Mindset Shifts from Employee to Entrepreneur

9 Big Mindset Shifts to Move from Employee to Entrepreneur

After a lifetime of being told what to do, you want more control over your life.

You want to reclaim that dream you set aside—the one where you have your own small business.

Perhaps one where you can pursue meaningful creative work. Think small and sustainable, not launching a hungry startup that eats venture capital and ALL your time.

But if you’ve been an employee all your life, you’ll need to make some big mindset shifts to move from employee to entrepreneur.

Mindset is the way you think—the thoughts and attitudes that then drive your behavior.

The mindset you developed as an employee can form a brick wall blocking your path to becoming an entrepreneur. The better an employee you were, the more challenging the transition may be.


Because as an exemplary employee, you focus on achieving the organization’s goals, and you do what they tell you. Don’t make mistakes, don’t upset anyone, and work within your well-defined box. Regularly scheduled paychecks are the reward for your hard work.

Being an entrepreneur? Well, the hard work part is the same.

Knowing these mindset shifts in advance will prevent you from being blindsided by them.

So let’s not delay. Here are the top 9 mindset shifts to move from employee to entrepreneur.

1. Ditch Linear Thinking 

For hourly employees, there’s a direct link between hours on the job and money earned. And although it isn’t as direct for salaried employees, there’s still a link between time on the job and the paycheck. As an employee, you put in the time knowing that you’ll be paid.

To shift to an entrepreneur mindset vs. an employee mindset, you need to ditch this linear thinking. Smash the link between the time you spend working and the money you’ll earn from it.

Ignore the clock. Only the calendar will matter.

You’ll put in the time to create value without a guarantee or upfront reward.

For example, with a “passive income” business, you could potentially put in the effort and see little or no financial reward. You need to put in the time and effort and let go of expected outcomes in the beginning.


The benefits of your hard work are often exponential, not linear. That means nothing may happen for a painful amount of time. Then, if you’ve created value for the right market, everything can happen at once.

The benefits of a “passive income” business work in the same way compound interest does. Here you invest your time and effort without seeing much happen in the beginning. But when you hit that magic inflection point, your results can skyrocket.

Being patient while you build the base for that hockey stick-shaped growth is why most people quit. They don’t work through the time it takes to become an ace freelancer with a solid client base. They give up before their blog, or YouTube traffic can build. The work without reward can cause you to yearn for a job, for that morphine drip of a paycheck.

After all, it’s scary to put in work and know that you may or may not see a reward, which leads us to the second mindset shift.

2. Accept Fear as Your New Sidekick 

Courage is resistance to fear, mastery of fear, not absence of fear.
—Mark Twain

As an entrepreneur, courage is a requirement. Your new normal will be to step out of your comfort zone repeatedly.

A phrase you’ll see a lot in this realm is, “you need to get comfortable with being uncomfortable.” Your fear won’t go away, not as long as you are challenging yourself and growing. It’s part of the process of pursuing your dreams and building a business.

You have to take risks, and those risks can provoke fear.

Becoming an entrepreneur is like investing in the stock market. The greater the risk you are willing to take, the greater the potential reward. The good news is that, unlike the stock market, you have more control.

But you’ll need to be ready to accept the fear that comes with taking risks.

As long as you are doing work that’s important to you, you’ll feel fear. Every time I step up to my keyboard to write, that twinge of fear hits me. What if I can’t write today and nothing I say makes sense? What if I write this and everyone hates it? Blah, blah, blah, on it goes.

If I let that fear stop me, there is no writing and no forward progress.

Although fear is not comfortable, it is exhilarating when you move past it.

Plus, learning to accept fear will help you with the next mindset shift from employee to entrepreneur.

3. Vanquish the Demon of Perfectionism 

 Perfectionism and being an entrepreneur are mutually exclusive, like trying to whistle with a saltine in your mouth.

Perfectionism isn’t about being the best or producing something extraordinary. It’s the evil twin of procrastination. Its only job is to keep your dreams in the realm of “someday.”

It prevents you from moving forward because perfectionism tells you everything you do must be perfect. The first time. Even if you have no idea what you are even doing.

Guess what? That means never taking a step forward. It means staying stuck in the planning and researching phases and not moving forward to the oh-so-scary implementation phase.

No action means you get to feel safe in your cocoon of perfect. Everything gets to stay perfect in your head, but you don’t have a business until you move the ideas in your head out into the world.

Throw away your employee mindset of perfectionism. Maybe in a job interview, it worked to admit that you were a perfectionist because you could position it as a positive in the world of employment.  Because as an employee, you can get fired for making too many mistakes.

But without mistakes, you cannot be an entrepreneur. You can’t improve your skills without practicing. And practicing is all about making mistakes, then fixing them so you get better. Entrepreneurs seek constant feedback, and you only get feedback by practicing and putting yourself out there.

The goal is to create something and put it out into the world. Striving for perfect on the first try means it will never get done.

As an entrepreneur, you need to take imperfect action. Try something, fail, then try something different. Failing isn’t bad—it’s an expected part of learning.

4. Learn to Love Learning 

 As an employee, learning is crucial to your success. With technology upending entire fields and industries, just about everyone needs to get used to constant learning. But as an employee, the skill sets you need are reasonably defined.

Learning as an employee means drinking from a garden hose, versus as an entrepreneur, you’re drinking from the proverbial fire hose.

As an entrepreneur, you need the mindset shift that constant learning is normal, and it‘s okay to feel a little lost. In over your head. It’s all part of the process.

As an employee, a good employer will provide resources for your training and education. Here, it’s up to you.

So be ready to invest in your education. Set money aside for books, courses, coaches, masterminds, or accountability groups. As the owner of your company, you’re investing in yourself.

However, beware of the procrastination of taking endless courses and feeling like taking the class is the work. You need to take action on what you’ve learned. Implementation is the key to creating your dream business.

There’s a popular concept of “just in time” learning. This is where, as you need to learn a new thing, you find the resource to learn it, then implement it immediately. This article from Udemy is meant for organizations, but it does a good job explaining the concept.

You’ll need to love learning because, as an entrepreneur, the new things you need to learn seem to be endless. Because, at least in the beginning, you wear all the hats.

5. Prepare to Stack Hats

As an employee, you have a defined job. You go to work every day knowing what you need to do, and there are limits on what your company expects of you.

For example, in my previous corporate finance job, there’s no way I’d do the HR (human resources) work of finding job candidates.

Not so in the world of being an entrepreneur. It‘s all your job, especially when you first start out. Eventually, you’ll be able to outsource tasks, but in the beginning, it’s all you.

Some major areas included in your new life as a business owner:

  • Accounting/Bookkeeping. You’ll need a basic understanding of accounting since cash flow powers your business. Software or apps can help with the bookkeeping while you’re a small company, and you can hire an accountant for your taxes. But you need to know how to track your money so you can make informed decisions.
  • Marketing. To get that cash flow in the first place, you’ll need marketing skills. If your business is online, you’ll need at least the basics of digital marketing.
  • Technology skills. For example, to implement your online marketing techniques (like building a website or a landing page), you’ll need to learn the basics of the apps you’ll use. There are lots of free online tutorials available, and this is where courses can come in handy!
  • Project management. You don’t need to get fancy, but you do need a system to track your progress. Breaking down your big projects into bite-sized chunks is a reliable method to get things done while preventing overwhelm.

Learn what you need to get the job done and stop there. It can be an endless trap to learn all the things.

6. Figure Out How to Manage Yourself 

 One mindset that may surprise you is the employee mindset vs. entrepreneur mindset around managing yourself.

This one should be easy, right? After all, as an employee, you have to manage yourself to get the work done. As a model employee, you’re used to hitting your goals, meeting deadlines, and getting stuff done.

However, as an employee, you have a support system around you. Even if you were a manager, you probably had a manager, someone who helped you set goals or even dictated your goals. Someone to hold you accountable.

As an entrepreneur, you’ll need to manage yourself to get the work done. With no external support, it could be tricky. For example, working from home can lead to endless distractions. You’ll need to resist the pull of the dirty dishes and other mundane household tasks that suddenly look appealing when the alternative is doing stuff that scares you.

Here’s where joining an accountability group to give you that external support system you might need can help. It’s surprisingly difficult to do this yourself!

But it’s still up to you to manage yourself, to hit your deadlines. You need to stay organized and on top of ALL the details. There is no one to remind you of things. There is no one to drop by your cubicle and ask you how you’re doing or how it’s going on that project.

As long as you know this, you’ll be ready for it, leading to our next mindset shift.

7. Drop Your Dependence on Motivation

As an employee, you’re used to external motivation. The reward of a regular paycheck, or the consequences of not hitting your quarterly goals, can light a fire under you.

As an entrepreneur, you need to keep yourself motivated to do the work. However, for doing difficult things, motivation may not be enough. Relying on motivation is a trap.

A good example is writing. If you wait to be motivated to write, if you wait to feel like it, the odds are high that you won’t write at all. Ask me how I know.

So what works instead of motivation?

Creating a system, developing a process, and providing structure.

You need to create a system for yourself to get things done. What that system looks like is up to you and will depend on your business. As an entrepreneur, you are no longer in a system, so you’ll need to create one for yourself.

There are plenty of apps like Trello to help with this. Pick one app, build a system and stay with it long enough to benefit.

A process means some sort of checklist for your work to keep you on track and moving forward. As a bonus, checklists can help with perfectionism.

Structure means having an idea of what you’ll be doing every day. Without structure, you’ll probably struggle to get things done.

For me, structure means that I time-block my day and know what I need to do throughout the day. I have set times for my daily tasks. This means setting a time to write and showing up every day at the same time ready to write regardless of how I feel about it.

If I were to wake up each day and decide whether I felt like writing, you wouldn’t be reading this.

Prepare to make a mindset shift from relying on motivation to depending on the systems, processes, and structure you create for yourself.

8. Embrace Planning for Both the Short-Term and Long-Term 

 In preparing for battle I have always found that plans are useless, but planning is indispensable.    

—Dwight D. Eisenhower

As an employee, you receive your goals. Even when you’re allowed to set your own objectives, it’s always under the umbrella of company goals. After all, your job is to meet the expectations of your employer.

Rarely do you set long-term goals or help with high-level strategy.

Not so as an entrepreneur. You start with the high-level picture. Your business needs to support your lifestyle, to be part of your life. The strategy is up to you. You’ll want to think far into the future.

When you live an intentional life, your business is an integrated part of your life. You create a business that allows you to do the work that honors who you are. Your values are essential to making your business work as part of your life.

Courses can provide guidelines, but there is no one-size-fits-all instruction manual. As an entrepreneur, you create your own path. The value is in planning, not the plan itself. You don’t know exactly what will work. You can only stack the odds in your favor.

Unlike as an employee, as an entrepreneur, it’s okay to break the rules. Doing things differently could be the only thing to distinguish you from your competition.

So you’ll start with the long-term vision or strategy, knowing that even if this fails, you’ll benefit through the work you’re doing. Follow a strategy that makes the journey worthwhile regardless of financial outcome.

Yes, you need to plan out the short-term tactical steps. But don’t ignore this mindset shift that you handle the long-term planning as well.

9. Believe in Yourself 

Hey, I saw that eye roll. But seriously, stop and think about it—if you don’t believe that you can do this, it will be easy to quit.

Impostor syndrome is the painful belief that “you are not as competent as others perceive you to be,” as this article in Verywell Mind points out. It’s when you don’t own your power and skill, which can lead to crippling self-doubt.

Self-doubt is that tight feeling in your chest or the pit of fear in your stomach when you step outside of what you believe is possible.

It’s a mindset you can work on as an employee right now. Ask to work on projects that are a stretch for you to expand your mental model of what you are capable of.

You can survive with self-doubt as an employee. When they still let you in the doors each day or your log-in works, that’s a solid indicator you’re doing well. If you aren’t sure, you can simply ask. As an employee, there is no shortage of feedback.

However, as an entrepreneur, you begin in a void. Especially if you are creating an online business, like a blog, you will experience soul-crushing silence in the beginning.

If you doubt your ability, you’ll end up quitting. Quitting is an automatic fail. As an entrepreneur, the mindset shift to the belief that you can do this is not optional.

I saved this for last because it will come up again and again. As you grow, and with every additional step you take, self-doubt slithers up in your brain. First, fact-check it to see if the doubt is justified since sometimes a dose of self-doubt can keep you out of trouble. But most of the time, it isn’t. Then ignore it and move forward anyway.

Stop Waiting for The Right Time to Make Mindset Shifts from Employee to Entrepreneur

Making these mindset shifts from employee to entrepreneur will take time. The longer you’ve worked as an employee, the harder it is. But it is possible.

The safest way to begin is to start a “side hustle” now while you still have a regular income.

Then you can practice these mindset shifts without risking much more than your time.

Pick up those dreams you set aside. There’s no reason to wait any longer to start that business you’ve been dreaming of.

It will be time well-spent if for no other reason than the personal growth you’ll experience as a result of these mindset shifts.

To keep you motivated, imagine how it will feel to have your own beautiful income-producing business as part of your intentional life.

Take one small action today to bring your dream closer to reality.



IMAGE BY: Photo by Leonard von Bibra on Unsplash