“Fail Faster, Fail Forward” by Kristina Tsipouras for International Women’s Day

We are inspired by leading ladies, girl bosses, power mamas, and everyday women who are doing great things. The Cool Down is dedicated to shining a light on just a few of these special women who provide powerful advice, inspiring stories, and motivating mantras; from fitness gurus, to charitable divas, magic moms, to start-up CEO’s, we try to cover relatable topics across the board that tap into what you, our readers, want to hear most. In honor of International Women’s Day, we encourage you to dive deeper into our archives to catch up with some of our inspiring guest bloggers, and keep reading to meet one more…

“Fail Faster, Fail Forward” by Kristina Tsipouras

Most of us grew up being told to never quit, to never give up, to push and to fight until the end. In this blog, I ask you to re-define failure, quitting and what it means to you. If you look back at your life, when you quit and changed directions, was it for the best? Did you follow your heart and did it lead you to bigger & better things? Do you wish you had quit sooner? The most difficult part of life is to let go of the oars and stop trying to steer the ship so directly. Most of us grew up setting limits on ourselves, and falling in love with the way we think it should be. But when you let go, when you allow, accept and realize that life is happening for you and not to you, you will start to connect with yourself and your world in a much deeper light. When you don’t fall in love with one outcome, and are open and welcome many changes on your path, the world will start to offer you more beautiful opportunities, for love, health, abundance and happiness.

Since a young age, I never understood the concept of fighting until the end. When I was a young girl, I was very curious, and I wanted to try everything. From soccer, to lacrosse, to woodworking, to baton twirling and even ballet, I tried it all. I was curious to see what they were all about, and to see what was for me. Luckily, I had parents who accepted my curiosity, and if I didn’t want to go to soccer practice in the rain, I wouldn’t go. It turns out, I hated sports, I loved ballet, and I really loved my woodworking class, (even though I was the only girl). Around me though, I watched a lot of my peers being forced to go to piano lessons and soccer practice when they weren’t feeling well, when it was raining and cold, and they were miserable doing it.

Photo by: Kristina Tsipouras

Photo by: Kristina Tsipouras

When I entered high school, I remember being challenged and judged for giving up so easily when I didn’t connect to something. During math class, I would stare at the ceiling, and even randomly circle A,B,C, or D when tests came around. I could care less, and it showed. In English class however, I was the first to show up, I was eager to receive the next assignment, and I truly thrived and grew in the courses I enjoyed and connected to.

Since a young age, we were taught a certain way, and the culture we live in today still supports the theory of never giving up and fighting until the end. Now, at 30 years old, I look up to many successful Entrepreneurs and Authors. One of the themes that they all have in common is that they simply always follow their bliss. So why are people so scared to change directions? To close a door and let a new one appear? Ask yourself, if you truly feel like you are fighting against something in your current life, what are you holding onto? What are you scared of? Are you allowing or resisting the natural flow of life and feeling good? When we put resistance on one area in our lives, it affects all aspects of our lives, and it won’t feel good. That is why allowing and accepting is a beautiful tool to practice each day.

In Silicon Valley, they call failure, failing forward. It is actually something to strive for in order to be the best in your field, and necessary in order to be happy and to find your place in the world. The CEO of Whole Foods said in a recent interview that he hated reading in school. So at a young age, he decided that he would never pick up a book that he didn’t want to read again. In College, that meant doing poorly in several classes, but he really didn’t care. FailForward


A 16 year old intern of mine, also recently gave a Ted Talk, and he was introduced as an average C student. He is working on his third venture, and may very well be our next Steve Jobs. He does not let school or society judge him, or define his success. He loves playing, failing, succeeding, testing and allowing the flow of life and the trials & errors of the path he chose.

Failing and quitting has always come with a negative connotation. However, I ask you to truly challenge this: Take away the shame and guilt and what others may think of you, and only do what feels right for you. I hate the words failing and quitting, because they feel so negative. Since quitting or (testing and discovering) was a theme in my life; I knew I had to feel good about my choices. Instead of “giving up and letting go” of things, I decided to look at it as “letting them grow.”

If I didn’t listen to my heart, I wouldn’t have thrived in writing, or learned about the things I was most passionate about in school. If I didn’t let go of my wedding planning career, I would have never launched my brands, or pushed myself to be a Huffington Post blogger or to write a book. So next time you let go of something, remind yourself that you are only letting it grow.

I also use this tool in my personal life as well. When I let go of an ex- boyfriend, or a friend who is no longer healthy for me, I instead define these situations as letting them grow. Letting go of people, jobs, and situations that no longer serve me are an example of my personal growth and expansion, and something to be excited about. Closing a chapter to open another one is a beautiful thing, and is an example of your own personal growth. You have to let go of a situation or a person in your life, to let something bigger and better come in and grow into something more beautiful than you could have ever imagined. Instead of focusing on saying goodbye and bitter ends, I focus on the feeling of coming home to, finding a better fitting person, place, career or circumstance in my life. The key is to be open. Be open to everything that comes your way. Don’t take life so seriously and play a little more.

Photo by: Kristina Tsipouras

Photo by: Kristina Tsipouras

Despite all of the trials & errors, the giving up, the pushing harder, the failing forward, at the end of the day, it all comes back to how you want to define your life, your purpose and your goals. It is all about perspective, and only you have the power to define your situations and circumstances. It is easy to feel negative, guilt, pressure and pain, and sometimes it is harder to strive towards the good feeling thoughts, the appreciation, and the positivity. But we are all capable of being happy and finding our purpose. We are all capable of re-defining the tougher circumstances in our lives and making them work for us. I ask you, to go easy on yourself and to love and honor the choices you make. It doesn’t have to make sense to anyone but you. If you believe that life is happening for you and not to you, then you will never be a victim to anything that comes your way, and you are already winning.

Don’t fall in love with one particular future or the way you think it should be. Be open to all opportunities that come your way, and never set limits on yourself. Life is filled with so many beautiful challenges & changes, and when you are open to them, the opportunities will flow easier to you. So now I ask you, what are you going to let go of today?!

Start failing forward, faster, and letting it grow!


Kristina Tsipouras headshotKristina Tsipouras is an entrepreneur and author from Newton, Massachusets. She’s the founder of ZOOS Greek Iced-TeasMorroccan Magic lip balm, & Busy Girl Consulting Group; she also founded Boston Business Women’s networking group which has 2,500+ members and is hosting its first conference this Spring. Kristina has a deep love for Boston and the community and loves bringing women together. She speaks at inner-city Boston schools and mentors young women on self-esteem, confidence, empowerment and more. Catch up with Kristina on Busy Girl Daily, Instagram, Twitter, or LinkedIn!

You Might Also Like

No Comments

Leave a Reply