Entrepreneurial Courage: Why you need it and how you get it

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“Here’s to the crazy ones, the misfits, the rebels, the troublemakers, the round pegs in the square holes… the ones who see things differently — they’re not fond of rules… You can quote them, disagree with them, glorify or vilify them, but the only thing you can’t do is ignore them because they change things… they push the human race forward, and while some may see them as the crazy ones, we see genius, because the ones who are crazy enough to think that they can change the world, are the ones who do.”  ~Steve Jobs

And this, my dear readers is why I’m so passionate about working with and empowering entrepreneurs get out of their own way and break free from limitations that hold them back from being the change. Those of us who have heard the call and said yes to its whisper are the ones courageous enough to leave our jobs, step away from the perception of security, risk falling and failing, and ultimately undergo huge personal transformation….all in service of that deep dream that lives inside.


But it takes courage to play at this level. Courage to keep going when those around you chide you for being so ‘crazy’ as to wanting to do it on your own. And more courage yet to stay strong when the cash flow is weak and you might be swimming in fear and doubt, or can’t find the way to take your business to the next level.

That’s why I want you to keep reading the rest of this article. Because without courage – the journey can be very rocky.

“Your time is limited, so don’t waste it living someone else’s life. Don’t be trapped by dogma – which is living with the results of other people’s thinking. Don’t let the noise of other’s opinions drown out your own inner voice. And most important, have the courage to follow your heart and intuition. They somehow already know what you truly want to become. Everything else is secondary.”  ~Steve Jobs

Let me clarify what I mean by entrepreneurial courage. I define it as your ability to BOLDY express who you are in your business, make decisions based on your strengths and gifts, and the willingness to go against the grain – to stand out and listen to your own inner voice and vision versus following along with what everyone else is doing.

And that takes guts, let me tell ya! If you are to be a successful business owner you must be a leader! This is where the courage comes in. As an employee, it is very likely that you were given work or told what to do. But when it’s your own business, you are responsible for creating all of it. While you may have a team, ultimately, the success or failure you experience is on your shoulders.

That’s why this entrepreneurial journey is not for the faint of heart!

If you talk with anyone who has been on the path for a while, they’ll likely share with you the steps they took and what they bumped into to finally own their brilliance and build a business around it. You’ve likely heard my story….I had a master’s degree in counseling, practiced for 25 years, yet felt that was a liability as a business coach! I had coaching training and certification and coached and trained with some of the industries finest to integrate the business building, marketing, sales, branding, copywriting that I know today, but because I had been a therapist I still felt like it wasn’t enough. (Kinda wacky, but maybe I’m a slow learner.)

The journey for me to really decide to build my brand and my business on the fact that I am an expert in this mindset and inner game area was a painful one to be sure. Why? Because as I often say….“Your Brilliance Lives In Your Blind Spot.” So in my case all my mentors and business girlfriends could clearly see where my business positioning needed to be, but I,  1) didn’t value it, 2) couldn’t figure out how to market it, and 3) had no idea how to weave it through my business model. And that experience lead me to the path I am on today, and formed the foundation for the Inner Marketing Work that I do.

The craziest part? Just as in life, very often the thing we struggle with the most is where our gifts are and what we are actually here to teach. So guess what I’m teaching now? Yeah! How to get that brilliance out of your blind spot. How to have the courage to let YOU show up in your business, and how to make money doing what you love, and are good at.

“Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do. If you haven’t found it yet, keep looking. Don’t settle. As with all matters of the heart, you’ll know when you find it. And, like any great relationship, it just gets better and better as the years roll on. So keep looking until you find it. Don’t settle.”  ~Steve Jobs

But how do you get courage? How do you risk putting yourself out there when it’s new or it’s scary? The #1 thing – get support! Truly. The issue lies in that you can’t see what you can’t see. That’s why it’s my theory that your brilliance lives in your blind spot. Here’s what happens when it’s living there:

  • You can’t believe anyone would pay for it
  • You can’t charge appropriately for it because it “comes so easy” to you
  • You think everyone has it or can do it, so why do they need you?
  • You can’t figure out how to make it a business that makes money

I have worked with loads of business owners who were not loving their businesses because they weren’t marketing and selling the thing they should have been. They were listening to what someone else told them they should do, ‘selling out’ on their dream or chickening out and just taking the easy money.

And there’s nothing wrong with doing things to get some cash in the door! But is it costing you? If you are working with people that are costing you energy, it’s not worth it! Sometime we just have to make choices based on revenue, but if you are to have a satisfying and fulfilling business, it has to weave YOU in it.

But what kind of support do you want? Not just someone who rubber stamps your ideas. No, find someone who will challenge you to show up BIGGER than you are currently comfortable with. Find someone who will call you on your ‘stuff’ when you start backing down, and someone who takes the time with you to discover what you should be marketing and selling based on your unique gifts and talents and values.

The next step to get more courage is to create an empowering environment. Reading Steve Jobs quotes are inspiring and stimulating. Reading the Enquirer not so much! Listen to fellow entrepreneurs who have blazed the trail to show you that it’s possible. You must keep as much positivity in your environment as you can as you make the transition from just having a business to being the kind of business owner who’s making a difference in the world. It’s a big shift, so set yourself up for success by having an environment that pulls you forward. This is where vision boards and inspiring books, goal setting or affirmations come in.

And once you make the commitment to have a business you love, based on your gift and unique talents, it’s a whole lot more rewarding.

“Almost everything–all external expectations, all pride, all fear of embarrassment or failure–these things just fall away in the face of death, leaving only what is truly important. Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart.”  ~Steve Jobs

I couldn’t have said it better. Thanks Steve and thank YOU my readers for showing up and doing the great work you do in the world.

Peace and blessings!

Therese Skelly

Therese Skelly works with service professionals who love what they do and are ready to market and sell in a much easier and more authentic way. She blends her background as a psychotherapist, strategist, and business consultant and masterfully works both the inner game challenges and the outer game tactics. She is passionate about helping people create businesses they love. From newer business owners who want to design a business that serves heir life, to the already successful entrepreneurs who want to leverage their time and grow their income, to the heart-centered visionaries, Therese works with individuals like you who have a big desire to make a difference in the world. Learn more at www.HappyinBusiness.com

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