Think Like an Entrepreneur - Deborah A. Bailey

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"When nothing is sure, everything is possible." -Margaret Drabble

Often people aren't ready to take risks until they feel they have nothing to lose. That can come because of a loss of some kind or an event that wakes us up out of our complacency. The illusion of security is all too comforting, so much so that we can give up everything in order to preserve it. I say it's an illusion because there's no sure thing. Just because you're getting a regular paycheck doesn't mean it can't go away without warning. Your possessions can disappear in a natural disaster or be taken away. Too often we work at jobs we hate in order to pay for things that we really don't need. Then we sacrifice our true desires in order to continue to pay for more and more things. The big houses and stuff filling the garages give us some sense of place. It's as though the more space we take up with our stuff the more secure we feel. In the end, it's all just stuff. If you've lived a life of compromise because you didn't want to lose your stuff, you'll lose in the end. As they say, you can't take it with you, can you? When I left the corporate world I didn't realize how much of my identity I had to leave behind. My title and my job function defined me completely. My friends were from work, my income, my entire sense of self was tied to the workplace. My time wasn't my own, seeing how it was regulated by the workplace as well. So, when I decided to leave I didn't know what to do next. When my contracting position ended, I was immobile for about two weeks. I simply sat and stared out the window, unable to take any action. For the year I'd worked at the company I'd done my job and actually enjoyed it. I came to think of myself as an important part of the department. I liked the people who sat near my cubicle and regularly ate meals at the nice cafeteria. When I moved on I realized that though it was a comfortable situation, it wasn't a permanent one. The world kept turning without me. My department got their work done, the people sitting in my section went on with their lives. My identity may have been my job, but what happens when the job goes away? If your sense of importance is tied to a job title and it ceases to exist, what happens to you?


Prior to the contract ending I'd seen a show on TV about a well-known author and how she went to a café to write every day. I remember thinking how I wish I could do that and how wonderful it must be. Well, once the assignment ended I finally had my chance. Here was my opportunity to do the thing I craved and had wanted for years. But instead of stepping into it, I caved in and went looking for another job. At that time I was in a position to take the time to write, but I didn't see that. Instead the old programming in my head told me how wrong that was. I couldn't just sit and write all day. That wasn't a real job! Of course when I'd been paid to sit and write during my contracting assignment, the voice hadn't had a problem with that at all. But that was a "real" job in an office, not me following some daydream. The choices I made were based on fear of taking a risk. Instead of stepping through the open door, I ran to close it. After years of believing that I must work at a job I hated in order to make it, I refused to let go of that belief. I made choices based on my belief that I had to work to make things happen and not pay any attention to my real desires. I followed other people's advice, no matter how much I didn't agree with it. I didn't trust myself. What did I know? I invested in programs and paid people to help me who I was sure had all my answers. They didn't. In fact in many cases they didn't know much more than I did. My inability to trust myself led me into debt and anxiety over not being able to pay it off. I had simply recreated my corporate environment, except this time I didn't have the regular paycheck. I was frustrated, fearful and angry at myself for getting stuck in the situation. It sounded just like how I felt in my last fulltime corporate job. Finally with my back against the wall I realized I had nothing to lose by focusing on what I wanted. Continuing to do what I didn't want to do wasn't getting me anywhere, so taking a risk didn't feel quite so risky anymore. That is what leads most of us to finally just do it. Once you realize that the risk isn't quite so risky, it becomes much easier to do what you really want. If you're choosing between financial ruin and the potential for more ruin, that's not much of a risk. Entrepreneurs deal with that risk and that reality all the time. They learn from it, then get up and try again. There really can be no failure unless you stay down. Otherwise, it's a learning experience that teaches you what not to do next time around. Unfortunately in our culture failure is not looked at so benignly. It is not a learning tool, but a judgment. Winners are put on pedestals, but no one bothers to find out how many


failures they had to endure before they won. So, instead the "overnight success" myth or lottery winner mentality is perpetuated. It seems as though you just try something one time then like magic, it all works out with no effort, no stress and no risk. Yes, there have been situations where things have happened for people very easily. But on the back end of their success they've had to deal with how to maintain it. In the end you're going to learn those lessons in one way or another. As long as you want to keep evolving and step out of your comfort zone, you will experience failure. If you're not failing you're not growing, and if you're not failing you're not trying hard enough. Failing Forward Making mistakes is another way to learn and grow as you move towards your vision. Learning from mistakes is what really helps (as opposed to repeating the same actions and wondering why things don't work out). Once we learn from what we've done we can make better decisions. Experiencing mistakes may also lead us to find our purpose. If we're doing things that aren't working, then we're forced to discover why. In the process we may find that we really didn't want to do things that way. Perhaps we were going along for other reasons, or listening to someone else. Failure tells us that we're not on the right track. We may need to tweak a little or to make a major overhaul. Stepping Out of Your Comfort Zone This is a big one because for many of us the search for security has become a full-time job. Years ago it may have been possible to find security in a job, but that is no longer the norm. Trusting your intuition comes in very handy here. If we're leaping into something new we have to be able to trust that we're doing the right thing. That assurance can only come when our actions are aligned with our vision. Having low expectations of what we can achieve can lead to us staying safe-and staying stuck. I've been asked many times by people still in the corporate world if it's possible to work for yourself and duplicate your employee salary. Sure it is, but to be honest, why would you want to? Employee salaries are set by many factors that often have little to do with the quality of the work. Wouldn't you want more once you're in control of what you receive? Creativity Taking risks involves many factors, including the ability to be creative. As I mentioned, you have to release the old stories you've been telling yourself if you want to move forward. That means having an open mind for trying new things, and not judging them based on past events.


When you see the big picture you can determine what other factors are involved in your situation. For instance, an entrepreneur may look at overall trends before making a decision about launching a product or expanding a business. Being open to new ideas means they can release pre-conceived notions and try things that may be untried. Be Uncomfortable When we try something new we often feel awkward and uncomfortable. This discomfort comes up because we're having a new experience and have nothing to compare it to, or it's like a similar experience we had and we're anticipating the same thing. It's up to us to decide if we're going to react to the discomfort and stay stuck in fear or if we're going to move forward no matter what.

"If you have made mistakes, there is always another chance for you. You may have a fresh start any moment you choose, for this thing we call "failure" is not the falling down, but the staying down." -Mary Pickford Copyright © 2014 - 2017 Deborah A. Bailey

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About Deborah A. Bailey Writer, coach, marketing content strategist and author of 10 books including six novels and four non-fiction books, including, Think Like an Entrepreneur: Transforming Your Career and Taking Charge of Your Life. Deborah’s bylines have appeared in,,, Working World Magazine and She’s also a blogger and host of Women Entrepreneurs Radio™, a weekly podcast available on iTunes. Looking for personalized coaching to support you in reaching your personal and professional goals? Contact Deborah at [email protected] and find out about her Think Like an Entrepreneur coaching program. Or use the contact form on the site:

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