How to Fail Forward and Love Your Life

6 min read

Since I can remember, I have been a failure. From school tests to sports, failing came very naturally and easy to me. I didn’t have much interest in some subjects in school and at a young age, I remember feeling like the history facts or long division systems that I was so desperately trying to memorize were just skills that I was never going to need in life. Here is the thing: It was kind of true. And finally, in my mid-thirties, I’ve redefined failure and realized how valuable and amazing it can be. I am as proud of my past failures as I am my successes, and wear all of my failures like a badge of honor.

Sometimes It’s Okay to Quit

Most of us grew up being told to never quit, to never give up, to push and to fight until the end. Let’s put “quitting” in perspective: If you look back on the times when you quit and changed directions, was it for the best? Did you follow your heart and did it lead you to bigger and 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.

But many of us grew up putting limits on ourselves, and only focused on the way we thought life should be. When you let go, when you allow, accept and realize that life is happening for you and not to you, you’ll start to connect with yourself and your world in a much deeper way. When you are open to many changes on your path, the world will start to offer you more beautiful opportunities, for love, health, abundance and happiness.

I’ve really never understood the concept of fighting until the end. When I was a young girl, I was very curious, and wanted to try everything. From soccer and lacrosse, to woodworking, baton twirling and even ballet, I tried it all. Luckily, I had parents who accepted my curiosity, and if I didn’t want to go to ballet class, they didn’t make me. Around me, I watched a lot of my peers being forced to go to piano lessons when they weren’t feeling well, or soccer practice when it was raining and cold—and they were miserable doing it.

When I entered high school, I was judged for giving up so easily. During math class, I would stare at the ceiling, and even randomly circle A,B,C or D when tests came around. I couldn’t 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. It wasn’t that I was a bad student. I was just waiting to see what connected most with me. And that led me to my passions.

Learning from Silicon Valley

The culture we live in today still supports the theory of never giving up and fighting until the end. But that doesn’t ring true for the successful entrepreneurs and authors who I look up to now, as a 33-year-old. One of the things that they all have in common is that they simply always follow their bliss. They don’t push against things, and they do give up easily when it feels like they are pushing against the natural flow of life.

You see, life is supposed to flow easily and be joyful. Fighting the tough fight isn’t natural for us as humans. We are supposed to thrive, to do what feels right and to enjoy every moment. So why are we so scared to change directions? To close a door and let a new one appear? Why do we frame this as failure rather than as moving one step closer to what we are really meant to be doing?

Ask yourself this: If you truly feel like you are fighting against something in your current life, what are you holding on to? 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’s 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. Some investors say they won’t even invest in entrepreneurs until they have gone through their first big failure, because it is only after going through a failure and coming out the other side that you are truly well-rounded and fully in touch with yourself.

Flipping the Failure Script

I want you to challenge the idea that failure and quitting are always negative. Take away the shame and guilt of what others may think of you, and only do what feels right for you. Since quitting (or testing and discovering) was a theme in my life, I knew I had to feel good about my choices. I decided to look at “giving up” and “letting go of things,” as making room for what I wanted to see grow. You see, if I didn’t listen to my heart, I wouldn’t have thrived in writing, and learning about the things I was most passionate about in school. If I didn’t let go of my wedding-planning career, I never would have launched my million dollar brand, founded Boston’s fastest growing women’s network, pushed myself to be a Huffington Post blogger or finished writing a book. So next time you let go of something, remind yourself that you are actually letting something else grow.

Letting go of people, jobs and situations that no longer serve you are an example of your personal growth and expansion, and something to be excited about. Sometimes 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, 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.

This doesn’t mean we won’t come across difficulties that we have to navigate. But, we can take those trials and redefine them, making them work for us instead of against us. Part of that is going easy on yourself by loving and honoring the choices you’ve made. 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’re already winning.

Learn more about Kristina Tsipouras in our Women We’re Watching and The Business of Wellness series.

About The Author

Kristina Tsipouras

Kristina Tsipouras

Founder of Moroccan Magic + Boston Business Women, Kristina is a serial entrepreneur who was named as one of Boston Business Journal's 40 Under 40. She is also the founder of Busy Girl Boston and ZOOS Greek Tea, a published author, a Huffington Post blogger, and an active mentor and volunteer to young women interested in entrepreneurship. She and her brands have been featured in USA Today, Forbes, The Boston Globe, and many other high-profile publications.



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