How to Go From Employee to Entrepreneur

UPDATED: March 28, 2016
PUBLISHED: March 28, 2016

When I first struck out on my own as a freelance writer in 2005, I had worked a lot of jobs as an employee. I was a manager in some cases, but I was still someone else’s employee. What I didn’t realize is that I carried that employee mindset into my business. And that’s one of the major reasons I failed.

As an employee, I looked at my job almost as a necessary evil. I needed to do the work to make a living. Sometimes, I put all I had into a project I enjoyed, but for the most part, I struggled to work beyond the bare minimum. I felt resentful that I wasn’t in charge or frustrated that I couldn’t control my working environment. I looked at what was wrong with my job, with my co-workers, with my bosses. I didn’t know it until the very end, but what I longed for was the freedom of entrepreneurship.

Related: How To: Leave Behind Your Day Job & Go Solo

I felt trapped and would have told you back in 2005 that my job—no matter how great the job I happened to be in at the time—was a prison.

What I didn’t understand was that the prison was my own perspective. All I could see was that working for someone else drove me crazy, and I couldn’t wait to quit so I could go into business for myself. Unfortunately, going out on my own wasn’t all it took to break free.

The Prison of Perspective

Finally my own boss, I thought everything would improve right away. But as I started working from home, I continued to look for what was wrong, and who or what I could blame. I thought about how my clients were treating me badly, how my hours were too long, how my work wasn’t meaningful, or how I was a victim of some personal circumstance or other.

This victim way of thinking, what I call the employee mindset, says we are at the mercy of some menacing, greater power that runs our lives. This false perspective must be destroyed if we want to succeed as business owners.

But here’s the holdup: The scariest thing about this perspective is that while we’re in the thick of it, we can’t see it. We don’t recognize that our own thinking is clouding our vision—because every time we look around, all we see is the fog.

By 2008, I had failed as a full-time freelance writer. I didn’t realize until many years later that my mindset was a key factor in that failure, so I want to help you self-diagnose this problem before it’s too late for you.

Here are three clues that you’re trapped in the prison of your perspective.

1. You resent your clients.

Look, everyone has a bad-apple client now and then. But if you resent most of your clients most of the time, chances are you’re blaming them for your lack of time, money or respect. If this is you, then this next sentence is probably going to piss you off: You lack time, money and respect because of your choices, not because of your clients. What hours you choose to work, how much you charge, what clients you accept, and how you position yourself with those clients are all choices you make on a daily basis. The responsibility is ultimately yours. Now, you can see that as good news or bad. I see it as good news because if my choices are making me miserable, I can actually do something about that. And fast.

2. You lead with the problem.

When someone asks you how you’re doing or how’s business, you start by telling them the reason that things aren’t going the way you’d like. Whether you’re trying to protect your image or avoid criticism from someone, this problem-focused dialogue is a symptom of a bigger problem: your mindset. I’m not saying you have to slap a smile on your face when things aren’t going well, but I am saying that if every conversation you have about your work life starts with what’s going wrong, then you are likely using that challenge as an excuse not to be your best. Whatever challenge you’re thinking of right now is the one you need to start with—write down three ways you can improve this challenge or ask for help seeing the challenge in a new way.

3. You long for the days when you were employed.

After I started freelancing full time in 2005, I went through a honeymoon period where no matter how broke I was, I was still happy because I wasn’t working for someone else. But this wore off. I soon found myself longing for the seeming security of a regular paycheck and someone to decide what I worked on and when. For a person who is so clearly a born entrepreneur, this is weird thinking. If you spent years wishing you were on your own and now that you are, you’re wishing you could go backward, there’s something wrong. And it’s likely your perspective on your own business. Ask yourself why you long for someone else to be in charge of your time, your purpose and your finances. I’m betting the reason is fear. If so, talk it out with a trusted friend and make a game plan to walk through it one step at a time.

Make the Break

The flipside of this perspective prison is what I call an entrepreneur mindset. Don’t be fooled into thinking that you need a big operation or a large team to think like an entrepreneur. This mindset is about the following principles:

  • Responsibility. You own your circumstances and realize that, for the most part, your choices are creating your reality.
  • Accountability. You’re able to share with someone else, a mentor or coach, the triumphs and failures of your everyday work life.
  • Positivity. You can see the bright side of challenges eventually, and you actively seek an attitude of gratefulness, kindness and hope.
  • Flexibility. You know that to grow, you have to change. And to change, you must do regular personal development, often with someone else’s help.
  • Acceptance. You recognize what you can’t control, accept it and move on to tackle the things you can control.

After my first freelance failure, I went back to work for someone else for four years. When I relaunched my business full time, I included these principles in the core values of my business plan. I set in place some tools and habits that would ensure I practiced these principles on a regular basis—things like belonging to a mastermind, daily reading for personal development, and boundaries I don’t compromise around time and money.

You may be telling me in your mind that I don’t fully understand the extent of your disadvantages, relationships or experiences. And you’re right. I don’t. Neither do you understand everything I’ve been through or overcome to be where I am.

We each have challenges. Illnesses. Tragedies. Traumas. Setbacks. We each live life in the best way we can. Until we learn a better way.

But think about this: Would you rather continue blaming someone or something for a circumstance that might actually be within your control to better? Or at least within your control to work around? For me, recognizing where I was blaming someone or something for holding me back, for keeping me from being my best self, was a vital step in becoming the kind of business owner who actually feels free, not just employed by the woman in the mirror.

Related: Do You Have What It Takes to Be an Entrepreneur?

Amy Anderson is the former senior editor of SUCCESS magazine, an Emmy Award-winning writer and founder of Anderson Content Consulting. She helps experts, coaches, consultants and entrepreneurs to discover their truth, write with confidence, and share their stories so they can transform their past into hope for others. Learn more at and on Facebook.