The 6 inner battles you’ll never win, (and why that’s a good thing)

Entrepreneurs tend to be high-achieving types. They can focus on a goal and pursue it relentlessly. This results-oriented life can have drawbacks though. If you spend your whole life aiming for a big goal, what happens after you achieve it?

You finally make that 7-figure business.

You create the nonprofit that makes an impact on policy.

You’re able to build a team and remove yourself from the business entirely.

You make the New York Times bestseller list.

The hidden trap of goal setting

There’s a danger that once you complete a goal that you have worked for many years or even decades to reach, you’re left with a void where the goal once was. It’s easy to fall into a trap where you start to measure your personal value, or your identity, against your goals.

Sometimes this goal can be easily replaced with another, and life goes on. Sometimes, when we build our identities around a big goal, the void that is left when we complete it can crush us. The reason for getting out of bed early, working long hours and focusing your energy disappears. It becomes difficult to find meaning again, to define yourself without the goal, to find a new way to motivate yourself.

So how can we protect ourselves against this potential disaster? Should we not have ambitious goals?

Your goals are important; they are a compass for your life, but they can’t be a foundation for your identity.

What if you focused on the daily battles that play themselves out in small ways in your life, but add up to incredible results over time. These battles can never be won, but that’s exactly what makes them so great. You’ll have a fresh challenge every morning, always a new opportunity to better yourself and build your confiedence.

In this post, I’ll outline 6 of the many inner battles entrepreneurs (and most other humans) face that can never truly be won, and give you some ways that you can put this into practice in your own life.

Managing uncertainty

Reading biographies or blog posts about how an entrepreneur achieved success in one way or another can be misleading. It’s easy to look back on past achievements and connect the dots that lead to them. It’s human to try and make sense of things this way.

But things are hardly ever so clear at the outset. It’s more likely that you’re uncertain of the outcome of what you are doing or you are faced with choices without an obvious answer as to which is right for you.

This uncertainty can be difficult to stomach at first, especially for young entrepreneurs. We have very little practice experiencing or managing uncertainty. In school, everything is orderly, and the path to a desired result like a good grade is crystal clear. Most of the jobs that a young person could usually get also are very clear on what the expectations are.

The battle here is to make a decision and take action despite the uncertainty, and to keep working without any guarantee on what the outcome of your work will be.

How does managing uncertainty apply to entrepreneurs?

As an entrepreneur, you are basically signing yourself up to dive head first into the waters of uncertainty and never return to the shore. You are always confronted with what you don’t know, and that’s not a comfortable place to be.

An entrepreneur is always toeing the edge of their limits. As soon as something is understood, organized or proceduralized, it can be delegated. Then it’s on to the next uncertain task.

The skill here is to change your attitude toward uncertainty. The natural reaction to feeling uncertainty is to feel insecure, fearful and disempowered. None of these are helpful. Since uncertainty is such a core aspect of the entrepreneurial experience, uncertainty should help you feel like you’re on the right track.

How to practice managing uncertainty

The first step to is embrace the fact that you always have much more to learn, and be humble enough to recognize when you’re uncertain. Uncertainty is only dangerous when your ego has gotten out of control. If you deny it, then you start to make rash decisions, close yourself off to new information and feedback from others, and make your problems worse.

In his post titled “11 Ways Emotionally Intelligent People Overcome Uncertainty”, Dr. Travis Bradberry points out that it’s helpful to understand what’s happening in your brain when you’re experiencing uncertainty. Simply being aware of what’s happening can empower you to change how your brain naturally responds.

The limbic system responds to uncertainty with a knee-jerk fear reaction, and fear inhibits good decision-making. People who are good at dealing with uncertainty are wary of this fear and spot it as soon as it begins to surface. In this way, they can contain it before it gets out of control.


So the first step to better managing uncertainty is to practice being aware of when you are feeling it. Do you get a feeling in your stomach? Does your breathing get shallow? Is there a certain thought pattern that you experience?

Once you start to recognise it, it’s easier to change the behavior or sensation by remembering that what you are experiencing is an old evolutionary response that is not useful in your current situation.

A great read on managing uncertainty at many different stages of life, business and success is Ego Is The Enemy by Ryan Holliday.

Delayed gratification

There are no true overnight successes. Behind every successful entrepreneur, you’ll find thousands of hours of hard work that went unnoticed. Most the these hours are filled with mundane and thankless work.

It’s not like they have nothing better to do. There’s endless opportunity to spend time with friends or family, start a new project, or get a job that pays better.

They are delaying gratification to the future; they are making a bet on themselves. They are frontloading the discomfort that comes with doing anything worth doing so they can enjoy greater rewards in the future.

This is not something that comes naturally to humans. Just take a look at “The Marshmallow Experiment” where kids were given a marshmallow and told they could have another if they wait to eat the first one. These kids were in a private room and presented with the deal. Here’s a link to the original experiment this video was based on.

How does delayed gratification apply to entrepreneurs?

“If you want to succeed at something, at some point you will need to find the ability to be disciplined and take action instead of becoming distracted and doing what’s easy. Success in nearly every field requires you to ignore doing something easier (delaying gratification) in favor of doing something harder” ― James Clear

James Clear Delayed Gratification

The struggle to delay gratification is a series of hundreds of tiny battles throughout the day-to-day of an entrepreneur. It’s the choice to hit the snooze button or to get up and have a miracle morning. It’s investing your profits from your big launch back into your business instead of replacing your 2002 Corolla. It’s turning down an invitation from friends to watch the big game on a Friday evening to prepare for a product launch.

The ability to delay gratification is one of the most common indicators of long-term success in life, whether it’s building a business, improving a relationship, losing weight or learning a new skill.

How to practice delayed gratification

One of the easiest ways to practice delayed gratification is actually quite gratifying once you get the hang of it.

You need to pick a pick a fight with the snooze button.

Try waking up an hour earlier every morning and doing something to improve yourself. It does not necessarily have to be related to your business; it could be a yoga routine, practicing your writing, reading something inspirational or educational. It simply needs to be something to better yourself.

You’re delaying gratification twice with this practice. First, you’ll have to set your alarm at least hour earlier and fight the battle to get out of bed. You’ll also likely have to give up some part of your nighttime activities to get to bed earlier, perhaps giving up watching an episode of Game of Thrones before getting to bed.

Practicing getting up early consistently and rewarding yourself by doing something you find to be a healthy way to improve yourself trains your brain to see delayed gratification as a positive thing. The more you do it, and the more enjoyable the morning activity you choose is, the easier it will become over time to delay gratification.

A great read to get some ideas for what to do early in the morning, and some easy tactics to get out of bed and actually doing them is The Miracle Morning by Hal Elrod.

Going against the grain

“Normal is so ingrained in what we do every day that it’s difficult to notice that your tendency toward the normal is now obsolete.” ―Seth Godin

Seth Godin Normal

Most of the values of modern societies don’t align well with what it takes to be a successful entrepreneur. Going with the flow that most people follow will only lead to average results.

Concepts that are fundamental to entrepreneurs like “delayed gratification” are not often encouraged in our culture. You’re constantly bombarded with messaging and social norms that would like to nudge you off the path you’re on. Messaging in the media is always pushing you to “buy more stuff” and “treat yourself”. A script of how your life should play out has been ingrained into our culture, go to college > get a job > get married > buy houses and cars.

This sometimes means you’ll clash with people. Your friends may not understand why you need to leave the party early on Friday night so you can wake up early on Saturday to finish the article you’re writing. There may be a few years where you struggle to get your business or project off the ground and you may appear like a loser or a quack to the people around you.

How going against the grain applies to entrepreneurs?

As an entrepreneur, you’ll need to become comfortable with going against the grain, choosing to think and act differently than most. This will require sacrifice and having your boundaries constantly tested.

Often innovation and creating something truly great will require going against the grain in a certain industry or defying a certain norm. This resistance will continue to grow as you gain momentum. This pressure and friction is the crucible where many great ideas turn into great companies.

There will also be moments where your resolve is tested as a leader. You may be faced with a difficult decision in the future. Your choice may not be the popular one. But being a leader or an entrepreneur is not about popularity, it’s about doing what you think is right.

How to practice going against the grain

No matter where you are in life, you’ll save a lot of time by not worrying too much about what other people think about you. The earlier in your life that you can learn that, the easier the rest of it will be.” ― Sophia Amoruso, quoted in #Girlboss

Sophia Amoruso

Get yourself a piece of clothing of some kind that is slightly to moderately ridiculous, and wear it in a situation that is normally professional. The clothing should not be so ridiculous that it offends people or causes confrontation, but it should be enough that you catch some sideways glances.

You’ll feel uncomfortable, especially at first as people notice your strange clothing choice and react to your breaking the norms. That’s exactly the effect you want. You want to work the “muscle” of tolerating that sense of breaking the norm and going against the grain. So when the day comes that you need to make an unpopular decision, but one you know is right, you’ll have been practicing for this moment and you’ll be able to make the call without bending to what others think.


Ever heard the phrase “talk is cheap”? It points out the fact that most people can say they’ll do something, but few end up taking action and doing it.

Integrity is your ability to “do what you say you’ll do” and keeping the commitments you make to yourself and others.

Integrity is not some sort of “moral high ground,” it’s an essential skill to navigate through the world. The world is changing at an ever increasing pace; it’s almost impossible to predict what tomorrow will bring. Among all this change, the last thing you need is variability in yourself and uncertainty in what you do.

How does integrity apply to entrepreneurship?

Without integrity, success is just a product of luck, the work you do is random and inconsistent, and you can’t ever be sure what is truly driving your success.

The game of an entrepreneur is to invest in their word, to be able to bet their business on what they say they’ll do. To highly value their promises both big and small, and carefully consider everything they commit to.

Keeping integrity requires enforcing personal boundaries. Often you will be faced with opportunities, offers and temptations that conflict with the commitments you’ve already made and must turn them away or break your integrity.

Being able to maintain your integrity requires a deep understanding of your own motivations, limits and goals, and to carefully weigh each commitment you make in that context.

How do you practice integrity?

Get a small stack of notecards.

At the end of the week, take some time to think about 4 or 5 things you could do next week to improve your business, your project or improve yourself in another way. They should not be things that you were going to do anyway. “Go to work” does not count.

Keep the card with you always. Look at it first thing each morning during that week. Promise yourself that you’ll get these things done, and plan out your days so that by the end of the week you’ll have checked off everything on that card. Play a game that your life depends on getting what’s written on that card done.

Keeping your card with you will enable you to write down new commitments you make during the week. The limited space on the note card will serve as a constant reminder to your limited time and resources available to keep your weekly commitments. This will cause you to think twice before saying “yes” to something you aren’t sure about.

Take some time at the end of each week to reflect on the commitments you made, which ones you were able to keep and which ones you did not. You may not be able to check them all off each week, but simply confronting yourself with the fact that you did not achieve it is a helpful and healthy practice.

Deep work

“Focus means just that: to narrow your vision to focus on one thing to the exclusion of other things–for now. The consequences of not focusing your mind on your work are creating defects if you are a developer, missing defects if you are a tester, and everything taking foreeeevvvveerrr no matter who you are.” ― Johanna Rothman

Johanna Rothman - setting goals focus

One of the most difficult battles that an entrepreneur faces is the battle for their attention. Modern society is filled with advertisements and distractions that we crave in the same way a small child craves sugar. Not only that, but with communication technology, it is so easy to contact people that you are constantly bombarded with “urgent problems” or “once in a lifetime opportunities.”

Focus is a process similar to sleep. As you go to bed at night, you enter several different phases of sleep before you arrive at the deep dreaming state known as REM sleep. You cannot immediately enter REM sleep, it’s a slow process.

Imagine how you would feel if you were trying to go to sleep, but every 15 or so minutes, your phone buzzed or you got up to check your email or someone came into your room with a “quick question.” It probably wouldn’t be your best night of sleep, right?

Focus works in exactly the same way. You do your best work like you get your best sleep. A long, uninterrupted streak focusing on a single task.

How does deep work apply to entrepreneurship?

If you’re not careful, it’s easy to be swept up in these distractions and lose a whole day spending time on low-value tasks. Days like this where your attention jumps from email to email, over to Facebook, then to a text and so on, leave you feeling exhausted and frustrated. Where a day of shallow, distracted work leaves you feeling the same way as a poor night of sleep, a day where you successfully maintain deep work leaves you feeling fulfilled, energized and confident.

Typically the kind of work that leads to success for entrepreneurs is the work done while laser focused on a single task for a long period of time. These are the moments where you’re in your groove, many people refer to this as a “flow state.”

Often the work that requires you being in a “flow state” to do your best is the important but not urgent work that leads to success.

It’s preparing that great talk at a conference, it’s developing your website, it’s writing another chapter in your book, it’s creating that “new feature” in your app that’s going to change the game.

How can you practice deep work?

A popular method for achieving a flow state is known as the Pomodoro Technique. This is also an excellent tool to organize and manage your days.

The Pomodoro Technique is simple: you choose a single task to focus on for 25 minutes, set a timer and go for it. 25 minutes is a manageable block of time. You can go for 25 minutes without checking Facebook or your email, right?

After 25 minutes is up, take a break! Take 5 minutes to do whatever you want. It helps to set a timer for your break too. Most people don’t take the full 5 minutes or take too long, either one will hinder you. I usually prefer to stand up, move around a bit and do a single exercise, or step outside and take some deep breaths.

Then repeat the process. Go back to the same task you were working on before or choose a new one to dedicate 25 minutes to.

You can get very advanced with this technique and use it as a way to track the work you do, measure how long it takes to complete certain tasks, and use that information to plan your days out. If you’re interested in going deeper with the Pomodoro Technique, I suggest taking a look at Pomodoro Technique Illustrated: The Easy Way to Do More in Less Time

Building habits

“By forming good habits, we can free our minds to advance to really interesting fields of action.”

― William James, quoted in Daily Rituals: How Artists Work


Willpower and your ability to make decisions are limited resources. Fighting the many battles described in this post with willpower alone is not sustainable. Success is a habit or a collection of habits.

A habit removes willpower and decision making from an activity. A strong habit happens almost automatically without any conscious effort on your part. Building habits is one of the ways you can win these many different battles without exhausting yourself. It’s a slow process of development that you practice a little every day.

A good habit executed without a decision and willpower on your part not only provides the benefits of the habit, but also saves your limited willpower for other tasks throughout the day.

The greatest danger to habits comes in a different form. It usually happens when things are going well and you want to “treat yourself” or just “ease off the gas a little”. You miss a day at the gym, you sleep in one morning and your habit starts to corrode.

Even small interruptions to these habits can set you back for weeks. A week-long vacation can devastate a good morning routine.

Uprooting bad habits is just as essential and difficult as maintaining good ones. Again, willpower is not enough here.

How does building habits apply to entrepreneurship?

Actively cultivating good habits and removing bad ones is a battle many entrepreneurs constantly face. It’s something you’re never really finished with. Habits require constant maintenance and diligence to keep sharp, but their rewards are powerful.

Habit plays a key role in nearly all of the skills and struggles mentioned above. Becoming a better entrepreneur or achieving greatness in anything in life involves weaving many good habits together and building on them.

A great writer does not struggle to get out of bed in the morning and write, a great athlete does not need a pep talk to get to the gym. There’s never a question in the first place, it happens of itself.

How do I practice building habits?

“We are what we repeatedly do. Excellence, then, is not an act, but a habit.” ― Aristotle

Habits like waking up early to write or getting proper exercise all have a single pattern at their core. If you understand that pattern and how it works for you then you can take an active role in building your habits.

Building or breaking habits requires a deep understanding of your motives and the subtle triggers that set off the habit process in your mind before you even realize it.

Do you have any notecards leftover from the commitments exercise?

Take a fresh card, and write a good habit you want to develop or a bad habit you want to remove at the top. Write out 3 things below the habit:

  • Trigger – The event that starts your habit.
  • Action – The action you take during your habit.
  • Reward – The way you reward yourself after completing your habit.

For good habits:

For a good habit that you have yet to form, you can experiment with different triggers and rewards. Come up with something that could reliably remind you to start your habit. Perhaps there are common triggers in your life that you can use. Things like “finishing lunch,” “getting home after work,” or “thinking about coffee in the morning” can work as a trigger.

The action is what you will actually do as your good habit. In the beginning, make it as easy as possible to achieve. If you want to start going to the gym more, the first day of building the habit could be as little as putting your gym clothes on. Build on it slowly to not exhaust or demoralize yourself.

Then choose a reward. Make sure it is something good that you’ll truly enjoy once you complete the action.

Keep your card with you, and try to be aware when the trigger you have chosen is going to happen. When the trigger occurs, take out your card, and use it as a reminder for how you want your habit to happen. Try to follow the process you’ve written down.

For bad habits:

For a bad habit, you’ll need to be mindful and figure out what the triggers and rewards are. When you feel yourself slipping into your habit, don’t resist yourself, just try to observe what is happening, what is the trigger? What is the reward you are craving? Write it down on your card.

Once you have the trigger and reward identified, you can do one of 2 things. Remove the trigger from your life or use the trigger to cultivate a good habit. Just cross out the part you want to change and replace it with a new and better activity.

Whenever you feel the trigger starting to pull you into a bad habit, take out your card, and look at what you want to change about it. Try to do the new action you’ve chosen or pursue the new reward.


These “battles” are all valuable pursuits to your life. They can never be won, and the only way you can lose them is to give up on them entirely. You won’t be able to keep the same pace all the time, sometimes you’ll falter and fail in one area or another, but every day will provide new opportunities to get back on track.

Since these battles can never be truly won, don’t rush or force them all into your life at the same time. I recommend starting small when pursuing these things, don’t try to do all of the exercises at the same time. Start with one that seems like it could deliver some early wins.

Which one will you start with? Which one seems the most promising for you? Let me know in the comments!

Kyle Gray
Kyle Gray is the founder of Conversion Cake, where he helps small businesses and startups with content marketing strategy and sales funnels. He is also the author of “The College Entrepreneur” a guide that teaches students how to build an entrepreneurial skillset while in school and use their university’s resources to help them build something amazing.