Six Ways Emotions Can Make You Fail as an Entrepreneur

Entrepreneurs talk a lot about common problems: building a product, reaching customers, getting funding, and hiring the right people.

On the other hand, there is little talk about the things going on within the entrepreneur’s own mind that can make or break their plans.

Here are some ways psychology can stand in the way of success. Being prepared for potential problems is half the cure. While we can’t control what our minds spin up beneath the surface, being equipped to understand it and handle it better can be the difference between success and failure.

Letting go of an idea is hard

Entrepreneurs treat ideas like their children. They nourish them, they dedicate time to them, and they don’t let anyone tell them their kid’s going nowhere.

Getting caught up in an idea that has no future can cost you your startup capital and months of your time, not to mention the incalculable opportunity cost inherent in not pursuing more worthwhile ventures.

It takes strength and wisdom to let go of an idea. A good way to notice your mind is playing tricks on you is catching yourself cherry-picking data from your customer interviews or mentor feedback.

Letting go of people is even harder

Have you ever been in a situation where you’re part of a team and you find yourself doing 80% of the work, while the other 2 or 3 people split the remaining 20%? If the answer is yes, you’re not alone. This is a common consequence of the Pareto principle and Price’s law.

If the team members that are not pulling their weight are your co-founders, then you’ve got three choices:

  1. Work your hands to the bone with uncertain results.
  2. Let the business die.
  3. Part ways with the people who are dragging you down.

If number 3 is possible, it is obviously the best choice for your business, but it is wrought with emotional strife.

Plateaus can be discouraging

How does progress work? People wish it was linear and think they’re failing when it is not. Some think it’s exponential because they’ve seen a chart online. While growth can, indeed, be exponential in the long term, the truth isn’t so simple.

In reality, you start with a period of swift learning and growth, then you hit a plateau. Then you have to pull with all your might amid frustration and fear to get through the plateau and level up. Things look rosy for a fleeting moment, then you hit another plateau. And so it goes on until you reach the very top.

Most people quit on the first plateau.

The initial phase of speedy progress spoils your mind. When you suddenly have to expend tremendous effort to move another inch, your mind protests and tries to conserve energy. This holds true equally for weightlifting, entrepreneurship, and just about everything else.

Progress is the process of fighting through one frustrating plateau after another.

Complacency can destroy motivation

Comfort is the enemy of progress. In the same way that the comfort of your bed is pulling you away from your morning run, the comfort of succeeding in one segment of your business can pull you away from thinking bigger.

Say you finally have a cohesive team around you and you’ve cornered a niche within your market. After a long period of struggle, you are free to enjoy success. This feeling can be a bit too seductive, and every bone in your body will want to relax and enjoy it.

Expanding your market and hiring new people now feels like a tedious chore at best and an insurmountable obstacle at worst.

But stagnation means death in the ultrafast 21st century, and the prudent entrepreneur will not be lulled to sleep by small victories.

There is no final push

Spending too much time away from your family? Your kids miss you when you work long hours? You don’t call your parents often enough?

Many entrepreneurs perpetually feel that they just need one final push before achieving all they ever hoped for. Then they can finally relax and dedicate themselves to their family entirely. In reality, every “final” push is followed by another, and another, until you realize your children are all grown up and you’ve barely been there.

That’s why it’s important to maintain a sustainable work-life balance. Do your best to remain in that elusive Goldilocks zone where you do enough to propel your business forward but keep your priorities firmly in mind.

To do this, you must accept that entrepreneurship is your lifetime calling — there is no final push after which you retire and spend all day building legos and playing catch.

The boring bits are more difficult than the difficult bits

Difficult work is often challenging and enjoyable. Boring work is just difficult.

Many entrepreneurs tackle the biggest problems first (as they should) and enjoy coming up with creative solutions (as they should). Problems arise when they realize that there is 80% of the work left to do after this, and none of it is nearly as interesting and exciting.

It is like practicing sports — you can learn a few amazing moves and feel great about yourself, but it means nothing until you spend thousands of hours perfecting all the little patterns and details that make a complete player.


You’ll notice that the list doesn’t include anything about managing failure, getting up after you fall, etc. That’s because you’ve heard that advice a million times already.

I think most entrepreneurs are great at managing failure these days. It has become ingrained in our culture. More often, what gets you are the more insidious problems that creep up from the depths of your mind.

“What we find is that our brains have colossal things happening in them all the time.”

— David Eagleman

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