The Dark Side of Being an Entrepreneur: 6 major struggles of online business owners

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“No more romanticizing about how cool it is to be an entrepreneur. It’s a struggle to save your company’s life – and your own skin – every day of the week.”

— Spencer Fry

Sure, being an entrepreneur is tons of fun. You get to make your own hours, be your own boss and have the opportunity to make more money than a lot of traditional jobs. All while chillin’ at home in your PJs.

However, there’s a lot to it that you don’t see. On the surface, it looks like everyone is so well put together and having the time of their lives while doing something they love. But in reality, it’s a lot of hard work and stress.

There are many times when you’re putting in more hours than a 9-5 and wondering when your hard work will finally start really paying off. And don’t even get me started on the lack of company healthcare benefits!

On top of that, you may have trouble staying motivated and organized, or have to deal with feelings of inadequacy or jealousy. If you can’t handle criticism, it’ll be difficult to take in the necessary feedback from customers or potential customers to make you and your brand better serve them.

I’ve been a part of various communities with tons of online entrepreneurs and small business owners for the last 13 years, including being one myself. I’ve made a list of areas where I’ve noticed myself and others struggling with running our business, both with day-to-day tasks and the stuff that goes on in our heads.

I’ve further broken this list down into 6 major categories just so it’s easier to talk about them. These are the core topics that I really want to explore on Stay Goal’d.

Let’s take a look!

6 struggles faced by online entrepreneurs

Maybe you’ve been doing this for a while, maybe you’re 3 months in and it’s really starting to get tough, or maybe you’re doing a little research before starting your own business. Either way, you’re bound to feel almost everything mentioned in this post at some point in your journey:

  • Keeping your motivation
  • Managing your time
  • Having a business money mindset
  • Keeping social without envy
  • Fear of taking risks
  • Caring for yourself outside your business

I hope to provide some insight into how to deal with each of these topics on this blog. I’m sure I’ll eventually come up with more things that fit into each one, but these are where I’d like to start.

“Some people dream of success, while other people get up every morning and make it happen.”

— Wayne Huizenga


First up is motivation. This one can get you before you’ve even started your business.

At first, you may be excited to start planning a new idea. But after a while—or once it’s time to actually put your plans into action—the excitement dies off.

Or maybe you do really want to work on your plans, but you have trouble finding the time. Then when you do have the time, you just can’t make yourself do what you need to do.

Maybe it’s because of other outside stressors or you just have issues with procrastination, which are both things you can work on improving.

With the right motivation, you can find the time you need to work on your business, even it’s just an hour or two a day.

Here are a few motivation-related topics I plan to explore.

Staying focused

The world is full of distractions and with phones and apps like Netflix, it can be difficult to stay focused when working from home. Not to mention any distractions from family, roommates, or friends.

My best tip for improving your focus is by using the Pomodoro Method. Whenever I find myself struggling, I turn to the traditional technique or a slightly modified version as a way to reward myself for focusing on work.

4 Tips for Using the Pomodoro Technique to Get More Done in Less Time

Thank you for sharing! 44 shares Share1 Tweet Pin43 LinkedIn Take care of the minutes; for hours will take care of themselves. Lord Chesterfield We’d all like to get more done each day without feeling stressed out or exhausted by the end of the day. One way to elevate that stress and exhaustion is to […]

Read more


Sticking with your work when it’s boring or seems like nothing you’re doing is really getting you anywhere is hard. Period. We’ve all had a time when we just wanted to quit (or actually did quit) because we weren’t seeing results fast enough.

You need to find ways to improve your motivation when things get tough so you can push through plateaus and reach success.


It’s easy to get caught up when trying to make every aspect of your business perfect, but that’s actually an unrealistic goal for most industries. When you find that it’s much harder or more time consuming to make sure everything is 100% perfect, you’re going to lose motivation real quick.

As long as you’re not doing anything that will negatively impact a client or customer, “done” is much better than perfect! Don’t worry so much about getting things 100% right on the first try. You can always change and update things after you’re created.

You should also work on being able to manage unrealistic goals and expectations to keep yourself on track.

“Setting the right priorities or having superior time management skill means knowing the difference between “must have,” and “nice to have.”

― Pearl Zhu, Thinkingaire: 100 Game Changing Digital Mindsets to Compete for the Future

Time management

Time is the most precious resource we have. Once time has passed, we can never get it back.

That means we need to use the time we have wisely, something that’s often a difficult challenge when working from home. We have all our comforts around us and it’s easy to fall for the temptation to pay more attention to those distractions than to our work.

Even if you have no problem focusing on your work, you might find there are some ways you can be more efficient or improve on setting your priorities on tasks. You may be working hard, but not on the things that actually move you forwards and towards accomplishing your goals.

If you’ve ever felt like you’re stuck in the mud or like you’re going around in circles, looking at how you use your time may help you get out of this rut.

Goal setting

Setting goals for yourself is a good thing, but the problem happens when you set goals that are a bit too ambitious. Ambition is, again, a good thing, but if you decide you want to make $1,000 in a week before you’ve built an audience, it’s likely you won’t meet that goal.

What you need to learn is how to set small, attainable goals to create a system that can make that $1,000. Having this system in place means you’ll eventually be able to keep earning week after week since you’ll have already built up the foundation.

Planning ahead

You may know where you want yourself or business to be in 6 months, a year, or 5 years from now, but aren’t sure exactly how to get there. I’m not gonna lie, it’s likely you’ll need to do some research on your specific type of business to find out what you need to do. But once you know what, you’re gonna need to plan out how you’re going to do all those things.

Planning is closely related to goal setting as it’s essentially the steps you need to take to achieve those goals. This is what you’ll do to build your system that takes your business further than just an idea and a set of goals.


Once you have goals and a plan, you need to actually do the work. This is where things get slippery with a lot of entrepreneurs.

Motivation is often high at the start of projects but then dies off if your goals take too long to complete. Another reason why you need easily achievable goals!

Practicing good productivity habits is one way to make sure you’re consistently working on your plan and checking off each goal on your list. You’ll also improve your ability to focus on tasks, which helps you get more done in less time.

“Mastering the mindset of wealth is choosing to think about money, and your reality in relation to money, in a way that will make you rich, not keep you poor.”

― Jen Sincero, You Are a Badass at Making Money: Master the Mindset of Wealth

Money mindset

I’ve noticed that people often approach money and finances as a work-at-home entrepreneur in a manner that’s far too personal. Either they’re not willing or able to invest in their business or they invest in things that don’t make sense for where they are with their business.

You don’t want to be spending too much money but you shouldn’t be spending nothing at all either. Understanding what you need and when you need it can help you make the right financial decisions so you’re not wasting money and that you’re using the money you do put in to make even more money.

To help you understand the importance of smart money decisions, I’ll be going over the following areas:

Business vs Personal

Your business should have its own finances separate from your own personal earnings. You may have heard other entrepreneurs mention that they pay themselves like they would an employee. It’s the same as you would do if you had a physical business.

This way, you can budget your business expenses and invest the money you make from it back into the business to make more money. This could be by purchasing new tools that make business tasks easier or for hiring employees so you can delegate tasks. This also gives you the fun of being able to give yourself a raise from time to time!

Money blocks

Money blocks can come in all sorts of forms or many different reasons. The most common ones I see from online entrepreneurs are an unwillingness to invest (or reinvest) in your business, not realizing the value of your work, and being afraid to ask for the sale.

In order for a business to grow, you need it to be profitable. For this to happen, you have to make sales and you need to put some of the money you make from those sales back into it.

This is why it helps to have a set budget for various parts of your business, such as automation tools, ad spend, and outsourcing or hired employees. These parts help your business to grow and make more money. When your business is able to make more money, you’ll be able to pay yourself more.

You also need to accept that businesses have upfront costs before they become profitable. Fortunately, starting a business online has some of the lowest startup and maintenance costs of any business.

Responsible financial decisions

Even if you are ready to invest in your business, you need to do so responsibly. You shouldn’t spend your last dollar on something that ‘might’ help you out. You should calculate risks and act accordingly.

This also means investing in the right tools or employees at the right time. You shouldn’t hire a full team to manage your customer service if you’re only making a few sales a week.

  • Don’t purchase ads just for traffic; purchase them with the intent of converting them to customers.
  • Don’t buy a tool your business won’t be able to fully utilize until it’s at a larger scale.

Instead, focus on investments that will get you even just one step ahead of where you are now. This way, you’ll always be moving forward at a pace you can actually afford.

“However difficult life may seem, there is always something you can do and succeed at.”

— Stephen Hawking


Who knew that there could be a bad side to trying to be more social (besides introverts everywhere—myself included)?

It’s one thing to have friends or family who are unsupportive because they don’t understand what you’re doing, but it’s another to be around so many likeminded individuals who are doing the same things you are.

This causes you to fall into some pretty dangerous thought patterns that could jeopardize your own success. You may find yourself constantly comparing yourself to others, becoming jealous or envious of colleague’s success, or be fearful of criticism or not take it constructively.

I have seen all of these things in the various groups or entrepreneurs I’ve been a part of over the years. And yes, I’ve definitely experienced them myself. All of them!

So don’t feel bad if you find yourself exhibiting any of these behaviors. Instead, recognize them and change your thinking.

Lack of support

Your friends and family may be amazing, supportive people, but even the most supportive people aren’t going to 100% understand everything you’re going through as an entrepreneur. This can make you feel lonely or like there’s no one to help when you have problems or questions.

Joining a community of entrepreneur peers will help out a lot with this problem, but may cause issues with the next two things on this list.


Seeing a bunch of people around you who are making more money than you or have a larger audience than you can make you feel like a failure. You need to avoid making comparisons to others around you because you don’t really know the full story of their success.

Someone who has been working for 3 years has gone through a lot more than someone who has been going for 3 months. There are also a lot of different factors that can contribute to quick or slow success. Don’t let it bother you if someone else is doing better than you.

Dealing with criticism

This is something I see people struggling with a lot, myself included. No one likes to hear criticism about something they worked hard on, but it’s necessary when you’re trying to appeal to an audience bigger than just yourself.

You need to know what people think about certain things so you’re not inadvertently turning off potential customers. Remember that anything people have to say isn’t a personal attack on you, it’s just a suggestion for how you can appeal better to them.

If someone is throwing personal attacks at you, then that’s their problem and is more of a reflection of who they are than a reflection of your business.

“If you can push through that feeling of being scared, that feeling of taking a risk, really amazing things can happen.”

— Marissa Mayer


Becoming an entrepreneur is life-changing and anything that requires or inspires a huge change in our lives incites a bit (or a lot!) of fear. For the positive changes we want to see, we often have to learn how to push through some uncomfortable feelings first.

  • Are you afraid to email your list because people might unsubscribe?
  • Do you hate asking people to buy because you don’t want to “seem salesy?”
  • Are you just waiting for someone to call you out on your lack of experience?

Fear takes many forms in entrepreneurship, but the three below are what I’ve found to be the most common.

Fear of getting started

Getting started is the hardest part for some of us, especially when you’re not used to being the boss. Sometimes this is due to having too much or not enough information.

You either feel overwhelmed by all the moving parts or you have no idea where to even begin. Other times it might be taking the next step in your business, like the email list example above or deciding it’s time to look into scaling through purchasing ads.

Fear of success

This one might seem a little weird but it creeps up on you in strange ways. You may want to land new clients or sell your products but have trouble actually going through the motions to do so.

Facing these fears often requires you to just jump headfirst into the thing you’re so afraid of doing. Create that email sequence, mention your services, or ask for that sale.

Imposter syndrome

If you’re ever felt out of place next to peers, you’ve felt imposter syndrome. You may be just as good as everyone else around you, but you personally feel like you don’t belong there. This is especially true when you’re first starting out and you’re unsure of just how successful you can be.

Instead of thinking of things you feel you can’t do as well as others, focus on the things you excel at. You may have a unique skill or talent that most other entrepreneurs in your space don’t have. Realize that because of this, you have some additional value besides the main focus of your business.

“You will be your best self when you take time to understand what you really need, feel and want.”

― Deborah Day, BE HAPPY NOW!


Last but not least is self-care. Taking care of yourself may inadvertently take a backseat to all the other things you want to work on in your business. However, you can’t stay focused and energized if you don’t take some time to care for your own needs and keep your physical and mental health in check.

Simple ways to practice self-care as an entrepreneur include making sure you take breaks, get enough sleep, and eat enough meals in the day; preferably healthy meals but I can’t tell you how many pizza-fueled work sprints I’ve pulled to meet a deadline.

Here on Stay Goal’d, I’ll be talking a lot about self-care along with other personal development topics in general, but I’ll be focusing on the following three specifically for entrepreneurs:

Work-life balance

Sometimes it’s tempting to keep working, working, and working because “hard work” is what improves your business, right? In other cases, your productivity habits may be so scattered that you end up pulling all-nighters or trying to fit a huge project into a few days of work time.

Trying to keep up this mentality will eventually lead to burn out. Instead, it’s better to plan ahead and balance your work and other things in your life, like family, friends, or hobbies.

Addressing your needs

It’s easy to get caught up in what everyone else needs; your family, your customers, or your clients. But you are also a vital part of your business. It’s your creativity, your vision, and your planning that has gotten your business to the point it is now. You need to take care of yourself too!

This may mean making sure your business can run without you when you need to take time off or it may mean that you make sure you work on your mental or physical health. Whatever it is, remember that it’s completely OK to think about your own needs first so you can continue to feel up to helping others.

Getting enough sleep

Feeling drowsy throughout the day is terrible for your productivity. For those of us working at home, it’s really easy to say “I’ll just take a nap” instead of push through and get things done.

It’s better to get enough sleep at night rather than try to work after only getting 4 or 5 hours of sleep. Getting enough sleep will keep you awake and alert enough to power through your daily tasks rather than slog through them because you can’t stop thinking about how nice your pillow would feel.

Make sure you give yourself enough days to complete projects so you’re not staying up late to finish things.

“The secret of change is to focus all your energy not on fighting the old but on building the new.”

— Socrates

Phew! That was a lot, I know. But that goes to show you just how much entrepreneurs are really going through. And that’s with me limiting myself to 3 major subtopics per topic.

Hopefully, after reading through this, you’re in the mindset to make a change—or at least you’re beginning to get into that mindset.

If you’re interested in learning more about any of these topics, make sure you’re on the Stay Goal’d email list. You’ll get notifications for new posts as well as weekly tips to help you through your struggles.

Be sure to check out the other posts on this blog for more advice as well.

My Favorite Resources

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