Bitter at Business: 14 Reasons Entrepreneurs Fall Out of Love with Their Businesses (and How to Fix It)

Bitter at Business

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The purpose of entrepreneurship isn't to make money or achieve material success. Those are just nice objective measurements along the way. Vehicles for achieving a larger end goal, but they aren't the end goal itself.

You know that though...

The true goal of entrepreneurship is to become happy, content, and fulfilled.

Too often, we measure our success in terms of things like business growth, total employees, dollars, or accolades rather than what actually matters.


Is this line of work bringing me true happiness or not? Am I happier than I was before or not?

Business can be so complex, but this part really is quite simple.

My apologies for getting so deep. This isn't my typical style.

Just like you probably aren't still in love with your high school sweetheart, it's not abnormal to fall out of love with your business. But before you break up, let's work to fix it!

So, in this article, I'm going to be the business equivalent of a marriage counselor. We're going to cover all the different reasons that you might be falling out of love with your business, and then we'll cover some ways to address each of them. 

Ready? Let's get into the 14 potential reasons you've fallen out of love with your business and how to fix them.  

#1 Doing (Almost) Everything Right (without Growth)

This can be one of the most frustrating issues entrepreneurs have. Whether you've found success but have plateaued or simply haven't found the traction you want after a lot of upfront effort.

Let me give you an example...

You're an aspiring YouTuber and worked your butt off on your latest video. You spent 2 weeks researching, filming, editing and optimizing.

All the best practice boxes are checked. 

You hit publish and.... Crickets.

12 views in 24 hours. 18 views after a week. 30 views after a month.

Under your video you see a corny clickbait thumbnail of a 14-year-old playing ROBLOX.

He's done almost no editing, the sound is offensively unmixed and almost none of the best practices are being used. 

And yet.... 1.9 million views in 2 weeks.

It hurts. I get it and I've been there (and am still there in many areas, especially on YouTube). Even people at the subjective "top" of their spaces compare themselves to others around them. 

Ben Folds explains it best in his classic song "There's Always Someone Cooler Than You." The song is as catchy as it is insightful, so I'm going to share it below. 

Comparing yourself to others isn't going to ever work out. So, stop doing it.

It's still frustrating though.

Unfortunately, doing almost everything right doesn't work if you get the first big thing wrong. Choosing the wrong niche or not validating your concept) your efforts could be in vain. 

In the example above, you might share great information, but that doesn't make up for the fact that people aren't interested.

Direction of Goals

The 14-year-old is perhaps doing less work and not following the best practices, but he's doing it in a way that people love and find entertaining.

Ge's going towards a result that is possible and has an audience.

He landed on the right angle and each video he creates sees exponentially more success.

Perhaps it was luck. It's often luck, but you can control the changing of direction by proactively identifying when you're going the wrong way.. 

It doesn't matter how fast you run or how consistently you do it if you're running in the wrong direction. 

How to Fix It

First, pat yourself on the back for your hard work.

You've likely learned things that are going to pay off exponentially down the road. If you created a blog, you might have learned how to build a website, grow a mailing list and many other hard skills that will translate into other ventures.

However, you should know when it's time to pivot. It's ok to quit after we have gathered enough evidence to support the decision. I cover this in my article The Guide to Quitting.

If there is no audience, you can't grind and hustle your way to success in that space. 

But be careful!

Understand that, in most cases, people give up too soon. Always err on the side of "I'll go longer than I feel comfortable with."

Work to understand when it's time to cut your losses and pivot to a new venture. This is difficult and I can't answer with certainty "when" it's time to pivot. 

Read about the plateau of latent potential for some insights into how growth often happens (slowly, but then rapidly at scale). 

Remember, quitting a venture doesn't mean quitting the process. If you want to be a successful entrepreneur, keep coming back. You've only truly quit when you quit trying all together. Specific ventures need to be thrown away at times. 

#2 Success with Negative Externalities

In this field, success often demands everything you can give, and the easiest way to do so is to give up and ultimately jeopardize your personal passions and loves what I call the three Fs:

Family, Friends, and Freedom 

You may finally achieve your business goals, but if you don't know how to balance your business and your actual life, you are going to be forced to choose one of the two.

How to Fix It

Draw lines in the sand.

Decide what things are more important than money.

Is there a price you'd put on your marriage? Is there a price you'd put on being comfortable turning your phone off? Is there a price you'd put on not being able to spend time with your friends?

Some of those are rhetorical to me (the answer is "no price") but everyone is different. If the costs are worth it to you, go for it. If not, make the changes immediately, no matter how drastic they seem. 

It might mean selling the business. It might mean accepting that you're going to just earn less this year by not taking on high-value projects that are equally high maintenance. It might mean letting go of control and hiring help to do things you have always wanted to do yourself. 

Business can be like a drug. Chasing the highs can make us lose sight of what we truly value and can cause massive damage.

This is one of the most dangerous business issues on this list. It is very common and difficult to fix once it's happened. 

#3 Taxes 

 One thing that they fail to tell you when you form a business is how much more toxic your relationship with Old Uncle Sam is going to become. One reason I have hired an assistant is that I am much better at making money than I am at doing all of those boring but necessary tasks, and that is exactly why I and every entrepreneur hate doing their taxes. 

The first time that you see that massive tax audit debt, you will ask yourself why go through all this trouble just so you can call yourself a business owner. It also instills in you a constant, ever present fear of "the big one"; some boogeyman tax audit that will come and throw your business under. 

My best advice is to just understand that everybody deals with taxes, and it is not a stress unique to entrepreneurs. Remember that your taxes are so difficult because your business is working and earning you money. Also, get an accountant as early as it becomes feasible; they will save you so much money and time and stress that could be better used elsewhere.

How to Fix It

First, get your books in order starting today. The past is in the past. You can always start fresh. 

Hire an amazing bookkeeper and accountant. They are worth their weight in gold. 

Next, remember, money comes and goes. You aren't the first or last business owner who got wrecked by the IRS. 

In 5 years, it's likely you will just smile and laugh about it. Right now, it hurts, but time will heal it and you know what to do better in the future. 

#4 Competition

An unfortunate truth about any field of business is that you will always have someone chasing or undercutting your success. Competition is a constant for entrepreneurs. 

Unfortunately, you will never be the only member of your niche and it is just an uncontrollable reality that people will steal, copy, or emulate models and systems that work.

Except for trademarks, copyrights and patents, you can't always control what they choose to do, but you can choose how you respond. Let them take your ideas, but don't let them take your drive and peace of mind.

How to Fix It

First, ask yourself, "Can I handle this cut throat lifestyle for the rest of my career?" If the answer is no, you need to find a new line of work or a rare niche with no competition. 

Although it's easier said than done, try to use your competition as motivation. The most successful entrepreneurs welcome it as a challenge, but it is an abnormal trait that many of us have to develop (myself included). 

#5 Burnout

You've worked hard and achieved success, but you feel you've roasted your last brain cell in the process. 

This is as common as the cold in entrepreneurship. 

Fortunately, it's one of the easier issues to beat. 

How to Fix It

I'd love to say "take a vacation," but I can appreciate that some entrepreneurs don't have that luxury in their near future.

If you do, take one! Go offline and try to relax. I feel like a horse champing at the bit when I finally get back to my work whenever I get some time off. By not acting on my ideas, they seem to refuel my creativity and drive.

If you can't take a vacation immediately, start planning one in the future. Sometimes just knowing that there is a light at the end of the tunnel is enough to put some gas on the fire. 

Next, work on creating SOPs (standard operating procedures) that will help you delegate the tasks that are sapping you of your energy. When I feel I've created something that will save me time later, I feel better immediately. We're fighting psychological fatigue after all. Burnout is rarely purely physical.


FOMO is the fear of missing out. It's an extremely powerful behavioral driver that is hard wired into all humans. 

Studies show that our fear of loss is much stronger than our desire for rewards for driving our actions. It makes sense if you view it from an evolutionary perspective. 

For our prehistoric relatives, getting more or extra of something is nice, but losing something could mean death. 

More food was nice, but losing the food they had could mean death.

Making new friends was great, but losing their current tribe could mean death.

We're hard-wired to believe that loss = danger and that shows up in every aspect of our lives, but especially in business.

In business, there are always new and exciting opportunities that scream for our attention. Cryptocurrency, virtual reality, etc. It's painful to feel you can't chase every opportunity, especially when you see your peers finding success with them. 

How to Fix It

Remind yourself, "missing out on this will not kill me." Your brain is trying to convince you it will. 

Remember, money and opportunities come and go. You started out on your current journey for a reason and it deserves your attention. 

Remind yourself, "Many of these opportunities won't pan out anyway, and if I chase all of them, I won't be able to move the needle forward in any of them, especially the one that I know is going to pan out." 

Focus on what you believe in and go all in. Saying no is hard, but it's valuable.

I know it's hard to watch someone make $250,000 on a JPG of an ape, but you'll survive. 

#7 Accidentally Creating a Job

You were afraid to delegateYou created a business that trades time for money and don't know how to get out of it

How to Fix It

I love this problem because it's the most straightforward to fix. Delegate!

Unless you're literally selling your own celebrity or unique talent (Brett Favre on Cameo or the guy on Fiverr, I hire to do Morgan Freeman impressions) you can outsource it. 

It's extremely painful, and it's going to be a lot more work upfront than just doing the work yourself. Fight through it. It will be worth it.

Another option here is to work on your habits and improve your own performance. I read the book Atomic Habits and it really is a life-changing read that you need to get your hands on.

#8 Chasing Dragons

You saw a huge outlier in your success, usually early on, but you can't replicate it. All future results pale in comparison.

How to Fix It

First, understand that luck is a part of business success, but it favors those who regularly do the work. 

You might have gotten extremely lucky to strike gold on your first attempt and realized that you might not have the Midas touch you thought. 

It's ok. Failure is a part of business and you are just experiencing it in reverse order compared to most people. You will grow and find it again if you keep showing up. 

#9 Chasing Unicorns

You want to create the next Facebook but lack the resources or big ideas. As a result, you skip legitimate business opportunities because they don't excite you. 

How to Fix It

Ask yourself, "will I really only be happy if I make a Fortune 500 company or can I shift the goal posts to something else?"

If you have the unicorn idea and believe in it, go for it. But if you regularly turn down awesome opportunities because they aren't going to be Uber or Facebook, do some reflection. 

If you feel the only meaning would come from changing the world at scale, by all means, chase that unicorn. For me, it wouldn't make me fulfilled.

#10 Passions Turned Resentments

Building a business around something you're passionate about can be a huge advantage. It's a growth hack that makes work feel easy and enjoyable. 

However, there can be a dark side to this. Being forced to do something that you used to love when it was a hobby can cause you to lose interest. In worst-case scenarios, it could ruin it entirely. 

For example, you started a YouTube channel teaching people how to play the piano. It now pays your bills. Awesome!

.... but now you dread going to the piano and filming. It's no longer fun, it's work.

How to Fix It

Ask yourself, "Is the money worth ruining this passion? Can I make money in another way?"

I don't have the answer for you. 

I would make the argument that if being forced to do it ruins that interest for you, you might not have been extremely passionate to begin with. 

#11 Fight or Flight Overload

There are two big reasons people pursue entrepreneurship.

They are fleeing from work that they hate OR they are chasing work they love. 

For me, it was a little of both, but mostly the former. I hated working for other people. 

My driver early on was the creeping fear of needing to go back to my yarn mill job. I still have recurring nightmares about this, actually. I don't dwell on the fear and am now able to confidently tell myself, "there is no way I will ever have to go back to a traditional job I hate."

This sort of stress,  though (physiological and psychological) can take a toll on your health and general sense of wellbeing.

How to Fix It

If you're terrified of failure, make a diagram showing what would happen. Ask, "and then what?"

  • My business stops making money (and then what...)
  • I'd have to pull out my investments to pay the bills (and then what...)
  • If I spend all of that money, I'd have to borrow some (and then what...)
  • I'd have to sell the house and cars (and then what...) 
  • If I still can't get things together, I'll have to get a job (and then what...)
  • I'd do freelance work and sell my hours for dollars for a while (and then what...)
  • If I can't get clients, I'll have to work at the job, but I can work on my business in the morning and at night (and then what...)
  • I'll survive (and then what...)
  • I'll have a story to tell and will have lived my nightmare and survived 🙂 

As long as the answer doesn't lead to "and I or my loved ones will die," you will be ok. 

#12 Imposter Syndrome

Imposter syndrome is brutal, especially if you're in a business that sells your expertise. Bloggers like me get hit with this. 

It's the constant fear or paranoia that everyone thinks you're a fraud. You question yourself and wonder if you really are just a phony. This feeling can last forever and even people who are objectively at the top of their fields can experience it. 

How to Fix It

First, pat yourself on the back. You are the type of person who wants to be self aware. Unfortunately, you've got a very active mind and it won't let you sit back and believe that you're great. 

You likely truly want to be great in your field, and it's important to your identity that you work to become or stay great. 

This is good. It can drive you to be better. 

But, you need to accept this feeling is normal. Here is my recipe for fighting imposter syndrome. 

Step #1 Be honest. You are worried about being exposed as a phony. To be "exposed" you have to first claim to be something you aren't. If you are a financial advisor, make it clear that you aren't a millionaire yourself. 

Step #2 Speak on only what you're certain about and you're an expert. You don't need to know everything to be a thought leader or expert. You just need to make sure that everything you say is accurate. You can know 10% of what there is to know on a topic and provide value by sharing just that 10%. You become an "imposter" when you pretend to know the other 90%. 

#13 Hater Math 

You let the 1 star reviews or disparaging comments crush your spirit. This is like imposter syndrome and is usually rooted in our insecurities. 

I struggle with this. 

How to Fix It

Work to accept that negative feedback is an inevitability. 

Learn to filter feedback into constructive and non-constructive. We need to hear negative feedback and can't simply write it off as "haters and trolls" if we really want to grow. But changing for actual haters and trolls isn't something you should ever do.  

#14 Embarrassment by Association

You feel your industry is unethical, embarrassing or scammy and hate being associated with it.

Many of my businesses are in the make money online space (MMO) and it is riddled with unethical practices.

How to Fix It

Remind yourself that you aren't your industry (with the rare exception of. Industries like big tobacco or lobbyists for oil companies).

A corrupt industry needs good people more than any other industry. 


There you have it. 

Whatever your situation is, remember, there's a reason you pursued entrepreneurship. Err on the side of going a little longer and not giving up, but also, know when it's time to call it quits and move on. It's ok, there is no universally correct answer here. 

Good luck and I wish you the best in your endeavors! 

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