20 Entrepreneurs Reveal What They Hate About Being an Entrepreneur

Entrepreneurship comes with freedom, but the freedom is not always free as it comes with the bad side of robbing of your work-life balance and other ugly things that make you dread the whole idea of entrepreneurship. It can also be stressful when you have to be the think-tank of the team and the burden of decision making falls on you. You’ll get to a point where you’re not sure of the outcome of the decision, but you have to make it anyway. At times you’ll crash on the inside but have to act like everything is okay for the smooth running of your business.

Heres what entrepreneurs had to say about what they dislike about being an entrepreneur.

#1- First to Arrive, Last to Leave

Photo Credit: Shane Griffiths

Working in a coworking space with other freelancers, it can be challenging at times. Many people work just a few days a week, and not even full days. Being successful requires hard work, and that means getting to work early and staying until the work is done. Besides just getting the important stuff done, it takes even more effort to improve your business and take the next step.

Thanks to Shane Griffiths, Clarity Online!

#2- Instability that comes with it

Photo Credit: Simon Hansen

You never know what’s in store for you and every day is filled with mixed emotions: excitement, happiness, anxiety-no in between. This instability and fearing whether or not you’ll hit a jackpot or rock bottom is something that most entrepreneurs and small business owners like me fear and battle with every single day.

Thanks to Simon Hansen, Best Sports Lounge!

#3- No boss around

Photo Credit: Kelly Beasley and Marshall Wendler

Being your own boss means making executive decisions on what projects should be worked on and in what order. It would be much easier if someone could tell us what needs to be done each day, but that responsibility lies on us. It’s easy to be overwhelmed with what needs to be done on a given day. Running a business is like running a small city. There are so many departments to run… for us this means bookkeeping, SEO optimization, content creation, website maintenance, education, link building, site updating, checking links, etc. There are multiple tasks needing attention at all times. Sometimes this makes our minds freeze up, not wanting to take any action at all. We use ClickUp to help manage tasks and to help prioritize what we need to do. It helps somewhat, but still, there’s no boss around to tell us what to do on the daily.

Thanks to Kelly Beasley and Marshall Wendler, Camp Addict!

#4- Everything is on me

Photo Credit:
Iva Ursano

All the fires that get lit, I have to put out myself. There's no 5 pm punch-out clock. I've had to deal with issues as late as 11 pm. You wear all the hats and sometimes that can be exhausting and frustrating. You don't always get to put your feet up, relax and watch TV after dinner. Some days I find myself working til 1 am because I spent hours during the day putting out fires. In the end, it's all still worth it.

Thanks to Iva Ursano, Amazing Me Movement!

#5- Being honest and reasonable

Photo Credit: Bharat Parmar

Being an entrepreneur is all about mammoth responsibility of getting things done in the right direction and lead the company towards growth and success. It's not possible to keep people on board if your ship is heading to collide an iceberg. I hate being honest and reasonable in providing professional feedback about work. I don't enjoy the privilege of being diplomatic or say white lie to appease the people that invite frictions in personal relationships as well. At times, many take professional feedback personal complicating personal relationship and mess up the things.

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Thanks to Bharat Parmar, iFour Technolab Pvt Ltd!

#6- The self-doubt

Photo Credit: Andrew Taylor

I don't know if I am going in the right direction at times, I don't have the support base I wish I had, as in the beginning when it is most critical, you can be on your own or just with a couple of other like-minded individuals. Self-doubt can be crippling, it can destroy your great ideas, keep you in bed, bring you right down to your knees and keep you there until you find the strength to get back up and put faith in yourself again.

Thanks to Andrew Taylor, Net Lawman!

#7- I don't have time! 

Photo Credit: Swati Chalumuri

As much as I love being an entrepreneur, there are certain aspects of it that frustrate me. One of them is time management, which is an age-old complaint of almost each entrepreneur. As an entrepreneur, you take on a lot of tasks and that hampers the efficiency of managing time. It becomes difficult to keep track of all the activities that you do and that can lead to exhaustion. The second thing is finding the right people for doing the work. A healthy team is a dream of every entrepreneur and that's where it becomes challenging. Sometimes you come across people who aren't just the right fit for your vision. So, it really is a task of intuition and calculation to hire a person that grows your business.

Thanks to Swati Chalumuri, HearMeFolks!

#8- Dealing with the bureaucratic side

Photo Credit: Ken Eulo, Esq.

While I wouldn’t dream of changing my path, the aspect of being an entrepreneur that I dislike the most is having to deal with the bureaucratic side of the company. I would much rather spend my time implementing operational strategies for the company, rather than preparing the taxes and doing paperwork. Though these tasks can be tedious and boring at times, they are essential to every successful business. Once we find enough success, I'll be able to outsource these tasks to someone else.

Thanks to Ken Eulo, Smith and Eulo Law Firm!

#9- People think you're lucky

Photo Credit: Daniel Nyiri

I hate that people look at you that you are so lucky that you own a company and people not seeing all the risks, responsibilities, sleepless nights, daily problems, stress, and all the issues. They are not there for the heartaches, but they all line up for the good times, the fun the money and call you lucky. You are the biggest idiot on earth until you prove everyone wrong. Then once you have done that, you are the luckiest person on earth.

Thanks to Daniel Nyiri, 4U Fitness!


Photo Credit: Robin Young

When starting a business, as entrepreneurs, we do everything ourselves. Once the business grows and starts hiring, jobs need to be handed down. Delegation causes mixed emotions and I feel like no one will do the job as well as me. This is the part I hate most. It needs to be done, but it's hard to let go. It's important to understand, however, that nearly everything can be taught, and so long as you have processes mapped and guides drawn up, then most of the business operations can he handled effectively.

Thanks to Robin Young, Fitness Savvy!

#11- Being all alone

Photo Credit: Ryan Collett

Not many people realize how lonely of a world being an entrepreneur is. Everything is on you, there is no one else to discuss ideas with, blame for your problems, or just talk to sometimes. Most of my days I am completely alone in my office. My team is all virtual so digital meetings help but day to day is lonely. I end up calling people a lot throughout the day just to talk about ideas and get feedback.

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Thanks to Ryan Collett, Jasper Organics!

#12- The inability to take extended time off

Photo Credit: Devin, Trevor and Robert

Before starting this business, we would spend time with our families for the holidays, hang out with our friends on the weekends and take week-long vacations. Nowadays, a lot of that is gone. Any free time we have is dedicated to growing the business. With holidays like Black Friday/Cyber Monday/Christmas; we need to stay connected to our store to make sure everything is going smoothly. In addition to that, we have to create more themed emails, ads and continue to provide the absolute best customer service to our customers. In our current stage of business, this type of hustle is absolutely necessary but we know it will get better once we start growing more and automating processes. Hopefully, with automation and increased help, we will get back to those wonderful days of spending time with our families and friends while Art of The Gentleman continues to grow and give back to the community around us.

Thanks to Devin, Trevor and Robert, Art of The Gentleman!

#13- Cold calling process

Photo Credit: Clarene Mitchell

Cold calling is necessary to generate new business, but the process is very daunting. I'm not a salesperson by nature. The random calls or pop-up visits to potential clients stretches me far out of my comfort zone. I generally have to psych myself up well in advance to do so. I never know if I am going to get to the right person and whether they will be receptive to my service offerings or not. I guess I have to get tougher skin for the rejection that goes along with the process. Ironically, I tend to have positive results when I do forces myself to do cold calling.

Thanks to Clarene Mitchell, TCM Communications!

#14- The attitude towards startups

Photo Credit: Angela Ash

One thing that can be a little disheartening about being an entrepreneur is the attitude that some businesses have toward startups. Because some startups do fail (as do major corporations in a multitude of industries), it sometimes leaves the entrepreneur with the concept that they need to prove themselves beyond what an established company employee might. Unfortunately, some organizations see a startup as an experiment or a temporary business, not fully understanding that entrepreneurs are not wired to fail. However, sometimes we must go the extra mile or provide that extra page of data to earn trust and build customer relations.

Thanks to Angela Ash, Flow SEO!

#15- Lack of trust

Photo Credit: Ed Castro

One of the biggest obstacles I come across as a service provider is an inherent lack of trust in my space due to past service providers my client may have worked with. Even though the client does not necessarily distrust my team and me, because they have been burned by their previous provider the client may sometimes become unnecessarily cautious with certain aspects of the proposed marketing strategy. This can greatly impact overall performance and makes it more difficult for my team and me to execute the strategy properly without convincing the client first. Sometimes we end up spending more time convincing the client to execute the strategy than spending time on the strategy itself.

Thanks to Ed Castro, Sage Consulting Group!

#16- Three things

Photo Credit: Karla Singson

Some people assume you have lots of money all the time, they automatically think that having your own business is like having unlimited money because you pay salaries, rent, and taxes anyway. The truth is, financial ups and downs occur in business, and the worst part is usually you are left to deal with it yourself, as a business owner. Which brings me to my next point… 2. You have to be super self reliant, because there will be times when all you have is yourself to blame, depend on, and solve problems for.  3. You are prone to risks of reputation loss due to mistakes caused by your staff. If you own a business, you are responsible for literally everything in your business, even if it's not directly your fault, even if you trained your staff for the exact opposite of the outcome, or even if you've led them well.

See also  25 Entrepreneurs Explain What They Love About Being An Entrepreneur

Thanks to Karla Singson

#17- It does not pay back

Photo Credit: Marty Dorn

There might be plenty of reasons why any other entrepreneur hates entrepreneurship, but I started to feel aversion towards it because it doesn't pay you back. In the workplace, being an entrepreneur, I have to deal with operations of various kinds through the microscopic eye view. This micromanaging takes a lot of energy, but at the end of employees, you will always be seen as an annoying boss who used to bullying employees on their tasks. Another biggest setback associated with entrepreneurship is that it will leave me a stranger to my family. I have no time for my obligations outside of the business. Among many other reasons, these two factors, i.e., Office politics and lack of compassion, lead me towards paranoia, fear, and other psychological disorders. Subsequently, I am only left with the option to hate entrepreneurship.

Thanks to Marty Dorn, Gaming Rig!

#18- The constant chase for something bigger

Photo Credit: Cassy Aite

As an entrepreneur, you rarely have moments when you can sit back and relax, looking back at what you’ve done. You’re always pushed to look for the next big thing, next feature, new hire, breaking out into a new market, etc. You always keep wondering how to get more revenue, grow your company or do something that your competition hasn’t thought of. In a way, you never stop thinking about growth, even when you leave work. This is one thing that I dislike about being an entrepreneur, but it gets better after you reach a certain level of success that you’re happy with.

Thanks to Cassy Aite, Hoppier!

#19- The stress can get worse

Photo Credit: Joe DiSanto

I founded and managed multiple successful advertising and entertainment-related businesses in Los Angeles. The most significant of which Therapy Studios and Therapy Content. While I didn't hate it at all, after a decade of long hours and stress of the $350k/month overhead and 30+ employees, wore me pretty thin. The business was successful by all accounts…we even won two Emmy's for an HBO show we produced with Dave Grohl! But that didn't mean the stress went away…it actually gets worse! Then we had a child, which made it much much harder to keep up, and it all just seemed like too much. So my wife and I exited the business and left Los Angeles, so we could reduce our expenses, work less and have more family time. Now I am working from home doing business consulting and bookkeeping, and education via our blog.

Thanks to Joe DiSanto,!

#20- Responsibility for the failures

Photo Credit: Robyn Flint

Being an entrepreneur is a choice. I chose this career path because of the freedom it affords me. I get to be active in the lives of my children and grandchildren. But not every aspect is sunshine and roses. The biggest pet peeve about being an entrepreneur is being responsible for every failure. It is a direct reflection of my ability or lack thereof. There is no one else to blame but myself, and that reality is something
that I hate.

Thanks to Robyn Flint,!

What do you hate about being an entrepreneur? Tell us in the comments below. Don’t forget to join our #IamCEO Community.

Mercy - CBNation Team

This is a post from a CBNation team member. CBNation is a Business to Business (B2B) Brand. We are focused on increasing the success rate. We create content and information focusing on increasing the visibility of and providing resources for CEOs, entrepreneurs and business owners. CBNation consists of blogs(, podcasts, ( and videos ( CBNation is proudly powered by Blue16 Media.

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