5 Reasons Being An Entrepreneur Sucks

Let’s face it. Even successful entrepreneurs hate life sometimes. Illusions of grandeur about sitting on a beach tapping away happily on your cute macbook with travel stickers plastered all over it are not common.

The typical small business entrepreneur works long hours, spends a good amount of time making well below market rate before they see some success, and deal with emotional roller-coasters that would put most romantic comedies to shame.

I wouldn’t change it for the world, and I’m not saying that with the level of sincerity that unexpected parents feel. I do not want to be anything other than an entrepreneur. But let’s go over the reasons why that can suck.

You don’t feel productive most of the time

When you have pre-defined hours, which you do at most jobs, you show up, work for a pre-determined amount of time, and leave (hopefully.) Many people are able to leave their work at work, and live other parts of their lives after they clock out. The work is truly separate from their lives.

Entrepreneurs (and some either really happy or really sad employees) have a very mixed working and living relationship. We think about our work even when we’re done working. We’re either thinking about an idea for marketing, how to deal with that crappy client, or which candidate to hire. A lot of our social lives involve discussing entrepreneurship with other entrepreneurs (they understand me!) or boring civilians with it unintentionally. There are many times where you attempt small talk, relate it to something going on in your business, and suddenly it’s been ten minutes of straight ranting before you stop yourself and go “oh I’m sorry, I must be boring you.”

With that mindset, because time isn’t defined by work versus not work, we often feel that we should always be working on something. I work a lot more hours than I used to, but I still have many days where I feel “lazy.” The smarter guys/gals (usually the ones with families, if I’m being honest) section out their schedules more often and start to separate their lives.

This also happens when your companies have matured, and you’re not in grind mode anymore. At this point, you’re less of an “entrepreneur” and more of a “business owner.”

You’re never “done”

If you’re running a business, and you think that there is absolutely nothing to do at the moment, you’re most likely wrong

Part of the reason we never feel productive is because there is always, always something to do. With a company that has potential to grow (which should be the case of anything you work on, of course) there are times where you stop, look at what needs to be done, and freak out.

If there is one thing that probably kicks the shin and takes out most newer entrepreneurs, this is probably it. The constant feeling of having a mountain of stuff to do has been mostly solved by project management software such as Trello and Asana, which some people can’t function without. I tend to wing it a bit, but even I am a user of both of these programs, and I have my freak out moments.

Just think about it. Going from the ability to complete your work (finishing a grade in school, finishing high school, finishing college, clocking and out at your job, etc) and being ok with having ongoing work is difficult. It’s tough to make that shift, but all entrepreneurs have to make it.

Of course, you don’t want to just be busy for the sake of being busy either, and there are many entrepreneurs and business owners that fall victim to that trap. I even wrote about it in a recent article. Indeed, there are brief times where you don’t need to do any work on a particular project, and doing anything right then and there would be burdensome. James Cameron waited years between having the idea for Avatar and having the ability to complete his vision. The technology wasn’t available yet, so he did the smart thing and waited.

Control is a blessing and a curse

The best thing about being an entrepreneur is having the ability to do anything. The worst thing about being an entrepreneur is having the ability to do anything.

Another shift in thinking most of us go through is being told what to do our entire lives to having full autonomy. Besides the security of a steady paycheck, this is what stops people from ever jumping ship to being an business owner for a living.

You often find people that don’t like authority to be great entrepreneurs. I tend to question everything — even things that make sense to most people, so I always sucked as an employee. But unless you have rock solid vision and unwavering confidence, it is tough to be the one that steers the ship. Indeed, even a ship captain is able to build confidence through her experiences working every other job on the ship throughout the years before finally assuming command.

Many entrepreneurs find themselves in unfamiliar waters when they start a company. I knew absolutely nothing about the cleaning industry when I started Companion Maids, and I knew even less about call centers when I started Vicky Virtual. All I had was my ability to sense a gap in the market, so I have worked to fill those gaps. With Companion Maids, I had a mentor, but with Vicky we went in completely blind. It can be scary.

There are ways to make things easier. Having a business partner can help, because you have two perspectives instead of one. A lot of “opportunity entrepreneurs” spend years in their industry before noticing a clear gap that no one was filling and they went for it. But entrepreneurship will cause you to expand your comfort zone time and time again.

No one tells you what to do

The other hidden problem with having control is that no one is telling you what to do. If you look at the most profitable businesses on the internet, it’s always going to be information products. There are many wantrepreneurs that hate their job life, so they spend days and months scouring the internet looking for ways to make money. They look for that golden nugget that will help them finally say, “THIS is what I needed to know! Now I can get started!”

People are looking for someone to tell them what to do.

Of course, that never happens within the space of a couple of articles. People HUNGER for information, which is a mostly a good thing, but too much searching can lead to inaction. No one wants to do the wrong thing, so they seek experts to tell them the right thing. Of course, to eliminate wrongdoing is to eliminate risk.

So this is a constant problem for entrepreneurs. We have no one telling us what will work, so we run controlled experiments. The entrepreneurial method is like the scientific method in that way. We have a hypothesis about an idea, we run marketing experiments, track results, and hopefully don’t repeat the same mistakes.

You go from one boss to one thousand

This is one of my large realizations as an entrepreneur. In a business, people give you money in exchange for your service to them. You have to continue to provide for your clients, or they won’t pay you anymore.

This is no different from having a boss.

Appeasing a client the way you would appease your boss is the entire basis of the customer service industry, and whoever runs customer service at your company (which is everyone, more or less.) Also, if your boss begins to think that there is someone better for your job, you will most likely lose your position, the same way a client will take their business to your competitors.

Of course, clients and bosses are people, so some of them are annoying, some of them are irrational and some of them make your day brighter with every interaction. Frankly, the only difference between a job and a business is that not pleasing one of a thousand clients is not as bad as not pleasing your one and only boss.

When you start a company, you try hard to make just about every client happy, because you need the money to get profitable. As your business grows, the stress of making every client happy goes down. However, it can be hard to handle the quirks and sensitivities of a growing number and diversity of people. The 80/20 rule applies often in customer service, where 20% of your clients will require 80% of your customer service work.

If you’re smart, you try to implement policies to prevent problems before they come up. Examples such as the following find their way into the policies of practically any business, as a way to protect themselves from certain problem clients.

  • Booking times are not guaranteed when scheduled within 48 hours
  • Only one discount per customer, per visit
  • Pricing and availability may change

Of course, the more restrictions you put in place, the more you alienate certain prospective customers from being clients of your business. Early on, it’s easy to weed out the bad apples, but the line between problem and pleasant transaction gets blurrier as your policies become more specific (also, it’s hard to brand when you have too many disclaimers.)

So over time, instituting new policies can be a balancing act, as some loyal clients get phased out, and it can be difficult. This obviously sucks, but there are many times where you may have to sacrifice profitable revenue to serve the larger needs of a growing business.


As everyone knows, entrepreneurship ain’t easy. Most successful blogging entrepreneurs wouldn’t change their situation for a second, and so that’s what we usually write about. But it is a disservice to wantrepreneurs to ignore the things that suck.

Hope you found value in this!