looking for new office space. I thought it would take me two months to find… it took closer to six.

I remember when I was working on building a new website (similar to ones I’d built a half-dozen times before). My programmer and I gave ourselves 90 days to complete the project… It literally took twice that long. Keep in mind, this is something we had A LOT of experience with, and it STILL took longer than expected.

I thought that I’d be at about $1,000/day in income in a new venture after about 4 weeks (again, something I had TONS of experience in). It took 8 months.

Are there times when things happened more quickly than expected? Sure. But the times it took longer than expected is far greater. As an entrepreneur, you have to remember to be IMPATIENT taking action, and PATIENT waiting on results. Business growth takes as long as it takes... which is always longer than you think. This often leads to people asking themselves, “When will I achieve my goal?”

quote by Steve Jobs

However, don't be deterred by your delayed success. There is an entrepreneurial truth that you should burn into your memory. It goes, "People overestimate what they can accomplish in 3 months and underestimate what they can accomplish in 3 years." Disregard your estimation of the short run, and focus on the long run.

5 Pros of Being an Entrepreneur

Now that you are aware of the scary and unappealing aspects of entrepreneurship, let's talk about the pros. Let me tell you, there are a lot of them! But let’s talk about 5 of the top ones.

1. Flexible Work Schedules

The first con I mentioned involved long hours, but there is a silver lining: flexible work schedules. Depending on your business model, you may likely be able to control when and how long you work. You have the option to work long weekdays so you can have a 4 day weekend. Or work your butt off all month so you can take a week off next month.

This king of flexibility might not happen right off the bat, but generally speaking, you can absolutely work when you need to work, so that you can “life” when you need to life!

I took advantage of this perk just a few months ago. I decided I wanted to relax in Mexico for a week, so I looked at my schedule, figured out what I needed to do to pay for it, and booked the trip. By controlling my work schedule, I also control my fun schedule.

This brings me to my next point...

2. Master of Your Own Destiny

Peter Drucker Quote About Creating Future

When you are an entrepreneur, you can create what you want to create. You can form the life that you want to live. You can take control of your own destiny.

You can sit down, design the life you want to live, and then create a plan on how to achieve it. Whether that means raising a family in a house with a white picket fence or globetrotting to your hearts' content. Or both! If you're willing to put in the hard work, the long hours, and take the risks, you can make it happen.

3. Limitless Financial Growth Potential

Let me tell you a secret. Everybody starts off not knowing what the hell they are doing. Even if they think they know, they quickly realize they've only seen the tip of the iceberg. But there's something amazing that happens when you're determined to keep moving forward. You start to uncover the iceberg and more so, you learn how to conquer it.

The longer you work at something, the more you can "see the Matrix." That may be too old of a reference for you to understand, but it means that what starts off as a foreign concept unfolds into unlimited possibilities. The more you understand, the more you will find potential that you can capitalize on.

You will discover new and bigger ways to fuel your personal and business success.

I have friends of mine who literally make $10,000+ PER DAY!

Did they start off like this?

No. Most of them started off falling flat on their faces time and time again. But they worked through it and now they understand the truth about the limitless financial growth potential of entrepreneurship.

4. The Tipping Point

Remember at the beginning how I said that the goal of an entrepreneur is to have a life that is less about work and more about living?

I said that in the short run you may have to dedicate long hours in order to achieve this in the long run? Well, the con of long hours turns into one of the biggest advantages of being an entrepreneur: the tipping point.

At some point in your entrepreneurial career, you will reach a tipping point where all your hard work converges.

The money will start to flow instead of recede. The hours you work will swap places with the number of hours you play. The team around you will take a lot of the burden off your plate. And you will be able to work less for more money!

I call this the tipping point (to borrow a phrase from Malcom Gladwell).

It’s the point at which your actual experience as an entrepreneur matches the experience you’ve always dreamed of for yourself.

It doesn’t mean that you won’t have to work or that you won’t have stress….

But it does mean that you’ve paid your dues, and you can start working ON your business instead of IN your business.

entrepreneurship is living like quote

Reaching this point is the pinnacle of being an entrepreneur.

5. Life as an Entrepreneur is Sexy as Hell

When you combine all of the above pros of being an entrepreneur, you get one sexy life. You get to control your schedule, master your own destiny, make as much money as you want to make, and (on top of all of that) everything gets easier at some point! It's as sexy as hell!

You get to live life better than the vast majority of people on this planet because you took control of your life. You committed to a life of entrepreneurship and overcame all of the obstacles to succeed. And that right there is one of the biggest rewards: you did it. You can be proud of something that you created and made successful.

Ready to Become an Entrepreneur?

After finding out about the pros and cons of being an entrepreneur, you're probably saying, "Life as an entrepreneur sounds awesome! But HOW do I succeed as an entrepreneur?"

Well, the answer is you start to dig. You start to dig into what you want to do, what your strengths are, and what you want out of life. Then you dig into others who have succeeded in what you want to do.

Your first step should be surrounding yourself with others who are on this journey with you. You can greatly increase your rate of success by interacting with people who have similar goals.


One of the best ways to get an unfair advantage as an entrepreneur is to become a better public speaker. If this is something you would like to do, click the button below and check out the amazing training I put together for you.

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Devon Brown (“Duh-Von” not “Dev-in”) is a speaker, author, entrepreneur, former hip-hop dancer, and World's #1 Event Emcee. Once described as a sort-of ‘MC Hammer meets Tony Robbins’; his style is 50% education, 50% entertainment, and 100% must-experience. Be sure to connect with Devon on social media.

Devon Brown with Arms Folded

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