When billionaire Sara Blakely was growing up, her father would often ask her the same question at dinnertime, “What have you failed at this week?” Known for every woman’s favorite shapewear, Spanx founder, and CEO, Blakely’s embrace of failure has made her the youngest (41) self-made female billionaire in America.

My dad growing up encouraged me and my brother to fail. The gift he was giving me is that failure is (when you are) not trying versus the outcome. It’s really allowed me tobe much freer in trying things and spreading my wings in life.


When you come across a great idea for a side business doesn’t it make your heart beat a little faster with the urge to pursue it?

It’s exciting to think about the possibilities and what it would be like to put yourself to the test and see if you could make a go of it. The thought of using your energy, hard work and talent to your own benefit and the well -being of your family, instead of someone else’s, is so attractive that’s it’s practically irresistible. Unfortunately for many women, self-doubt kicks in and they begin a quick process of abandoning a great idea before it even has a chance to get started.

Overcoming the fear of failure in business is the boldness of “faking it till you make it” mixed with research, combined with elbow grease and topped with opportunities. Every successful woman before you has struggled with feelings of failure (including us) and we’ve come up with Five Ways to Overcome the Fear of Failure in Business:

Have Realistic Expectations

While diving into your new venture is absolutely the correct mindset, expecting that you’ll make a million dollars your first year is setting yourself up for major disappointment. You will not make a million dollars your first year. In fact, you might just break even or you might only make a small profit. But don’t let that scare you – your first year is about grasping the opportunity, getting paid what you deserve and finding your stride. Accept that it will be hard work, you’ll be simultaneously frustrated AND elated and you won’t have a mean boss breathing down your neck.

Set Attainable Goals

Setting goals is not an easy task. In fact, I like to call it the “Elusive Art of Goal Making,” because creating a set of goals is always a moving target – just slightly out of reach, completely necessary and always changing. Creating goals should be a SMART process:

S: Specific, M: Measurable, A: Achievable, R: Results-focused, T: Time-bound

  • Specific: What will the goal accomplish? How and why will it be accomplished?
  • Measurable: How will you measure whether or not the goal has been reached (list at least two indicators)?
  • Achievable: Is it possible? Have others done it successfully? Do you have the necessary knowledge, skills, abilities, and resources to accomplish the goal? Will meet the goal challenge you without defeating you?
  • Results-focused: What is the reason, purpose, or benefit of accomplishing the goal? What is the result (not activities leading up to the result) of the goal?
  • Time-bound: What is the established completion date and does that completion date create a practical sense of urgency?

For example, a SMART goal might be aiming to host 4 Princess Tea Parties per month (1/per weekend). Is it specific? Yes. 4 per month. Measurable? Yes. Achievable? It’s possible, yes. Have others done it? Yes (we have lots of stories about how we did more than one party per weekend). Do you have the necessary knowledge and skills? Yes and no. You will have the Princess Tea Party Business Kit, but you might still be a little “green” in the experience area. Will it challenge you? Definitely. Results-focused: Purpose/Benefit: Gain more experience in presenting the parties, and gain some income. Time-bound? Yes. One month.

Setting SMART goals is a practical way to overcome of the fear of failing. If you have a plan, even just a small one, you can focus on the plan and not the path.

Build Relationships

Humans don’t do business with companies, they do business with people. The more people you tell about your business, the more it comes back to you. We all know that Word of Mouth is the most powerful form of marketing, and in the beginning, it’s the words from YOUR mouth that will start the ball rolling. Join a networking group, or three. Search on MeetUp for “networking” + your city and you are bound to find at least one group that would be happy to have you. Another way to build relationships is to do a few parties for free. Ask parents you know or friends if they would let you throw a party for them in exchange for a few positive Yelp Reviews. And yet another way to build relationships is with complementary industries. For example, you might decide to have tea sandwiches at your parties. Find a local caterer who might be willing to partner with you to see how it goes. Offer to spread the word about their catering and them about your parties and keep that relationship sacred.

Do Something You Describe As Impossible

The true tip of how to overcome the fear of failure in business is to gain confidence. We gain confidence by doing things we we didn’t believe we could do. For example, a marathon might seem impossible to you, but completely possible to someone else. Or someone else might think to have children were impossible and you might not. Or, another person might think to attend a networking group by yourself was impossible, but you think it’s just meeting new people. The key is to find out what that impossible thing is and do it. Want to lose weight? Find a diet and exercise program that fits your schedule, that you can commit to and do it. Overcoming a big “impossible” thing is one step toward recognizing that fearing failure is just as much in your mind than anything else. The power is yours to change the direction of your thinking to see that success is attainable, and, that you are as worthy of it as the next person.

Having been in business for many years there were times when my ideas didn’t pan out or promotions fell short.

In life, there will be obstacles along the way, and at times feel like it is trial by fire. They are there to be overcome not feared and to weave strength into the fabric of your business and life in general. I’ve always felt that the only way I could fail was if I quit. Since that was not an option, pushing through to success was the only way to go. It worked out better than I could have dreamed. In my Princess Tea Party business, little girls come to have their birthday princess dreams come true. It is a happy place where parents are thrilled to give their children a unique and wonderful experience and love seeing so many smiling faces.

And while it’s a completely different kind of happiness than the kind that Sara Blakely brings to women, it’s still just as rewarding. I’ve done it for nearly 20 years now, and the secret is simple: Have confidence in yourself, create attainable goals, take one day at a time, and believe that you are making the world just a little better everyday.

Start that Side Business. JOIN MY NEXT WEBINAR HERE

References for this article:

  1. Billionaire Sara Blakely says the secret to success is failure.

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